Sinuladiterpenes A–F, New Cembrane Diterpenes from Sinularia flexibilis

Abstract

Chromatographic investigation of the octocoral Sinularia flexibilis afforded six new cembrane diterpenes, sinuladiterpenes A-F (1-6, resp.), in addition to four known cembranolides, 11-episinulariolide acetate, 11-dehydrosinulariolide, 11-episinulariolide, and sinulariolide. Their structures were elucidated by spectroscopic analysis, especially 2D-NMR and HR-ESI-MS. Compound 2 exhibited significant in vitro cytotoxic activity against human colon adenocarcinoma (WiDr) cell line.

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.…”

Peroxy natural products

“…117 The same group provided two further structurally-related ε-lactones sinuladiterpenes A 207 and B 208 from the same species. 118 The Taiwanese soft coral S. manaarensis contained four cembrane-type diterpenoids, manaarenolides A 209 and B 210 and manaarenolides E 211 and F 212, which were discovered for the first time as the hydroperoxycembranolides possessing a δ-lactone ring. 123 The same source, S. crassocaule, provided three further cembranoid sarcocrassocolides F 227, G 228, and J 229, all of which inhibited LPS-induced upregulation of the pro-inammatory protein iNOS.…”

Cembrane Diterpenes Chemistry and Biological Properties

“…Chromatographic investigation of the octocoral Sinularia flexibilis afforded eight new diterpenes, sinuladiterpenes A-H (406-413), Compound 407 exhibited in vitro cytotoxic activity against human colon adenocarcinoma (WiDr) cell line with ED 50 8.37 μg/ml [69,121]. Moreover, a series of analogs were also isolated from Sinularia flexibilis, including sinulaflexiolides B-D, J, and K (414-418) [43], flexilarins D-J (419-425) [70], sinulariolone (426) [122], sandensolide monoacetate (427) and flexibolide (428) [123], and sinulariolide (429) [124].…”