Show legend Show as text

Structure type: oligomer

• Article ID: 2571
  Carter GT, Phillipson DW, Goodman JJ, Dunne TS, Borders DB "LL-E19020 α and β, novel growth promoting agents: isolation, characterization and structures" - The Journal of Antibiotics 41 (1988) 1511-1514
  

  No abstract available

  NCBI PubMed ID: 3192501
  Publication DOI: 10.7164/antibiotics.41.1511
  Journal NLM ID: 0151115
  Publisher: London: Nature Publishing Group
  Institutions: American Cyanamid Company, Medical Research Division, Lederle Laboratories, Pearl River, NY, USA
  
   
  
  Streptomyces
  CSDB ID 131641 (all data & tools)

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Structure type: oligomer ; 1209.5958 [M+Na]+
C₆₁H₉₀N₂O₂₁
Trivial name: lobophorin C
Compound class: glycoside

• Article ID: 5650
  Wei RB, Xi T, Li J, Wang P, Li FC, Lin YC, Qin S "Lobophorin C and D, new kijanimicin derivatives from a marine sponge-associated actinomycetal strain AZS17" - Marine Drugs 9(3) (2011) 359-368
  

  Marine sponge Hymeniacidon sp. was collected from coastal waters of the East China Sea to isolate symbiotic microorganisms. The resulting sponge-associated actinomycete, Streptomyces carnosus strain AZS17, was cultivated in a 20 L volume of medium for production of bioactive secondary metabolites. Bioassay-guided isolation and purification by varied chromatographic methods yielded two new compounds of kijanimicin derivatives, AS7-2 and AS9-12. Their structures were elucidated by spectroscopy and comparison with literatures. Results showed these two compounds were structurally similar to the previously reported compounds lobophorin A and B, yet differed in specific bond forms, stereochemistry and optical activities. The two novel compounds were named lobophorin C and D. In vitro cytotoxicity investigation by MTT assay indicated their selective activities. Lobophorin C displayed potent cytotoxic activity against the human liver cancer cell line 7402, while lobophorin D showed significant inhibitory effect on human breast cancer cells MDA-MB 435

  actinomycete, marine sponge, cytotoxic activity, lobophorin C and D

  NCBI PubMed ID: 21556165
  Publication DOI: 10.3390/md9030359
  Journal NLM ID: 101213729
  Publisher: Basel, Switzerland: Molecular Diversity Preservation International
  Correspondence: Wei RB ; Wang P ; Xi T ; Li FC ; Li J ; Qin S
  Institutions: College of Marine Science, Zhejiang Ocean University, Zhoushan, China, Marine Drugs Research Centre, China Pharmaceutical University, Nanjing, China, Open Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao, China, School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou, China
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, ESI-MS, UV, extraction, microscopy, optical rotation measurement, elemental analysis, CC, cell growth, HR-ESI-MS, cytotoxicity assay, sonication, MTT
  
   
  
  Streptomyces carnosus AZS 17
  CSDB ID 48081 (all data & tools)

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Structure type: oligomer
Trivial name: lobophorin D
Compound class: glycoside

• Article ID: 5650
  Wei RB, Xi T, Li J, Wang P, Li FC, Lin YC, Qin S "Lobophorin C and D, new kijanimicin derivatives from a marine sponge-associated actinomycetal strain AZS17" - Marine Drugs 9(3) (2011) 359-368
  

  Marine sponge Hymeniacidon sp. was collected from coastal waters of the East China Sea to isolate symbiotic microorganisms. The resulting sponge-associated actinomycete, Streptomyces carnosus strain AZS17, was cultivated in a 20 L volume of medium for production of bioactive secondary metabolites. Bioassay-guided isolation and purification by varied chromatographic methods yielded two new compounds of kijanimicin derivatives, AS7-2 and AS9-12. Their structures were elucidated by spectroscopy and comparison with literatures. Results showed these two compounds were structurally similar to the previously reported compounds lobophorin A and B, yet differed in specific bond forms, stereochemistry and optical activities. The two novel compounds were named lobophorin C and D. In vitro cytotoxicity investigation by MTT assay indicated their selective activities. Lobophorin C displayed potent cytotoxic activity against the human liver cancer cell line 7402, while lobophorin D showed significant inhibitory effect on human breast cancer cells MDA-MB 435

