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1. Compound ID: 20889
|
b-D-AltpA-(1-19)-Subst
Subst = isopimara-7,15-diene-2α,3β,19-triol = SMILES C[C@@]1(CCC2[C@@](C)(C[C@@H](O)[C@@H]([C@@]3({19}CO)C)O)C3CC=C2C1)C=C |
Show graphically |
Structure type: monomer
C26H40O9
Trivial name: virescenoside F
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 6181
Hussain H, Mamadalieva NZ, Ali I, Elizbit, Green IR, Wang D, Zou L, Simal-Gandara J, Cao H, Xiao J "Fungal glycosides: Structure and biological function" -
Trends in Food Science and Technology 110 (2021) 611-651
Background: Natural products acquire vast and intriguing structural diversity and have been recognized as a tremendously diverse source of new lead compounds. Numerous bioactive secondary metabolites are present in the form of glycosylated molecules in which the sugar parts are normally associated with the interaction along with molecular recognition of the cellular target. Scope and approach: The presence of sugar entities are crucial as well as in some cases necessary, for therapeutic effects. Establishing novel and potent glycosylated secondary metabolites has formed a main goal in the natural product field from fungi and bacteria. These compounds possess a diverse range of sugar units. Key findings and conclusions: Fungi is considered one of the important sources for approved drugs with a diverse range of mode of action. The sugar part in numerous pharmacologically active natural products enhances bioavailability, biological potential, reduce toxicity, and improve stability. The vast majority of glyocosides showed antimicrobial effects, cytotoxic, antiviral and antiinflammatory effects. Notably, numerous fungal glycosides presented in this review illustrate significant antimicrobial effects towards various microorganisms especially against plant pathogens. The antimicrobial effects of these fungal glycosides indicate that these metabolites could be employed as natural preservatives in food in order to abolish or control the growth of pathogenic and spoilage microorganisms.
glycoside, antimicrobial, fungi, food preservative, secondary metabolites
Publication DOI: 10.1016/j.tifs.2021.02.029Journal NLM ID: 9426004Publisher: Cambridge, UK: Elsevier Trends Journals
Correspondence: Hussain H
; Hussain H ; Xiao J ; Xiao J
Institutions: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Halle (Saale), Germany, Institute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent, Uzbekistan, School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan, China, Department Materials Engineering, National University of Sciences and Technology (NUST) H12, Islamabad, Pakistan, Department of Chemistry and Polymer Science, University of Stellenbosch, Matieland, South Africa, Key Laboratory of Coarse Cereal Processing, Ministry of Agriculture and Rural Affairs, Chengdu University, Chengdu, China, Nutrition and Bromatology Group, Department of Analytical Chemistry and Food Science, Faculty of Food Science and Technology, University of Vigo - Ourense Campus, Ourense, Spain
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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2. Compound ID: 20890
|
b-D-AltpA-(1-19)-Subst
Subst = isopimara-7,15-diene-3β,19-diol = SMILES C[C@](C1)(C=C)CCC2C1=CCC3[C@]2(C)CC{3}C(O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
C26H40O8
Trivial name: virescenoside G
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 6181
Hussain H, Mamadalieva NZ, Ali I, Elizbit, Green IR, Wang D, Zou L, Simal-Gandara J, Cao H, Xiao J "Fungal glycosides: Structure and biological function" -
Trends in Food Science and Technology 110 (2021) 611-651
Background: Natural products acquire vast and intriguing structural diversity and have been recognized as a tremendously diverse source of new lead compounds. Numerous bioactive secondary metabolites are present in the form of glycosylated molecules in which the sugar parts are normally associated with the interaction along with molecular recognition of the cellular target. Scope and approach: The presence of sugar entities are crucial as well as in some cases necessary, for therapeutic effects. Establishing novel and potent glycosylated secondary metabolites has formed a main goal in the natural product field from fungi and bacteria. These compounds possess a diverse range of sugar units. Key findings and conclusions: Fungi is considered one of the important sources for approved drugs with a diverse range of mode of action. The sugar part in numerous pharmacologically active natural products enhances bioavailability, biological potential, reduce toxicity, and improve stability. The vast majority of glyocosides showed antimicrobial effects, cytotoxic, antiviral and antiinflammatory effects. Notably, numerous fungal glycosides presented in this review illustrate significant antimicrobial effects towards various microorganisms especially against plant pathogens. The antimicrobial effects of these fungal glycosides indicate that these metabolites could be employed as natural preservatives in food in order to abolish or control the growth of pathogenic and spoilage microorganisms.
