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1. Compound ID: 21410
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b-D-Glcp-(1-7)-Subst
Subst = naringenin = SMILES O=C1CC(C2=CC={54}C(O)C=C2)OC3=C{7}C(O)={6}C{5}C(O)=C13 |
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Structure type: monomer
Trivial name: prunin
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8625
Penso J, Cordeiro KC, da Cunha CR, da Silva Castro PF, Martins DR, Lião LM, Rocha ML, de Oliveira V "Vasorelaxant activity of 7-β-O-glycosides biosynthesized from flavonoids" -
European Journal of Pharmacology 733 (2014) 75-80
In this work we report the vasorelaxant activity of 7-β-O-glycosides obtained with biosynthesis of naringenin-7-β-O-glycoside (3) and quercetin-7-β-O-glycoside (4). These compounds were obtained from naringenin (1) and quercetin (2) glycosylation catalyzed by Beauveria bassiana ATCC 7159. Screening of the best strain as a catalyst for glycosylation was carried out and the reaction conditions established. Cultures were grown in PDSM medium for 7 days at 27 °C. After purification by reverse-phase preparative HPLC, naringenin-7-β-O-glycoside (3) and quercetin-7-β-O-glycoside (4) were identified by (1)H and (13)C NMR. The right position and β-configuration of the glucose was determined through HSQC and HMBC experiments. The vasorelaxation potential of naringenin, quercetin and its glycosylated derivatives was evaluated using isolated aorta in vitro models. Interestingly, results suggest that vasorelaxation properties of naringenin, rutin and its glycosides are due to different pathways.
glycosylation, quercetin, Beauveria bassiana, aorta relaxation, naringenin
NCBI PubMed ID: 24704375Publication DOI: 10.1016/j.ejphar.2014.03.014Journal NLM ID: 1254354Publisher: Amsterdam: Elsevier
Correspondence: de Oliveira V
Institutions: Laboratório de Ressonância Magnética Nuclear, Instituto de Química, Universidade Federal de Goiás, Campus Samambaia, Goiânia, Brazil, Laboratório de Bioconversão, Faculdade de Farmácia, Universidad eFederal de Goiás, Setor Universitário,Brazil, Laboratório de Farmacologia Cardiovascular, Faculdade de Farmácia, Universidade Federal de Goiás, Setor Universitário, Brazil
Methods: 13C NMR, 1H NMR, HMBC, HPLC-UV, biological studies
- Article ID: 8898
Sordon S, Popłoński J, Tronina T, Huszcza E "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca" -
Bioorganic Chemistry 93 (2019) ID 102750
In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.
biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones
NCBI PubMed ID: 30755333Publication DOI: 10.1016/j.bioorg.2019.01.046Journal NLM ID: 1303703Publisher: Orlando, FL: Academic Press
Correspondence: Sordon S
; Popłoński J ; Tronina T ; Huszcza E
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
- Article ID: 9140
Ahmad R, Lim CK, Marzuki NF, Goh Y-K, Azizan KA, Goh YK, Goh KJ, Ramzi AB, Baharum SN "Metabolic profile of Scytalidium parasiticum-Ganoderma boninense co-cultures revealed the alkaloids, flavonoids and fatty acids that contribute to anti-Ganoderma activity" -
Molecules 25(24) (2020) ID 5965
In solving the issue of basal stem rot diseases caused by Ganoderma, an investigation of Scytalidium parasiticum as a biological control agent that suppresses Ganoderma infection has gained our interest, as it is more environmentally friendly. Recently, the fungal co-cultivation has emerged as a promising method to discover novel antimicrobial metabolites. In this study, an established technique of co-culturing Scytalidium parasiticum and Ganoderma boninense was applied to produce and induce metabolites that have antifungal activity against G. boninense. The crude extract from the co-culture media was applied to a High Performance Liquid Chromatography (HPLC) preparative column to isolate the bioactive compounds, which were tested against G. boninense. The fractions that showed inhibition against G. boninense were sent for a Liquid Chromatography-Time of Flight-Mass Spectrometry (LC-TOF-MS) analysis to further identify the compounds that were responsible for the microbicidal activity. Interestingly, we found that eudistomin I, naringenin 7-O-β-D-glucoside and penipanoid A, which were present in different abundances in all the active fractions, except in the control, could be the antimicrobial metabolites. In addition, the abundance of fatty acids, such as oleic acid and stearamide in the active fraction, also enhanced the antimicrobial activity. This comprehensive metabolomics study could be used as the basis for isolating biocontrol compounds to be applied in oil palm fields to combat a Ganoderma infection.
metabolomics, Biological control, Ganoderma boninense, LC-TOF-MS analysis, Scytalidium parasiticum, anti-Ganoderma
NCBI PubMed ID: 33339375Publication DOI: 10.3390/molecules25245965Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: Ahmad R
; Azizan KA ; Ramzi AB ; Lim CK ; Marzuki NF ; Goh Y-K ; Goh YK ; Goh KJ ; Baharum SN
Institutions: Metabolomics Research Laboratory, Institute of Systems Biology (INBIOSIS), Universiti Kebangsaan Malaysia, UKM, Bangi, Malaysia, Advanced Agriecological Research Sdn Bhd, Petaling Jaya, Malaysia
Methods: MS/MS, extraction, RP-HPLC, cell growth, sonication, centrifugation, antifungal activity test, HPLC-TOF-MS
- Article ID: 12167
Felgines C, Texier O, Morand C, Manach C, Scalbert A, Régerat F, Rémésy C "Bioavailability of the flavanone naringenin and its glycosides in rats" -
American Journal of Physiology. Gastrointestinal and Liver Physiology 279(6) (2000) G1148-G1154
Naringenin, the predominant flavanone in grapefruit, mainly occurs as glycosides such as naringenin-7-rhamnoglucoside or naringenin-7-glucoside. This study compared kinetics of absorption of naringenin and its glycosides in rats either after a single flavanone-containing meal or after adaptation to a diet for 14 days. Regardless of the diet, circulating metabolites were glucurono- and sulfoconjugated derivatives of naringenin. The kinetics of absorption of naringenin and naringenin-7-glucoside were similar, whereas naringenin-7-rhamnoglucoside exhibited a delay in its intestinal absorption, resulting in decreased bioavailability. After naringenin-7-glucoside feeding, no glucoside was found in the cecum. However, after feeding naringenin-7-rhamnoglucoside, some naringenin-7-rhamnoglucoside accumulated in cecum before being hydrolyzed by intestinal microflora. Adaptation to flavanone diets did not induce accumulation of plasma naringenin. Moreover, flavanone cecal content markedly decreased after adaptation, and almost no naringenin-7-rhamnoglucoside was recovered after naringenin-7-rhamnoglucoside feeding, suggesting that an adaptation of cecal microflora had occurred. Overall, these data indicate that flavanones are efficiently absorbed after feeding to rats and that their bioavailability is related to their glycosidic moiety.
