Found 211 structures.
Displayed structures from 1 to 15
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1. Compound ID: 13293
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b-D-Olip-(1-4)-b-Rhop-(1-4)-a-L-Rhap-(1-13)-Subst
Subst = SMILES CC[C@@H](C)[C@@H](O)[C@@H]1O[C@H]1C[C@H](C)/C=C/C=C(C)\c2cc(O)c4c(c2)oc3ccc(CC[C@@H](C){13}CO)c(O)c34 |
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Structure type: oligomer
Trivial name: fulicineroside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
The structure is contained in the following publication(s):
- Article ID: 5261
Zhou ZY, Liu JK "Pigments of fungi (macromycetes)" -
Natural Product Reports 27(11) (2010) 1531-1570
This review surveys the chemical, biological and mycological literature dealing with the isolation, structure elucidation, biological activities, and synthesis of pigments manufactured by those fungi that produce conspicuous fruiting bodies (macromycetes).
pigment
NCBI PubMed ID: 20694228Publication DOI: 10.1039/c004593dJournal NLM ID: 8502408Publisher: London: Royal Society of Chemistry
Institutions: State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming, China
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2. Compound ID: 13482
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b-D-Olip-(1-4)-a-Rhop-(1-4)-b-D-1dOlip-(1C-9)-Subst-(12-1)-a-Rhop
Subst = urdamycinone E aglycon = SMILES O=C1C2=C(C=C(SC)[C@@](C[C@](O)(C)C3)(O){12}[C@]2(O)C3=O)C(C4=C(O){9}C=CC=C41)=O |
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Structure type: oligomer
Trivial name: urdamycin E
Compound class: C-glycoside
The structure is contained in the following publication(s):
- Article ID: 5352
Supong K, Thawai C, Suwanborirux K, Choowong W, Supothina S, Pittayakhajonwut P "Antimalarial and antitubercular C-glycosylated benz[α]anthraquinones from the marine-derived Streptomyces sp. BCC45596" -
Phytochemistry Letters 5(3) (2012) 651-656
Three naturally new C-glycosylated benz[α]anthraquinone derivatives, urdamycinone E (1), urdamycinone G (2), dehydroxyaquayamycin (3) have been isolated from the marine Streptomycetes sp. BCC45596. Urdamycin E (4), the possible biosynthetic precursor of 1-3, has also been identified after a re-cultivation of the strain. These compounds (1-4) exhibited potent anti-Plasmodium palcifarum K1 strain with IC50 values in a range of 0.0534-2.93 μg/mL and anti-Mycobacterium tuberculosis with minimum inhibition concentrations (MICs) in a range of 3.13-12.50 μg/mL. Cytotoxicity against KB, MCF-7, NCI-H187, and Vero cells was also evaluated.
Streptomyces, benz[α]anthraquinones, urdamycinone, dehydroxyaquayamycin, antimalarial, anti-TB
Publication DOI: 10.1016/j.phytol.2012.06.015Journal NLM ID: 101513432Publisher: Amsterdam: Elsevier
Correspondence: Pittayakhajonwut P
Institutions: Department of Biology, Faculty of Science, King Mongkut's Institute of Technology Ladkrabang, Bangkok, Thailand, Center for Bioactive Natural Products from Marine Organisms and Endophytic fungi (BNPME), Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand, Department of Pharmacognosy and Pharmaceutical Botany, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, Thailand, National Center for Genetic Engineering and Biotechnology (BIOTEC), Thailand Science Park, Klong Luang, Thailand
Methods: 13C NMR, 1H NMR, NMR-2D, IR, ESI-MS, biological assays, HPLC, UV, extraction, optical rotation measurement, CD, CC, cell growth, HR-ESI-MS
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3. Compound ID: 13524
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b-D-Olip-(1-4)-a-Rhop-(1-3)-b-D-1dOlip-(1C-9)-Subst-(12-1)-a-Rhop
Subst = SMILES CC2(O)CC(=O){12}[C@]1(O)c4c(/C=C\[C@]1(O)C2)c(=O)c3c(O){9}cccc3c4=O |
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Structure type: oligomer
; 867 [M+Na]+
C43H56O17
Trivial name: kerriamycin B
Compound class: glycoside
The structure is contained in the following publication(s):
- Article ID: 5373
Hayakawa Y, Iwakiri T, Imamura K, Seto H, Otake N "Studies on the isotetracenone antibiotics. II. Kerriamycins A, B and C, new antitumor antibiotics" -
The Journal of Antibiotics 38(7) (1985) 960-963
During the course of screening program for new antitumor antibiotics, three active substances has been isolated which were named kerriamycins A, B and C, respectively, from the culture broth of a streptomycete. These antibiotics inhibit the growth of Gram-positive bacteria and prolong the survival periods of mice bearing Ehrlich ascites carcinoma.