glycoside, antimicrobial, fungi, food preservative, secondary metabolites
Publication DOI: 10.1016/j.tifs.2021.02.029Journal NLM ID: 9426004Publisher: Cambridge, UK: Elsevier Trends Journals
Correspondence: Hussain H
; Hussain H ; Xiao J ; Xiao J
Institutions: Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Halle (Saale), Germany, Institute of the Chemistry of Plant Substances of the Academy Sciences of Uzbekistan, Tashkent, Uzbekistan, School of Pharmaceutical Sciences and Key Laboratory for Applied Technology of Sophisticated Analytical Instruments of Shandong Province, Shandong Analysis and Test Center, Qilu University of Technology (Shandong Academy of Sciences), Jinan, China, Department Materials Engineering, National University of Sciences and Technology (NUST) H12, Islamabad, Pakistan, Department of Chemistry and Polymer Science, University of Stellenbosch, Matieland, South Africa, Key Laboratory of Coarse Cereal Processing, Ministry of Agriculture and Rural Affairs, Chengdu University, Chengdu, China, Nutrition and Bromatology Group, Department of Analytical Chemistry and Food Science, Faculty of Food Science and Technology, University of Vigo - Ourense Campus, Ourense, Spain
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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3. Compound ID: 20891
|
b-D-AltpA6Me-(1-19)-Subst
Subst = isopimara-7,15-diene-2α,3β,19-triol = SMILES C[C@@]1(CCC2[C@@](C)(C[C@@H](O)[C@@H]([C@@]3({19}CO)C)O)C3CC=C2C1)C=C |
Show graphically |
Structure type: monomer
C26H40O9
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
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4. Compound ID: 20892
|
b-D-AltpA6Me-(1-19)-Subst
Subst = isopimara-7,15-diene-3β,19-diol = SMILES C[C@](C1)(C=C)CCC2C1=CCC3[C@]2(C)CC{3}C(O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
C26H40O8
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
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5. Compound ID: 20893
|
b-D-AltpA2Ac3Ac4Ac6Me-(1-19)-Subst3Ac
Subst = isopimara-7,15-diene-3β,19-diol = SMILES C[C@](C1)(C=C)CCC2C1=CCC3[C@]2(C)CC{3}C(O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
C26H40O8
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 8347
Ceccherelli P, Cagnoli-Bellavita N, Polonsky J, Baskevitch Z "Structures des virescenosides F et G, nouveaux metabolites de Oospora virescens (Link) Wallr." -
Tetrahedron 29(2) (1973) 449-454
Several glycosides (virescenosides) have been isolated from Oospora virescens (Link) Wallr. Virescenosides A, 1a, B, 1b and C, 1c, are β-D-altropyranosides of virescenol A, 2a, B, 2b and C, 2c. Here we describe the isolation of two metabolites, virescenosides F (3a), C26H40O9, and G (3b), C26H40O8. They are the first natural glycosides of altruronic acid. Virescenosides F and G readily undergo lactonisation. Two types of lactones have been isolated for which structures 5a, 5b and 7a, 7c are proposed
glycosides, Oospora virescens, virescenosides
Publication DOI: 10.1016/S0040-4020(01)93316-2Journal NLM ID: 2984170RPublisher: Pergamon Press
Institutions: Instituto di Chimica Organica, Facolta Farmacia dell'Università, Perugia, Italy, Institut de Chimie des Substances Naturelles, C.N.R.S., Gif sur Yvette, France
Methods: 1H NMR, methylation, IR, TLC, acid hydrolysis, MS, UV, optical rotation measurement, acetylation, reduction, CC, precipitation
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6. Compound ID: 22021
|
b-D-AltpA-(1-19)-Subst
Subst = virescenoside Z10 aglycon = SMILES C=C[C@@]1(C)CC/C2=C(C1)/C(=O)C[C@@H]3[C@]2(C)CC{3}[C@H](O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
