Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Sarcoeleganolides C-G, Five New Cembranes from the South China Sea Soft Coral Sarcophyton elegans.

ABSTRACT: Five new cembranes, named sarcoeleganolides C-G (1-5), along with three known analogs (6-8) were isolated from soft coral Sarcophyton elegans collected from the Yagong Island, South China Sea. Their structures and absolute configurations were determined by extensive spectroscopic analysis, QM-NMR, and TDDFT-ECD calculations. In addition, compound 3 exhibited better anti-inflammation activity compared to the indomethacin as a positive control in zebrafish at 20 μM.

SUBMITTER: Wang C

PROVIDER: S-EPMC9506240 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Sarcoeleganolides C-G, Five New Cembranes from the South China Sea Soft Coral Sarcophyton elegans.

Wang Cili C Zhang Jiarui J Shi Xing X Li Kai K Li Fengling F Tang Xuli X Li Guoqiang G Li Pinglin P

Marine drugs 20220910 9

Five new cembranes, named sarcoeleganolides C-G (1-5), along with three known analogs (6-8) were isolated from soft coral Sarcophyton elegans collected from the Yagong Island, South China Sea. Their structures and absolute configurations were determined by extensive spectroscopic analysis, QM-NMR, and TDDFT-ECD calculations. In addition, compound 3 exhibited better anti-inflammation activity compared to the indomethacin as a positive control in zebrafish ...[more]

PMID: 36135763

Similar Datasets

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

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

New Cembrane-Type Diterpenoids from the South China Sea Soft Coral Sarcophyton ehrenbergi.

Project description:Chemical investigation on the soft coral Sarcophyton ehrenbergi collected from the Xisha Islands of the South China Sea have led to the isolation of eight cembranoids including five new ones, sarcophytonoxides A-E (1-5). The structures of new cembranoids (1-5) were determined by spectroscopic analysis and comparison of the NMR data with those of related analogues. The cytotoxicities of compounds 1-8 against human ovarian cancer cell line A2780 were also evaluated.

| S-EPMC6273003 | biostudies-literature

Bioactive polyoxygenated steroids from the South China sea soft coral, Sarcophyton sp.

Project description:Seven new polyoxygenated steroids (1-7) were isolated together with seven known analogues (8-14) from the South China Sea soft coral, Sarcophyton sp. The structures of the new compounds were identified on the basis of extensive spectroscopic analysis and comparison with reported data. All the steroids are characterized with 3β,5α,6β-hydroxy moiety, displaying carbon skeletons of cholestane, ergostane, gorgostane and 23,24-dimethyl cholestane. In the in vitro bioassay, metabolites exhibited different levels of antimicrobial activity against bacterial species Escherichia coli and Bacillus megaterium, and fungal species Microbotryum violaceum and Septoria tritici. No inhibition was detected towards microalga Chlorella fusca. Preliminary structure-activity analysis suggests that the 11α-acetoxy group may increase both antibacterial and antifungal activities. The terminal-double bond and the cyclopropane moiety at the side chain may also contribute to the bioactivity.

| S-EPMC3705369 | biostudies-literature

Cembrane-type diterpenoids from the South China Sea soft coral Sarcophyton mililatensis.

Project description:Eight cembrane-type diterpenoids, namely, (+)-(6R)-6-hydroxyisosarcophytoxide (1), (+)-(6R)-6-acetoxyisosarcophytoxide (2), (+)-17-hydroxyisosarcophytoxide (3), sarcomililatins A-D (4-7), and sarcomililatol (8), were isolated from the soft coral Sarcophyton mililatensis collected from Weizhou Island, Guangxi Autonomous Region, together with 2 known related analogues, (+)-isosarcophytoxide (9) and (+)-isosarcophine (10). The structures of these compounds were elucidated by a combination of detailed spectroscopic analyses, chemical methods, and comparison with reported data. The absolute configuration of compound 1 was established by the modified Mosher׳s method, while the absolute configurations of compounds 4 and 5 were assigned by electronic circular dichroism (ECD) spectroscopy and that of compound 8 was established by time-dependent density functional theory electronic circular dichroism (TD-DFT ECD) calculation. In in vitro bioassays, compound 9 displayed significant cytotoxicity against the human cancer cell lines human promyelocytic leukemia cells (HL-60) and human lung adenocarcinoma cells (A-549) with IC50 values of 0.78±0.21 and 1.26±0.80 μmol/L, respectively. Compounds 4 and 9 also showed moderate inhibitory effects on the TNFα-induced Nuclear factor kappa B (NF-κB, a therapeutical target in cancer) activation, showing IC50 values of 35.23±12.42 and 22.52±4.44 μmol/L, respectively.

| S-EPMC6251813 | biostudies-literature

Structurally Diverse Diterpenes from the South China Sea Soft Coral Sarcophyton trocheliophorum.

