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2 results on '"24-isopropenylcholesterol"'

1. C-24 Stereochemistry of Marine Sterols: (22E)-24-(Isopropenyl)-22-dehydrocholesterol and 24-Isopropenylcholesterol

Author

Yoshinori Fujimoto, Carmenza Duque, Noriyuki Hara, Gladys Jeanette Carderon, and Shizue Echigo

Subjects
Magnetic Resonance Spectroscopy, Stereochemistry, Chemistry, Molecular Conformation, Stereoisomerism, Colombian Caribbean sponge, General Chemistry, General Medicine, Reference Standards, Sensitivity and Specificity, Nmr data, Porifera, Sterols, Dehydrocholesterols, Species Specificity, 24-isopropenyl-22-dehydrocholesterol, Drug Discovery, Topsentia ophiraphidites, Animals, Organic chemistry, 24-isopropenylcholesterol
Abstract

The C-24 configuration of (22E,24xi)-24-isopropenyl-22-dehydrocholesterol (1), which was recently isolated from the Colombian Caribbean sponge, Topsentia ophiraphidites, was investigated. Synthesis of the stereodefined (24R)- and (24S)-(22E)-24-isopropenyl-22-dehydrocholesterols (1a, 1b) followed by (1)H- and (13)C-NMR data comparison of these sterols established the (24R)-configuration of 1. In addition, (24R)- and (24S)-24-isopropenylcholesterols (2a and 2b) were also synthesized and their NMR data are provided. The C-24 configurations of the samples of 24-isopropenylcholesterol reported previously are discussed.

Published
2006

2. New 24-Isopropylcholesterol and 24-Isopropenylcholesterol Sulfate from the Marine Sponge Epipolasis Species

Author

Shigenobu Arihara, Seiichi Ito, Akemi Umeyama, and Kanako Adachi

Subjects
Magnetic Resonance Spectroscopy, Optical Rotation, Spectrophotometry, Infrared, Stereochemistry, medicine.medical_treatment, Pharmaceutical Science, Polasterol B sulfate, Gas Chromatography-Mass Spectrometry, Analytical Chemistry, Steroid, chemistry.chemical_compound, Epipolasis, Japan, Drug Discovery, medicine, Animals, Sulfate, Pharmacology, biology, Chemistry, Organic Chemistry, biology.organism_classification, Porifera, Sponge, Cholesterol, Complementary and alternative medicine, Chromatography, Gel, Molecular Medicine, Spectrophotometry, Ultraviolet, Steroids, Triol, Enone, 24-isopropenylcholesterol
Abstract

Two novel steroids, polasterol A (1) and polasterol B sulfate (2), along with two known compounds, 22(E),24-isopropylcholesta-5, 22-dien-3 beta-ol (3) and halistanol sulfate (4), have been isolated from the Japanese marine sponge Epipolasis sp. The structures of 1 and 2 were determined as 3 beta-hydroxy-24-isopropylcholesta-5, 22(E)-dien-7-one and 24xi-isopropenylcholesta-22(Z), 28(29)-diene-2 beta,3 alpha,6 alpha-triyl trisodium sulfate on the basis of spectroscopic investigations and a chemical conversion.

Published
2000

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