Trivial name: virescenoside Z10
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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7. Compound ID: 22022
|
b-D-AltpA-(1-19)-Subst
Subst = virescenoside Z11, Z15 aglycon = SMILES C=C[C@@]1(C)CC/C2=C(C1)/C(=O)C[C@@H]3[C@]2(C)C{2}[C@@H](O){3}[C@H](O)[C@]3(C){19}CO |
Show graphically |
Structure type: monomer
Trivial name: virescenoside Z11
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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8. Compound ID: 22023
|
b-D-AltpA6Me-(1-19)-Subst
Subst = virescenoside Z12, Z18 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO){3}[C@@H](O)CC[C@]12C)C3 |
Show graphically |
Structure type: monomer
Trivial name: virescenoside Z12
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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9. Compound ID: 22024
|
b-D-AltpA6Me-(1-19)-Subst
Subst = virescenoside Z13, Z17 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO){3}[C@@H](O){2}[C@H](O)C[C@]12C)C3 |
Show graphically |
Structure type: monomer
Trivial name: virescenoside Z13
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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10. Compound ID: 22025
|
b-D-AltpA6Me-(1-19)-Subst
Subst = virescenoside V, Z14 aglycon = SMILES C=C[C@]3(C)/C=C\2C(=O)C[C@H]1[C@@](C)({19}CO){3}[C@@H](O){2}[C@H](O)C[C@]1(C)[C@H]2CC3 |
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Structure type: monomer
Trivial name: virescenoside Z14
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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11. Compound ID: 22026
|
b-D-AltpA6Me-(1-19)-Subst
Subst = virescenoside Z11, Z15 aglycon = SMILES C=C[C@@]1(C)CC/C2=C(C1)/C(=O)C[C@@H]3[C@]2(C)C{2}[C@@H](O){3}[C@H](O)[C@]3(C){19}CO |
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Structure type: monomer
Trivial name: virescenoside Z15
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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12. Compound ID: 22027
|
b-D-AltpA6Me-(1-19)-Subst
Subst = virescenoside Z16 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO)C(=O)CC[C@]12C)C3 |
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Structure type: monomer
Trivial name: virescenoside Z16
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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13. Compound ID: 22028
|
b-D-AltpA6Bu-(1-19)-Subst
Subst = virescenoside Z13, Z17 aglycon = SMILES C=C[C@@]3(C)CC[C@H]1/C(=C\C[C@H]2[C@@](C)({19}CO){3}[C@@H](O){2}[C@H](O)C[C@]12C)C3 |
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Structure type: monomer
Trivial name: virescenoside Z17
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 8911
Zhuravleva OI, Antonov AS, Oleinikova GK, Khudyakova YV, Popov RS, Denisenko VA, Pislyagin EA, Chingizova EA, Afiyatullov SS "Virescenosides from the holothurian-associated fungus Acremonium striatisporum Kmm 4401" -
Marine Drugs 17(11) (2019) ID 616
Ten new diterpene glycosides virescenosides Z9-Z18 (1-10) together with three known analogues (11-13) and aglycon of virescenoside A (14) were isolated from the marine-derived fungus Acremonium striatisporum KMM 4401. These compounds were obtained by cultivating fungus on wort agar medium with the addition of potassium bromide. Structures of the isolated metabolites were established based on spectroscopic methods. The effects of some isolated glycosides and aglycons 15-18 on urease activity and regulation of Reactive Oxygen Species (ROS) and Nitric Oxide (NO) production in macrophages stimulated with lipopolysaccharide (LPC) were evaluated.