  actinomycete, marine sponge, cytotoxic activity, lobophorin C and D

  NCBI PubMed ID: 21556165
  Publication DOI: 10.3390/md9030359
  Journal NLM ID: 101213729
  Publisher: Basel, Switzerland: Molecular Diversity Preservation International
  Correspondence: Wei RB ; Wang P ; Xi T ; Li FC ; Li J ; Qin S
  Institutions: College of Marine Science, Zhejiang Ocean University, Zhoushan, China, Marine Drugs Research Centre, China Pharmaceutical University, Nanjing, China, Open Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao, China, School of Chemistry and Chemical Engineering, Sun Yat-sen University, Guangzhou, China
  Methods: 13C NMR, 1H NMR, NMR-2D, IR, TLC, ESI-MS, UV, extraction, microscopy, optical rotation measurement, elemental analysis, CC, cell growth, HR-ESI-MS, cytotoxicity assay, sonication, MTT
  
   
  
  Streptomyces carnosus AZS 17
  CSDB ID 48082 (all data & tools)
• Article ID: 5654
  Gomes NGM, Buttachon S, Kijjoa A "Meroterpenoids from marine microorganisms: potential scaffolds for new chemotherapy leads" - Book: Handbook of Anticancer Drugs from Marine Origin (2015) Chapter 16, 323-366
  

  Meroterpenoids, including several biologically active metabolites from marine microorganisms mainly fungi and actinomycete bacteria, represent promising structural scaffolds with not only diverse biological activities such as antimicrotubule, cytotoxic and antiproliferative but also different mechanisms of action. In this chapter, an overview on structural diversity and anticancer activity of mixed biogenesis terpenoid derivatives (meroterpenoids) from marine microorganisms is presented with highlight on individual examples of the most promising candidates in cancer chemotherapy and prevention

  cytotoxicity, Marine bacteria, marine microorganisms, anticancer activities, marine-derived fungi, marine-derived actinomycetes, meroterpenoids, terpenyl alkaloids, terpenyl glycosides, terpenyl polyketides

  Publication DOI: 10.1007/978-3-319-07145-9_16
  Publisher: Cham: Springer
  Correspondence: ankijjoa@icbas.up.pt
  Editors: Kim S-K
  Institutions: ICBAS—Instituto de Ciências Biomédicas Abel Salazar and Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Porto, Portugal
  
   
  
  Streptomyces carnosus AZS 17
  CSDB ID 48113 (all data & tools)

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Structure type: oligomer
C₆₇H₁₀₀N₂O₂₄
Trivial name: kijanimicin
Compound class: glycoside

• Article ID: 5651
  Mallams AK, Puar MS, Rossman RR, McPhail AT, Macfarlane RD "Kijanimicin. 2. Structure and absolute stereochemistry of kijanimicin" - Journal of the American Chemical Society 103(13) (1981) 3940-3943
  

  Kijanimicin, the major component of a complex of antibiotics produced by Actinomadura kijaniata nov. sp., has been shown to have the novel tetronic acid structure. Kijanimicin has antitumor activity and is active against P.acnes and is a member of a new class of tetronic acid containing antibiotics of which the tetrocarcins and antlermicins are the only other known members. The latter differ in the structure of the aglycon as well as in the structures of some of the glycosidic components, and full structures for these antiobiotics have not yet been published.

  antibiotic, kijanimicin, Actinomadura kijaniata

  Publication DOI: 10.1021/ja00403a063
  Journal NLM ID: 7503056
  Publisher: American Chemical Society
  Institutions: Research Division, Schering-Plough Corporation, Bloomfield, USA, Paul M. Gross Chemical Laboratory, Duke University, Durham, USA, Department of Chemistry, Texas A&M University College Station, Texas, USA
  Methods: 13C NMR, 1H NMR, EI-MS, IR, X-ray, acid hydrolysis, PD-MS, HPLC, UV, optical rotation measurement, CI-MS, FD-MS, derivatization
  
