(22E)-Ergosta-6,22-diene-3β5α8α-triol: A new polyhydroxysterol isolated from Lentinus edodes (Shiitake)

Natural Product Research

Volumn 23, Issue 3, 2009, Pages 293-300

  Rivera, A ^a   Benavides, O L ^b   Rios Motta, J ^a  

^a UNIVERSIDAD NACIONAL DE COLOMBIA   (Colombia)

^b UNIVERSIDAD DE NARIÑO   (Colombia)

Author keywords

GIAO; Lentinus edodes; Mushrooms; Polyhydroxysterols; Shiitake

Indexed keywords

22 ERGOSTA 4,67,8(14),22 TETRAEN 3 ONE; 22 ERGOSTA 5,7,9(11),22 TETRAEN 3BETA OL; 22 ERGOSTA 6,22 DIENE 3BETA,5ALPHA,8ALPHA TRIOL; 22 ERGOSTA 6,8,22 TRIEN 3BETA OL; 22 ERGOSTA 7,9(11),22 TRIEN 3BETA OL; 22 NORERGOSTA 5,7,9,22 TETRAEN 3BETA OL; 3BETA,5ALPHA DIHYDROXY 22 ERGOSTA 7,22 DIEN 6 ONE; ALCOHOL; ERGOSTEROL; ERGOSTEROL PEROXIDE; LENTINUS EDODES EXTRACT; PLANT EXTRACT; PLANT MEDICINAL PRODUCT; STEROL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG IDENTIFICATION; DRUG ISOLATION; DRUG STRUCTURE; LENTINUS EDODES; MUSHROOM; PROTON NUCLEAR MAGNETIC RESONANCE;

CHOLESTENONES; ERGOSTEROL; HYDROXYSTEROIDS; MOLECULAR STRUCTURE; PHYTOSTEROLS; SHIITAKE MUSHROOMS;

BASIDIOMYCOTA; LENTINULA EDODES;

EID: 62249172216     PISSN: 14786419     EISSN: 14786427     Source Type: Journal    
DOI: 10.1080/14786410802038671     Document Type: Article

References (24)

1. Bai, S., Fan, B. and Yan, F. (2005) Sterol constituents of Doellingeria scaber. Chemical Abstract, 144, p. 484623.
2. Bonzom, PMA, Nicolaou, A., Zloh, M., Baldeo, W. and Gibbons, WA (1999) NMR lipid profile of Agaricus bisporus. Phytochemistry, 50:8, pp. 1311-1321.
3. Cheesemann, JR, Trucks, GW, Keith, TA and Frisch, MJ (1996) A comparison of models for calculating nuclear magnetic resonance shielding tensors. The Journal of Chemical Physics, 104:14, pp. 5497-5509.
4. Dalton, F. and Meakins, GD (1961) Proof of rear approach in the oxidation of ergosterol. Journal of the Chemical Society, pp. 1880-1884.
5. Ditchfield, R., Hehre, WJ and Pople, JA (1971) Self-consistent molecular-orbital methods. IX. An extended gaussian-type basis for molecular-orbital studies of organic molecules. The Journal of Chemical Physics, 54:2, pp. 724-728.
6. Finley, JW and Stephens, PJ (1995) Density functional theory calculations of molecular structures and harmonic vibrational frequencies using hybrid density functionals. Journal of Molecular Structure (Theochem), 357:3, pp. 225-235.
7. Frisch, MJ, Trucks, GW, Robb, MA, Schlegel, HB, Scuseria, GE Cheeseman, JR et al. (1998) Gaussian 98, Revision A.9, Gaussian, Pittsburgh, PA
8. Gunatilaka, AAL, Gopichand, Y., Schmitz, FJ and Djerassi, C. (1981) Minor and trace sterols in marine invertebrates. 26. Isolation and structure elucidation of nine new 5α,8α-epidoxy sterols from four marine organisms. The Journal of Organic Chemistry, 46:19, pp. 3860-3866.
9. Han, Y-F, Pan, J., Gao, K. and Jia, ZJ (2005) Sesquiterpenes, nortriterpenes and other constituents from Ligularia tongolensis. Chemical and Pharmaceutical Bulletin, 53:10, pp. 1338-1341.
10. Hata, K., Sugawara, F., Ohisa, N., Takahashi, S. and Hori, K. (2002) Stimulative effects of (22E,24R)-ergosta-7,22-diene-3β,5α,6β-triol from fruiting bodies of Tricholoma auratum, on a mouse osteoblastic cell line, MC3T3-E1. Biological and Pharmaceutical Bulletin, 25:8, pp. 1040-1044.
11. Lafont, R. (1997) Ecdysteroids and related molecules in animals and plants. Archives of Insect Biochemistry Physiology, 35, pp. 3-20.
12. McLafferty, FW and Stauffer, DB (1994) Registry of mass spectral data, New York, Wiley
13. Ohnuma, N., Amemiya, K., Kakuda, R., Yaoita, Y., Machida, K. and Kikuchi, M. (2000) Sterol constituents from two edible mushrooms, Lentinula edodes and Tricholoma matsutake. Chemistry and Pharmaceutical Bulletin, 48:5, pp. 749-751.
14. Wan, H., Sun, R., Wu, D. and Guo, B. (1999) Three sterols from Gyroporus castaneus. Chemical Abstract, 133, p. 190274.
15. Wojtas, M., Bienkowski, T., Tateyama, S., Sagami, H., Chojnacki, T. Danikiewicz, W. et al. (2004) Polyisoprenoid alcohols from the mushroom Lentinus edodes. Chemistry and Physics of Lipids, 130:2, pp. 109-115.
16. Wolinski, K., Hilton, KJF and Pulay, P. (1981) Efficient implementation of the gauge-independent atomic orbital method for NMR chemical shift calculations. Journal of the American Chemical Society, 112:23, pp. 8251-8260.
17. Yang, D., Tang, X., Zhang, Y. and Xu, S. (2000) Chemical constituents of Gyroporus castaneus. Chemical Abstract, 134, p. 14976.
18. Yang, L., Wang, M., Zhao, Y. and Tu, Y. (2004) Studies on chemical constituents in rhizome of Matteuccia struthiopteris. Chemical Abstract, 144, p. 484591.
19. Yaoita, Y., Amemiya, K., Ohnuma, H., Furumura, K., Masaki, A. Matsuki, T. et al. (1998) Sterol constituents from five edible mushrooms. Chemistry and Pharmaceutical Bulletin, 46:6, pp. 944-950.
20. Yaoita, Y., Endo, M., Tani, Y., Machida, K., Amemiya, K. Furumura, K. et al. (1999) Sterol constituents from seven mushrooms. Chemistry and Pharmaceutical Bulletin, 47:6, pp. 847-851.
21. Yaoita, Y., Matsuki, K., Idima, T., Nakano, S., Kakuda, R. Machida, K. et al. (2001) New sterols and triterpenoids from four edible mushrooms. Chemistry and Pharmaceutical Bulletin, 49:5, pp. 589-594.
22. Yue, J-M, Chen, S-N, Lin, Z-W and Sun, H-D (2001) Sterols from the fungus Lactarium volenus. Phytochemistry, 56:8, pp. 801-806.
23. Zhu, Y., Zhu, QX and Jia, ZJ (2000) Epoxide sesquiterpenes and steroids from Cremanthodium discoideum. Australian Journal of Chemistry, 53:10, pp. 831-834.
24. Zilliken, FW (1980) Ergostadientriols and compositions containing them., U.S. Pat. No. 4,157,984, USA. Z-L Limited Partnership, Janesville