metabolism, plasma, rats, naringenin, grapefruit, naringenin-7-rhamnoglucoside
NCBI PubMed ID: 11093936Publication DOI: 10.1152/ajpgi.2000.279.6.G1148Journal NLM ID: 100901227Publisher: Bethesda, MD: American Physiological Society
Correspondence: Catherine.FELGINES@u-clermont1.fr
Institutions: Laboratoire de Pharmacognosie, Faculté de Pharmacie, Clermont-Ferrand, France, Laboratoire des Maladies Métaboliques et des Micronutriments, Institut National de la Recherche Agronomique de Clermont-Ferrand/Theix, Saint-Genès-Champanelle, France
Methods: biological assays, HPLC, enzymatic digestion, extraction, evaporation, sonication, centrifugation
- Article ID: 12457
Mato M, Onozaki T, Ozeki Y, Higeta D, Itoh Y, Yoshimoto Y, Ikeda H, Yoshida H, Shibata M "Flavonoid biosynthesis in white-flowered Sim carnations (Dianthus caryophyllus)" -
Scientia Horticulturae 84(3-4) (2000) 333-347
Analysis of flavonoid composition and gene expression of enzymes involved in anthocyanin synthesis in flowers of four acyanic and one cyanic cultivar of Sim carnation showed that the acyanic flower cultivars are divided into three types. The first includes two normal white cultivars, ‘U Conn Sim’ and ‘White Sim’; the second includes a nearly pure white cultivar, ‘Kaly’; and the third includes a nearly pure white cultivar, ‘White Mind’. ‘U Conn Sim’ and ‘White Sim’ accumulated flavonol glycosides and lacked anthocyanins. The transcription of the several genes of enzymes involved in flavonoid biosynthesis were reduced at a later flowering stage than the cyanic cultivar, especially the genes encoding dihydroflavonol 4-reductase and anthocyanidin synthase. ‘Kaly’ accumulated flavanone glycosides and a small amount of flavonol and flavone glycosides by blocking the transcription of the gene encoding flavanone 3-hydroxylase, in addition to the transcriptional reduction of the genes for flavonoid biosynthesis at a later flowering stage. Although ‘White Mind’ contains little flavonoid, the position of the block on flavonoid biosynthesis in ‘White Mind’ is not known.
flavonoid, Dianthus caryophyllus, white flower, flavanone 3-hydroxylase, dihydroflavonol 4-reductase, anthocyanidin synthase
Publication DOI: 10.1016/S0304-4238(99)00140-5Journal NLM ID: 9882883Publisher: Amsterdam, International Society for Horticultural Science
Correspondence: Mato M
Institutions: Department of Floriculture, National Research Institute of Vegetables, Ornamental Plants and Tea, Ano, Japan, Department of Biotechnology, Tokyo University of Agriculture and Technology, Koganei, Japan, Japan Tobacco Inc., Applied Plant Research Laboratory, Oyama, Japan
- Article ID: 12476
Merken HM, Beecher GR "Measurement of food flavonoids by high-performance liquid chromatography: a review" -
Journal of Agricultural and Food Chemistry 48(3) (2000) 577-599
The flavonoids are plant polyphenols found frequently in fruits, vegetables, and grains. Divided into several subclasses, they include the anthocyanidins, pigments chiefly responsible for the red and blue colors in fruits, fruit juices, wines, and flowers; the catechins, concentrated in tea; the flavanones and flavanone glycosides, found in citrus and honey; and the flavones, flavonols, and flavonol glycosides, found in tea, fruits, vegetables, and honey. Known for their hydrogen-donating antioxidant activity as well as their ability to complex divalent transition metal cations, flavonoids are propitious to human health. Computer-controlled high-performance liquid chromatography (HPLC) has become the analytical method of choice. Many systems have been developed for the detection and quantification of flavonoids across one, two, or three subclasses. A summary of the various HPLC and sample preparation methods that have been employed to quantify individual flavonoids within a subclass or across several subclasses are tabulated in this review.
antioxidant; flavonoids; HPLC; mass spectrometry; polyphenols
NCBI PubMed ID: 10725120Publication DOI: 10.1021/jf990872oJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: merken@bhnrc.usda.gov
Institutions: Food Composition Laboratory, Beltsville Human Nutrition Research Center Agricultural Research Service, U.S. Department of Agriculture, Beltsville, USA
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2. Compound ID: 21445
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b-D-Glcp-(1-7)-Subst
Subst = genistein = SMILES O=C1C(C2=CC={54}C(O)C=C2)=COC3=C1{5}C(O)={6}C{7}C(O)={8}C3 |
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Structure type: monomer
Trivial name: genistin, genistein glucoside
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8632
Sordon S, Popłoński J, Tronina T, Huszcza E "Microbial glycosylation of daidzein, genistein and biochanin A: two new glucosides of biochanin A" -
Molecules 22(1) (2017) E81 (1-9)
Biotransformation of daidzein, genistein and biochanin A by three selected filamentous fungi was investigated. As a result of biotransformations, six glycosylation products were obtained. Fungus Beauveria bassiana converted all tested isoflavones to 4″-O-methyl-7-O-glucosyl derivatives, whereas Absidia coerulea and Absidia glauca were able to transform genistein and biochanin A to genistin and sissotrin, respectively. In the culture of Absidia coerulea, in addition to the sissotrin, the product of glucosylation at position 5 was formed. Two of the obtained compounds have not been published so far: 4″-O-methyl-7-O-glucosyl biochanin A and 5-O-glucosyl biochanin A (isosissotrin). Biotransformation products were obtained with 22%-40% isolated yield.
fungi, genistein, microbial glycosylation, daidzein, biochanin A, isoflavones
NCBI PubMed ID: 28054950Publication DOI: 10.3390/molecules22010081Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: Popłoński J
; Tronina T ; Huszcza E ; Sordon S
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland, Department of Chemistry,Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, TLC, HPLC, CC, HR-ESI-MS, HMBC, COSY, HSQC
- Article ID: 10875
Gagnon H, Tahara SL, Ibrahim RK "Biosynthesis, accumulation and secretion of isoflavonoids during germination and development of white lupin (Lupinus albus L)" -
Journal of Experimental Botany 46 (1995) 609-616
Journal NLM ID: 9882906Publisher: Oxford University Press
- Article ID: 12225
He X-G "On-line identification of phytochemical constituents in botanical extracts by combined high-performance liquid chromatographic–diode array detection–mass spectrometric techniques" -
Journal of Chromatography A 880(1-2) (2000) 203-232
It is necessary to determine all of the phytochemical constituents of botanical extracts in order to ensure the reliability and repeatability of pharmacological and clinical research, to understand their bioactivities and possible side effects of active compounds and to enhance product quality control. HPLC chromatographic fingerprints can be applied for this kind of documentation. Combined HPLC-diode array detection-MS techniques can provide on-line UV and MS information for each peak in a chromatogram. In most cases, direct identification of the peaks is possible, based on comparison with published data or with standard compounds. This review will primarily focus on electrospray and thermospray ionization MS and their applications for the qualitative analyses of phenolic compounds, saponins, alkaloids and other classes of natural products in botanical extracts. Twenty-one of the most commonly used herbal examples, their phytochemical analyses and characteristics of their mass spectra are described.
