Bioactive Cembranoids from the Soft Coral Sinularia crassa

Abstract

Eight new cembranoids, crassarines A–H (1–8) were isolated from the Formosan soft coral Sinularia crassa. Compounds 1–3 represent the rare cembranoids with a 1,12-oxa-bridged tetrahydrofuran ring, while 4 and 5 are the firstly discovered 1,11-oxa-bridged tetrahydropyranocembranoids. The absolute configuration of 6 was determined using the Mosher’s method. Compounds 6 and 8 were found to significantly inhibit the expression of both pro-inflammatory iNOS and COX-2 proteins at 10 μM, respectively, while compounds 4–8 were found to be non-cytotoxic toward the selected human liver cancer cells.

Diterpenoids from the Soft Coral <i>Sinularia maxima</i> and Their Inhibitory Effects on Lipopolysaccharide-Stimulated Production of Pro-inflammatory Cytokines in Bone Marrow-Derived Dendritic Cells

“…The methanol extract of the soft coral S. maxima yielded twelve diterpenes (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12), including nine new compounds, termed sinumaximols A−I (1−3, 5-9, 12), and three known compounds: sethukarailin (4), 13) (1S,2E,4S,6E,8S,11R)-2,6,12(20)-cembratriene-4,8,11-triol (10), 14) and isomandapamate (11). 15) Compound 1 was obtained as a colorless oil.…”

“…In continuation of our interest in evaluating the biological potential of natural compounds and searching for novel anti-inflammatory agents from natural products, we evaluated the effects of all isolated compounds (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12) in the inflammatory response by bone marrow derived dendritic cells (BMDCs). We first used a colorimetric In our experiments, DCs were incubated in 48-well plates at a density of 2×10 5 cells/mL, and then treated for 1 h with the compounds at concentrations ranging from 0 to 50 µM, then stimulated with LPS (10 ng/mL; Fig.…”

“…2) Sinularia is one of the most widely distributed soft corals in the order Alcyonacea; these corals are prolific and constitute a dominant portion of the biomass in the tropical reef environment. 3) Previous investigations have indicated that diterpenes, a main constituent of the genus Sinularia, exhibit various biological activities, such as anti-inflammatory, [4][5][6][7][8] antiviral, 6) and cytotoxic [9][10][11][12] effects.…”

Antiosteoporotic and antioxidant activities of diterpenoids from the Vietnamese soft corals Sinularia maxima and Lobophytum crassum

“…The genera of Sinularia and Lobophytum (Phylum: Coelenterata, Family: Alcyoniidae, Class: Anthozoa, Order: Alcyonacea) are two of the most widely distributed of their genera, constituting a dominant portion of the biomass in tropical reef environments (Anjaneyulu and Rao, 1997;Lakshmi and Kumar, 2009). Previous studies have indicated that diterpenes, a main constituent of the genus Sinularia and Lobophytum (most are derived from the 14-membered cembrane nucleus), exhibit various biological activities, such as anti-inflammatory (Chao et al, 2011;Cheng et al, 2010;Lu et al, 2010;Su and Wen, 2011), antiviral (Cheng et al, 2010), and cytotoxic (Grote et al, 2008;Kamel et al, 2007;Lo et al, 2009;Su et al, 2009) effects.…”

A New Cubitane Diterpenoid from the Soft Coral Sinularia crassa

“…Moreover, Formosan soft corals of the genus Sinularia have been shown to be rich sources of structurally unique and bioactive natural products [2,3,4,5,6]. In the investigation of secondary metabolites in marine invertebrates, the diterpenoid cubitane was first reported in 1984 as being obtained from the Caribbean gorgonian octocoral Eunicea calyculata [7].…”