antibiotics, kerriamycins, Streptomyces violaceolatus
NCBI PubMed ID: 3839784Publication DOI: 10.7164/antibiotics.38.960Journal NLM ID: 0151115Publisher: London: Nature Publishing Group
Institutions: Institute of Applied Microbiology, The University of Tokyo, Tokyo, Japan, Applied Bioscience Laboratory Kirin Brewery Co. Ltd., Maebashi, Japan
Methods: 13C NMR, IR, FAB-MS, acid hydrolysis, composition analysis, UV, extraction, optical rotation measurement, CC, cell growth, melting point determination, antibacterial assay, antitumor activity assay, evaporation, antifungal activity test
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4. Compound ID: 13525
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b-D-Olip-(1-4)-a-Rhop-(1-3)-b-D-1dOlip-(1C-9)-Subst
Subst = SMILES CC2(O)CC(=O)[C@]1(O)c4c(/C=C\[C@]1(O)C2)c(=O)c3c(O){9}cccc3c4=O |
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Structure type: oligomer
; 753 [M+Na]+
C37H46O15
Trivial name: kerriamycin C
Compound class: C-glycoside
The structure is contained in the following publication(s):
- Article ID: 5373
Hayakawa Y, Iwakiri T, Imamura K, Seto H, Otake N "Studies on the isotetracenone antibiotics. II. Kerriamycins A, B and C, new antitumor antibiotics" -
The Journal of Antibiotics 38(7) (1985) 960-963
During the course of screening program for new antitumor antibiotics, three active substances has been isolated which were named kerriamycins A, B and C, respectively, from the culture broth of a streptomycete. These antibiotics inhibit the growth of Gram-positive bacteria and prolong the survival periods of mice bearing Ehrlich ascites carcinoma.
antibiotics, kerriamycins, Streptomyces violaceolatus
NCBI PubMed ID: 3839784Publication DOI: 10.7164/antibiotics.38.960Journal NLM ID: 0151115Publisher: London: Nature Publishing Group
Institutions: Institute of Applied Microbiology, The University of Tokyo, Tokyo, Japan, Applied Bioscience Laboratory Kirin Brewery Co. Ltd., Maebashi, Japan
Methods: 13C NMR, IR, FAB-MS, acid hydrolysis, composition analysis, UV, extraction, optical rotation measurement, CC, cell growth, melting point determination, antibacterial assay, antitumor activity assay, evaporation, antifungal activity test
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5. Compound ID: 15956
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b-D-Olip-(1-4)-b-Rhop-(1-4)-a-L-Rhap-(1-4')-Subst
Subst = fulicinerine = SMILES CC[C@H]({111}[C@@H](O)[C@H]1[C@H](C[C@@H](/C=C/C=C(C2=C{1}C(O)=C3C(OC4=C3{9}C(O)=C(CC[C@H]({54}CO)C)C=C4)=C2)\C)C)O1)C |
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Structure type: monomer
Trivial name: fulicineroside
Compound class: glycoside
Contained glycoepitopes: IEDB_136105,IEDB_225177,IEDB_885823
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
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6. Compound ID: 15981
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b-D-Olip-(1-4)-a-Rhop-(1-3)-b-D-1dOlip-(1C-9)-Subst
Subst = urdamycinone E aglycon = SMILES O=C1C2=C(C=C(SC)[C@@](C[C@](O)(C)C3)(O){12}[C@]2(O)C3=O)C(C4=C(O){9}C=CC=C41)=O |
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Structure type: oligomer
; 799.2612 [M+Na]+
C38H48O15S
Trivial name: urdamycin W
