Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Oxygenated ylangene-derived sesquiterpenoids from the soft coral Lemnalia philippinensis.

ABSTRACT: Chemical examination of a Taiwanese soft coral Lemnalia philippinensis led to the isolation of three oxygenated ylangene-derived sesquiterpenoids 1-3, including two new metabolites, philippinlins A and B (1 and 2). The structures of these compounds were elucidated on the basis of detailed spectroscopic data. Compound 1 was shown to exhibit cytotoxicity against HepG2, MDA-MB231 and A549 cancer cell lines.

SUBMITTER: Xio YJ

PROVIDER: S-EPMC3826132 | biostudies-literature | 2013 Oct

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Oxygenated ylangene-derived sesquiterpenoids from the soft coral Lemnalia philippinensis.

Xio Yun-Jie YJ Su Jui-Hsin JH Chen Bo-Wei BW Tseng Yen-Ju YJ Wu Yang-Chang YC Sheu Jyh-Horng JH

Marine drugs 20130930 10

Chemical examination of a Taiwanese soft coral Lemnalia philippinensis led to the isolation of three oxygenated ylangene-derived sesquiterpenoids 1-3, including two new metabolites, philippinlins A and B (1 and 2). The structures of these compounds were elucidated on the basis of detailed spectroscopic data. Compound 1 was shown to exhibit cytotoxicity against HepG2, MDA-MB231 and A549 cancer cell lines. ...[more]

PMID: 24084789

Similar Datasets

Oxygenated eremophilane- and neolemnane-derived sesquiterpenoids from the soft coral Lemnalia philippinensis.

Project description:Five sesquiterpene-related metabolites (1-5), including two new eremophilane-type compounds, philippinlins C and D (1 and 2) and a 4,5-seconeolemnane philippinlin E (3), were isolated from the organic extract of a Taiwanese soft coral Lemnalia philippinensis. The structures of the new metabolites were determined on the basis of extensive spectroscopic analysis and by comparison of NMR data with those of related metabolites. Compound 3 was suggested to be derived from the neolemnane skeleton.

| S-EPMC4145327 | biostudies-other

Oxygenated Cembranoids from the Soft Coral Sinularia flexibilis.

Project description:Chemical examination of the Taiwanese soft coral Sinularia flexibilis led to the isolation of five cembrane-based diterpenoids 1-5, including two new metabolites, 11-acetylsinuflexolide (1) and 11-acetyldihydrosinuflexolide (2). The structures of the new metabolites were determined based on extensive spectroscopic analysis, particularly mass spectrometry and 2D NMR (1H-1H COSY, HMQC, HMBC, and NOESY) spectroscopy. Metabolites 1, 3 and 4 exhibited moderate to weak cytotoxicity to human tumor cell lines, HeLa, HEp-2, MCF-7 and MDA-MB-231.

| S-EPMC3588100 | biostudies-literature

nardosinane-type sesquiterpenoids from the formosan soft coral Paralemnalia thyrsoides.

Project description:Five new nardosinane-type sesquiterpenoids, paralemnolins Q-U (1-5), along with three known compounds (6-8), were isolated from the Formosan soft coral Paralemnalia thyrsoides. The structures of new metabolites were elucidated on the basis of extensive spectroscopic methods, and the absolute configuration of 1 was determined by the application of Mosher's method on 1. Among these metabolites, 1 and 3 are rarely found nardosinane-type sesquiterpenoids, possessing novel polycyclic structures. Compounds 1, 3, 6 and 7 were found to possess neuroprotective activity.

| S-EPMC3225934 | biostudies-literature

New 19-oxygenated steroids from the soft coral Nephthea chabrolii.

Project description:In order to search for novel bioactive substances from marine organisms, we investigated the acetone extract of the soft coral Nephthea chabrolii collected at San-Hsian-Tai, Taitong County, Taiwan. From this extract three new 19-oxygenated steroids, nebrosteroids N-P (1-3) were isolated. The structures of these compounds were elucidated by extensive spectroscopic analyses.

| S-EPMC3397439 | biostudies-literature

Parathyrsoidins A-D, four new sesquiterpenoids from the soft coral Paralemnalia thyrsoides.

Project description:Four new nardosinane-type sesquiterpenoids, parathyrsoidins A-D (1-4) were isolated from the soft coral Paralemnalia thyrsoides. The structures of parathyrsoidins A-D (1-4) were determined by extensive spectral analysis and their cytotoxicity against selected cancer cell lines as well as antiviral activity against human cytomegalovirus (HCMV) were evaluated in vitro.

| S-EPMC3736437 | biostudies-literature

Chondrosterins A-E, triquinane-type sesquiterpenoids from soft coral-associated fungus Chondrostereum sp.

