Abstract
Chemical investigation of Junceella juncea has resulted in the isolation of three new briaranes designated juncenolides M–O (1–3). The structures of these compounds were determined by spectroscopic analysis including 2D-NMR (COSY, HMBC and NOESY) and HRMS. Compound 1 is a new chlorinated briarane while compound 3 contains a rare methyl ester at C-16. The anti-inflammatory activities tested on superoxide anion generation and elastase release by human neutrophils in response to FMLP/CB were evaluated.
Highlights
Gorgonian corals of the genus Junceella (Ellisellidae) are common in subtropical and tropical waters in a number of places around the world, such as the South China Sea and Indo-Pacific Ocean, and are well known as a source of highly oxidized diterpenes of the briarane class (3,8-cyclized cembranoids) [1].Many in vitro and in vivo studies on diterpenes isolated from gorgonians showed a variety of biological activities including anti-tumor, anti-inflammatory, antiplasmodial, antibacterial, antiviral, antimalarialMar
The presence of a γ-lactone ring was ascertained by the carbonyl carbon at δC 175.3 (C-18), and the O-bearing carbons at δC 78.5 (C-7) and 81.2 (C-8), and confirmed the HMBC correlations (Figure 2) of Me-19/C-8, C-17, C-18 and C-7/C-8, C-18 [16,17]
Connectivities between CH-2/CH-3/CH-4, CH-6/CH-7, CH-9/CH-10, CH2-12/CH-13/CH-14 (Figure 1), suggested that compound 1 possesses 8-hydroxybriarane-type diterpenoid skeleton together with an exocyclic epoxy group which was corroborated by HMBC correlations of CH2-12/C-11, C-20
Summary
Gorgonian corals of the genus Junceella (Ellisellidae) are common in subtropical and tropical waters in a number of places around the world, such as the South China Sea and Indo-Pacific Ocean, and are well known as a source of highly oxidized diterpenes of the briarane class (3,8-cyclized cembranoids) [1]. Juncins O–ZII, were isolated from the EtOH/CH2Cl2 extract of a. A bioassay-guided fractionation of the acetone extract of a Taiwanese collection of J. juncea led to the identification of seven new diterpenoids, juncenolides A–G [8,9,10,11]. A chemical investigation of the Indian Ocean gorgonian J. juncea resulted in the isolation of eight new briarane-type diterpenoids, juncins G–N [12,13,14]. The relative stereochemistry of the chiral centers and the geometry of the double bonds were deduced from NOESY spectra
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