Compound class: C-glycoside, angucycline polyketide glycoside
The structure is contained in the following publication(s):
- Article ID: 6197
Anh CV, Kwon JH, Kang JS, Lee HS, Heo CS, Shin HJ "New Angucycline Glycosides from a Marine-Derived Bacterium Streptomyces ardesiacus" -
International Journal of Molecular Sciences 23(22) (2022) 13779
Chemical investigation of the ethyl acetate extract from the culture broth of the marine-derived actinobacterium Streptomyces ardesiacus 156VN-095 led to the isolation of three hitherto undescribed angucycline glycosides, including urdamycins W and X (1 and 2) and grincamycin U (9), as well as their seven known congeners. The structures of the new compounds were elucidated by means of spectroscopic methods (HRESIMS, 1D and 2 D NMR) and comparison of their experimental data with literature values. Compounds 1-3 and 9 were evaluated for their anti-Gram-positive bacterial effect and cytotoxicity against six cancer cell lines. Compound 1 displayed significant cytotoxicity against all the tested cell lines with GI50 values of 0.019-0.104 µM. Collectively, these findings highlight the potential of angucycline glycosides as leading structures for the development of new anti-cancer drugs.
cytotoxicity, anti-bacterial, grincamycin, Streptomyces ardesiacus, urdamycin
NCBI PubMed ID: 36430256Publication DOI: 10.3390/ijms232213779Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: H.J. Shin
Institutions: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea, Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Korea
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, isolation
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7. Compound ID: 15983
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b-D-Olip-(1-4)-a-Rhop-(1-3)-b-D-1dOlip-(1C-6)-Subst
Subst = fridamycin E = SMILES O=C1C2=C(C=CC(C[C@@](C)(O)CC(O)=O)=C2O)C(C3=C1C=C{6}C=C3O)=O |
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Structure type: oligomer
; 753.2734 [M+Na]+
C37H46O15
Trivial name: grincamycin U
Compound class: C-glycoside, angucycline polyketide glycoside
The structure is contained in the following publication(s):
- Article ID: 6197
Anh CV, Kwon JH, Kang JS, Lee HS, Heo CS, Shin HJ "New Angucycline Glycosides from a Marine-Derived Bacterium Streptomyces ardesiacus" -
International Journal of Molecular Sciences 23(22) (2022) 13779
Chemical investigation of the ethyl acetate extract from the culture broth of the marine-derived actinobacterium Streptomyces ardesiacus 156VN-095 led to the isolation of three hitherto undescribed angucycline glycosides, including urdamycins W and X (1 and 2) and grincamycin U (9), as well as their seven known congeners. The structures of the new compounds were elucidated by means of spectroscopic methods (HRESIMS, 1D and 2 D NMR) and comparison of their experimental data with literature values. Compounds 1-3 and 9 were evaluated for their anti-Gram-positive bacterial effect and cytotoxicity against six cancer cell lines. Compound 1 displayed significant cytotoxicity against all the tested cell lines with GI50 values of 0.019-0.104 µM. Collectively, these findings highlight the potential of angucycline glycosides as leading structures for the development of new anti-cancer drugs.