secondary metabolites, Acremonium striatisporum, Diterpene glycosides, Marine fungi, urease activity
NCBI PubMed ID: 31671910Publication DOI: 10.3390/md17110616Journal NLM ID: 101213729Publisher: Basel, Switzerland: Molecular Diversity Preservation International
Correspondence: Zhuravleva OI
; Antonov AS ; Oleinikova GK ; Khudyakova YV <161070@rambler.ru>; Popov RS ; Denisenko VA ; Pislyagin EA ; Chingizova EA ; Afiyatullov SS
Institutions: G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, Vladivostok, Russia, School of Natural Science, Far Eastern Federal University, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, NMR-2D, inhibition studies, TLC, biological assays, UV, extraction, gel chromatography, optical rotation measurement, CID-MS, CC, RP-HPLC, cell growth, HR-ESI-MS, determination of NO production, macrophage activity assay, evaporation
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14. Compound ID: 22722
|
b-D-AltpA-(1-19)-Subst
Subst = 3-oxo-isopimara-7(8),15-diene-19-ol = SMILES C[C@@]1(CCC2[C@@](C)(CCC([C@@]3({19}CO)C)=O)C3CC=C2C1)C=C |
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Structure type: monomer
; 501.2437 [M+Na]+
C26H38O8
Trivial name: virescenoside Z4
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 9389
Afiyatullov SS, Kalinovsky AI, Antonov AS "New virescenosides from the marine-derived fungus Acremonium striatisporum" -
Natural Product Communications 6(8) (2011) 1063-1068
Five new diterpene glycosides, virescenosides Z4-Z8 (1-5) have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined by HRESI-MS and 1D and 2D NMR. Virescenosides Z4-Z8 contain rare altruronic acid 4C1 and 1C4 conformations as their carbohydrate components. Virescenosides Z5 and Z7 exhibit an unusual 16-chloro, 15-hydroxyethylgroup as their side chains.
altruronic acid, Acremonium striatisporum, marine-derived fungus, virescenosides
NCBI PubMed ID: 21922899Journal NLM ID: 101477873Publisher: Natural Product Communications
Correspondence: afiyat@piboc.dvo.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, TLC, GC, HPLC, UV, extraction, optical rotation measurement, reduction, CC, cell growth, HR-ESI-MS, evaporation, LC, HR-MALDI-TOF
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15. Compound ID: 22723
|
b-D-AltpA-(1-19)-Subst
Subst = virescenoside Z5 aglycon = SMILES C[C@@]1(C(CC=C2C1CC[C@@]({20}[C@@H](O)CCl)(C)C2)[C@@]3(C){19}CO)CCC3=O |
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Structure type: monomer
; 529.2227 [M-H]-
C26H39O9Cl
Trivial name: virescenoside Z5
Compound class: glycoside, diterpene glycoside
The structure is contained in the following publication(s):
- Article ID: 9389
Afiyatullov SS, Kalinovsky AI, Antonov AS "New virescenosides from the marine-derived fungus Acremonium striatisporum" -
Natural Product Communications 6(8) (2011) 1063-1068
Five new diterpene glycosides, virescenosides Z4-Z8 (1-5) have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures were determined by HRESI-MS and 1D and 2D NMR. Virescenosides Z4-Z8 contain rare altruronic acid 4C1 and 1C4 conformations as their carbohydrate components. Virescenosides Z5 and Z7 exhibit an unusual 16-chloro, 15-hydroxyethylgroup as their side chains.
altruronic acid, Acremonium striatisporum, marine-derived fungus, virescenosides
NCBI PubMed ID: 21922899Journal NLM ID: 101477873Publisher: Natural Product Communications
Correspondence: afiyat@piboc.dvo.ru
Institutions: Pacific Institute of Bioorganic Chemistry, Far East Branch of the Russian Academy of Sciences, Vladivostok, Russia
Methods: 13C NMR, 1H NMR, methylation, NMR-2D, TLC, GC, HPLC, UV, extraction, optical rotation measurement, reduction, CC, cell growth, HR-ESI-MS, evaporation, LC, HR-MALDI-TOF
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Next 15 structure(s)
Total list of structure IDs on all result pages of the current query:
Total list of corresponding CSDB IDs (permanent record IDs):
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