alkaloids, saponins, plant materials, flavonoids, phenolic compounds, reviews
NCBI PubMed ID: 10890521Publication DOI: 10.1016/s0021-9673(00)00059-5Journal NLM ID: 9318488Publisher: Amsterdam; New York: Elsevier
Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA
- Article ID: 12405
Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, Cordell GA "LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense)" -
Journal of Agricultural and Food Chemistry 48(2) (2000) 354-365
High-performance liquid chromatography−electrospray ionization−mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their malonate-free extracts, ∼20 flavonoid glycoside malonates were detected in the flower extract. Eight were identified as genistin 6‘‘-O-malonate (39), formononetin 7-O-β-D-glucoside 6‘‘-O-malonate (40), biochanin A 7-O-β-D-glucoside 6‘‘-O-malonate (41), trifoside 6‘‘-O-malonate (42), irilone 4‘-O-β-D-glucoside 6‘‘-O-malonate (43), pratensein 7-O-β-D-glucoside 6‘‘-O-malonate (44), isoquercitrin 6‘‘-O-malonate (45), and 3-methylquercetin 7-O-β-D-glucoside 6‘‘-O-malonate (46). About 15 other flavonoids and clovamides were proved to be present in this extract. The study also found that the flowers contained flavones as the major flavonoids, whereas the leaves had isoflavones as the major flavonoids. This is the first detection of the six malonates (39 and 42−46) in the extracts of red clover, and among them, 42, 43, and 46 are new compounds.
flavonoids, Leguminosae, Trifolium pratense, red clover, flavonoid glycoside malonates, clovamides, LC-ESI-MS analysis
NCBI PubMed ID: 10691640Publication DOI: 10.1021/jf991002+Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: longze.lin@amtbotanicals.com
Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL, USA
Methods: LC-ESI-MS
- Article ID: 12661
Scalbert A, Williamson G "Dietary intake and bioavailability of polyphenols" -
The Journal of Nutrition 130(8S) (2000) ID 2073S-2085S
The main dietary sources of polyphenols are reviewed, and the daily intake is calculated for a given diet containing some common fruits, vegetables and beverages. Phenolic acids account for about one third of the total intake and flavonoids account for the remaining two thirds. The most abundant flavonoids in the diet are flavanols (catechins plus proanthocyanidins), anthocyanins and their oxidation products. The main polyphenol dietary sources are fruit and beverages (fruit juice, wine, tea, coffee, chocolate and beer) and, to a lesser extent vegetables, dry legumes and cereals. The total intake is ∼1 g/d. Large uncertainties remain due to the lack of comprehensive data on the content of some of the main polyphenol classes in food. Bioavailability studies in humans are discussed. The maximum concentration in plasma rarely exceeds 1 μM after the consumption of 10–100 mg of a single phenolic compound. However, the total plasma phenol concentration is probably higher due to the presence of metabolites formed in the body's tissues or by the colonic microflora. These metabolites are still largely unknown and not accounted for. Both chemical and biochemical factors that affect the absorption and metabolism of polyphenols are reviewed, with particular emphasis on flavonoid glycosides. A better understanding of these factors is essential to explain the large variations in bioavailability observed among polyphenols and among individuals.
metabolism, flavonoid, Antioxidant, bioavailability, glucosidase, flavonoid glycoside, dietary intake, polyphenol, phenolic acid, gut absorption, colonic microflora
NCBI PubMed ID: 10917926Publication DOI: 10.1093/jn/130.8.2073SJournal NLM ID: 0404243Publisher: Rockville, MD: American Society for Nutrition
Institutions: Institute of Food Research, Norwich Research Park, Colney, UK, Laboratoire des Maladies Métaboliques et Micronutriments, INRA, Saint-Genès-Champanelle, France
- Article ID: 12698
Singletary K, Faller J, Li JY, Mahungu S "Effect of extrusion on isoflavone content and antiproliferative bioactivity of soy/corn mixtures" -
Journal of Agricultural and Food Chemistry 48(8) (2000) 3566-3571
The present studies were conducted to determine changes in the quantities of select isoflavones and in the bioactivity (ability to inhibit proliferation of human breast cancer cell lines) of extracts from blends of soy protein and cornmeal during extrusion processing. The extrusion of samples resulted in an average 24% decrease in the concentration of total isoflavones for all samples. Although the amounts of specific genistein-derived and daidzein-derived forms changed following extrusion, the content of the aglycones genistein and daidzein per g sample generally did not change. The extrusion of samples generally resulted in decreased antiproliferative action toward breast cancer cells, although antiproliferative activity was not eliminated. Therefore, extrusion of soy protein/cornmeal-containing foods are likely to retain a considerable portion of their isoflavone content and some of the health benefits associated with soy.
extrusion; isoflavones; soy; corn; antiproliferative
NCBI PubMed ID: 10956151Publication DOI: 10.1021/jf991312sJournal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: Singletary K
Institutions: University of Illinois, Department of Food Science and Human Nutrition, Urbana, USA
Methods: HPLC, extraction, MTT, proliferation assay
- Article ID: 12721
Strick R, Strissel PL, Borgers S, Smith SL, Rowley JD "Dietary bioflavonoids induce cleavage in the MLL gene and may contribute to infant leukemia" -
Proceedings of the National Academy of Sciences of the USA 97(9) (2000) 4790-4795
Chromosomal translocations involving the MLL gene occur in about 80% of infant leukemia. In the search for possible agents inducing infant leukemia, we identified bioflavonoids, natural substances in food as well as in dietary supplements, that cause site-specific DNA cleavage in the MLL breakpoint cluster region (BCR) in vivo. The MLL BCR DNA cleavage was shown in primary progenitor hematopoietic cells from healthy newborns and adults as well as in cell lines; it colocalized with the MLL BCR cleavage site induced by chemotherapeutic agents, such as etoposide (VP16) and doxorubicin (Dox). Both in vivo and additional in vitro experiments demonstrated topoisomerase II (topo II) as the target of bioflavonoids similar to VP16 and Dox. Based on 20 bioflavonoids tested, we identified a common structure essential for topo II-induced DNA cleavage. Reversibility experiments demonstrated a religation of the bioflavonoid as well as the VP16-induced MLL cleavage site. Our observations support a two-stage model of cellular processing of topo II inhibitors: The first and reversible stage of topo II-induced DNA cleavage results in DNA repair, but also rarely in chromosome translocations; whereas the second, nonreversible stage leads to cell death because of an accumulation of DNA damage. These results suggest that maternal ingestion of bioflavonoids may induce MLL breaks and potentially translocations in utero leading to infant and early childhood leukemia.
doxorubicin, acute myelogenous leukemia, acute lymphoblastic leukemia, etoposide, topoisomerase II
NCBI PubMed ID: 10758153Publication DOI: 10.1073/pnas.070061297Journal NLM ID: 7505876Publisher: National Academy of Sciences
Correspondence: Strick R
; Strissel PL
Institutions: University of Chicago, Department of Medicine, Section of Hematology/Oncology, Chicago, IL, USA
Methods: biological assays
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3. Compound ID: 21446
|
b-D-Glcp-(1-7)-Subst4'Me
Subst = genistein = SMILES O=C1C(C2=CC={54}C(O)C=C2)=COC3=C1{5}C(O)={6}C{7}C(O)={8}C3 |
Show graphically |
Structure type: monomer
; 445.1151 [M-H]-
C22H22O10
Trivial name: sissotrin
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8632
Sordon S, Popłoński J, Tronina T, Huszcza E "Microbial glycosylation of daidzein, genistein and biochanin A: two new glucosides of biochanin A" -
Molecules 22(1) (2017) E81 (1-9)
Biotransformation of daidzein, genistein and biochanin A by three selected filamentous fungi was investigated. As a result of biotransformations, six glycosylation products were obtained. Fungus Beauveria bassiana converted all tested isoflavones to 4″-O-methyl-7-O-glucosyl derivatives, whereas Absidia coerulea and Absidia glauca were able to transform genistein and biochanin A to genistin and sissotrin, respectively. In the culture of Absidia coerulea, in addition to the sissotrin, the product of glucosylation at position 5 was formed. Two of the obtained compounds have not been published so far: 4″-O-methyl-7-O-glucosyl biochanin A and 5-O-glucosyl biochanin A (isosissotrin). Biotransformation products were obtained with 22%-40% isolated yield.