   
  
  Actinomadura kijaniata
  CSDB ID 48085 (all data & tools)
• Article ID: 5652
  Mallams AK, Puar MS, Rossman RR "Kijanimicin. 1. Structures of the individual sugar components" - Journal of the American Chemical Society 103(13) (1981) 3938-3940
  

  Kijanimicin, the major component of a complex of antibiotics produced by Actinomadura kijaniata nov. sp., has been shown to have the novel tetronic acid structure. Kijanimicin has antitumor activity and is active against P.acnes and is a member of a new class of tetronic acid containing antibiotics of which the tetrocarcins and antlermicins are the only other known members. The latter differ in the structure of the aglycon as well as in the structures of some of the glycosidic components, and full structures for these antiobiotics have not yet been published.

  antibiotic, kijanimicin, Actinomadura kijaniata

  Publication DOI: 10.1021/ja00403a062
  Journal NLM ID: 7503056
  Publisher: American Chemical Society
  Institutions: Research Division, Schering-Plough Corporation, Bloomfield, USA
  Methods: 13C NMR, 1H NMR, EI-MS, IR, acid hydrolysis, UV, optical rotation measurement, CI-MS, CD, reduction, melting point determination, derivatization
  
   
  
  Actinomadura kijaniata
  CSDB ID 48086 (all data & tools)

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Structure type: oligomer
Trivial name: lobophorin A
Compound class: glycoside

• Article ID: 5653
  Jiang ZD, Jensen PR, Fenical W "Lobophorins A and B, new antiinflammatory macrolides produced by a tropical marine bacterium" - Bioorganic and Medicinal Chemistry Letters 9(14) (1999) 2003-2006
  

  Two new antiinflammatory macrolides, lobophorins A and B (1 and 2), have been isolated from fermentation broths of a marine bacterium isolated from the surface the Caribbean brown alga Lobophora variegata (Dictyotales). The new compounds, distantly related to antibiotics of the kijanimicin class, are potent inhibitors of topical PMA-induced edema in the mouse ear assay when administered either topically or IP

  lobophorins, antiinflammatory activity, Lobophora variegata

  NCBI PubMed ID: 10450970
  Publication DOI: 10.1016/s0960-894x(99)00337-6
  Journal NLM ID: 9107377
  Publisher: Elsevier
  Institutions: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, USA
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, acid hydrolysis, biological assays, HPLC, extraction, acetylation, CC, cell growth, DEPT, HR-FAB-MS
  
   
  
  (Actinomycetaceae) sp. CNB-837
  CSDB ID 48087 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lobophorin B
Compound class: glycoside

• Article ID: 5653
  Jiang ZD, Jensen PR, Fenical W "Lobophorins A and B, new antiinflammatory macrolides produced by a tropical marine bacterium" - Bioorganic and Medicinal Chemistry Letters 9(14) (1999) 2003-2006
  

  Two new antiinflammatory macrolides, lobophorins A and B (1 and 2), have been isolated from fermentation broths of a marine bacterium isolated from the surface the Caribbean brown alga Lobophora variegata (Dictyotales). The new compounds, distantly related to antibiotics of the kijanimicin class, are potent inhibitors of topical PMA-induced edema in the mouse ear assay when administered either topically or IP

  lobophorins, antiinflammatory activity, Lobophora variegata

  NCBI PubMed ID: 10450970
  Publication DOI: 10.1016/s0960-894x(99)00337-6
  Journal NLM ID: 9107377
  Publisher: Elsevier
  Institutions: Center for Marine Biotechnology and Biomedicine, Scripps Institution of Oceanography, University of California, San Diego, USA
  Methods: 13C NMR, 1H NMR, methylation, NMR-2D, acid hydrolysis, biological assays, HPLC, extraction, acetylation, CC, cell growth, DEPT, HR-FAB-MS
  
   
  
  (Actinomycetaceae) sp. CNB-837
  CSDB ID 48088 (all data & tools)

