Blazeispirol X and Y, two novel carbon skeletal sterols from the cultured mycelia of the fungus Agaricus blazei

Tetrahedron Letters

Volumn 41, Issue 26, 2000, Pages 5107-5110

  Hirotani, Masao ^a   Hirotani, Seiko ^a   Yoshikawa, Takafumi ^a  

^a KITASATO UNIVERSITY   (Japan)

Author keywords

Fungi; Natural products; NMR; Steroid

Indexed keywords

BLAZEISPIROL X; BLAZEISPIROL Y; STEROL DERIVATIVE; UNCLASSIFIED DRUG;

AGARICUS BLAZEI; ARTICLE; DRUG ISOLATION; DRUG STRUCTURE; MYCELIUM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

AGARICACEAE; AGARICUS BLAZEI; FUNGI;

EID: 0034709613     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00783-8     Document Type: Article

References (12)

1. Hirotani, M.; Hirotani, S.; Takayanagi, H.; Yoshikawa, T. Tetrahedron Lett. 1999, 40, 329-332.
2. Kosemura, S.; Uotsu, S.; Yamamura, S. Tetrahedron Lett. 1995, 36, 7481-7482.
3. Koshino, H.; Yoshihara, T.; Sakamura, S.; Shimanuki, T.; Sato, T.; Tajimi, A. Phytochemistry 1989, 28, 771-772.
4. Kawahara, N.; Sekita, S.; Satake, M. Phytochemistry 1995, 38, 947-950.
5. Emke, A.; Midgley, J. M.; Whalley, W. B. J. Chem. Soc., Perkin Trans. 1 1980, 1779-1781.
6. Hussler, G.; Albrecht, P. Nature 1983, 304, 262-263.
7. Hirotani, M.; Asaka, I.; Ino, C.; Furuya, T.; Shiro, M. Phytochemistry 1987, 26, 2797-2803.
8. Demarco, P. V.; Farkas, E.; Doddrell, D.; Mylari, B. L.; Wenkert, E. J. Am. Chem. Soc. 1968, 90, 5480-5486.
9. Turner, W. B.; Aldridge, D. C. Fungal Metabolites II; Academic Press: London, 1983; pp. 225-366.
10. + (34), 339 (24), 321 (16), 265 (25), 256 (100), 242 (29), 221 (23), 209 (22), 165 (28), 97 (53).
11. + (23), 433 (24), 370 (69), 351 (25), 295 (32), 256 (32), 197 (100), 179 (51), 137 (72), 109 (53), 97 (99), 85 (78).
12. 1 our proposed structure of blazeispirol A was correct, but the description of 4′R was a typographical error. We have corrected the description to the S-configuration and, additionally, we have changed the nomenclature (2S,3S,3′R,4R,4aR,4′S,10bR) (3,4,4′,5′)-tetrahydro-3′-hydroxy-8-methoxy-(3,4′,4a, 5′,5′,7)-hexamethylspiro[2H-4,10b-ethanonaphtho[1,2-b]pyran-2, 2′(3′H)-furan] to (20S,22S,23R,24S)-14β,22:22,25-diepoxy-5-methoxy-des-A-ergosta-5,7,9,11- tetraen-23-ol for the structure of blazeispirol A in this paper.