Project description:The marine fungus Chondrostereum sp. was collected from a soft coral Sarcophyton tortuosum from the South China Sea. This fungus was cultured in potato dextrose broth medium and the culture broth was extracted with EtOAc. Five new triquinane-type sesquiterpenoids, chondrosterins A-E (1-5), and the known sesquiterpenoid hirsutanol C (6), were isolated. The structures were elucidated mainly on the basis of NMR, MS, and X-ray single-crystal diffraction data. Chondrosterin A (1) showed significant cytotoxic activities against cancer lines A549, CNE2, and LoVo with IC(50) values of 2.45, 4.95, and 5.47 ?M, respectively.

| S-EPMC3347020 | biostudies-literature

Crannenols A-D, Sesquiterpenoids from the Irish Deep-Sea Soft Coral <i>Acanella arbuscula</i>.

Project description:Four undescribed sesquiterpenoids, crannenols A-D (1-4), have been isolated from CHCl2 and MeOH extracts of the deep-sea bamboo coral Acanella arbuscula. The corals were collected from a submarine canyon on the edge of Ireland's Porcupine Bank via a remotely operated vehicle. The structure elucidation of these (Z,E)-α-farnesene derivatives was achieved using a combination of 1D and 2D NMR, electron impact (1, 2), and electrospray ionization (3, 4) mass spectrometry.

| S-EPMC9623587 | biostudies-literature

Harnessing enzyme plasticity for the synthesis of oxygenated sesquiterpenoids.

Project description:8-Methoxy-?-humulene, (E)-8-methoxy-?-farnesene, 12-methoxy-?-sesquiphellandrene and 12-methoxyzingiberene can be synthesised in amorphadiene synthase-catalysed reactions from 8- and 12-methoxyfarnesyl diphosphates due to the highly plastic yet tightly controlled carbocationic chemistry of this sesquiterpene cyclase.

| S-EPMC6774066 | biostudies-literature

Isolation of Sesquiterpenoids and Steroids from the Soft Coral Sinularia brassica and Determination of Their Absolute Configuration.

Project description:Two undescribed rearranged cadinane-type sesquiterpenoids (1-2), named sinulaketol A-B, together with one new chlorinated steroid (3), one new gorgosterol (4), one known sesquiterpene (5), one known dibromoditerpene (6) and two known polyhydroxylated steroids (7-8) were isolated from the soft coral Sinularia brassica. The structures of these compounds were established by extensive spectroscopic analysis, including HRESIMS, 1D, and 2D NMR spectroscopy. Their absolute configurations were also determined by the ECD calculations and DP4+ probability analysis. Antileishmanial activity of compounds 1-8 was evaluated in vitro against the amastigote forms of Leishmania donovani, in which compounds 3, 6, and 7 inhibited the growth of L. donovani by 58.7, 74.3, 54.7%, respectively, at a concentration of 50 μM. Antimicrobial effect of the isolated compounds were also evaluated against Candida albicans, Staphylococcus aureus, and Escherichia coli. Compound 6, a brominated diterpene, exhibited antimicrobial effect against S. aureus.

| S-EPMC8466225 | biostudies-literature

Clavukoellians G-K, New Nardosinane and Aristolane Sesquiterpenoids with Angiogenesis Promoting Activity from the Marine Soft Coral Lemnalia sp.

Project description:The chemical examination of the marine soft coral Lemnalia sp., collected at the Xisha islands in the South China Sea, resulted in the isolation of four new nardosinane-type sesquiterpenoids, namely clavukoellians G-J (1-4), and one new aristolane sesquiterpene, namely clavukoellian K (5), together with five known compounds, 6-10. The structure elucidation of the isolated natural products was based on various spectroscopic techniques including HRESIMS and NMR, while their absolute configurations were resolved on the basis of comparisons of the ECD spectra with the calculated ECD data. The isolated new compounds 1-5 were evaluated for their anti- and pro- angiogenesis activities in a transgenic fluorescent zebrafish (Tg(vegfr2:GFP)) model. Quantitative analysis revealed that compound 5 displayed pro-angiogenesis activity in a PTK787-induced vascular injury zebrafish model at 2.5 μM. Data showed that compound 5 significantly promoted the angiogenesis in a dose-dependent manner.

| S-EPMC7143192 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data