Show legend Show as text

Structure type: oligomer
Trivial name: lobophorin C
Compound class: glycoside

• Article ID: 5654
  Gomes NGM, Buttachon S, Kijjoa A "Meroterpenoids from marine microorganisms: potential scaffolds for new chemotherapy leads" - Book: Handbook of Anticancer Drugs from Marine Origin (2015) Chapter 16, 323-366
  

  Meroterpenoids, including several biologically active metabolites from marine microorganisms mainly fungi and actinomycete bacteria, represent promising structural scaffolds with not only diverse biological activities such as antimicrotubule, cytotoxic and antiproliferative but also different mechanisms of action. In this chapter, an overview on structural diversity and anticancer activity of mixed biogenesis terpenoid derivatives (meroterpenoids) from marine microorganisms is presented with highlight on individual examples of the most promising candidates in cancer chemotherapy and prevention

  cytotoxicity, Marine bacteria, marine microorganisms, anticancer activities, marine-derived fungi, marine-derived actinomycetes, meroterpenoids, terpenyl alkaloids, terpenyl glycosides, terpenyl polyketides

  Publication DOI: 10.1007/978-3-319-07145-9_16
  Publisher: Cham: Springer
  Correspondence: ankijjoa@icbas.up.pt
  Editors: Kim S-K
  Institutions: ICBAS—Instituto de Ciências Biomédicas Abel Salazar and Centro Interdisciplinar de Investigação Marinha e Ambiental (CIIMAR), Universidade do Porto, Porto, Portugal
  
   
  
  Streptomyces carnosus AZS 17
  CSDB ID 48112 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1157.6359 [M+H]+
C₆₁H₉₂N₂O₁₉
Trivial name: lobophorin A
Compound class: glycoside

• Article ID: 6462
  Shi J, Peng D, Peng FF, Zhang QB, Duan YW, Huang Y "The Isolation and Structure Elucidation of Spirotetronate Lobophorins A, B, and H8 from Streptomyces sp. CB09030 and Their Biosynthetic Gene Cluster" - Molecules 28(8) (2023) 3597
  

  Lobophorins (LOBs) are a growing family of spirotetronate natural products with significant cytotoxicity, anti-inflammatory, and antibacterial activities. Herein, we report the transwell-based discovery of Streptomyces sp. CB09030 from a panel of 16 in-house Streptomyces strains, which has significant anti-mycobacterial activity and produces LOB A (1), LOB B (2), and LOB H8 (3). Genome sequencing and bioinformatic analyses revealed the potential biosynthetic gene cluster (BGC) for 1-3, which is highly homologous with the reported BGCs for LOBs. However, the glycosyltransferase LobG1 in S. sp. CB09030 has certain point mutations compared to the reported LobG1. Finally, LOB analogue 4 (O-β-D-kijanosyl-(1→17)-kijanolide) was obtained through an acid-catalyzed hydrolysis of 2. Compounds 1-4 showed different antibacterial activities against Mycobacterium smegmatis and Bacillus subtilis, which revealed the varying roles of different sugars in their antibacterial activities.

  Streptomyces, lobophorins, anti-mycobacterial activity, spirotetronate, transwell

  NCBI PubMed ID: 37110828
  Publication DOI: 10.3390/molecules28083597
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: Y.W. Duan ; Y. Huang ;
  Institutions: Xiangya International Academy of Translational Medicine, Central South University, Changsha 410013, China, School of Pharmaceutical Sciences, Changsha Health Vocational College, Changsha 410100, China, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China, Hunan Engineering Research Center of Combinatorial Biosynthesis and Natural Product Drug Discovery, Changsha 410011, China, National Engineering Research Center of Combinatorial Biosynthesis for Drug Discovery, Changsha 410011, China, Institute of Health and Medicine, Hefei Comprehensive National Science Center, Hefei 230093, China
  Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, bioinformatic analysis, CC, RP-HPLC, fermentation, phylogenetic analysis, HR-ESI-MS, antibacterial assay, cytotoxicity assay, genome sequencing, HR-ESI-MS/MS
  
   
  
  Streptomyces sp. CB09030, Actinomyces sp. CNB-837, Streptomyces sp. SCSIO 01127, Streptomyces pactum SCSIO 02999, Streptomyces sp. MS100061
  CSDB ID 22314 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 1209.5921 [M+H]+
C₆₁H₉₀N₂O₂₁
Trivial name: lobophorin B
Compound class: glycoside

