Natural product chemistry of gorgonian corals of the genus Junceella

Sung, Ping‐Jyun; Gwo, H.-H.; Fan, Tung‐Yung; Li, Jan-Jung; Dong, Jiancheng; Han, Ching-Chih; Wu, Shwu-Li; Fang, Lee‐Shing

doi:10.1016/s0305-1978(03)00132-7

Cited by 33 publications

(19 citation statements)

References 14 publications

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“…The Et 2 O-soluble portion (13.0 g) of the acetone extract was chromatographed repeatedly over silica gel, Sephadex LH-20, and semi-preparative RP-HPLC, to afford compounds 1 – 11 . By extensive spectroscopic analysis combined with careful comparison with the reported data, the structures of the known compounds were determined as junceellolide A ( 5 ) [16], junceellin A ( 6 ) [1,10], praelolide ( 7 ) [16], juncin ZI ( 8 ) [17], junceellolide B ( 9 ) [16], junceellolide C ( 10 ) [16] and junceellolide D ( 11 ) [16]. Junceellin A ( 6 ) and juncin ZI ( 8 ) were once reported from J .…”

Section: Resultsmentioning

confidence: 99%

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

Zhou

Heng-Chao

et al. 2014

Marine Drugs

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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.

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Section: Resultsmentioning

confidence: 99%

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

Zhou

Heng-Chao

et al. 2014

Marine Drugs

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“…Briarane-type and the related cembranoid-based diterpenoids are a family of coral-derived natural products with unique scaffolds, which are characterized by the presence of a highly oxidized c-lactone-bearing bicyclo [8.4.0]tetradecane ring system. [1 -5] Biogenetically, briarane analogues are suggested to be originated from host corals rather than the endophytic microorganisms, [6] [7] while they are considered to be generated through 3,8-cyclization of cembranoids. [8] [9] Ecologically, briarane diterpenoids exhibited antifouling effects against the larval settlement of barnacle, antibiotic, and insecticide activities, [10] [11] whereas the weak cytotoxic effects of most analogues imply that some unknown ecological roles of the typical compounds for the chemical defense are waiting for uncovering.…”

Section: Introductionmentioning

confidence: 99%

Halogenated Briarane Diterpenes with Acetyl Migration from the Gorgonian Coral Junceella fragilis

Cheng

Yin

et al. 2017

Chemistry & Biodiversity

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Chemical examination of the gorgonian coral Junceella fragilis resulted in the isolation of four pairs of acetyl isomers belonging to briarane diterpenoids, including five new compounds. Their structures were determined on the basis of extensive spectroscopic (IR, MS, NMR, and single-crystal X-ray diffraction) analysis in association with the chemical conversion. Each pair of isomers featured by dynamical interconversion through as acetyl migration in 1,2-diol, which was postulated to be generated under the formation of a cyclic orthoacetate intermediate. All compounds exerted the inhibitory activities against the nitric oxide production in RAW264.7 macrophage cells.

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“…Members of the gorgonians, Junceella and Briareum , have yielded numerous and highly oxygenated briarane-type diterpenes with a γ-lactone ring, produced from 3,8-cyclized cembranoids [1,2,3]. Many of the briarane diterpenoids have been reported to exhibit interesting biological activities, such as cytotoxic [4,5,6], anti-inflammatory [7,8], antiviral [8], insecticidal [9] and immunomodulatory [10] activities.…”

Section: Introductionmentioning

confidence: 99%

Four New Briarane Diterpenoids from Taiwanese Gorgonian Junceella fragilis

Liaw

Lin

et al. 2013

Marine Drugs

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Four new 8-hydroxybriarane diterpenoids, frajunolides P–S (1–4), together with umbraculolide A, juncenolide C, junceellonoid A and juncin R, were isolated from the acetone extract of the gorgonian Junceella fragilis, collected from the southeast coast of Taiwan. Compound 1 contains an unusual pivaloyloxy group at C-2, while 3 is a rare compound having a chlorine atom on the olefinic carbon (C-6). The structures of the isolated compounds were established by extensive spectroscopic analysis, including 1D- and 2D-NMR, as well as HRMS data. Compound 1 was further confirmed by X-ray crystallographic analysis. In the anti-inflammatory test, compounds 1 and 2 exhibited moderate inhibition on superoxide anion generation and elastase release by human neutrophils in response to formylmethionylleucyl-phenylalanine/dihydrocytochalasin B (fMLP/CB).

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Natural product chemistry of gorgonian corals of the genus Junceella

Cited by 33 publications

References 14 publications

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

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

Halogenated Briarane Diterpenes with Acetyl Migration from the Gorgonian Coral Junceella fragilis

Four New Briarane Diterpenoids from Taiwanese Gorgonian Junceella fragilis

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