cytotoxicity, anti-bacterial, grincamycin, Streptomyces ardesiacus, urdamycin
NCBI PubMed ID: 36430256Publication DOI: 10.3390/ijms232213779Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: H.J. Shin
Institutions: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea, Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Korea
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, isolation
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8. Compound ID: 15984
|
b-D-Olip-(1-4)-a-Rhop-(1-3)-b-D-1dOlip-(1C-9)-Subst-(12-1)-a-Rhop
Subst = urdamycinone E aglycon = SMILES O=C1C2=C(C=C(SC)[C@@](C[C@](O)(C)C3)(O){12}[C@]2(O)C3=O)C(C4=C(O){9}C=CC=C41)=O |
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Structure type: oligomer
Trivial name: urdamycin E
Compound class: C-glycoside, angucycline polyketide glycoside
The structure is contained in the following publication(s):
- Article ID: 6197
Anh CV, Kwon JH, Kang JS, Lee HS, Heo CS, Shin HJ "New Angucycline Glycosides from a Marine-Derived Bacterium Streptomyces ardesiacus" -
International Journal of Molecular Sciences 23(22) (2022) 13779
Chemical investigation of the ethyl acetate extract from the culture broth of the marine-derived actinobacterium Streptomyces ardesiacus 156VN-095 led to the isolation of three hitherto undescribed angucycline glycosides, including urdamycins W and X (1 and 2) and grincamycin U (9), as well as their seven known congeners. The structures of the new compounds were elucidated by means of spectroscopic methods (HRESIMS, 1D and 2 D NMR) and comparison of their experimental data with literature values. Compounds 1-3 and 9 were evaluated for their anti-Gram-positive bacterial effect and cytotoxicity against six cancer cell lines. Compound 1 displayed significant cytotoxicity against all the tested cell lines with GI50 values of 0.019-0.104 µM. Collectively, these findings highlight the potential of angucycline glycosides as leading structures for the development of new anti-cancer drugs.
cytotoxicity, anti-bacterial, grincamycin, Streptomyces ardesiacus, urdamycin
NCBI PubMed ID: 36430256Publication DOI: 10.3390/ijms232213779Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: H.J. Shin
Institutions: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea, Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Korea
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, isolation
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9. Compound ID: 15986
|
b-D-Olip-(1-4)-a-Rhop-(1-3)-b-D-1dOlip-(1C-9)-Subst-(12-1)-a-Rhop
Subst = urdamycin A aglycon = SMILES O=C1C2=C(C(C3=C({9}C=CC=C31)O)=O)C=C[C@@](O)({12}[C@@]24O)C[C@](C)(CC4=O)O |
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Structure type: oligomer
Trivial name: urdamycin A
Compound class: C-glycoside, angucycline polyketide glycoside
The structure is contained in the following publication(s):
- Article ID: 6197
Anh CV, Kwon JH, Kang JS, Lee HS, Heo CS, Shin HJ "New Angucycline Glycosides from a Marine-Derived Bacterium Streptomyces ardesiacus" -
International Journal of Molecular Sciences 23(22) (2022) 13779
Chemical investigation of the ethyl acetate extract from the culture broth of the marine-derived actinobacterium Streptomyces ardesiacus 156VN-095 led to the isolation of three hitherto undescribed angucycline glycosides, including urdamycins W and X (1 and 2) and grincamycin U (9), as well as their seven known congeners. The structures of the new compounds were elucidated by means of spectroscopic methods (HRESIMS, 1D and 2 D NMR) and comparison of their experimental data with literature values. Compounds 1-3 and 9 were evaluated for their anti-Gram-positive bacterial effect and cytotoxicity against six cancer cell lines. Compound 1 displayed significant cytotoxicity against all the tested cell lines with GI50 values of 0.019-0.104 µM. Collectively, these findings highlight the potential of angucycline glycosides as leading structures for the development of new anti-cancer drugs.
