Tetrahydrobostrycin and 1-deoxytetrahydrobostrycin, two new hexahydroanthrone derivatives, from a marine-derived fungus Aspergillus sp.

Journal of Antibiotics

Volumn 61, Issue 7, 2008, Pages 415-419

  Xu, Jinzhong ^a,d   Nakazawa, Takahiro ^a   Ukai, Kazuyo ^a   Kobayashi, Hisayoshi ^b   Mangindaan, Remy E P ^c   Wewengkang, Defny S ^c   Rotinsulu, Henki ^c   Namikoshi, Michio ^a  

^a TOHOKU PHARMACEUTICAL UNIVERSITY   (Japan)

^b UNIVERSITY OF TOKYO   (Japan)

^c SAM RATULANGI UNIVERSITY   (Indonesia)

^d ZHEJIANG UNIVERSITY   (China)

Author keywords

1 deoxytetrahydrobostrycin; Abscisic acid; Aspergillus sp.; Bostrycin; Hexahydroanthrone; Marine derived fungus; Tetrahydrobostrycin

Indexed keywords

1 DEOXYTETRAHYDROBOSTRYCIN; ABSCISIC ACID; BOSTRYCIN; HEXAHYDROANTHRONE DERIVATIVE; NATURAL PRODUCT; TETRAHYDROBOSTRYCIN; UNCLASSIFIED DRUG; ANTHRAQUINONE DERIVATIVE; ANTIINFECTIVE AGENT; SEA WATER;

ANTIBACTERIAL ACTIVITY; ARTICLE; ASPERGILLUS; DRUG ISOLATION; DRUG STRUCTURE; ESCHERICHIA COLI; FUNGAL STRAIN; NONHUMAN; PRIORITY JOURNAL; STAPHYLOCOCCUS AUREUS; STRUCTURE ANALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG EFFECT; INDONESIA; ISOLATION AND PURIFICATION; MICROBIOLOGICAL EXAMINATION; MICROBIOLOGY;

ANTHOZOA; ASPERGILLUS SP.; ESCHERICHIA COLI; FUNGI; STAPHYLOCOCCUS AUREUS;

ABSCISIC ACID; ANTHRAQUINONES; ANTI-BACTERIAL AGENTS; ASPERGILLUS; ESCHERICHIA COLI; INDONESIA; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; SEAWATER; STAPHYLOCOCCUS AUREUS;

EID: 55449099336     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2008.57     Document Type: Article

References (27)

