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Biscembranoids are the distinctive tetraterpenoids owing a 14/6/14 membered tricyclic scaffold that have been mainly discovered in the soft corals, especially the genera Sarcophyton, Lobophytum and Sinularia. Recent findings have demonstrated the great anti-inflammatory potential of biscembranoid analogues in human neutrophils, motivating more chemical and biological explorations targeting these marine-derived natural products. In the current study, the chemical diversity of biscembranoids derived from the cultured-type Sarcophyton trocheliophorum von Marenzeller was illustrated through MS/MS molecular networking (MN) profiling approach. Based on the MN patterns, the prioritization of unknown biscembranoid derivatives was putatively analyzed. As a result, the biscembrane targeting isolation afforded two new metabolites, sarcotrochelides A (1) and B (2), along with six known analogues (3–8). Their structures and relative configurations were determined by spectroscopic methods. In vitro neutrophil inflammatory inhibition was further investigated for all isolates based on reduced superoxide anion (O2•−) generation detections. Compounds 5–8 showed significant dose-dependently inhibitory effects, suggesting the cruciality of 6,7-dihydrooxepin-2(5H)-one moiety and saturated γ-lactone ring in their reactive oxygen species (ROS)-dependent anti-inflammatory properties.

The ethyl acetate and dichloromethane-soluble fractions, from a soft coral Sarcophyton trocheliophorum total methanolic extract, exhibited significant anti-leishmanial and cytotoxic activities. These active fractions yielded a new cembranoid diterpene (1), two known analogues [sarcotrocheliol (2) and sarcophine (3)], and two sterols [(24S)-24-methylcholesterol (4) and gorgosterol (5)]. The structure of the new diterpene (1) was determined via a detailed analysis of its spectroscopic data. Compounds 3 and 5 demonstrated noticeable cytotoxicity on A549 (IC50 17.4 ± 1.9 µg/ml) and HepG2 (IC50 17.7 ± 1.5 µg/ml) cell lines, respectively. None of the isolates 1‒5 showed detectable anti-leishmanial activity (IC50 >100 µg/ml).

Two new cembranoids, ximaosarcophytols A (1) and B (2), together with three related known ones (3-5), were isolated from the soft coral Sarcophyton trocheliophorum collected off the Ximao Island, Hainan Province, China. Their structures including the absolute configurations were elucidated by extensive spectroscopic analysis, TDDFT/ECD (time-dependent density functional theory/electronic circular dichroism) calculations and comparison with the reported data.

Minor metabolic components, six new cembranoids sarcophytrols G – L (1 – 6) along with two known related analogues 7 and 8, were isolated from the South China Sea soft coral Sarcophyton trocheliophorum. Their structures were elucidated by extensive spectroscopic analyses (1D- and 2D-NMR, and ESI-MS.) as well as comparison with literature data. As part of our ongoing research project for discovering bioactive substances from Chinese marine invertebrates, compounds 1 – 8 were tested for their inhibitory activity against protein tyrosine phosphatase 1B (PTP1B), a key target for the treatment of Type-II diabetes and obesity. However, none of them exhibited potent PTP1B inhibitory activities. This article is protected by copyright. All rights reserved.

This review covers structural diversity and biological activities of terpenes from soft corals of the genus of Sarcophyton, reported from 1995 to July, 2011. During this period, besides undefined species, 16 species of the genus Sarcophyton, from different geographical areas, had been chemically examined. Two hundred and five terpenes had been isolated from this genus, including eleven sesquiterpenes, 165 diterpenes, 29 biscembranoids, some of which had novel skeletons. They exhibited various biological features, such as antifeedant, anti-inflammatory, antiviral, and antifouling activities.

The genetic connectivity of soft coral is influenced by current and distance between islands. The complexity of islands and geographical region in Indonesia might influence the distribution of soft corals. The information of genetic connectivity can be used to design marine protected areas and to avoid destruction and possible extinction. The objective of the present study was to analyze genetic connectivity of one species of soft coral, Sarcophyton trocheliophorum, in three populations spanning Java, Nusa Tenggara, and Sulawesi’s waters, and to describe its implication for marine protected area. The mitochondrial protein-coding gene (750 bp of ND2) was used to analyze genetic population structure and genetic connectivity. Genetic connectivity was found in all populations with Fst value of 0.227 to 0.558, indicating populations had the close genetic relationship. The local and Indonesian currents were expected to distribute the larva to islands as a stepping stone, they moved slowly to spread them self far away. Tanakeke island (Sulawesi population) might be a center connectivity of S. trocheliophorum populations. This island connected with islands in west and east Indonesia, therefore that area need to protect