cytotoxicity, anti-bacterial, grincamycin, Streptomyces ardesiacus, urdamycin
NCBI PubMed ID: 36430256Publication DOI: 10.3390/ijms232213779Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: H.J. Shin
Institutions: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea, Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Korea
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, isolation
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10. Compound ID: 15987
|
b-D-Olip-(1-4)-a-Rhop-(1-3)-b-D-1dOlip-(1C-9)-Subst
Subst = urdamycinone B aglycon = SMILES O=C1C2=C(C=CC(C[C@](C3)(O)C)C2C3=O)C(C4=C(O){9}C=CC=C41)=O |
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Structure type: oligomer
Trivial name: urdamycin B
Compound class: C-glycoside, angucycline polyketide glycoside
The structure is contained in the following publication(s):
- Article ID: 6197
Anh CV, Kwon JH, Kang JS, Lee HS, Heo CS, Shin HJ "New Angucycline Glycosides from a Marine-Derived Bacterium Streptomyces ardesiacus" -
International Journal of Molecular Sciences 23(22) (2022) 13779
Chemical investigation of the ethyl acetate extract from the culture broth of the marine-derived actinobacterium Streptomyces ardesiacus 156VN-095 led to the isolation of three hitherto undescribed angucycline glycosides, including urdamycins W and X (1 and 2) and grincamycin U (9), as well as their seven known congeners. The structures of the new compounds were elucidated by means of spectroscopic methods (HRESIMS, 1D and 2 D NMR) and comparison of their experimental data with literature values. Compounds 1-3 and 9 were evaluated for their anti-Gram-positive bacterial effect and cytotoxicity against six cancer cell lines. Compound 1 displayed significant cytotoxicity against all the tested cell lines with GI50 values of 0.019-0.104 µM. Collectively, these findings highlight the potential of angucycline glycosides as leading structures for the development of new anti-cancer drugs.
cytotoxicity, anti-bacterial, grincamycin, Streptomyces ardesiacus, urdamycin
NCBI PubMed ID: 36430256Publication DOI: 10.3390/ijms232213779Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: H.J. Shin
Institutions: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea, Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Korea
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, isolation
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11. Compound ID: 15988
|
b-D-Olip-(1-4)-a-Rhop-(1-3)-b-D-1dOlip-(1C-9)-Subst
Subst = 5-hydroxyurdamycin B aglycon = SMILES O=C1C2=C(C=C(C(C[C@](C)(C3)O)=C2C3=O)O)C(C4=C(O){9}C=CC=C41)=O |
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Structure type: oligomer
Trivial name: 5-hydroxyurdamycin B
Compound class: C-glycoside, angucycline polyketide glycoside
The structure is contained in the following publication(s):
- Article ID: 6197
Anh CV, Kwon JH, Kang JS, Lee HS, Heo CS, Shin HJ "New Angucycline Glycosides from a Marine-Derived Bacterium Streptomyces ardesiacus" -
International Journal of Molecular Sciences 23(22) (2022) 13779
Chemical investigation of the ethyl acetate extract from the culture broth of the marine-derived actinobacterium Streptomyces ardesiacus 156VN-095 led to the isolation of three hitherto undescribed angucycline glycosides, including urdamycins W and X (1 and 2) and grincamycin U (9), as well as their seven known congeners. The structures of the new compounds were elucidated by means of spectroscopic methods (HRESIMS, 1D and 2 D NMR) and comparison of their experimental data with literature values. Compounds 1-3 and 9 were evaluated for their anti-Gram-positive bacterial effect and cytotoxicity against six cancer cell lines. Compound 1 displayed significant cytotoxicity against all the tested cell lines with GI50 values of 0.019-0.104 µM. Collectively, these findings highlight the potential of angucycline glycosides as leading structures for the development of new anti-cancer drugs.
cytotoxicity, anti-bacterial, grincamycin, Streptomyces ardesiacus, urdamycin
NCBI PubMed ID: 36430256Publication DOI: 10.3390/ijms232213779Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: H.J. Shin
Institutions: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea, Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Korea
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, isolation
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12. Compound ID: 15990
|
b-D-Olip-(1-4)-a-Rhop-(1-3)-b-D-1dOlip-(1C-9)-Subst-(12-1)-a-Rhop
Subst = urdamycinone A aglycon = SMILES O=C1C[C@](C)(O)C[C@]2(O){12}[C@@]1(O)C(C(C3=CC={9}CC(O)=C3C4=O)=O)=C4[C@H](O)C2 |
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Structure type: oligomer
Trivial name: urdamycin F
Compound class: C-glycoside, angucycline polyketide glycoside
The structure is contained in the following publication(s):
- Article ID: 6197
Anh CV, Kwon JH, Kang JS, Lee HS, Heo CS, Shin HJ "New Angucycline Glycosides from a Marine-Derived Bacterium Streptomyces ardesiacus" -
International Journal of Molecular Sciences 23(22) (2022) 13779
Chemical investigation of the ethyl acetate extract from the culture broth of the marine-derived actinobacterium Streptomyces ardesiacus 156VN-095 led to the isolation of three hitherto undescribed angucycline glycosides, including urdamycins W and X (1 and 2) and grincamycin U (9), as well as their seven known congeners. The structures of the new compounds were elucidated by means of spectroscopic methods (HRESIMS, 1D and 2 D NMR) and comparison of their experimental data with literature values. Compounds 1-3 and 9 were evaluated for their anti-Gram-positive bacterial effect and cytotoxicity against six cancer cell lines. Compound 1 displayed significant cytotoxicity against all the tested cell lines with GI50 values of 0.019-0.104 µM. Collectively, these findings highlight the potential of angucycline glycosides as leading structures for the development of new anti-cancer drugs.