• Article ID: 6462
  Shi J, Peng D, Peng FF, Zhang QB, Duan YW, Huang Y "The Isolation and Structure Elucidation of Spirotetronate Lobophorins A, B, and H8 from Streptomyces sp. CB09030 and Their Biosynthetic Gene Cluster" - Molecules 28(8) (2023) 3597
  

  Lobophorins (LOBs) are a growing family of spirotetronate natural products with significant cytotoxicity, anti-inflammatory, and antibacterial activities. Herein, we report the transwell-based discovery of Streptomyces sp. CB09030 from a panel of 16 in-house Streptomyces strains, which has significant anti-mycobacterial activity and produces LOB A (1), LOB B (2), and LOB H8 (3). Genome sequencing and bioinformatic analyses revealed the potential biosynthetic gene cluster (BGC) for 1-3, which is highly homologous with the reported BGCs for LOBs. However, the glycosyltransferase LobG1 in S. sp. CB09030 has certain point mutations compared to the reported LobG1. Finally, LOB analogue 4 (O-β-D-kijanosyl-(1→17)-kijanolide) was obtained through an acid-catalyzed hydrolysis of 2. Compounds 1-4 showed different antibacterial activities against Mycobacterium smegmatis and Bacillus subtilis, which revealed the varying roles of different sugars in their antibacterial activities.

  Streptomyces, lobophorins, anti-mycobacterial activity, spirotetronate, transwell

  NCBI PubMed ID: 37110828
  Publication DOI: 10.3390/molecules28083597
  Journal NLM ID: 100964009
  Publisher: Basel, Switzerland: MDPI
  Correspondence: Y.W. Duan ; Y. Huang ;
  Institutions: Xiangya International Academy of Translational Medicine, Central South University, Changsha 410013, China, School of Pharmaceutical Sciences, Changsha Health Vocational College, Changsha 410100, China, South China Sea Institute of Oceanology, Chinese Academy of Sciences, Guangzhou 510301, China, Hunan Engineering Research Center of Combinatorial Biosynthesis and Natural Product Drug Discovery, Changsha 410011, China, National Engineering Research Center of Combinatorial Biosynthesis for Drug Discovery, Changsha 410011, China, Institute of Health and Medicine, Hefei Comprehensive National Science Center, Hefei 230093, China
  Methods: 13C NMR, 1H NMR, NMR-2D, acid hydrolysis, bioinformatic analysis, CC, RP-HPLC, fermentation, phylogenetic analysis, HR-ESI-MS, antibacterial assay, cytotoxicity assay, genome sequencing, HR-ESI-MS/MS
  
   
  
  Streptomyces sp. CB09030, Actinomyces sp. CNB-837, Streptomyces sp. SCSIO 01127, Streptomyces pactum SCSIO 02999, Streptomyces sp. MS100061
  CSDB ID 24840 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 747 [M-H]-
C₄₀H₆₀O₁₃
Trivial name: cynascyroside A
Compound class: glycoside

• Article ID: 11416
  Yeo H, Kim KW, Kim J, Choi YH "Steroidal glycosides of the 14,15-seco-18-nor-pregnane series from Cynanchum ascyrifolium" - Phytochemistry 49(4) (1998) 1129-1133
  

  Three new steroidal glycosides named cynascyrosides A-C were isolated from the roots of Cynanchum ascyrifolium. The structures of these compounds were determined on the basis of spectroscopic and chemical evidence as cynajapogenin A 3-O-alpha-D-oleandropyranosyl-(1 --> 4)-beta-L-cymaropyranosyl-(1 --> 4)-beta-D-digitoxopyranoside; cynajapogenin A 3-O-beta-D-glucopyranosyl-(1 --> 4)-alpha-L-cymaropyranosyl-(1 --> 4)-beta-L-cymaropyranosyl-(1 --> 4)-beta-L-cymaropyranoside cynajapogenin A 3-O-beta-D-glucopyranosyl-(1 --> 4)-alpha-L-cymaropyranosyl-(1 --> 4)-beta-D-digitoxopyranosyl-(1 --> 4)-beta-L-cymaropyranoside.

