24-Methylenecholest-5-ene-7-oxo-3β,19-diacetate 5 was synthesized starting from stigmasterol via twelve step reactions in 4.1% overall yield. It can be served as a key intermediate for the synthesis of 24-methylenech...24-Methylenecholest-5-ene-7-oxo-3β,19-diacetate 5 was synthesized starting from stigmasterol via twelve step reactions in 4.1% overall yield. It can be served as a key intermediate for the synthesis of 24-methylenecholest-5-ene-3β,7β,19-triol 1, a naturally occuring polyhydroxylated sterol with potential biological activity.展开更多
The blood-brain barrier permeability of 20（S） and 20（R）-protopanaxatriol epimers and dammar-20（22）E,24-diene- 313,6α,12β-triol were investigated using the MDCK-pHaMDR cell monolayer model. The bidirectional pe...The blood-brain barrier permeability of 20（S） and 20（R）-protopanaxatriol epimers and dammar-20（22）E,24-diene- 313,6α,12β-triol were investigated using the MDCK-pHaMDR cell monolayer model. The bidirectional permeability tests were carried out, and the apparent permeability coefficients （Papp） were calculated. The two protopanaxatriol epimers showed good permeability with Papp values of-10^-5 cm/s, whereas dammar-20（22）E,24-diene-3β,6α, 12β-triol showed poor permeability with Papp of 〈1 × 10^-7 cm/s. The three compounds showed differences in intracellular accumulations due to their different structures. Inhibition of P-gp with verapamil showed that the transport mechanisms in MDCK-pHaMDR cell monolayer for compounds 1 and 2 epimers were not only simple passive diffusion but also involving an effiux way mediated by P-gp. These findings provided new basis for the further study of compounds 1 and 2 acting on the brain.展开更多
Twelve steroids, including eight ergostane-type sterols and four mono-glucosides of ergostane-type sterols, were isolated from the ethyl acetate soluble fraction of the fungus Pleurotus ostreatus ( Jacq. : Fr.) Kummer...Twelve steroids, including eight ergostane-type sterols and four mono-glucosides of ergostane-type sterols, were isolated from the ethyl acetate soluble fraction of the fungus Pleurotus ostreatus ( Jacq. : Fr.) Kummer. A new compound 3-O-beta-D-glucopyranosyl-22E, 24R-ergosta-7, 22-diene-5alpha, 6beta, 9alpha-triol, was structurally elucidated by spectroscopic and chemical methods. The eleven known compounds were 22E, 24R-ergosta-7, 22-diene-3beta, 5alpha, 6beta, 9alpha-tetraol; 3-O-beta-D-glucopyranosyl-22E, 24R-ergosta-7, 22-diene-5alpha, 6beta-diol; 22E, 24R-ergosta-7, 22-diene-3beta, 5alpha, 6beta-triol; 22E, 24R-ergosta-5, 7, 22-trien-3beta-ol 3-O-beta-D-glucopyranoside; ergosterol; 22E, 24R-ergosta-7, 22-dien-3beta-ol 3-O-beta-D-glucopyranoside; 22E, 24R-ergosta-7, 22-diene-3beta-ol; 22E, 24R-ergosta-4, 6, 8, 22-tetraen-3-one; 22E, 24R-ergosta-7, 22-diene-3beta, 5alpha, 6alpha-triol; ergosterol peroxide; 22E, 24R-ergosta-7, 22-diene-3beta, 5alpha-diol-6-one.展开更多
Two new sterol have been isolated from the South China Sea marine organism. Compound 1 was isolated from the sponge Polymastia sobustia and compound 2 was obtained from the soft coral Sinularia inexplicata. Their stru...Two new sterol have been isolated from the South China Sea marine organism. Compound 1 was isolated from the sponge Polymastia sobustia and compound 2 was obtained from the soft coral Sinularia inexplicata. Their structures were established as 3 beta-hydroxy-stigmast-5en-7-one and 24-methylene cholestan -3 beta, 6 beta, 9 alpha, 19-tetrol by variety of spectral analysis such as IR, EIMS, 1DNMR, H-1-H-1 COSY, HMQC, HMBC, NOESY.展开更多
基金We are grateful to the National Natural Science Foundation of China (No. 29932030)the NationalHigh Technology Development Project (No. 2001AA624030)the Natural Science Foundationof Guangdong Province (No. 04300569) for financial support for this work.
文摘24-Methylenecholest-5-ene-7-oxo-3β,19-diacetate 5 was synthesized starting from stigmasterol via twelve step reactions in 4.1% overall yield. It can be served as a key intermediate for the synthesis of 24-methylenecholest-5-ene-3β,7β,19-triol 1, a naturally occuring polyhydroxylated sterol with potential biological activity.
基金The National New Drug R&D Program(Grant No.2011BAI07B082009ZX09301-010)of China
文摘The blood-brain barrier permeability of 20（S） and 20（R）-protopanaxatriol epimers and dammar-20（22）E,24-diene- 313,6α,12β-triol were investigated using the MDCK-pHaMDR cell monolayer model. The bidirectional permeability tests were carried out, and the apparent permeability coefficients （Papp） were calculated. The two protopanaxatriol epimers showed good permeability with Papp values of-10^-5 cm/s, whereas dammar-20（22）E,24-diene-3β,6α, 12β-triol showed poor permeability with Papp of 〈1 × 10^-7 cm/s. The three compounds showed differences in intracellular accumulations due to their different structures. Inhibition of P-gp with verapamil showed that the transport mechanisms in MDCK-pHaMDR cell monolayer for compounds 1 and 2 epimers were not only simple passive diffusion but also involving an effiux way mediated by P-gp. These findings provided new basis for the further study of compounds 1 and 2 acting on the brain.
文摘Two new sterol have been isolated from the South China Sea marine organism. Compound 1 was isolated from the sponge Polymastia sobustia and compound 2 was obtained from the soft coral Sinularia inexplicata. Their structures were established as 3 beta-hydroxy-stigmast-5en-7-one and 24-methylene cholestan -3 beta, 6 beta, 9 alpha, 19-tetrol by variety of spectral analysis such as IR, EIMS, 1DNMR, H-1-H-1 COSY, HMQC, HMBC, NOESY.