cytotoxicity, anti-bacterial, grincamycin, Streptomyces ardesiacus, urdamycin
NCBI PubMed ID: 36430256Publication DOI: 10.3390/ijms232213779Journal NLM ID: 101092791Publisher: Basel, Switzerland: MDPI
Correspondence: H.J. Shin
Institutions: Marine Natural Products Chemistry Laboratory, Korea Institute of Ocean Science and Technology, 385 Haeyang-ro, Yeongdo-gu, Busan 49111, Korea, Department of Marine Biotechnology, University of Science and Technology (UST), 217 Gajungro, Yuseong-gu, Daejeon 34113, Korea, Laboratory Animal Resource Center, Korea Research Institute of Bioscience and Biotechnology, 30 Yeongudanjiro, Cheongju 28116, Korea
Methods: 13C NMR, 1H NMR, NMR-2D, IR, HPLC, UV, fermentation, HR-ESI-MS, antibacterial assay, cytotoxicity assay, isolation
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13. Compound ID: 24619
|
Tig-(1-12)-+
|
b-D-Glcp-(1-4)-b-D-6dAllp3Me-(1-4)-b-D-Olip3Me-(1-3)-Subst11Ac
Subst = tenacigenin B = SMILES O{3}[C@H]1CC[C@@]2(C)[C@](CC[C@]3(O4)[C@]2([H]){11}[C@H](O){12}[C@@H](O)[C@@]5(C)[C@]34CC[C@@]5([H])C(C)=O)([H])C1;
Tig = tiglic acid |
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Structure type: oligomer
C48H74O19
Trivial name: tenacissoside A
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10115
Miyakawa S, Yamaura K, Hayashi K, Kaneko K, Mitsuhashi H "Studies on the constituents of Asclepiadaceae plants. Part 63. Five glycosides from the Chinese drug Tong-guang-san: the stems of Marsdenia tenacissima" -
Phytochemistry 25 (1986) 2861-2865
Five new glycosides were isolated from the Chinese crude drug ‘Tong-guang-san’: the stems of Marsdenia tenacissima (Roth.) Wight et Arn. (Asclepiadaceae). The structures of tenacissosides A-E were deduced on the basis of chemical and spectral evidence as tenacigenin B-I 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-β-D- allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-II 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy- β-Dallopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-III 3-O-β-Dglucopyranosyl-(1→4)-3-O-methyl-6- deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-IV 3-O-β-D-glucopyranosyl-(1→4)-3-O- methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside and tenacigenin B-V 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-allopyranosyl-(1→4)-β-D-oleandropyranoside, respectively.