  steroidal glycosides, Asclepiadaceae, Cynanchum ascyrifolium, cynascyrosides A-C, cynajapogenin A

  NCBI PubMed ID: 9788147
  Publication DOI: 10.1016/s0031-9422(97)01064-9
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: College of Pharmacy, Seoul National University, Seoul, South Korea, College of Pharmacy, Ewha Womans University, Seoul, South Korea
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, COSY
  
   
  
  Cynanchum ascyrifolium
  CSDB ID 61675 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 747 [M-H]-
C₄₇H₇₂O₁₈
Trivial name: cynascyroside B
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11416
  Yeo H, Kim KW, Kim J, Choi YH "Steroidal glycosides of the 14,15-seco-18-nor-pregnane series from Cynanchum ascyrifolium" - Phytochemistry 49(4) (1998) 1129-1133
  

  Three new steroidal glycosides named cynascyrosides A-C were isolated from the roots of Cynanchum ascyrifolium. The structures of these compounds were determined on the basis of spectroscopic and chemical evidence as cynajapogenin A 3-O-alpha-D-oleandropyranosyl-(1 --> 4)-beta-L-cymaropyranosyl-(1 --> 4)-beta-D-digitoxopyranoside; cynajapogenin A 3-O-beta-D-glucopyranosyl-(1 --> 4)-alpha-L-cymaropyranosyl-(1 --> 4)-beta-L-cymaropyranosyl-(1 --> 4)-beta-L-cymaropyranoside cynajapogenin A 3-O-beta-D-glucopyranosyl-(1 --> 4)-alpha-L-cymaropyranosyl-(1 --> 4)-beta-D-digitoxopyranosyl-(1 --> 4)-beta-L-cymaropyranoside.

  steroidal glycosides, Asclepiadaceae, Cynanchum ascyrifolium, cynascyrosides A-C, cynajapogenin A

  NCBI PubMed ID: 9788147
  Publication DOI: 10.1016/s0031-9422(97)01064-9
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: College of Pharmacy, Seoul National University, Seoul, South Korea, College of Pharmacy, Ewha Womans University, Seoul, South Korea
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, COSY
  
   
  
  Cynanchum ascyrifolium
  CSDB ID 61676 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 747 [M-H]-
C₄₆H₇₀O₁₈
Trivial name: cynascyroside C
Compound class: glycoside
Contained glycoepitopes: IEDB_142488,IEDB_146664,IEDB_983931,SB_192

• Article ID: 11416
  Yeo H, Kim KW, Kim J, Choi YH "Steroidal glycosides of the 14,15-seco-18-nor-pregnane series from Cynanchum ascyrifolium" - Phytochemistry 49(4) (1998) 1129-1133
  

  Three new steroidal glycosides named cynascyrosides A-C were isolated from the roots of Cynanchum ascyrifolium. The structures of these compounds were determined on the basis of spectroscopic and chemical evidence as cynajapogenin A 3-O-alpha-D-oleandropyranosyl-(1 --> 4)-beta-L-cymaropyranosyl-(1 --> 4)-beta-D-digitoxopyranoside; cynajapogenin A 3-O-beta-D-glucopyranosyl-(1 --> 4)-alpha-L-cymaropyranosyl-(1 --> 4)-beta-L-cymaropyranosyl-(1 --> 4)-beta-L-cymaropyranoside cynajapogenin A 3-O-beta-D-glucopyranosyl-(1 --> 4)-alpha-L-cymaropyranosyl-(1 --> 4)-beta-D-digitoxopyranosyl-(1 --> 4)-beta-L-cymaropyranoside.

  steroidal glycosides, Asclepiadaceae, Cynanchum ascyrifolium, cynascyrosides A-C, cynajapogenin A

  NCBI PubMed ID: 9788147
  Publication DOI: 10.1016/s0031-9422(97)01064-9
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: College of Pharmacy, Seoul National University, Seoul, South Korea, College of Pharmacy, Ewha Womans University, Seoul, South Korea
  Methods: 13C NMR, 1H NMR, IR, FAB-MS, acid hydrolysis, UV, extraction, optical rotation measurement, CC, melting point determination, HMBC, COSY
  
