Furanocembranoids from the Soft Corals Sinularia asterolobata and Litophyton arboreum

Abstract

The new cembranoid diterpene danielid (1) along with 3alpha-ethoxyfuranocembranoid 2, pukalide (3), 13alpha-acetoxypukalide (4), furanocembranoid 5, and furanosesquiterpene 6 have been isolated from the soft coral Sinularia asterolobata. The furanocembranoid diterpene 11beta,12beta-epoxypukalide (7) and the sesquiterpene (-)-bicyclogermacrene (8) have been obtained from the soft coral Litophyton arboreum. The structures were elucidated primarily by NMR spectroscopy. The furanocembranoids 2, 4, and 5 show good antiproliferative activities against the cell lines L-929 and K-562, and weak cytotoxic effects on HeLa cells.

Antibacterial and cytotoxic properties of isoprenoids from the red sea soft coral, <i>Lobophytum</i> sp

“…exp.) of 6 was found to be stereochemically similar with the structure of chalinasterol, a steroid isolated previously from a soft coral of Sinularia gibberosa and Lytophyton arboretum [28,29].…”

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.…”

Cembrane Diterpenes Chemistry and Biological Properties

“…Pukalide (472), isolated from the soft coral Sinularia abrupt, is a diterpenoid with a cembrane skeleton, bearing butenolide, epoxide, isopropenyl, and an unprecedented , -disubstituted furan--carboxylate function [141]. Thirteen highly oxygenated cembranolides, which are structurally similar to pukalide, were isolated including 13-acetoxypukalide (473), pukalide aldehyde (474) [138], 11b,12b-epoxypukalide (475), and unnamed furanocembranoid (476) [142], acerosolide (477) [143], sethukarailin (478), sethukarailide (479) [144], danielid (480), 3 -ethoxyfuranocembranoid (481) [145], unnamed furanocembranoid (482) [146], leptodiol(483), acetate of leptodiol(484), 8-epiLopholide (485) [147]. Three furanocembranolides, (Z)-deoxypukalide (486), (E)-deoxypukalide (487), and isopukalide (488) were isolated from Leptogorgia spp.…”