Ring B aromatic steroids from an endophytic fungus, Colletotrichum sp.

Natural Product Communications

Volumn 4, Issue 11, 2009, Pages 1449-1454

  Zhang, Wen ^a   Draeger, Siegfried ^b   Schulz, Barbara ^b   Krohn, Karsten ^c  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

^b TECHNICAL UNIVERSITY OF BRAUNSCHWEIG   (Germany)

^c UNIVERSITY OF PADERBORN   (Germany)

Author keywords

Antimicrobial activity; Aromatic ring B; Colletotrichum sp.; Endophytic fungus; Ergosteroids; Ilex canariensis

Indexed keywords

19(10-6) ABEO ERGOSTA 5,7,9,22 TETRAEN 3BETA OL; 3 ACETOXY 19(10-6) ABEO ERGOSTA 5,7,9,22 TETRAEN 3BETA OL; 3,6 DIACETOXY ERGOSTA 7,22 DIEN 3BETA,5ALPHA,6BETA TRIOL; 5ALPHA,8ALPHA EPIDIOXYERGOSTA 6,22 DIEN 3BETA OL; 6 ACETOXY ERGOSTA 7,22 DIEN 3BETA,5ALPHA,6BETA TRIOL; AROMATIC COMPOUND; CHEMICAL COMPOUND; ERGOSTA 4,6,8(14),22 TETRAEN 3 ONE; ERGOSTA 4,7,22 TRIEN 3 ONE; ERGOSTA 7,22 DIEN 3BETA,5ALPHA,6BETA TRIOL; ERGOSTEROL; STEROID; UNCLASSIFIED DRUG; ANTIINFECTIVE AGENT;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ARTICLE; BACILLUS MEGATERIUM; BIOSYNTHESIS; COLLETOTRICHUM; DRUG ISOLATION; ENDOPHYTE; ERGONOMICS; ESCHERICHIA COLI; FUNGUS; FUNGUS CULTURE; ILEX; METABOLITE; NONHUMAN; SPECTROSCOPY; ACETYLATION; ALGA; BACTERIUM; CHEMISTRY; CULTURE MEDIUM; DRUG EFFECT; MICROBIOLOGICAL EXAMINATION; MICROBIOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; THIN LAYER CHROMATOGRAPHY;

'CHLORELLA' FUSCA; ALGAE; BACILLUS MEGATERIUM; COLLETOTRICHUM SP.; ESCHERICHIA COLI; FUNGI; ILEX CANARIENSIS; MICROBOTRYUM VIOLACEUM;

ACETYLATION; ALGAE; ANTI-BACTERIAL AGENTS; BACTERIA; CHROMATOGRAPHY, THIN LAYER; COLLETOTRICHUM; CULTURE MEDIA; FUNGI; ILEX; MAGNETIC RESONANCE SPECTROSCOPY; MICROBIAL SENSITIVITY TESTS; STEROIDS;

EID: 75549084659     PISSN: 1934578X     EISSN: 15559475     Source Type: Journal    
DOI: 10.1177/1934578x0900401101     Document Type: Article

References (23)