1. Blunt JW, Copp BR, Hu W-P, Munro MHG, Northcote PT, Prinsep MR. Marine natural products. Nat Prod Rep 25: 35-94 (2008) and previous reports in this series.
2. Namikoshi M. Biologically active natural products from marine fungi. In Biomaterials from Aquatic and Terrestrial Organisms. Ed., M. Fingerman and R. Nagabhushanam, pp. 285-359, Science Publishers, Enfield (2006)
3. Bugni TS, Ireland CM. Marine-derived fungi: a chemistry and biologically diverse group of microorganisms. Nat Prod Rep 21: 143-163 (2004)
4. Noda T, Take T, Otani M, Miyauchi K, Watanabe T, Abe J. Structure of bostrycin. Tetrahedron Lett 9: 6087-6090 (1968)
5. Noda T, Take T, Watanabe T, Abe J. The structure of bostrycin. Tetrahedron 26: 1339-1346 (1970)
6. Kelly TR, Saha JK. Bostrycin: structure correction and synthesis. J Org Chem 50: 3679-3685 (1985)
7. Beagly B, Larsen DS, Pritchard RG, Stoodley RJ. Revision of absolute configuration of (-)-bostrycin. J Chem Soc Chem Commun 1989: 17-19 (1989)
8. Furuya K, Shirasaka M. Antibiotics from fungi. IV Production of rhodosporin (bostrycin) by Nigrospora oryzae. Sankyo Kenkyusho Nempo 21: 165-168 (1969)
9. Van Eijk BW. Bostrycin, a tetrahydroanthraquinone pigment and some other metabolites from the fungus Arthrinium phaeospermum. Experientia 31: 783-784 (1975)
10. Charudattan R, Rao KV. Bostrycin and 4-deoxybostrycin: two nonspecific phytotoxins produced by Alternaria eichhorniae. Appl Environ Microbiol 43: 846-849 (1982)
11. Namikoshi M, Negishi R, Nagai H, Dmitrenok A, Kobayashi H. Three new chlorine containing antibiotics from a marine-derived fungus Aspergillus ostianus collected in Pohnpei. J Antibiot 56: 755-761 (2003)
12. Stoessl A, Stothers JB. Tetrahydroaltersolanol B, a hexahydroanthronol from Alternaria solani. Can J Chem 61: 378-382 (1983)
13. Okamura N, Mimura K, Haraguchi H, Shingu K, Miyahara K, Yagi A. Altersolanol-related compounds from the culture liquid of Alternaria solani. Phytochemistry 42: 77-80 (1996)
14. Xia X-K, Huang H-R, She Z-G, Shao C-L, Liu F, Cai X-L, Vrijmoed LLP, Lin Y-C. 1H and 13C-NMR assignments for five anthraquinones from the mangrove endophytic fungus Halorosellinia sp. (No. 1403). Mag Reson Chem 45: 1006-1009 (2007)
15. Suemitsu R, Horiuchi K, Kubota M, Okamatsu T. Production of alterporriols, altersolanols and macrosporin by Alternaria porri and A. solani. Phytochemistry 29: 1509-1511 (1990)
16. Stoessl A. Some metabolites of Alternaria solani. Can J Chem 47: 67-76 (1969)
17. Yagi A, Okamura N, Haraguchi H, Abo T, Hashimoto K. Antimicrobial tetrahydroanthraquinones from a strain of Alternaria solani. Phytochemistry 33: 87-91 (1993)
18. Okamura N, Haraguchi H, Hashimoto K, Yagi A. Altersolanol-related antimicrobial compounds from a strain of Alternaria solani. Phytochemistry 34: 1005-1009 (1993)
19. Okamura N, Mimura K, Haraguchi H, Shingu K, Miyahara K, Yagi A. Altersolanol-related compounds from the culture liquid of Alternaria solani. Phytochemistry 42: 77-80 (1996)
20. Alvi KA, Rabenstein J. Auxarthrol A and auxarthrol B: two new tetrahydroanthraquinones from Auxarthron umbrinum. J Ind Microbiol Biotechnol 31: 11-15 (2004)
21. Ivanova VB, Hoshino Y, Yazawa K, Ando A, Mikami Y, Zaki SM Gräfe U. Isolation and structure elucidation of two new antibacterial compounds produced by Chrysosporium queenslandicum. J Antibiot 55: 914-918 (2002)
22. Kettner M, Nemec P, Kovác S, Balanová J. Dactylarin, a new antiprotozoal antibiotic from Dactylaria luea. J Antibiot 26: 692-696 (1973)
23. Becker AM, Rickards RW, Schmalzl KJ, Yick HC. Metabolites of Dactylaria lutea the structures of dactylariol and the antiprotozoal antibiotic dactylarin. J Antibiot 31: 324-329 (1978)
24. Burns CJ, Gill M, Giménez A. Pigments of fungi. XXIV New trihydroxylated tetrahydroanthraquinones from an Australian fungus belonging to the genus Dermocybe. Aust J Chem 44: 11729-1736 (1991)
25. Wheeler MM, Wheeler DMS, Peterson GW Anthraquinone pigments from the phytopathogen Phomopsis juniperovora Hahn. Phytochemistry 14: 288-289 (1975)
26. Ge HM, Song YC, Shan CY, Ye YH, Tan RX. New and cytotoxic anthraquinones from Pleospora sp. IFB-E006, an endophytic fungus in Imperata cylindrical. Planta Med 71: 1063-1065 (2005)
27. Assante G, Nasini G. Identity of the phytotoxin stemphylin from Stemphylium botryosum with altersolanol A. Phytochemistry 26: 703-705 (1987)