The junceellolides, new anti-inflammatory diterpenoids of the briarane class from the chinese gorgonian junceella fragilis

Shin, Jongheon; Park, Minkyu; Fenical, William

doi:10.1016/s0040-4020(01)80026-0

Cited by 93 publications

(107 citation statements)

References 18 publications

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“…During the course of further searching for novel active compounds from gorgonians [10] [11], we undertook the investigation of the South China Sea gorgonian coral J. fragilis. Three new briarane diterpenes, junceellonoids C ± E 1 )(1 ± 3), along with six known briaranes, junceellin A (4) [4], praelolide (5) [12], and junceellolides A ± D (6 ± 9) [1], were isolated from the EtOH/CH 2 Cl 2 extracts of J. fragilis. In the cytotoxicity testing of a number of compounds (including compounds 1, 2, and other compounds that are not reported herein), we observed that 1 and 2 exhibited mild cytotoxicity against human galactophore carcinoma (MDA-mB-231 and MCF-7) cells at a concentration of 100 mm, but almost no activity at the concentration of 33.3 mm.…”

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confidence: 99%

“…The CHCl 3 extract was chromatographed over silica gel, and selected fractions were rechromatographed on Sephadex LH-20 and silica gel to yield compounds 1 ± 9. All of the compounds possessed a briarane-type skeleton, and compounds 4 ± 9 were identified as junceellin A (4) [4], praelolide (5) [12], and junceellolides A ± D (6 ± 9) [1] by comparison of their spectral data with literature values. The structures of 1 ± 3 are described below.…”

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New Briaranes from the South China Sea GorgonianJunceella fragilis

Zhang

Wen

et al. 2005

HCA

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New Briaranes from the South China Sea GorgonianJunceella fragilis

Zhang

Wen

et al. 2005

HCA

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“…The relative configuration of 2 was assigned to be the same as that of 1 by comparison of NMR data and analysis of the NOESY spectrum. Dichotellide H (3) had a molecular formula of C 38 H 51 ClO 16 by positive HRESIMS at m/z, 821.2786 [MþNa] þ (calcd for 821.2673).…”

Section: Resultsmentioning

confidence: 99%

“…The 1 H and 13 C NMR spectral data (Tables 1 and 2 Dichotellide K (6) was assigned the molecular formula C 38 H 52 O 16 by its HRESIMS at m/z 787.3145 [MþNa] þ . Its NMR spectroscopic data (Tables 1 and 2) were similar to those of 5 with the exception that the two acetate groups instead of two isovalerate groups.…”

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confidence: 99%

Antifouling briarane type diterpenoids from South China Sea gorgonians Dichotella gemmacea

et al. 2013

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“…Moreover, H-4 showed correlations with H-2 and one proton of the C-16 methylene (d H 5.32, H-16a) and a large coupling constant was found between H-4 and H-3 (Jϭ10.8 Hz), indicating that the dihedral angle between H-3 and H-4 is approximately 180°and H-4 has an a-orientation at C-4. It was found that the structure of 1 was similar to that of a known briarane, praelolide (4), 3,31,32) which was first isolated from the gorgonian coral Plexaureides praelonga collected off the South China Sea, 31) except that the signals corresponding to a 2b-acetoxy group in 4 was replaced by a 2b-hydroxy group in 1. Based on the above findings, the structure of 1 was established and the chiral centers of 1 were assigned as 1R*, 2R*, 3R*, 4R*, 6S*, 7R*, 8R*, 9S*, 10S*, 11R*, 14R*, and 17R*.…”

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confidence: 85%

Chlorinated Briarane Diterpenoids from the Sea Whip Gorgonian Corals Junceella fragilis and Ellisella robusta (Ellisellidae)

Wang

Chang

Chiang

et al. 2010

CHEMICAL & PHARMACEUTICAL BULLETIN

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Previous studies on the chemical constituents of sea whip gorgonian corals belonging to the genus Junceella and Ellisella (family Ellisellidae), collected in waters off Taiwan, yielded a series of interesting briarane diterpenoids. Briarane-type natural products are found only in marine organisms and mainly from octocorals. [27][28][29] Compounds of this type are suggested to be originally synthesized by host corals, 4,30) and confirmed to possess various bioactivities. 27-29)We have further isolated a new chlorinated briarane, fragilide J (1), from the sea whip gorgonian coral Junceella fragilis. Furthermore, two chlorinated briaranes, including a new compound, robustolide L (2), and a known metabolite, robustolide H (3), 24) were obtained from the sea whip gorgonian coral Ellisella robusta. In this paper, we describe the isolation, structure determination, and bioactivity of the above briaranes 1-3. Results and DiscussionFragilide J from J. fragilis Fragilide J (1) was isolated as a white powder. The molecular formula of 1 was estab- ). The IR spectrum of 1 showed bands at 3491, 1790, and 1741 cm Ϫ1 , consistent with the presence of hydroxy, g-lactone, and ester carbonyl groups. The 13 C-NMR and distortionless enhancement by polarization transfer (DEPT) spectra of 1 showed that this compound has 26 carbons (Table 1) H correlation spectroscopy (COSY) spectrum of 1, five different structural units, C-2/-3/-4, C-6/-7, C-9/-10, C-12/-13/-14, and C-17/-18, were identified (Table 1), which were assembled with the assistance of a heteronuclear multiple-bond coherence (HMBC) experiment (Table 1). The HMBC correlations between protons and quaternary carbons of 1, such as H-9, H-10, H 3 -15/C-1; H-4/C-5; H-4, H-17, H 3 -18/C-8; H-9, H-10, H 2 -12/C-11; and H-17, H 3 -18/C-19, permitted the elucidation of the carbon skeleton of 1. An exocyclic double bond at C-5 was confirmed by the allylic coupling between H-6 and H 2 -16 in the 1 H-1 H COSY experiment and by the HMBC correlations between H 2 -16/C-4, -6. The ring junction C-15 methyl group was positioned at C-1 A new chlorinated briarane, fragilide J (1), has been isolated from the sea whip gorgonian coral Junceella fragilis. In addition, the sea whip gorgonian coral Ellisella robusta yielded two chlorinated briaranes, including a new compound, robustolide L (2), and a known metabolite, robustolide H (3). The structures of these compounds were determined using spectroscopic methods. The structure, including the absolute configuration of 3, was further confirmed by X-ray data analysis for the first time.

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The junceellolides, new anti-inflammatory diterpenoids of the briarane class from the chinese gorgonian junceella fragilis

Cited by 93 publications

References 18 publications

New Briaranes from the South China Sea GorgonianJunceella fragilis

New Briaranes from the South China Sea GorgonianJunceella fragilis

Antifouling briarane type diterpenoids from South China Sea gorgonians Dichotella gemmacea

Chlorinated Briarane Diterpenoids from the Sea Whip Gorgonian Corals Junceella fragilis and Ellisella robusta (Ellisellidae)

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