New Cembranoid Diterpenes from Sarcophyton trocheliophorum

Bioactive Cembranoids from the Coral Sarcophyton trocheliophorum of Ximao Island

“…As the isolated compounds share a typical cembranoid skeleton, a plausible biosynthetic pathway was proposed (Figure S67). In brief, the cyclization of GGPP formed three different cembranoid scaffolds resulting from three deprotonations, forming double bonds: Δ 1 , Δ 1 (14) , and Δ 1 (15) . The isolated natural products would then be readily generated following a series of simple enzymatic reactions, for example, oxidation, acetylation, and methylation.…”

“…Its ultraviolet (UV) (λ max 286 and 204 nm) and infrared (IR) (ν max 1710 cm −1 ) spectra showed typical absorptions for a conjugated polyene pattern. The NMR spectra (Figures S2 and S3) of 34 To determine the stereochemistry of the four double bonds, namely, Δ 4 , Δ 8 , Δ 12 , and Δ 1 (14) , in indicated that the four double bonds in 1 are all E-configured.…”

“…Various functions, including epoxide, ester, furan, lactone, and so forth, were frequently found among these compounds. − Cembranoids are biologically synthesized from the C20 precursor geranylgeranyl diphosphate (GGPP). , The biological activities of cembranoids have made them fascinating candidates for drug development and chemical synthesis . Over the past decades, nearly 1500 cembranoids have been discovered from various organisms, especially soft corals. , Corals of the genus Sarcophyton are renowned for the production of a wide variety of bioactive terpenoids, especially cembranoids. − More than 90 cembranoids have been isolated from Sarcophyton trocheliophorum in the past decades. ,, In the course of our ongoing program toward the isolation of biologically active second metabolites from Chinese marine invertebrates, several geographically distinct soft coral S. trocheliophorum were chemically investigated, affording 33 new cembranoids from S.…”

“… 11 − 20 More than 90 cembranoids have been isolated from Sarcophyton trocheliophorum in the past decades. 13 , 14 , 16 In the course of our ongoing program toward the isolation of biologically active second metabolites from Chinese marine invertebrates, several geographically distinct soft coral S. trocheliophorum were chemically investigated, affording 33 new cembranoids from S. trocheliophorum collected off the Yalong Bay 18 , 21 − 25 and Ximao Island. 26 Among the isolates, sarcophytonolide N, sarcrassin E, 4 Z ,12 Z ,14 E -sarcophytolide, sartrolide H, cembrene-C, and ketoemblide showed potential to moderate inhibitory activities against the human protein tyrosine phosphatase 1B (PTP1B) enzyme, 18 , 22 which plays a major role in the dephosphorylation of the insulin receptor and the insulin receptor substrate (IRS-1) protein, representing a promising drug target for the treatment of type-II diabetes and obesity.…”

16-Hydroxycembra-1,3,7,11-tetraene, a new Cembrane Diterpene from Malaysian Soft Coral Genus Sarcophyton

“…Therefore, compound 1 was reported as (3E,7E,11E)-16-hydroxycembra-1,3,7,11-tetraene. Compounds 2-4 were identified as 15-hydroxycembra-1,3,7,11-tetraene (2), sarcophine (3) and sarcophytoxide (4) by comparing their spectroscopic data with those reported in the literature [6][7][8].…”