Ceramide and Cerebrosides from the Octocoral Sarcophyton ehrenbergi

Abstract

Chemical investigation of the octocoral Sarcophyton ehrenbergi, collected at the Dongsha Islands, Taiwan, has led to the isolation of a known ceramide (1) and two new cerebrosides, sarcoehrenosides A (2) and B (4), along with three known cerebrosides (3, 5, and 6). The structures of the new compounds were established by spectroscopic and chemical methods. Sarcoehrenoside A (2) differs from previously known marine cerebrosides in that it possesses a rare alpha-glucose moiety. Compounds 1-6 were evaluated for antimicrobial activity against a small panel of bacteria and for anti-inflammatory activity using RAW 264.7 macrophages.

<i>Drymaria cordata</i> (Linn.) Willd (Caryophyllaceae): Ethnobotany, Pharmacology and Phytochemistry

“…Ceramide plays the role of a lipid second messenger in cell signaling transductions [29]- [31] such as cell growth, differentiation [32], proliferation [33], senescence [34] and necrosis [35]. In recent years several different types of biological activities have been found for these compounds, including antifungal, antitumor, antiviral, cytotoxicity and immunomodulatory properties, anti-inflammatory and anti-microbial activities [36] [37]. Stigmasterol possesses analgesic and anti-inflammatory activities [38].…”

Glycolipids from Marine Invertebrates

“…Among several metabolites isolated from the soft coral Lobophytum sp., collected in the Indian Ocean, a pure unprecedented glucocerebroside was identified bearing the same diunsaturated sphingoid base as in the latter reports, and a saturated 2-hydroxy FA (Muralidhar et al, 2005). In addition to the a-glucocerebroside, the ceramide of which was composed of a triunsaturated branched sphingoid base, the octocoral Sarcophyton ehrenbergi harvested off the coasts of Taiwan contains b-glucocerebroside molecular species including a new compound (Cheng et al, 2009). This a further example of a 9-methyl-4E,8E-sphingadiene-type cerebroside.…”

“…Among these, oreacerebrosides A-C are glucocerebrosides containing a 4E,8E,10E-trienoic sphingoid base. The same triunsaturated sphingosine type, found as a part of the ceramide of an a-glucocerebroside, from the octocoral Sarcophyton ehrenbergi, also composed the ceramide moiety of a new b-glucocerebroside (Cheng et al, 2009).…”

“…Another a-GSL with glucopyranose was isolated along with some b-glucopyranosylceramides during an investigation of the soft coral Sarcophyton ehrenbergi, collected near Taiwan (Cheng et al, 2009). The fatty acyl chain proved to be monounsaturated and 2-hydroxylated (2 0 R,3 0 E), while the long-chain base (LCB) was (4E,8E,10E) triunsaturated and 9-methyl-branched.…”

Marine soft corals as source of lead compounds for anti-inflammatories

“…Compounds 23 and 24 reduced iNOS protein expression (47.3% ± 7.1%, 46.5% ± 5.3%, respectively), but did not inhibit COX-2 protein expression (Figure 4) [28]. Gyrosanolide B (18) Gyrosanolide C (19) Simplexin E (15) …”