fungi, genistein, microbial glycosylation, daidzein, biochanin A, isoflavones
NCBI PubMed ID: 28054950Publication DOI: 10.3390/molecules22010081Journal NLM ID: 100964009Publisher: Basel, Switzerland: MDPI
Correspondence: Popłoński J
; Tronina T ; Huszcza E ; Sordon S
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland, Department of Chemistry,Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, TLC, HPLC, CC, HR-ESI-MS, HMBC, COSY, HSQC
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4. Compound ID: 21981
|
b-D-Glcp-(1-7)-Subst
Subst = chrysin = SMILES O=C1C=C(OC2=C1{5}C(O)=C{7}C(O)=C2)C3=CC=CC=C3 |
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Structure type: monomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8898
Sordon S, Popłoński J, Tronina T, Huszcza E "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca" -
Bioorganic Chemistry 93 (2019) ID 102750
In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.
biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones
NCBI PubMed ID: 30755333Publication DOI: 10.1016/j.bioorg.2019.01.046Journal NLM ID: 1303703Publisher: Orlando, FL: Academic Press
Correspondence: Sordon S
; Popłoński J ; Tronina T ; Huszcza E
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
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5. Compound ID: 21982
Structure type: monomer
Trivial name: cosmosiin, apigenin 7-O-glucoside, rhoifolin, apigenin 7-glucoside, apigetrin
Compound class: glycoside, flavonoid glycoside, flavonol glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_613414,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8898
Sordon S, Popłoński J, Tronina T, Huszcza E "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca" -
Bioorganic Chemistry 93 (2019) ID 102750
In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.
biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones
NCBI PubMed ID: 30755333Publication DOI: 10.1016/j.bioorg.2019.01.046Journal NLM ID: 1303703Publisher: Orlando, FL: Academic Press
Correspondence: Sordon S
; Popłoński J ; Tronina T ; Huszcza E
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
- Article ID: 10744
Ofman DJ, Markham KR, Vilain C, Molloy BPJ "Flavonoid profiles of New Zealand kauri and other species of Agathis" -
Phytochemistry 38 (1995) 1223-1228
This paper describes the flavonoid constituents in Agathis australis from a wide geographic range and completes a comprehensive survey of the flavonoid chemistry/chemotaxonomy of New Zealand conifers begun in 1984. Flavonol 3-O-glycosides and biflavones of the cupressuflavone and agathisflavone types are shown to be the predominant flavonoids. NMR data for these biflavones with varying degrees of methylation are presented for the first time. The flavonoid profiles of A. australis and three other species of Agathis show a high level of uniformity, and in this respect are closely related.
chemotaxonomy, flavonoids, Agathis australis, Araucariaceae, biflavonoids, cupressuflavone, agathisflavone
Publication DOI: 10.1016/0031-9422(94)00783-PJournal NLM ID: 0151434Publisher: Elsevier
Institutions: New Zealand Institute for Industrial Research and Development, Lower Hutt, New Zealand, Manaaki Whenua-Landcare Research, Lincoln, New Zealand
Methods: 13C NMR, 1H NMR, TLC, LSI-MS, UV, 2D-PC
- Article ID: 10972
Ohe C, Sugino M, Minami M, Hasegawa C, Ashida K, Ogaki K, Kanamori H "Studies on the cultivation and evaluation of chamomilae flos. Seasonal variation in production of the head (capitula) and accumulation of glycosides in the capitula of Matricaria chamomilla L" -
Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 115 (1995) 130-135
Journal NLM ID: 0413613Publisher: Tokyo: Nihon Yakugakkai
- Article ID: 11595
Barakat HH "Chemical investigation of the constitutive phenolics of Ailanthus altissima; The structure of a new flavone glycoside gallate" -
Natural Product Sciences 4(3) (1998) 153-157
The aqueous ethanolic leaf extract of Ailanthus altissima was found to contain the new natural product, luteolin 7-O-β-(6'- galloylglucopyranoside), 13, along with fourteen known phenotic metabolites (1-12, 14 and 15). Structures of all compounds (1-15) were established by conventional methods of analysis and confirmed by FAB-MS, 1H- and 13C-NMR spectral analysis.
13C-NMR, FAB-MS, phenolics, Simaroubaceae, Ailanthus altissima, luteolin 7-O-β-(6'- galloylglucopyranoside)
Journal NLM ID: 9714997Publisher: Seoul, Korea: Korean Society of Pharmacognosy
Institutions: National Research Centre, Dokki, Cairo, Egypt
Methods: 13C NMR, 1H NMR, FAB-MS, acid hydrolysis, UV, extraction, CC
- Article ID: 11680
Kumar JK, Rao MS, Rao PS, Toth G, Balázs B, Duddeck H "Flavone glycosides from Polygala telephioides and Polygala arvensis" -
Natural Product Letters 14(1) (1999) 35-38
A novel flavone C-glucoside, telephioidin, was isolated from Polygala telephioides. Its structure was established by extensive 1D and 2D NMR measurements. Rhoifolin was isolated from Polygala arvensis and polygalitol from both plants.
flavones, Polygala telephioides, Polygala arvensis, telephioidin, rhoifolin, apigenin, polygalitol, C-glucoside
Publication DOI: 10.1080/10575639908045432Journal NLM ID: 9315615Publisher: Taylor & Francis Health Sciences
Institutions: Department of Chemistry, Kakatiya University, Warangal, 506009, Andra Pradesh, India, Technical Analytical Research Group of the Hungarian Academy of Sciences, Institute for General and Analytical Chemistry of the Technical University, Szent Gellért tér 4, H-1111, Budapest, Hungary, Universität Hannover, Institut für Organische Chemie, Schneiderberg 1B, D-30167, Hannover, Germany
Methods: 13C NMR, 1H NMR, IR, FAB-MS, TLC, UV, optical rotation measurement, HMBC, HMQC, COSY, sulfuric acid hydrolysis
- Article ID: 11700
Cimanga K, De Bruyne T, Hu JP, Cos P, Apers S, Pieters L, Tona L, Van Den Berghe D, Vlietinck AJ "Constituents from Morinda morindoides leaves as inhibitors of xanthine oxidase and scavengers of superoxide anions" -
Pharmacy and Pharmacology Communications 5(6) (1999) 419-424
Morinda morindoides (Kongobololo or Nkongabululu) is one of the most popular medicinal plants used in the Democratic Republic of Congo. Ten of its constituent flavonoids were evaluated in the xanthine-xanthine oxidase enzymatic system. The compounds were identified by spectroscopic methods as quercetin (1), quercetin 7,4' dimethylether (2), luteolin 7 glucoside (3), apigenin 7 glucoside (4), quercetin 3 rhamnoside (5), kaempferol 3 rhamnoside (6), quercetin 3 rutinoside (7), kaempferol 3 rutinoside (8), chrysoeriol 7 neohesperidoside (9) and kaempferol 7 rhamnosylsophoroside (10). The aglycones chrysoeriol (11), kaempferol (12), luteolin (13) and apigenin (14), obtained by acid hydrolysis of the corresponding glycosides, were also included. Compound 5 exhibited only scavenging activity, 9 and 11 were devoid of any effect against xanthine oxidase and scavenging activity, and the remaining flavonoids exhibited xanthine oxidase inhibiting and superoxide scavenging activity to varying extent. Study of structure activity relationships demonstrated that the activity was not only dependent on the nature of substituents and the substitution site, but also on the nature of the aglycone. These results partially explain and support the use of Morinda morindoides in the treatment of rheumatism.
