Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Bioactive Cembranoids from the Coral Sarcophyton trocheliophorum of Ximao Island.

ABSTRACT: Eight new cembranoids (sarcophytembranoids A-H, 1-8) and 10 known terpenoids (9-18) were obtained from the soft coral Sarcophyton trocheliophorum of Ximao Island. Notably, 11, 15, and 16 were obtained from a natural source for the first time. The structures of the new isolates were elucidated by extensive spectroscopic analysis, optical rotatory dispersion, and X-ray diffraction experiments. Although the isolated compounds did not show significant activity against the tested tumor cell lines, compounds 3, 7, 8, and 10-15 exhibited anti-inflammatory activities at 10 μM, and compounds 17 and 18 showed moderate protein tyrosine phosphatase 1B inhibition activities with the minimum inhibitory concentrations of 22.19 and 11.26 μM, respectively.

SUBMITTER: Zeng ZR

PROVIDER: S-EPMC9670263 | biostudies-literature | 2022 Nov

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Bioactive Cembranoids from the Coral Sarcophyton trocheliophorum of Ximao Island.

Zeng Zi-Rong ZR Chen Jing J Wang Hong H Zhang Hai-Yan HY Li Jia J Xu Baofu B Guo Yue-Wei YW

ACS omega 20221102 45

Eight new cembranoids (sarcophytembranoids A-H, 1-8) and 10 known terpenoids (9-18) were obtained from the soft coral Sarcophyton trocheliophorum of Ximao Island. Notably, 11, 15, and 16 were obtained from a natural source for the first time. The structures of the new isolates were elucidated by extensive spectroscopic analysis, optical rotatory dispersion, and X-ray diffraction experiments. Although the isolated compounds did not show sign ...[more]

PMID: 36406568

Similar Datasets

New Bicyclic Cembranoids from the South China Sea Soft Coral Sarcophyton trocheliophorum.

Project description:Nine new bicyclic cembranoids, sarcophytrols M-U(1-9), were isolated from the South China Sea soft coral Sarcophyton trocheliophorum as minor components, along with one known related cembranoid 10. Their structures were elucidated by detailed spectroscopic analysis and chemical conversion. The chemical structures of these metabolites are characterized by the different patterns of the additional cyclization within the 14-member skeleton, which leading to the formation of furan, pyran, oxepane, and peroxyl rings, respectively. Among them, sarcophytrols R and S(6 and 7) share a rare decaryiol skeleton with an unusual C12/C15 cyclization. In addition, the absolute configurations of sarcophytrols M and T(1 and 8) were determined by the modified Mosher's method. The research of these new secondary metabolites provided a further understanding of the diversity of cyclized cembranoids from the title species.

| S-EPMC5399464 | biostudies-literature

Bioactive cembranoids from the dongsha atoll soft coral Sarcophyton crassocaule.

Project description:Seven new cembranoids, sarcocrassocolides F-L (1-7), have been isolated from a soft coral Sarcophyton crassocaule. Their structures were determined by extensive spectroscopic analysis. Most new compounds exhibited significant cytotoxic activity against a limited panel of cancer cell lines, and the structure-activity relationship was studied. Compounds 1-7 were found to display significant in vitro anti-inflammatory activity in LPS-stimulated RAW264.7 macrophage cells by inhibiting the expression of the iNOS protein. Compound 4 was also found to effectively reduce the level of COX-2 protein.

| S-EPMC3131557 | biostudies-literature

Bioactive hydroperoxyl cembranoids from the Red Sea soft coral Sarcophyton glaucum.

Project description:A chemical investigation of an ethyl acetate extract of the Red Sea soft coral Sarcophyton glaucum has led to the isolation of two peroxide diterpenes, 11(S) hydroperoxylsarcoph-12(20)-ene (1), and 12(S)-hydroperoxylsarcoph-10-ene (2), as well as 8-epi-sarcophinone (3). In addition to these three new compounds, two known structures were identified including: ent-sarcophine (4) and sarcophine (5). Structures were elucidated by spectroscopic analysis, with the relative configuration of 1 and 2 confirmed by X-ray diffraction. Isolated compounds were found to be inhibitors of cytochrome P₄₅₀ 1A activity as well as inducers of glutathione S-transferases (GST), quinone reductase (QR), and epoxide hydrolase (mEH) establishing chemo-preventive and tumor anti-initiating activity for these characterized metabolites.

| S-EPMC3280536 | biostudies-literature

Bioactive cembranoids from the South China Sea soft coral Sarcophyton elegans.

Project description:Four new cembranoids, sarcophelegans A-D (1-4) and six known analogues (5-10) were isolated from the South China Sea soft coral Sarcophyton elegans. Their structures were elucidated through detailed spectroscopic analysis, and the absolute conﬁguration of 1 was conﬁrmed by single-crystal X-ray diffraction. The antimigratory potential of compounds 1-10 were evaluated and compounds 2 and 6 were found to inhibit human breast tumor MDA-MB-231 cell migration at 10 μM.

| S-EPMC6331945 | biostudies-literature

Bioactive cembranoids, sarcocrassocolides P-R, from the Dongsha Atoll soft coral Sarcophyton crassocaule.

