ABSTRACT
Three new polyoxygenated steroids, michosterols A-C (1-3), and four known compounds (4-7) were isolated from the ethyl acetate (EtOAc) extract of the soft coral Lobophytum michaelae, collected off the coast of Taitung. The structures of the new compounds were elucidated on the basis of spectroscopic analyses and comparison of the nuclear magnetic resonance (NMR) data with related steroids. The cytotoxicity of compounds 1-3 against the proliferation of a limited panel of cancer cell lines was assayed. Compound 1 was found to display moderate cytotoxicity against adenocarcinomic human alveolar basal epithelial (A549) cancer cells. It also exhibited potent anti-inflammatory activity by suppressing superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-stimulated human neutrophils. Furthermore, 3 could effectively inhibit elastase release, as well.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/chemistry , Steroids/chemistry , A549 Cells , Animals , Anti-Inflammatory Agents/pharmacology , Cell Line, Tumor , Cell Proliferation/drug effects , Cytochalasin B/pharmacology , Cytotoxins/chemistry , Cytotoxins/pharmacology , Humans , Magnetic Resonance Spectroscopy/methods , N-Formylmethionine Leucyl-Phenylalanine/pharmacology , Neutrophils/drug effects , Neutrophils/metabolism , Pancreatic Elastase/metabolism , Steroids/pharmacology , Superoxides/metabolismABSTRACT
A continuing chemical investigation of the ethyl acetate (EtOAc) extract of a reef soft coral Sinularia brassica, which was cultured in a tank, afforded four new steroids with methyl ester groups, sinubrasones A-D (1-4) for the first time. In particular, 1 possesses a ß-D-xylopyranose. The structures of the new compounds were elucidated on the basis of spectroscopic analyses. The cytotoxicities of compounds 1-4 against the proliferation of a limited panel of cancer cell lines were assayed. The anti-inflammatory activities of these new compounds 1-4 were also evaluated by measuring their ability to suppress superoxide anion generation and elastase release in N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLP/CB)-induced human neutrophils. Compounds 2 and 3 were shown to exhibit significant cytotoxicity, and compounds 3 and 4 were also found to display attracting anti-inflammatory activities.
Subject(s)
Anthozoa/chemistry , Steroids , Acetates/chemistry , Animals , Anti-Inflammatory Agents, Non-Steroidal/pharmacology , Humans , N-Formylmethionine Leucyl-Phenylalanine/chemistry , Neutrophils/drug effects , Pancreatic Elastase/drug effects , Steroids/chemistry , Steroids/isolation & purification , Steroids/pharmacology , Superoxides/metabolism , Xylose/analogs & derivatives , Xylose/chemistryABSTRACT
Continuing study of the ethyl acetate (EtOAc) extract of the cultured soft coral Sinularia brassica afforded five new withanolides, sinubrasolides H-L (1-5). The structures of the new compounds were elucidated on the basis of spectroscopic analysis. The cytotoxicities of new compounds 1-5 and a known compound sinubrasolide A (6) against the proliferation of a limited panel of cancer cell lines were assayed. The anti-inflammatory activities of compounds 1-6 were evaluated by measuring their ability to suppress N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLP/CB)-induced superoxide anion generation and elastase release in human neutrophils.
Subject(s)
Anthozoa/chemistry , Anti-Inflammatory Agents/chemistry , Anti-Inflammatory Agents/pharmacology , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Withanolides/chemistry , Withanolides/pharmacology , Animals , Anti-Inflammatory Agents/isolation & purification , Antineoplastic Agents/isolation & purification , Cell Line, Tumor , Cytochalasin B/immunology , Humans , Models, Molecular , Neoplasms/drug therapy , Neutrophils/drug effects , Pancreatic Elastase/immunology , Superoxides/immunology , Withanolides/isolation & purificationABSTRACT
New steroids, klyflaccisteroids K-M (1-3), were isolated from a soft coral Klyxum flaccidum. Their structures were elucidated on the basis of extensive spectroscopic analysis. Klyflaccisteroid K (1) is the unique 9,11-secosteroid with a 5,8-epidioxy-9-ene functional group. Klyflaccisteroid L (2) has an unusual 11-norsteroid skeleton and is the first example of 11-oxasteroid isolated from natural sources. Cytotoxicity assay showed that 1 and 3 possessed moderate to weak cytotoxicity against these cancer cells. Compound 1 was also found to display significant anti-inflammatory activity of suppressing superoxide anion generation (O2-) and elastase release, and compound 3 was found to show notable anti-inflammatory activity toward inhibition of elasstase release, too.