flavonoid glycoside, Morinda morindoides, xanthine oxidase inhibition, superoxide anion scavanger
Publication DOI: 10.1211/146080899128735009Journal NLM ID: 9807134Publisher: London: Pharmaceutical Press
Institutions: Department of Pharmaceutical Sciences, University of Antwerp, Universiteitsplein 1, B 2610, Wilrijk, Antwerp, Belgium, Faculty of Pharmacy, University of Kinshasa, B.P. 212, Kinshasa XI, Congo
Methods: statistical analysis, antioxidant activities
- Article ID: 11779
Shalaby NMM, Maghraby AS, El-Hagrassy AM "Effect of Daucus carota var. boissieri extracts on immune response of Schistosoma mansoni infected mice" -
Folia Microbiologica 44(4) (1999) 441-448
Isolation and structure elucidation was carried out of flavonoid constituents found in fractionated extracts of the seeds and green leaves of Daucus carota L. var. boissieri (Apiaceae). The flavonoids are mainly apigenin, luteolin, their glycosidic precursors and 2,4,5-trimethoxybenzaldehyde. Fatty acids, hydrocarbons and sterols were identified by GLC. The effect of various carrot extracts on the immune responses of Schistosoma mansoni infected mice was studied. The rate of reduction in worm infestation in mice injected with some fractions indicated a strong protection. Some extracts induced humoral immune response through raising the IgG level at 2, 4 and 6 weeks post-infection as compared with infected control. The phenotypic analysis of the cellular immune response in spleen and mesenteric lymph nodes was accomplished by direct immunofluorescence. The data showed that some extracts stimulated the blastogenesis of CD4+-T splenocytes and mesenteric lymph node cells.
flavonol glycoside, luteolin, apigenin, mesenteric lymph node, praziquantel, worm burden
NCBI PubMed ID: 10983240Publication DOI: 10.1007/bf02903720Journal NLM ID: 0376757Publisher: New York: Springer
Institutions: Laboratory of Natural Products, National Research Centre, Dokki, Cairo, Egypt, Laboratory of Therapeutical Chemistry, National Research Centre, Dokki, Cairo, Egypt
Methods: 1H NMR, GLC, UV, PC
- Article ID: 12048
Calvo MI, Crespo A, Fernández M "Seasonal variations of the iridoids, flavonoids and verbascoside content from Verbena officinalis L" -
Acta Horticulture 516(516) (2000) 169-176
The aim of this work is the quantitative determinations of iridoids, flavonoids and verbascoside by HPLC in leaves of Verbena officinalis during three vegetative periods. The effects of plant age, date of harvest, type of soil, climate, as well as a comparision between two different locations, Ilundain and Lezaun, are been investigated in order to evaluate the development and content of major compounds in Verbena leaves, verbenalin mainly, because it is the active principle. The highest amount of iridoids and flavonoids was found in the leaves during the pre-flowering period. After flowering the total compound content in the leaves decreases, whereas verbascoside content increases. The amount of iridoids and phenolic components are increasing by the years. Verbenalin content is greater in Lezaun than in Ilundain every vegetative cycle.
HPLC, flavonoids, Verbenaceae, verbascoside, Iridoids, Verbena officinalis, experimental field, verbenalin
Publication DOI: 10.17660/ActaHortic.2000.516.20Institutions: Institut de pharmacognosie et phytochimie, Ecole de Pharmacie, Université de Lausanne, Lausanne, Switzerland, Dpto. Farmacia y Tecnologiá Farmaceútica (Farmacognosia), Facultad de Farmacia, Universidad de Navarra, Pamplona, Spain
Methods: HPLC, UV, extraction, derivatization, evaporation
- Article ID: 12238
Ho CT, Wang M, Wei GJ, Huang TC, Huang MT "Chemistry and antioxidative factors in rosemary and sage" -
BioFactors 13(1-4) (2000) 161-166
Rosemary and sage are common spices used in food. In our recent search of cancer chemopreventive agents from spices, the alcohol extracts of rosemary and sage showed strong antumorigenic activities. Rosemary and sage extracts contain active antioxidative factors such as phenolic diterpenes, flavonoids and phenolic acids. Here we discuss chromatographic methods used to separate and purify compounds from these spices and MS and NMR spectrometry to identify the isolated compounds. Several new compounds isolated from sage were determined to be 6-O-caffeoyl-β-D-fructofuranosyl-(2→1)-β-glucopyranoside, 1-O-caffeoyl-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, 1-O-p-hydroxybenzoyl-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside, 1-O-(3-methyl-2,3,4-trihydroxybutyl)-6-O-feruloyl-β-D-glucopyranoside, 4-hydroxyacetophenone 4-O-[5-O-(3,5-dimethoxy-4-hydroxybenzoyl)-β-D-apiofuranosyl]-(1→2)-β-D-glucopyranoside and 1-O-[2-hydroxy-5-(2-hydroxyethyl)phenyl]-6-O-trans-caffeoyl-β-D-glucopyranoside.
Antioxidant activity, phenolic glycosides, flavonoids, rosemary, sage
NCBI PubMed ID: 11237177Publication DOI: 10.1002/biof.5520130126Journal NLM ID: 8807441Publisher: Oxford; Washington, DC: IRL Press, International Union of Biochemistry
Correspondence: Ho CT
Institutions: Department of Food Science, Rutgers University, New Brunswick, NJ, USA, Department of Food Science and Technology, National Pingtung University of Science and Technology, Pingtung, Taiwan, Laboratory for Cancer Research, College of Pharmacy, Rutgers University, Piscataway, USA
- Article ID: 12258
Inagaki I, Hisada S, Nishibe S, Sakushima A "Studies on the constituents of the leaves of Trachelospermum asiaticum var. intermedium. I. Isolation of flavones and flavone glycosides" -
Yakugaku Zasshi = Journal of the Pharmaceutical Society of Japan [Japanese] 93(9) (1973) 1231-1234
The methanol extract of the leaves of Trachelospermum asiaticum NAKAI var. intermedium NAKAI was treated (Chart 1) and from the ethyl acetate-soluble fraction, succinic acid, apigenin, luteolin, arctigenin, apigenin 7-glucoside, luteolin 7-glucoside, and luteolin 4'-glucoside were isolated and identified respectively with authentic samples.
