Briarane Diterpenes from the South China Sea Gorgonian Coral, Junceella gemmacea

Wei Zhou,William Gerwick,Hui-Ming Hua,Heng-Chao E,Hua Tang,Wen Zhang,Bao-Shu Liu,Jiao Li

doi:10.3390/md12020589

Abstract

Four new briarane diterpenoids, junceellolides M–P (1–4), were isolated together with seven known analogs (5–11) from the South China Sea gorgonian, Junceella gemmacea. The structures of these compounds were elucidated by detailed spectroscopic analysis and comparison with the reported data. The absolute configuration of compounds 1–3 were determined based on an ECD experiment, while the absolute configuration of compound 4 was genetically determined. All the compounds were isolated for the first time from J. gemmacea. These compounds showed no growth inhibitory activity against A549, MG63 and SMMC-7721 cell lines in an in vitro bioassay.

Highlights

IntroductionGorgonian corals of the genus Junceella (phylum, Cnidaria; class, Anthozoa; order, Gorgonacea; family, Ellisellidae) are widely distributed in the subtropical and tropical waters of the Indo-Pacific
Gorgonian corals of the genus Junceella are widely distributed in the subtropical and tropical waters of the Indo-PacificOcean as whip-shaped unbranched colonies of variable colors
Chemical investigation on the acetone extract of these animals resulted in the isolation of four new briarane diterpenes, junceellolides M–P (1–4), together with seven known ones, namely junceellolide A (5), junceellin A (6), praelolide (7), juncin ZI (8), junceellolide B (9), junceellolide C

Summary

Introduction

Gorgonian corals of the genus Junceella (phylum, Cnidaria; class, Anthozoa; order, Gorgonacea; family, Ellisellidae) are widely distributed in the subtropical and tropical waters of the Indo-Pacific. Chemical investigation on the acetone extract of these animals resulted in the isolation of four new briarane diterpenes, junceellolides M–P (1–4), together with seven known ones, namely junceellolide A (5), junceellin A (6), praelolide (7), juncin ZI (8), junceellolide B (9), junceellolide C (10) and junceellolide D (11) (Figure 1). The structures of these compounds were elucidated by extensive spectroscopic analysis (1H and 13C NMR, DEPT, HSQC, HMBC, NOESY, 1H–1H COSY and HRESIMS) and comparison with the reported analytical data for the known compounds. We report the isolation, structural determination and bioactivities of these new compounds

Results and Discussion

General Experimental Procedures

Animal Material

Extraction and Isolation

Cytotoxicity Assay

Conclusions