Muriceanol, a 24(28)‐Epoxide Sterol Link in the Carbon Flux Toward Side‐Chain Dealkylation of Sterols

European Journal of Organic Chemistry - Tập 2006 Số 3 - Trang 582-585 - 2006
Manuel Lorenzo1,2, Mercedes Cueto2, Luis D’Croz3,4, Juan L. Maté5, Aurelio San-Martı́n6, José Dárias2
1Departamento de Química, Facultad de Ciencias, Universidad de Magallanes, Centro de Estudios del Cuaternario, Avenida Bulnes 01855, Casilla 113-D, Punta Arenas, Chile
2Instituto de Productos Naturales y Agrobiología del CSIC, Avda. Astrofísico F. Sánchez, 3, Apdo. 195, 38206 La Laguna, Tenerife, Spain
3Departamento de Biología Marina y Limnología, Universidad de Panama, Panama
4Smithsonian Tropical Research Institute (STRI), P. O. Box 0843‐03092, Balboa, Panama
5Smithsonian Tropical Research Institute (STRI), P. O. Box 0843-03092, Balboa, Panama
6Departamento de Química, Facultad de Ciencias, Universidad de Chile, Santiago de Chile, Chile

Tóm tắt

AbstractSide‐chain‐oxidized C‐28‐sterol 1 and one new pregnane metabolite 2 were isolated from eastern Pacific Muricea spp. The C‐24(28)‐epoxide functionality is a key intermediate in the C‐24‐dealkylation mechanism of the conversion of phytosterol to cholesterol by phytophagous insects. Certain marine invertebrates share this dealkylation pathway; however, such a key epoxide feature has not yet been found in a naturally occurring sterol from marine invertebrates. The unusual oxidation pattern of the side chain of 1 encourages speculation about its biogenesis and converts this non‐zooxanthellate gorgonia into an interesting candidate organism for biosynthetic studies on C‐24‐dealkylation of phytosterols in octocorals. The (22S)‐22‐hydroxy group, after 24‐dealkylation of 1, may be an advantageous functionalization in the side‐chain cleavage to C‐21‐pregnane steroids in Muricea spp. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

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Tài liệu tham khảo

Svoboda J. A., 1985, Comprehensive Insect Physiology Biochemistry and Pharmacology

10.1046/j.1444-2906.2001.00354.x

10.1016/0014-5793(77)80614-5

10.1021/ar00012a003

10.1016/0039-128X(77)90029-0

10.1039/P19790002064

10.1016/S0031-9422(00)89083-4

PCModel version 7.0 Serena Software Bloomington IN.

10.1021/bi00547a003

10.1021/np980366d

10.1111/j.1432-1033.1978.tb20931.x

10.1074/jbc.M303359200

10.1021/bk-1992-0497.ch010

10.1021/cr00021a010

10.1039/np9910800465

10.1002/(SICI)1521-3765(19980210)4:2<193::AID-CHEM193>3.0.CO;2-Q

10.1016/j.jsbmb.2004.12.040

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European Journal of Organic Chemistry

Tập 2006 Số 3

582-585

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