flavonoid glucosides, Trachelospermum asiaticum
NCBI PubMed ID: 4797583Publication DOI: 10.1248/yakushi1947.93.9_1231Journal NLM ID: 0413613Publisher: Tokyo: Nihon Yakugakkai
Institutions: Faculty of Pharmaceutical Sciences, Nagoya City University, Nagoya, Japan
Methods: 13C NMR, 1H NMR, IR, TLC, UV, extraction, elemental analysis, CC, melting point determination
- Article ID: 12298
Kisiel W, Zielińska K "Sesquiterpenoids and phenolics from Lactuca perennis" -
Fitoterapia 71(1) (2000) 86-87
flavonoids, sesquiterpene lactone glycosides, Lactuca perennis, phenolic acid esters
NCBI PubMed ID: 11449481Publication DOI: 10.1016/s0367-326x(99)00112-4Journal NLM ID: 16930290RPublisher: Elsevier
Correspondence: Kisiel W
; Kisiel W
Institutions: Department of Phytochemistry, Institute of Pharmacology, Polish Academy of Sciences, Krakow, Poland
- Article ID: 12405
Lin LZ, He XG, Lindenmaier M, Yang J, Cleary M, Qiu SX, Cordell GA "LC-ESI-MS study of the flavonoid glycoside malonates of red clover (Trifolium pratense)" -
Journal of Agricultural and Food Chemistry 48(2) (2000) 354-365
High-performance liquid chromatography−electrospray ionization−mass spectrometry (LC-ESI-MS) was applied to the analysis of the flavonoids and their glycoside malonates of the flowers and leaves of red clover (Trifolium pratense). Through LC-MS comparative studies on the plant extracts and their malonate-free extracts, ∼20 flavonoid glycoside malonates were detected in the flower extract. Eight were identified as genistin 6‘‘-O-malonate (39), formononetin 7-O-β-D-glucoside 6‘‘-O-malonate (40), biochanin A 7-O-β-D-glucoside 6‘‘-O-malonate (41), trifoside 6‘‘-O-malonate (42), irilone 4‘-O-β-D-glucoside 6‘‘-O-malonate (43), pratensein 7-O-β-D-glucoside 6‘‘-O-malonate (44), isoquercitrin 6‘‘-O-malonate (45), and 3-methylquercetin 7-O-β-D-glucoside 6‘‘-O-malonate (46). About 15 other flavonoids and clovamides were proved to be present in this extract. The study also found that the flowers contained flavones as the major flavonoids, whereas the leaves had isoflavones as the major flavonoids. This is the first detection of the six malonates (39 and 42−46) in the extracts of red clover, and among them, 42, 43, and 46 are new compounds.
flavonoids, Leguminosae, Trifolium pratense, red clover, flavonoid glycoside malonates, clovamides, LC-ESI-MS analysis
NCBI PubMed ID: 10691640Publication DOI: 10.1021/jf991002+Journal NLM ID: 0374755Publisher: American Chemical Society
Correspondence: longze.lin@amtbotanicals.com
Institutions: Research Laboratory of Natural Products Chemistry, A. M. Todd Botanicals, Eugene, USA, Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, The University of Illinois at Chicago, Chicago, IL, USA
Methods: LC-ESI-MS
- Article ID: 12423
Lu K-L, Ku Y-R, Wen K-C, Ho L-K, Chang Y-S "Analysis of flavonoids and coumarins in Ixeris laevigata var. oldhami by HPLC" -
Journal of Liquid Chromatography & Related Technologies 23(16) (2000) 2573-2583
Tao-shang-tsao is the dried entire plant of Ixeris laevigata var. oldhami (Compositae) and a commonly used folk herb in Taiwan. To evaluate the quality of I. laevigata var. oldhami, a simple, rapid, and accurate high-performance liquid chromatographic (HPLC) method was developed for the assay of four flavonoids, apigenin, apigenin-7-O-glucoside, luteolin, and luteolin-7-O-glucoside, and two coumarins, esculetin and esculin. The present HPLC system uses an Inertsil ODS-2 column by gradient elution with acetonitrile and 0.1% (v/v) phosphoric acid as the mobile phase. Ethylparaben was used as an internal standard and detected at 254 nm. Regression equations revealed good linear relationships (correlation coefficients: 0.9998–0.9999) between the peak-area ratios of each constituent to ethylparaben. The relative standard deviations of these six constituents ranged between 0.56–3.04% (intra-day) and 0.79–4.39% (inter-day). The contents of six constituents of I. laevigata var. oldhami in 7 crude drugs have been determined. This study also compared their constituents with those of similar folk herbs, I. chinensis and Taraxacum formosanum, commonly used as an adulterant, by their HPLC chromatograms.
HPLC, coumarins, flavonoids, esculin, esculetin, Ixeris laevigata var. oldhami
Publication DOI: 10.1081/JLC-100100511Journal NLM ID: 9605507Publisher: Monticello, NY: Marcel Dekker
Institutions: Institute of Chinese Pharmaceutical Sciences, China Medical College, Taichung, Taiwan, China, National Laboratories of Foods and Drugs, Department of Health, Executive Yuan, Nankang, Taipei, Taiwan, China, Chung Hwa Institute of Technology, Jen-Teh Hsiang, Taiwan, China, Department and Institute of Pharmacology, National Yang-Ming University, Taipei, Taiwan, China
Methods: HPLC, extraction
- Article ID: 12579
Panizzi L, Catalano S, Miarelli C, Cioni PL, Campeol E "In vitro antimicrobial activity of extracts and isolated constituents of Geum rivale" -
Phytotherapy Research 14(7) (2000) 561-563
The antimicrobial activity of extracts of Geum rivale (Rosaceae) and that of some isolated constituents, on bacteria and fungi, was evaluated. The activity was concentrated in the triterpenes fraction and, for gram+ and gram- bacteria, also in the flavonoids fraction.
Geum rivale; Rosaceae; triterpenes; flavonoids; tannins; antimicrobial activity
NCBI PubMed ID: 11054853Publication DOI: 10.1002/1099-1573(200011)14:7<561::aid-ptr651>3.0.co;2-hJournal NLM ID: 8904486Publisher: Chichester: Wiley
Institutions: Dipartimento di Bioorganica e Biofarmacia, Università di Pisa, Pisa, Italy, Sezione di Biotossicologia, Dipartimento di Prevenzione A.U.S.L., Livorno, Italy
Methods: biological assays
- Article ID: 12598
Pieroni A, Pachaly P, Huang Y, Van Poel B, Vlietinck AJ "Studies on anti-complementary activity of extracts and isolated flavones from Ligustrum vulgare and Phillyrea latifolia leaves (Oleaceae)" -
Journal of Ethnopharmacology 70(3) (2000) 213-217
Polar fractions and flavones isolated from methanolic extracts of the leaves of Ligustrum vulgare and Phillyrea latifolia (Oleaceae), whose popular use as an anti-inflammatory is well-known in Mediterranean historical medicine and ethnobotany, showed significant in vitro complement inhibiting effect on the classical pathway of the complement system. Among the isolated flavonoidic structures, apigenin-7-O-glucoside, apigenin-7-O-rutinoside, luteolin-4'-O-glucoside, luteolin-7-O-glucoside and ligustroflavone presented remarkable activity.
