Several new cembranoid diterpenes from three soft corals of the red sea

Structural and Stereochemical Studies of α-Methylene-γ-lactone-Bearing Cembrane Diterpenoids from a South China Sea Soft Coral Lobophytum crassum

“…Four new R-methylene-γ-lactone-bearing cembranoids, 20-acetylsinularolide B (6), presinularolide B (7), 3-dehydroxylpresinularolide B (8), and 3-dehydroxyl-20-acetylpresinularolide B (9), together with five known analogues, sinularolides B-E (1-4) and 20-acetylsinularolide C (5), were isolated from a South China Sea soft coral Lobophytum crassum. Their structures and relative stereochemistry were established by a combination of detailed spectroscopic data analysis and chemical correlations.…”

Cembrane Diterpenes Chemistry and Biological Properties

“…An investigation of the Caribbean octocoral Eunicea tourniforti collected along the southwest coast of Barbados afforded four new cembrane diterpenes (36)(37)(38)(39) [19]. Alcyonols A-C (40)(41)(42) were reported by Zvia Kinamoni and his coworkers from Alcyonium utinumii [20], while gibberosenes B-G (43)(44)(45)(46)(47)(48) were identified from the Formosan soft coral, Sinularia gibberosa [21]. Two new cembrane-type diterpenoids, 14-0-acetylsarcophytol B(49) and 14-0-acetylsarcophytol J (50), were isolated from the Okinawan soft coral Sinularia sp.…”

“…Two unprecedented cembranoids, methyl tetrahydrosarcoate (18) and methyl tetrahydroisosarcoate (19), have been isolated [12]. Chemical investigation of the octocoral Sarcophyton ehrenbergi led to the isolation of three new simple cembranoids, ehrenberoxides A-C (20)(21)(22) [13]. Moreover, sarcophytol T (23), was isolated from the same species by Konig and his coworker [14].…”

“…Four new cembranoid diterpenes, 11,12-epoxy-1(E),3(E),7(E)-cembratrien-15-ol (117), 3,4:11,12-diepoxy-15-methoxy-1(E),7(E)-cembradiene (118), 1(E),3(E),7(E),11(E)-cembratetraene-14,15-diol (119), and 3,14-epoxy-1(E),7(E),11(E)-cembratriene-4,15-diol (120), have been isolated from the soft coral Sinularia gibberosa [42]. A series of analogs were isolated from the soft coral Sinularia flexibilis (121) [43], Sinularia gibberosa (122) [44], Sarcophyton decaryi (123,124) [45,46], Nephthea brassica (125) [47], Lobopbytum pauciflorum (126)(127) [20,48], Sarcophyton mililatensis (130) [49]. Three novel cembrane diterpenoids, decaryiols B-D (130-132), characterized by a bicyclic skeleton of the decaryiol-type, have been isolated from the Indonesian soft coral Lobophytum sp., meanwhile, a analogue, namely decaryiol (133), have been isolated from the soft coral Sarcophyton decaryi [50].…”

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“…They were identified by detailed spectral data and chemical studies (mainly ozonolysis). 16 Investigation of the terpenoid content of the Red Sea soft corals Xenia macrospiculata, Xenia obscuronata, and Xenia lilielae resulted in the isolation of eight diterpenes. Two of them belonged to the xeniolides, xenialactol-D (32) and xeniolide-E (33), while the other six belonged to the xeniaphylanes (prenylated caryophyllanes), namely 4,14-diepoxyxeniaphyllene (34), 4,5-epoxyxeniaphyllan-14,15-diol (35), 4,14 diepoxyxeniaphyllenol-A (36), xeniaphyllenol-B (37), xeniaphyllenol-C (38), and xeniaphyllantriol (39).…”