Bioactive Steroids with Methyl Ester Group in the Side Chain from a Reef Soft Coral Sinularia brassica Cultured in a Tank

Abstract

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 β-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.

Metabolites from the Paracel Islands Soft Coral Sinularia cf. molesta

“…Since 1975 [1,2], over 50 species of the genus Sinularia have been chemically investigated, showing a wide range of structure diversities in diterpenes (especially cembrane diterpenes) [3,4], sesquiterpenes [5,6], polyhydroxylated steroids [7,8], polyamines [9,10], cyclopentenones [6,8,11,12], and butenolides [11,12]. Many of these metabolites exhibited a wide range of biological activities, including cytotoxic [13,14], anti-inflammatory [15], antimicrobial [16], antifouling [17], and antifeedant activities [18].…”

The Holo-Transcriptome of the Zoantharian Protopalythoa variabilis (Cnidaria: Anthozoa): A Plentiful Source of Enzymes for Potential Application in Green Chemistry, Industrial and Pharmaceutical Biotechnology

“…Sponges, cnidarians, tunicates and other marine invertebrates can harbor a great diversity of microbial symbionts [ 17 , 18 , 19 ]. Despite the microbial origin of many compounds derived from the holobiont assemblage, the own coral tissues comprise unique resources of diverse chemicals with distinct pharmacological activities, such as anti-inflammatory and anti-proliferative activities [ 20 , 21 , 22 ]. Therefore, prospecting biopharmaceuticals from unusual marine species, as sources of unique enzymes, focusing particularly on improved and novel biocatalysts, is also warranted.…”

Marine Pharmacology in 2016–2017: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…SF-5976 [192]; a novel halogenated 5α-iodozoanthenamine (171) isolated from the colorful Taiwanese zoanthid Zoanthus kuroshio [193]; two novel steroids klyflaccisteroid J and K (172, 173) isolated from the Taiwanese soft coral Klyxum flaccidum [194,195]; a known lobane diterpenoid (174) isolated from a Taiwanese soft coral Lobophytum varium [196]; two new bioactive steroids petasitosterones B and C (175, 176) isolated from the Taiwanese soft coral Umbellulifera petasites [197]; two new sterols (177,178) [198], and novel 9,11-secosterols pinnigorgiol A (179) [199], pinnigorgiol E (180) [200], pinnisterol A (181) [201] and pinnisterol H (182) [202] isolated from the Taiwanese gorgonian coral Pinnigorgia sp. ; a new pyrrole oligoglycoside plancipyrroside B (183) isolated from an extract of the Vietnamese starfish Acanthaster planci [203]; a novel steroidal glycoside protolinckioside A (184) isolated from an Arabian sea starfish Protoreaster lincki [204]; a known terpenoid sarcophytonolide O (185) isolated from the Chinese soft coral Lobophytum crassum [205]; two novel norcembranoids sinulerectols A and B (186, 187) isolated from South China Sea soft coral Sinularia erecta [206]; a known terpenoid sinubrasolide A (188) and the steroid sinubrasone D (189) isolated from the Taiwanese "cultivation pool" soft coral Sinularia brassica [207,208]; and the novel diterpenes uprolides N, O and P (190)(191)(192) isolated from the Panamanian octocoral Eunicea succinea [209].…”

“…As shown in Table 2 and Figure 2, in 2016-2017, the preclinical nervous system pharmacology of marine compounds (206)(207)(208)(209)(210)(211)(212)(213)(214)(215)(216)(217)(218)(219)(220)(221)(222)(223)(224)(225) reported several mechanisms of action involving potassium (K + ) channels, nicotinic acetylcholine, calcium (Ca 2+ ) and serotonin receptors, as well as in vivo models of antinociception and neuroprotection.…”

“…Goda and colleagues conducted detailed studies that determined that the marine xanthophyll carotenoid astaxanthin (207) reversed the toxicity of the calcium-dependent Maxi-K (BK) K + channel antagonist food mycotoxin penitrem A (PA) "by restoring normal levels of the targeted neurotransmitters" both in Schwann cells CRL-2765 in vitro and in both the nematode Caenorhabditis elegans and rat in vivo models thus concluding astaxanthin might be useful "for in vivo prevention of PA-induced brain toxicity [224]. Mendez and colleagues investigated the marine guanidine alkaloid crambrescidin 816 (208) produced by the Mediterranean sponge Crambe crambe and known to block voltage dependent L-type Ca 2+ channels, and observed that cytotoxicity was concomitant with an increase of cytosolic Ca 2+ in a primary culture of cortical neurons by a mechanism that "was mediated by both NMDA and AMPA glutamate receptor subtypes" activation [225]. Jiang and colleagues discovered a novel O-conotoxin GeXXVIIA linear peptide (209) from the venom of the South China sea cone snail Conus generalis that potently inhibited the human α9α10 nicotinic acetylcholine receptor (nACh), a nAChR receptor expressed in both the nervous system, as well as in other non-neuronal cells, by a non-competitive and voltage-independent mechanism.…”