Ligustrum vulgare; Phillyrea latifolia; mediterranean ethnomedicine; flavones; anti-complementary activity
NCBI PubMed ID: 10837985Publication DOI: 10.1016/s0378-8741(99)00169-5Journal NLM ID: 7903310Publisher: Limerick: Elsevier Sequoia
Correspondence: Pieroni A
Institutions: Department of Pharmaceutical Sciences, University of Antwerp (UIA), Antwerp, Belgium, Pharmazeutisches Institut der Rheinischen Friedrich-Wilhelms-Universität Bonn, Bonn, Germany, Dipartimento di Scienza del Suolo e Nutrizione della Pianta, Università degli Studi di Firenze, Firenze, Italy
Methods: inhibition studies, HPLC, extraction
- Article ID: 12647
Samuelsen AB "The traditional uses, chemical constituents and biological activities of Plantago major L. A review" -
Journal of Ethnopharmacology 71(1-2) (2000) 1-21
Plantago major L. leaves have been used as a wound healing remedy for centuries in almost all parts of the world and in the treatment of a number of diseases apart from wound healing. These include diseases related to the skin, respiratory organs, digestive organs, reproduction, the circulation, against cancer, for pain relief and against infections. P. major contains biologically active compounds such as polysaccharides, lipids, caffeic acid derivatives, flavonoids, iridoid glycosides and terpenoids. Alkaloids and some organic acids have also been detected. A range of biological activities has been found from plant extracts including wound healing activity, anti-inflammatory, analgesic, antioxidant, weak antibiotic, immuno modulating and antiulcerogenic activity. Some of these effects may attribute to the use of this plant in folk medicine.
traditional uses; chemical constituents; biological activities; Plantago major L
NCBI PubMed ID: 10904143Publication DOI: 10.1016/s0378-8741(00)00212-9Journal NLM ID: 7903310Publisher: Limerick: Elsevier Sequoia
Correspondence: a.b.samuelsen@farmasi.uio.no
Institutions: Department of Pharmacognosy, School of Pharmacy, University of Oslo, Oslo, Norway
- Article ID: 12751
Tattini M, Gravano E, Pinelli P, Mulinacci N, Romani A "Flavonoids accumulate in leaves and glandular trichomes of Phillyrea latifolia exposed to excess solar radiation" -
New Phytologist 148(1) (2000) 69-77
Experiments were conducted on Phillyrea latifolia plants grown under a dense overstorey of Pinus pinea (shade plants) or on seashore dunes (sun plants) in a coastal area of Tuscany (42° 46′ N, 10° 53′ E). Total integrated photon flux densities averaged 1.67 and 61.4 m mol/m^2/d for shade and sun sites, respectively. A leaf morphological–structural analysis, a qualitative and quantitative analysis of phenylpropanoids of leaf tissue and leaf surface, and a histochemical localization of flavonoids were conducted. The area of sun leaves reached 57% of that of shade leaves, whereas leaf angle (β), sclerophylly index (ratio of leaf d. wt:leaf area), and trichome frequency (trichome number mm−2 ) were markedly greater in leaves exposed to full solar radiation than in leaves acclimated to shade. The total thickness of sun leaves was 78% higher than that of shade leaves, mostly owing to a greater development of both palisade parenchyma and spongy mesophyll. The concentration, but not the composition, of leaf tissue phenylpropanoids varied significantly between sun and shade leaves, with a marked increase in flavonoid glycosides in sun leaves. Flavonoids occurred almost exclusively in the upper epidermal cells of shade leaves. By contrast, flavonoids largely accumulated in the upper and lower epidermis, as well as in the mesophyll tissue of leaves that were acclimated to full sunlight. Flavonoid glycosides were found exclusively in the secretory products of glandular trichomes of P. latifolia leaves exposed to high levels of light; luteolin 7-O- glucoside and quercetin 3-O-rutinoside were the major constituents. By contrast, verbascoside and an unidentified caffeic acid derivative constituted 72% of total phenylpropanoids secreted by glandular trichomes of shade leaves, whereas they were not detected in glandular trichomes of sun leaves. These findings suggest that the light-induced synthesis of flavonoids in glandular trichomes of P. latifolia probably occurs in situ and concomitantly inactivates other branch pathways of the general phenylpropanoid metabolism. This is the first report of the key role of glandular trichomes and of flavonoid glycosides in the integrated mechanisms of acclimation of P. latifolia to excess light.
phenylpropanoids, flavonol glycosides, Oleaceae, fluorescence microscopy, glandular trichomes
NCBI PubMed ID: 33863030Publication DOI: 10.1046/j.1469-8137.2000.00743.xJournal NLM ID: 9882884Publisher: Blackwell Publishing
Correspondence: tattini@ipsl.fi.cnr.it
Institutions: Dipartimento di Scienze Farmaceutiche, Università di Firenze, Florence, Italy, Istituto sulla Propagazione delle Specie Legnose - Consiglio Nazionale delle Ricerche, Scandicci, Italy, Dipartimento di Biologia Vegetale, Università di Firenze, Florence, Italy
Methods: ESI-MS, HPLC, UV, extraction, HPTLC, HPLC-MS, spectrophotometry
- Article ID: 12778
Upson TM, J Grayer R, Greenham JR, A Williams C, Al-Ghamdi F, Chen F "Leaf flavonoids as systematic characters in the genera Lavandula and Sabaudia" -
Biochemical Systematics and Ecology 28(10) (2000) 991-1007
A comprehensive survey of the leaf flavonoids of the genus Lavandula and the related Sabaudia group was carried out using two-dimensional paper chromatography and high-performance liquid chromatography. The flavonoid patterns obtained were found to be systematically informative at the infrageneric level. Three main groupings were identified: the first containing sections Lavandula, Dentata and Stoechas characterised by the accumulation of flavone 7-glycosides; the second containing sections Pterostoechas, Subnuda and Chaetostachys characterised by the accumulation of 8-hydroxylated flavone 7-and 8-glycosides; the third encompassing the Sabaudia group and accumulating both flavone and 8-hydroxylated flavone 7- glycosides. Such a grouping of taxa is congruent with data from other disciplines, although it is not recognised in any present classifications. The taxonomic and evolutionary implications of the flavonoid data are discussed.