Project description:New cembranoids, sarcocrassocolides P-R (1-3) and four known compounds (4-7) were isolated from the soft coral Sarcophyton crassocaule. The structures of the metabolites were determined by extensive spectroscopic analysis. Compounds 3-5 and 7 were shown to exhibit cytotoxicity toward a limited panel of cancer cell lines and all compounds 1-7 displayed potent in vitro anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 macrophage cells by inhibiting the expression of inducible nitric oxide synthase (iNOS) protein. Compound 7 also showed significant activity in reducing the accumulation of cyclooxygenase-2 (COX-2) protein in the same macrophage cells.

| S-EPMC3944518 | biostudies-literature

Biscembranoids and Cembranoids from the Soft Coral Sarcophyton elegans.

Project description:Two novel biscembranoids, sarelengans A and B (1 and 2), five new cembranoids, sarelengans C-G (3-7), along with two known cembranoids (8 and 9) were isolated from the South China Sea soft coral Sarcophyton elegans. Their structures were determined by spectroscopic and chemical methods, and those of 1, 4, 5, and 6 were confirmed by single crystal X-ray diffraction. Compounds 1 and 2 represent the first example of biscembranoids featuring a trans-fused A/B-ring conjunction between the two cembranoid units. Their unique structures may shed light on an unusual biosynthetic pathway involving a cembranoid-∆⁸ rather than the normal cembranoid-∆¹ unit in the endo-Diels-Alder cycloaddition. Compounds 2 and 3 exhibited potential inhibitory effects on nitric oxide production in RAW 264.7 macrophages, with IC50 values being at 18.2 and 32.5 μM, respectively.

| S-EPMC5408232 | biostudies-literature

Three new cembranoids from the Taiwanese soft coral Sarcophyton ehrenbergi.

Project description:In order to search for new bioactive substances from marine organisms, we have investigated the acetone extracts of the soft coral Sarcophyton ehrenbergi collected at San-Hsian-Tai, Taitong County, Taiwan. Chromatographic fractionation of the extracts of the octocoral S. ehrenbergi led to the isolation of three new cembranoids, (+)-12-ethoxycarbonyl-11Z-sarcophine (1), ehrenbergol A and B (2 and 3). The structures of these isolated metabolites were elucidated through extensive spectroscopic analyses. Moreover, metabolites 1-3 were evaluated in vitro for their cytotoxicity towards selected cancer cell lines and antiviral activity against human cytomegalovirus (HCMV).

| S-EPMC3407922 | biostudies-literature

Anti-Inflammatory Cembranoids from a Formosa Soft Coral Sarcophyton cherbonnieri.

Project description:The present investigation on chemical constituents of the soft coral Sarcophyton cherbonnieri resulted in the isolation of seven new cembranoids, cherbonolides F-L (1-7). The chemical structures of 1-7 were determined by spectroscopic methods, including infrared, one- and two-dimensional (1D and 2D) NMR (COSY, HSQC, HMBC, and NOESY), MS experiments, and a chemical reduction of hydroperoxide by triphenylphosphine. The anti-inflammatory activities of 1-7 against neutrophil proinflammatory responses were evaluated by measuring their inhibitory ability toward N-formyl-methionyl-leucyl-phenylalanine/cytochalasin B (fMLF/CB)-induced superoxide anion generation and elastase release in primary human neutrophils. The results showed that all isolates exhibited moderate activities, while cherbonolide G (2) and cherbonolide H (3) displayed a more active effect than others on the inhibition of elastase release (48.2% ± 6.2%) and superoxide anion generation (44.5% ± 4.6%) at 30 µM, respectively.

| S-EPMC7699541 | biostudies-literature

Sarcophyolides B-E, new cembranoids from the soft coral Sarcophyton elegans.

Project description:Four new cembrane-type diterpenoids, sarcophyolides B-E (1-4), along with 11 known analogues were isolated from the soft coral Sarcophyton elegans. The structures of new compounds 1-4 were established on the basis of spectroscopic analysis and chemical conversion. The new cembranoids sarcophyolides B (1) and lobocrasol were found to exhibit potent inhibition against A2780 human ovarian tumor cells.

| S-EPMC3801120 | biostudies-literature

New Cembranoids and a Biscembranoid Peroxide from the Soft Coral Sarcophyton cherbonnieri.

Project description:Six new cembranoids, cherbonolides A-E (1⁻5) and bischerbolide peroxide (6), along with one known cembranoid, isosarcophine (7), were isolated from the Formosan soft coral Sarcophyton cherbonnieri. The structures of these compounds were elucidated by detailed spectroscopic analysis and chemical methods. Compound 6 was discovered to be the first example of a molecular skeleton formed from two cembranoids connected by a peroxide group. Compounds 1⁻7 were shown to have the ability of inhibiting the production of superoxide anions and elastase release in N-formyl-methionyl-leucyl-phenyl-alanine/cytochalasin B (fMLF/CB)-induced human neutrophils.

| S-EPMC6117711 | biostudies-literature