A Novel Diterpenolide from the Soft Coral Sarcophyton solidun

Zhang, Min; Kanghou, Long; Huang, Sijia; Shi, K.; Mak, Thomas C. W.

doi:10.1021/np50089a018

Cited by 17 publications

(14 citation statements)

References 1 publication

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“…14,30 Among them, sarsolilides A−C represent the only three capnosanes containing an α,β-unsaturated ε-lactone moiety. 14,28 Bissubvilides A and B represent a novel heterodimeric skeleton formed by the coupling of a capnosane and a cembrane.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Bissubvilides A and B, Cembrane–Capnosane Heterodimers from the Soft CoralSarcophyton subviride

Sun

Jiao

et al. 2016

J. Nat. Prod.

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Two new biscembranoid-like compounds, bissubvilides A (1) and B (2), were isolated together with sarsolilide B (3), the proposed biogenetic precursor to 1, from the soft coral Sarcophyton subviride. The structures and absolute configurations were solved by spectroscopic analysis and TDDFT/ECD and DFT/NMR calculations. The bissubvilides represent a novel biscembranoid-like skeleton presumed to derive from a cembrane-type diene and a capnosane-type dienophile via a Diels-Alder reaction. These two molecules exerted no cytotoxicity against MG-63 or A549 tumor cells or HuH7 tumor stem cells.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Bissubvilides A and B, Cembrane–Capnosane Heterodimers from the Soft CoralSarcophyton subviride

Sun

Jiao

et al. 2016

J. Nat. Prod.

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“…In addition to the isolated new compounds ( 1 – 6 ), ten known cembrenoids ( 7 – 16 ) ( Figure 6 ) were also obtained from S. stellatum , including sarsolilide ( 7 ) [ 34 , 35 ], a hydroperoxide ( 8 ) obtained by autoxidation of dihydrofuranocembrenoid [ 36 ] (+)-sarcophine ( 9 ) [ 2 , 7 ], laevigatol B ( 10 ) [ 37 ], sarcophytonin E ( 11 ) [ 38 ], sarcophytonin C ( 12 ) [ 39 ], 17-hydroxysarcophytoxide ( 13 ) [ 40 , 41 ], 7β-acetoxy-8α-hydroxydeepoxysarcophine ( 14 ) [ 42 ], 7β,8α-dihydroxydeepoxy- ent -sarcophine ( 15 ) [ 43 ], and crassumol A ( 16 ) [ 38 ]. Among these cembranoids, compounds 8 and 14 were isolated from a natural source for the first time.…”

Section: Resultsmentioning

confidence: 99%

Isolation and Structure Elucidation of Cembranoids from a Dongsha Atoll Soft Coral Sarcophyton stellatum

et al. 2018

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Six new polyoxygenated cembrane-based diterpenoids, stellatumolides A–C (1–3), stellatumonins A and B (4 and 5), and stellatumonone (6), were isolated together with ten known related compounds (7–16) from the ethyl acetate (EtOAc) extract of soft coral Sarcophyton stellatum. The structures of the new compounds were established by extensive spectroscopic analyses, including 1D and 2D nuclear magnetic resonance (NMR) spectroscopy and data comparison with related structures. Compounds 8 and 14 were isolated from a natural source for the first time. The isolated metabolites were shown to be not cytotoxic against a limited panel of cancer cells. Compound 9 showed anti-inflammatory activity by reducing the expression of proinflammatory cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) proteins in lipopolysaccharide (LPS)-stimulated mouse leukaemic monocyte macrophage (RAW 264.7) cells.

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“…4 By comparison of their observed and reported NMR data, the known compounds ( Fig. 1) were identified as sarsolinone (2) Liang et al, 2014), methyl dihydrosarsolenoneate (3) (Liang et al, 2014), sarsolilide B (4) (Liang et al, 2014), sarsolilide A (5) (Zhang et al, 1992;Liang et al, 2014), emblide (6) (Toth et al, 1980), (4Z,8S,9R,12E,14E)-9-hydroxy-1-isopropyl-8,12-dimethyloxabicyclo[9.3.2]-hexadeca-4,12,14-trien-18-one (7) (Bowden et al, 1982;Gross et al, 2004), and ketoemblide (8) (Uchio et al, 1983).…”

Section: Structure Elucidationmentioning

confidence: 97%