1. 5,7,9-anthracholestatrien-x- ols. Journal of the American Chemical Society, 85, 1126-1131.
2. 5,8(14),9(11)-ergostatrien-3β-ol. Journal of the American Chemical Society, 85, 1131-1133.
3. Steele JA, Cohen LA, Mosettig E. (1963) The anthrasteroid rearrangement. X. Elucidation of the stereochemistry of the C/D ring fusion from chemical transformation and NMR data. Journal of the American Chemical Society, 85, 1134-1138.
4. 5,8(9)-steroidal azoester adducts. Tetrahedron Letters, 14, 813-816.
5. Bosworth N, Emke A, Midgley JM, Moore CJ, Whalley WB, Ferguson G, Marsh WC. (1977) Unsaturated steroids. Part 2. A novel route to anthrasteroids: x-ray crystal structure of 1(10→6) abeo-cholesta-5,7,9-trien-3-yl p-bromobenzoate. Journal of the Chemical Society, Perkin Transactions I, 805-812.
6. Emke A, Midgley JM, Whalley WB. (1980) Journal of the Chemical Society, Perkin Transactions I, 1779-1781.
7. 29 Monoaromatic anthrasteroid hydrocarbons in Cretaceous black shales. Nature, 304, 262-263.
8. Koshino H, Yoshihara T, Sakamura S, Shimanuki T, Sato T, Tajimi A. (1989) A ring B aromatic sterol from stromata of Epichloe typhina. Phytochemistry, 28, 771-772.
9. Bisseret P, Adam H, Rohmer M. (1987) Structural elucidation of ring B aromatic sterols of the soil amoeba Acanthamoeba polyphaga. Journal of the Chemical Society, Chemical Communications, 693-695.
10. Ondeyka JG, Jayasuriya H, Herath KB, Guan Z, Schulman M, Collado J, Dombrowski AW, Kwon SS, McCallum C, Sharma N, MacNaul K, Hayes N, Menke JG, Singh SB. (2005) Steroidal and triterpenoidal fungal metabolites as ligands of liver X receptors. Journal of Antibiotics, 58, 559-565. (Pubitemid 41512929)
11. Krohn K, Kouam SF, Kuigoua GM, Hussain H, Cludius-Brand S, Flörke U, Kután T, Pescitelli G, Di Bari L, Draeger S, Schulz B. (2009) Xanthones and new oxepino[2,3-b]chromones from three endophytic fungi, Chemistry - A European Journal, DOI: 10.1002/chem.200900749.
12. Schulz B, Draeger S, de la Cruz T, Rheinheimer J, Siems K, Loesgen S Bitzer J, Schloerke O Zeeck A, Ines Kock I, Hussain H, Dai J, Krohn K. (2008) Screening strategies for obtaining novel, biologically active secondary metabolite from marine habitats. Botanica Marina, 51, 219-234.
13. Goulston G, Ian Mercer E, Goad LJ. (1975) The identification of 24-methylene-24,25-dihydrolanosterol and other possible ergosterol precursors in Phycomyces blakesleeanus and Agaricus campestris. Phytochemistry, 14, 457-462.
14. Shepherd DA, Donia RA, Allan Campbell J, Johnson BA, Holysz RP, Slomp G, Stafford JE, Pederson RL, Ott AC. (1955) A Synthesis of progesterone from ergosterol. Journal of the American Chemical Society, 77, 1212-1215.
15. Tanaka N, Hosoi K, Tanaka D, Takahashi M. (1996) Photochemical reaction of ergosta-4,6,8(14),22-tetraen-3-one. Chemical & Pharmaceutical Bulletin, 44, 843-846.
16. Kang J, Chen R. (2005) Studies on chemical constituents in the mycelia from fermented culture of Flammulina velutipes. China Journal of Chinese Materia Medica, 30, 193-195.
17. Della Greca M, Mangoni L, Molinaro A, Monaco P, Previtera L. (1990) 5α,8α-Epidioxyergosta-6,22-dien-3β-ol from Typha latifolia. Gazzetta Chimica Italiana, 120, 391-392.
18. Gao H, Hong K, Zhang X, Liu HW, Wang NL, Zhuang L, Yao XS. (2007) New steryl esters of fatty acids from the mangrove fungus Aspergillus awamori. Helvetica Chimica Acta, 90, 1165-1178. (Pubitemid 47051330)
19. Lu H, Zou WX, Meng JC, Hu J, Tan RX. (2000) New bioactive metabolites produced by Colletotrichum sp., an endophytic fungus in Artemisia annua. Plant Science, 151, 67-73.
20. Cafieri F, Fattorusso E. (1985) 3β,5α,6β- Trihydroxysterols from the Mediterranean bryozoan Myriapora truncate. Journal of Natural Products, 48, 944-947.
21. Schulz B, Sucker J, Aust HJ, Krohn K, Ludewig K, Jones PG, Doering D. (1995) Biologically active secondary metabolites of endophytic Pezicula species. Mycological Research, 99, 1007-1015.
22. Krohn K, Flörke U, Rao MS, Steingröver K, Aust HJ, Draeger S, Schulz B. (2001) Metabolites from fungi 15. New isocoumarins from an endophytic fungus isolated from the Canadian thistle Cirsium arvense. Natural Product Letters, 15, 353-361. (Pubitemid 34071173)
23. Höller U, Wright AD, Matthée GF, Konig GM, Draeger S, Aust HJ, Schulz B. (2000) Fungi from marine sponges: diversity, biological activity and secondary metabolites. Mycological Research, 104, 1354-1365.