Three new capnosane type diterpenoids, sarcophytrols A–C (1–3), were isolated from the South China Sea soft coral Sarcophyton trocheliophorum. Among them, 1 and 2 share a dodecahydrocyclopenta[6,7]cycloundeca[1,2-b]oxirene ring system with an unusual 1Z-configuration, whereas 1 and 3 encompass a peculiar isopropyl alcohol moiety. Their structures were elucidated by extensive spectroscopic analysis and the absolute configuration of 1 was determined by an X-ray diffraction analysis with Cu Kα radiation on a single crystal.

Nineteen new cembranoids named trocheliophols A-S including the potent antibacterial compounds (I) and (II) are isolated from the soft coral of Sarcophyton trocheliophorum.

Two new sarsolenane diterpenes, dihydrosarsolenone (2), methyl dihydrosarsolenoneate (3), and two new capnosane diterpenes, sarsolilides B (5) and C (6), were isolated together with the known analogue, sarsolilide A (4), from the Hainan soft coral Sarcophyton trocheliophorum Marenzeller. Their structures were elucidated by detailed spectroscopic analysis and by comparison with reported data, leading to a structure revision of sarsolenone (1). The absolute configurations of 2 and 5 were determined by TDDFT ECD calculations, and they could be used as ECD reference compounds in the determination of the absolute configuration of their related derivatives. Compounds 4 and 5 exhibited inhibitory activity in vitro against protein tyrosine phosphatases 1B (PTP1B), representing the first report of PTP1B inhibitory activity for capnosane diterpenes.

The two new steroids zahramycins A (I) and B (II) are isolated from the coral Sarcophyton trocheliophorum.

A new cembranoidal diterpene, trocheliolide B (1), was isolated from the octocoral Sarcophyton trocheliophorum. The structure of 1 was elucidated on the basis of spectroscopic methods.

An investigation of metabolites from the soft coral Sarcophyton trocheliophorum collected at North East Reef, Orpheus Island, has yielded three simple cembranoid diterpenes , namely (7R,8R,14S,1E,3E,11E)-7,8-epoxycembra-1,3,11-trien-14-ol (1), (7R,8R,14S,1E,3E,11E)-14-acetoxy-7,8-epoxycembra-1,3,11-triene (2) and (7R,14S,1E,3E,8E,11E)-cembra-1,3,8,11-tetraene-7,14-diol(3), together with the known dihydrofuran sarcophytoxide (4). The diterpenes (2) and (3) were previously reported as synthetic derivatives of sarcophytol A, but this is the first report of their natural occurrence. The three mildly cytotoxic diterpenes (1)-(3) are structural modifications of the antitumour promotor sarcophytol A (5). Structures were established by high-resolution n.m.r. spectroscopy and interconversion. The absolute stereochemistries of the metabolites were determined by use of the Mosher n.m.r. method, and the stereochemistry at C14 was shown to be the same as that of sarcophytol A in each case. These results are in agreement with the published absolute stereochemistries of the metabolites determined by the Horeau method. Full n.m.r. assignments for (11S,12S,14S,1E,3E,7E)-11,12-epoxycembra-1,3,7-trien-14-ol (6) and (11S,12S,14S,1E,3E,7E)-14-acetoxy-11,12-epoxycembra-1,3,7-triene (7) are given.

A novel rearranged sesquiterpenoid, trocheliophorin (1) has been isolated from the soft coral Sarcophyton trocheliophorum besides the known compounds, sarcophytin, methyl arachidonate, and two polyhydroxy steroids (24S)-24-methylcholestane-3beta,5alpha,6beta,25-tetrol-25-monoacetate and (24S)-24-methylcholestane-3beta,5alpha,6beta,25-tetrol. The structure of the new sesquiterpenoid was elucidated by a study of its spectral data.

A new hydroperoxycembranoidal diterpene, trocheliolide A (1), was isolated from the octocoral Sarcophyton trocheliophorum. The structure of 1 was elucidated on the basis of spectroscopic and mass spectrometric methods.

The first enantioselective total synthesis of (−)-13-hydroxyneocembrene ( 1 ), a naturally occurring cembranoids isolated from soft coral Sarcophyton trocheliophorum, was achieved via a general approach by employing intramolecular McMurry coupling as a key step from (S)-(+)-carvone.