   
  
  Cynanchum ascyrifolium
  CSDB ID 61677 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 952 [M-H]-
C₄₈H₇₂O₁₉
Trivial name: stauntoside A
Compound class: saponin glycoside

• Article ID: 11748
  Zhu N, Wang M, Kikuzaki H, Nakatani N, Ho CT "Two C21-steroidal glycosides isolated from Cynanchum stauntoi" - Phytochemistry 52(7) (1999) 1351-1355
  

  Studies on the roots of Cynanchum stauntoi led to the isolation of two C21-steroidal glycosides, formally named stauntosides A and B. Their structures were elucidated on the basis of spectroscopic evidence, especially that from analysis of 2D-NMR spectra. They were found to possess an unusual skeleton and were identified as stauntogenin 3-O-α-L-diginopyranosyl-(1-4)-β-L-cymaropyranosyl-(1-4)-β-D-digitoxopyranosyl-(1-4)-β-D-thevetopyranoside and stauntogenin 3-O-α-L-cymaropyranosyl-(1-4)-β-D-digitoxopyranosyl-(1-4)-β-D-3-demethyl-2-deoxy-thevetopyranoside.

  NMR assignments, two-dimensional NMR techniques, Cynanchum stauntoi, Ascelepiadaceae, C21-steroidal glycosides, stauntoside A, stauntoside B

  NCBI PubMed ID: 10647217
  Publication DOI: 10.1016/S0031-9422(99)00439-2
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Food Science, Rutgers, The State University of New Jersey, 65 Dudley Road, New Brunswick, NJ 08901-8520, USA, Department of Food & Nutrition, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi, Osaka, Japan
  Methods: 13C NMR, 1H NMR, FAB-MS, TLC, HPLC, optical rotation measurement, HMBC, HMQC, COSY, NOESY, APCI-MS
  
   
  
  Cynanchum stauntoi
  CSDB ID 62764 (all data & tools)

Show legend Show as text

Structure type: oligomer ; 801 [M+Na]+
C₄₀H₅₈O₁₅
Trivial name: stauntoside B
Compound class: saponin glycoside

• Article ID: 11748
  Zhu N, Wang M, Kikuzaki H, Nakatani N, Ho CT "Two C21-steroidal glycosides isolated from Cynanchum stauntoi" - Phytochemistry 52(7) (1999) 1351-1355
  

  Studies on the roots of Cynanchum stauntoi led to the isolation of two C21-steroidal glycosides, formally named stauntosides A and B. Their structures were elucidated on the basis of spectroscopic evidence, especially that from analysis of 2D-NMR spectra. They were found to possess an unusual skeleton and were identified as stauntogenin 3-O-α-L-diginopyranosyl-(1-4)-β-L-cymaropyranosyl-(1-4)-β-D-digitoxopyranosyl-(1-4)-β-D-thevetopyranoside and stauntogenin 3-O-α-L-cymaropyranosyl-(1-4)-β-D-digitoxopyranosyl-(1-4)-β-D-3-demethyl-2-deoxy-thevetopyranoside.

  NMR assignments, two-dimensional NMR techniques, Cynanchum stauntoi, Ascelepiadaceae, C21-steroidal glycosides, stauntoside A, stauntoside B

  NCBI PubMed ID: 10647217
  Publication DOI: 10.1016/S0031-9422(99)00439-2
  Journal NLM ID: 0151434
  Publisher: Elsevier
  Institutions: Department of Food Science, Rutgers, The State University of New Jersey, 65 Dudley Road, New Brunswick, NJ 08901-8520, USA, Department of Food & Nutrition, Osaka City University, 3-3-138 Sugimoto, Sumiyoshi, Osaka, Japan
  Methods: 13C NMR, 1H NMR, FAB-MS, TLC, HPLC, optical rotation measurement, HMBC, HMQC, COSY, NOESY, APCI-MS
  
   
  
  Cynanchum stauntoi
  CSDB ID 62765 (all data & tools)