Lavandula; Sabaudia; lavender; Lamiaceae; flavonoids; chemotaxonomy
NCBI PubMed ID: 10996263Publication DOI: 10.1016/s0305-1978(00)00013-2Journal NLM ID: 0430442Publisher: Pergamon Press
Correspondence: christine.williams@reading.ac.uk
Institutions: Department of Botany, University of Reading, Reading, UK, Jodrell Laboratory, Royal Botanic Gardens, Richmond, UK
Methods: HPLC, UV, extraction, paper electrophoresis, PPC, 2D paper chromatography
- Article ID: 12877
Yoshikawa M, Uemura T, Shimoda H, Kishi A, Kawahara Y, Matsuda H "Medicinal foodstuffs. XVIII. Phytoestrogens from the aerial part of Petroselinum crispum Mill. (Parsley) and structures of 6''-acetylapiin and a new monoterpene glycoside, petroside" -
Chemical and Pharmaceutical Bulletin 48(7) (2000) 1039-1044
In the course of our screening for natural estrogenic compounds from Occidental medicinal herbs, the extracts of several herbs were found to show proliferative activity in MCF-7 (an estrogen-sensitive breast cancer cell line). Among these active herbs, the methanolic extract from the aerial parts of Petroselinum crispum (parsley) showed potent estrogenic activity, which was equal to that of isoflavone glycosides from soybean. Through bioassay-guided separation, we isolated several flavone glycosides and a new flavone glycoside, 6"-acetylapiin, with estrogenic activity together with a new monoterpene glucoside, petroside. The structures of 6"-acetylapiin and petroside were characterized by the chemical and physicochemical evidence. Estrogenic activities of these flavone glycosides were found to be enhanced by removal of their glycoside moieties. The EC50 values (concentration needed to enhance the MCF-7 proliferation 50% compared to non-estrogen treated cell) of their aglycones are as follows, apigenin (1.0 μM), diosmetin (2.9 μM), and kaempferol (0.56 μM). The estrogenic activities of these flavones are nearly equal to those of the isoflavones, daidzein (0.61 μM) and genistein (0.60 μM). The methanolic extract of parsley, apiin, and apigenin restored the uterus weight in ovariectomized mice when orally administered for consecutive 7 days.
flavone glycoside, phytoestrogen, Petroselinum crispum, 6"-acetylapiin, petroside, breast cancer cell line
NCBI PubMed ID: 10923837Publication DOI: 10.1248/cpb.48.1039Journal NLM ID: 0377775Publisher: Pharmaceutical Society Of Japan
Correspondence: Yoshikawa M
Institutions: Kyoto Pharmaceutical University, Kyoto, Japan, Research and Development Division, Morishita Jintan Co., Ltd., Osaka, Japan
Methods: 13C NMR, 1H NMR, NMR-2D, FAB-MS, TLC, ESI-MS, biological assays, HPLC, extraction, CC
- Article ID: 12900
Pieroni A, Pachaly P "Isolation and structure elucidation of ligustroflavone, a new apigenin triglycoside from the leaves of Ligustrum vulgare L." -
Die Pharmazie 55(1) (2000) 78-80
A new flavone, apigenin-7-O-β-(2",6"-di-α-rhamnopyranosyl)-glucopyranoside , named ligustroflavone, was isolated from the leaves of common privet (Ligustrum vulgare L., Oleaceae), whose popular use was well known in the Mediterranean historical medicine and ethnomedicine as anti-inflammatory. The structures of other five apigenin and luteolin derivates, isolated from the polar fractions of the methanolic leaf extracts, were elucidated.
NCBI PubMed ID: 10683879Journal NLM ID: 9800766Publisher: Eschborn: Govi-Verlag Pharmazautischer Verlag
Correspondence: Pieroni A
Institutions: Pharmaceutical Institute, University of Bonn, Bonn, Germany
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, enzymatic hydrolysis, acid hydrolysis, HPLC, optical rotation measurement, HR-FAB-MS
Expand this compound
Collapse this compound
6. Compound ID: 21983
|
b-D-Glcp-(1-7)-Subst
Subst = pinocembrin = SMILES O=C1CC(OC2=C1{5}C(O)=C{7}C(O)=C2)C3=CC=CC=C3 |
Show graphically |
Structure type: monomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8898
Sordon S, Popłoński J, Tronina T, Huszcza E "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca" -
Bioorganic Chemistry 93 (2019) ID 102750
In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.
biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones
NCBI PubMed ID: 30755333Publication DOI: 10.1016/j.bioorg.2019.01.046Journal NLM ID: 1303703Publisher: Orlando, FL: Academic Press
Correspondence: Sordon S
; Popłoński J ; Tronina T ; Huszcza E
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
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7. Compound ID: 21984
|
b-D-Glcp-(1-7)-Subst4'Me
Subst = eriodictyol = SMILES O=C1C[C@H](OC2=C1{5}C(O)=C{7}C(O)=C2)C3=C{53}C(O)={54}C(O)C=C3 |
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Structure type: monomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8898
Sordon S, Popłoński J, Tronina T, Huszcza E "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca" -
Bioorganic Chemistry 93 (2019) ID 102750
In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.
biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones
NCBI PubMed ID: 30755333Publication DOI: 10.1016/j.bioorg.2019.01.046Journal NLM ID: 1303703Publisher: Orlando, FL: Academic Press
Correspondence: Sordon S
; Popłoński J ; Tronina T ; Huszcza E
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
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8. Compound ID: 21985
|
b-D-Glcp-(1-3')-Subst4'Me
Subst = eriodictyol = SMILES O=C1C[C@H](OC2=C1{5}C(O)=C{7}C(O)=C2)C3=C{53}C(O)={54}C(O)C=C3 |
Show graphically |
Structure type: monomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8898
Sordon S, Popłoński J, Tronina T, Huszcza E "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca" -
Bioorganic Chemistry 93 (2019) ID 102750
In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.
biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones
NCBI PubMed ID: 30755333Publication DOI: 10.1016/j.bioorg.2019.01.046Journal NLM ID: 1303703Publisher: Orlando, FL: Academic Press
Correspondence: Sordon S
; Popłoński J ; Tronina T ; Huszcza E
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
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9. Compound ID: 21986
|
b-D-Glcp-(1-3')-Subst4'Me
Subst = luteolin = SMILES C1=C{54}C(={53}C(C=C1C2=CC(=O)C3={5}C({6}C={7}C({8}C=C3O2)O)O)O)O |
Show graphically |
Structure type: monomer
Compound class: glycoside, flavonoid glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 8898
Sordon S, Popłoński J, Tronina T, Huszcza E "Regioselective O-glycosylation of flavonoids by fungi Beauveria bassiana, Absidia coerulea and Absidia glauca" -
Bioorganic Chemistry 93 (2019) ID 102750
In the present study, the species: Beauveria bassiana, Absidia coerulea and Absidia glauca were used in biotransformation of flavones (chrysin, apigenin, luteolin, diosmetin) and flavanones (pinocembrin, naringenin, eriodictyol, hesperetin). The Beauveria bassiana AM 278 strain catalyzed the methylglucose attachment reactions to the flavonoid molecule at positions C7 and C3'. The application of the Absidia genus (A. coerulea AM 93, A. glauca AM 177) as the biocatalyst resulted in the formation of glucosides with a sugar molecule present at C7 and C3' positions of flavonoids skeleton. Nine of obtained products have not been previously reported in the literature.
biotransformation, Beauveria bassiana, Absidia coerulea, microbial glycosylation, Absidia glauca, flavanones, flavones
NCBI PubMed ID: 30755333Publication DOI: 10.1016/j.bioorg.2019.01.046Journal NLM ID: 1303703Publisher: Orlando, FL: Academic Press
Correspondence: Sordon S
; Popłoński J ; Tronina T ; Huszcza E
Institutions: Department of Chemistry, Wrocław University of Environmental and Life Sciences, Wrocław, Poland
Methods: 13C NMR, 1H NMR, NMR-2D, TLC, HPLC, biosynthetic methods, extraction, cell growth, HR-ESI-MS
Expand this compound
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Total list of corresponding CSDB IDs (permanent record IDs):
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