Project description:The present investigation of the South China Sea soft coral Sarcophyton trocheliophorum resulted in the discovery of six new polyoxygenated diterpenes, namely sartrocheliols A-E (1, 3, 5-8) along with four known ones, 2, 4, 9, and 10. Based on extensive spectroscopic data analysis, sartrocheliol A (1) was identified as an uncommon capnosane diterpene, while sartrocheliols B-E (3, 5-8) were established as cembrane diterpenes. They displayed diverse structural features not only at the distinctly different carbon frameworks but also at the various types of heterocycles, including the epoxide, γ-lactone, furan, and pyran rings. Moreover, their absolute configurations were determined by a combination of quantum mechanical-nuclear magnetic resonance (QM-NMR) approach, modified Mosher's method, and X-ray diffraction analysis. In the anti-tumor bioassay, compound 4 exhibited moderate cytotoxic activities against A549, H1975, MDA-MB-231, and H1299 cells with the IC50 values ranging from 26.3 to 47.9 μM.

| S-EPMC9960596 | biostudies-literature

Uncommon Capnosane Diterpenes with Neuroprotective Potential from South China Sea Soft Coral Sarcophyton boettgeri.

Project description:The first investigation of the South China Sea soft coral Sarcophyton boettgeri afforded five new capnosane diterpenes, sarboettgerins A-E (1-5), together with one known related compound, pavidolide D (6). Their structures, including absolute configurations, were elucidated by the extensive spectroscopic analysis, 13C NMR calculations, and X-ray diffraction. Among them, new compounds 1-5 were featured by the rarely encountered Z-geometry double bond Δ1 within the 5/11-fused bicyclic capnosane carbon framework. Plausible biogenetic relationships of all isolates were proposed, and they might give an insight into future biomimetic synthesis of these novel compounds. In an in vitro bioassay, compound 5 displayed potent anti-neuroinflammatory activity against LPS-induced NO release in BV-2 microglial cells, which might be developed as a new type of potential neuroprotective agent in future.

| S-EPMC9604702 | biostudies-literature

Cembranoid Diterpenes from South China Sea Soft Coral Sarcophyton crassocaule.

Project description:Cembranoid diterpenes are characteristic compounds of soft corals with diverse structures and significant activities, making them an important source of drug lead compounds. In this paper, five new cembranoid diterpenes, meijicrassolins A-E (1-5), were isolated from the soft coral Sarcophyton crassocaule, along with five previously reported compounds (6-10). The structures and absolute configuration for new compounds 1-5 were assigned by extensive spectroscopic analysis, single-crystal X-ray crystallography, quantum mechanical nuclear magnetic resonance (QM-NMR), and time-dependent density functional theory/electronic circular dichroism (TDDFT/ECD) calculations. Compounds 3, 4, and 9 showed moderate inhibition of nitric oxide generation in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. Overall, our research results have enriched the library of secondary metabolites from soft corals, providing more molecular entities for subsequent research and development of related compounds.

| S-EPMC11676429 | 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

Polyhydroxylated steroids from the South China Sea soft coral Sarcophyton sp. and their cytotoxic and antiviral activities.

Project description:Chemical investigation on the soft coral Sarcophyton sp. collected from the South China Sea yielded three new polyhydroxylated steroids, compounds (1-3), together with seven known ones (4-10). Their structures were established by extensive spectroscopic methods and comparison of their data with those of the related known compounds. All the isolates possessed the 3β,5α,6β-trihydroxylated steroidal nucleus. The cytotoxicities against selected HL-60, HeLa and K562 tumor cell lines and anti-H1N1 (Influenza A virus (IAV)) activities for the isolates were evaluated. Compounds 2, 3 and 5-8 exhibited potent activities against K562 cell lines with IC₅₀ values ranging from 6.4 to 10.3 μM. Compounds 1, 6-8 potently inhibited the growth of HL-60 tumor cell lines, and 6 also showed cytotoxicity towards HeLa cell lines. In addition, preliminary structure-activity relationships for the isolates are discussed. The OAc group at C-11 is proposed to be an important pharmacophore for their cytotoxicities in the 3β,5α,6β-triol steroids. Compounds 4 and 9 exhibited significant anti-H1N1 IAV activity with IC₅₀ values of 19.6 and 36.7 μg/mL, respectively.

| S-EPMC3877887 | biostudies-literature