Marsdenia tenacissima, Asclepiadaceae, pregnane glycosides, tenacissosides A-E
Publication DOI: 10.1016/S0031-9422(00)83756-5Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan
Methods: 13C NMR, 1H NMR, gel filtration, acid hydrolysis, HPLC, melting point determination
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14. Compound ID: 24620
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Tig-(1-11)-+
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b-D-Glcp-(1-4)-b-D-6dAllp3Me-(1-4)-b-D-Olip3Me-(1-3)-Subst
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Tig-(1-12)-+
Subst = tenacigenin B = SMILES O{3}[C@H]1CC[C@@]2(C)[C@](CC[C@]3(O4)[C@]2([H]){11}[C@H](O){12}[C@@H](O)[C@@]5(C)[C@]34CC[C@@]5([H])C(C)=O)([H])C1;
Tig = tiglic acid |
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Structure type: oligomer
Trivial name: tenacissoside B
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10115
Miyakawa S, Yamaura K, Hayashi K, Kaneko K, Mitsuhashi H "Studies on the constituents of Asclepiadaceae plants. Part 63. Five glycosides from the Chinese drug Tong-guang-san: the stems of Marsdenia tenacissima" -
Phytochemistry 25 (1986) 2861-2865
Five new glycosides were isolated from the Chinese crude drug ‘Tong-guang-san’: the stems of Marsdenia tenacissima (Roth.) Wight et Arn. (Asclepiadaceae). The structures of tenacissosides A-E were deduced on the basis of chemical and spectral evidence as tenacigenin B-I 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-β-D- allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-II 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy- β-Dallopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-III 3-O-β-Dglucopyranosyl-(1→4)-3-O-methyl-6- deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-IV 3-O-β-D-glucopyranosyl-(1→4)-3-O- methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside and tenacigenin B-V 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-allopyranosyl-(1→4)-β-D-oleandropyranoside, respectively.
Marsdenia tenacissima, Asclepiadaceae, pregnane glycosides, tenacissosides A-E
Publication DOI: 10.1016/S0031-9422(00)83756-5Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan
Methods: 13C NMR, 1H NMR, gel filtration, acid hydrolysis, HPLC, melting point determination
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15. Compound ID: 24621
|
Tig-(1-11)-+
|
b-D-Glcp-(1-4)-b-D-6dAllp3Me-(1-4)-b-D-Olip3Me-(1-3)-Subst12Bz
Subst = tenacigenin B = SMILES O{3}[C@H]1CC[C@@]2(C)[C@](CC[C@]3(O4)[C@]2([H]){11}[C@H](O){12}[C@@H](O)[C@@]5(C)[C@]34CC[C@@]5([H])C(C)=O)([H])C1;
Tig = tiglic acid |
Show graphically |
Structure type: oligomer
Trivial name: tenacissoside C
Contained glycoepitopes: IEDB_139965,IEDB_142488,IEDB_146664,IEDB_983931,SB_192
The structure is contained in the following publication(s):
- Article ID: 10115
Miyakawa S, Yamaura K, Hayashi K, Kaneko K, Mitsuhashi H "Studies on the constituents of Asclepiadaceae plants. Part 63. Five glycosides from the Chinese drug Tong-guang-san: the stems of Marsdenia tenacissima" -
Phytochemistry 25 (1986) 2861-2865
Five new glycosides were isolated from the Chinese crude drug ‘Tong-guang-san’: the stems of Marsdenia tenacissima (Roth.) Wight et Arn. (Asclepiadaceae). The structures of tenacissosides A-E were deduced on the basis of chemical and spectral evidence as tenacigenin B-I 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-β-D- allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-II 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy- β-Dallopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-III 3-O-β-Dglucopyranosyl-(1→4)-3-O-methyl-6- deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside, tenacigenin B-IV 3-O-β-D-glucopyranosyl-(1→4)-3-O- methyl-6-deoxy-β-D-allopyranosyl-(1→4)-β-D-oleandropyranoside and tenacigenin B-V 3-O-β-D-glucopyranosyl-(1→4)-3-O-methyl-6-deoxy-allopyranosyl-(1→4)-β-D-oleandropyranoside, respectively.
Marsdenia tenacissima, Asclepiadaceae, pregnane glycosides, tenacissosides A-E
Publication DOI: 10.1016/S0031-9422(00)83756-5Journal NLM ID: 0151434Publisher: Elsevier
Institutions: Faculty of Pharmaceutical Sciences, Hokkaido University, Sapporo, Japan
Methods: 13C NMR, 1H NMR, gel filtration, acid hydrolysis, HPLC, melting point determination
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