Dolabellane Diterpenoids from the South Atlantic Gorgonian Convexella magelhaenica.

J Nat Prod

UMYMFOR, Departamento de Química Orgánica, Facultad de Ciencias Exactas y Naturales, Universidad de Buenos Aires, Ciudad Universitaria, Pabellón 2 (1428), Buenos Aires, Argentina.

Published: October 2010

Two new dolabellane diterpenoids (1 and 2) were isolated from a small sample of the deep water gorgonian octocoral Convexella magelhaenica collected as a nontarget by-catch by dredging (-93 m) in commercial Patagonian scallop fishing grounds in the South Atlantic. The structures of the new compounds, which are major metabolites in the extract, were established by spectroscopic techniques and chemical transformations. Both compounds were cytotoxic against a human pancreatic adenocarcinoma cell line at micromolar concentrations.

Download full-text PDF

Source
http://dx.doi.org/10.1021/np100337jDOI Listing

Publication Analysis

Top Keywords

dolabellane diterpenoids
8
south atlantic
8
convexella magelhaenica
8
diterpenoids south
4
atlantic gorgonian
4
gorgonian convexella
4
magelhaenica dolabellane
4
diterpenoids isolated
4
isolated small
4
small sample
4

Similar Publications

Atranones and dolabellanes with cardiomyocyte protective activity against cold ischemic injury from a coral-associated fungus Stachybotrys chartarum.

Phytochemistry

September 2024

Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan, 430030, People's Republic of China. Electronic address:

Five undescribed atranones, namely atranones V-Z (1-5), three undescribed dolabellane-type diterpenoids, namely stachatranones D-F (7-9), together with four known congeners (6 and 10-12), were obtained from a coral-associated strain of the toxigenic fungus Stachybotrys chartarum. Their structures were elucidated via extensive spectroscopic analyses, mainly including the HRESIMS and NMR data, single-crystal X-ray diffraction analysis, electronic circular dichroism calculation, and [Mo(OAc)] induced circular dichroism spectrum. The cardiomyocyte protective activity assay revealed that compound 9 significantly ameliorated cold ischemic injury at 24 h post cold ischemia (CI) in a dose-dependent manner.

View Article and Find Full Text PDF

Five new eudensamane-type sesquiterpene lactones, clasamanes A-E (-), three new dolabellane-type diterpenes, clabellanes A-C (-), and fifteen known compounds (-) were isolated from the ethanolic extract of Taiwanese soft coral spp. The structures of all undescribed components (-) were determined by analysis of IR, mass, NMR, and UV spectroscopic data. The absolute configuration of new compounds was determined by using circular dichroism and DP4+ calculations.

View Article and Find Full Text PDF

Targeted Isolation of Dolabellane Diterpenoids from the Soft Coral Using Molecular Networking.

ACS Omega

June 2023

State Key Laboratory of Natural and Biomimetic Drugs, Ningbo Institute of Marine Medicine, Peking University, Beijing 100191, P.R. China.

LC-MS/MS-based molecular networking annotation coupled H NMR detection allowed the depiction of the soft coral to produce a profile of dolabellane-type diterpenoids. Chromatographic separation of the EtOAc fraction resulted in the isolation of 12 undescribed dolabellane-type diterpenoids, namely, clavirolides J-U (-) Their structures were characterized by the extensive analysis of the spectroscopic data, including the calculated ECD and X-ray diffraction for the configurational assignments. Clavirolides J-K are characterized by a 1,11- and 5,9-fused tricyclic tetradecane scaffold fused with a α,β-unsaturated-δ-lactone, and clavirolide L possesses a 1,11- and 3,5-fused tricyclic tetradecane scaffold, which extend the dolabellane-type scaffolds.

View Article and Find Full Text PDF

Extending the record of dolabellane-type diterpenoids from the soft coral Clavularia viridis: Structures and stereochemistry.

Phytochemistry

June 2023

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zu Chong Zhi Road, Zhangjiang Hi-Tech Park, Shanghai, 201203, China; School of Chinese Materia Medica, Nanjing University of Chinese Medicine, Nanjing, 210023, China; Shandong Laboratory of Yantai Drug Discovery, Bohai rim Advanced Research Institute for Drug Discovery, Yantai, Shandong, 264117, China; Collaborative Innovation Center of Yangtze River Delta Region Green Pharmaceuticals and College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou, 310014, China. Electronic address:

Five undescribed dolabellane-type diterpenoids (1-5), together with three related known ones (6-8), were isolated from the soft coral Clavularia viridis. Their structures and stereochemistry were elucidated by extensive spectroscopic analysis and NMR calculation with DP4+ probability analysis. The absolute configurations of 1 and 5 were unambiguously determined by X-ray crystallographic analysis.

View Article and Find Full Text PDF

The dolabellane-type diterpene dictyoxetane represents a significant challenge to synthetic organic chemistry. Methodology directed towards the total synthesis of naturally occurring (+)-dictyoxetane is reported. Catalytic asymmetric synthesis of the trans-hydrindane ring system is achieved through chemoselective deoxygenation of the Hajos-Parrish ketone.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!