11β,20β-Epoxybriaranes from the gorgonian coral Junceella fragilis (Ellisellidae)

Tung Pin Su; Tsu Jen Kuo; San Nan Yang; Gene Hsiang Lee; Yen Tung Lee; Yi Chen Wang; Jih Jung Chen; Zhi Hong Wen; Tsong Long Hwang; Ping Jyun Sung

doi:10.3390/md18040183

11β,20β-Epoxybriaranes from the gorgonian coral Junceella fragilis (Ellisellidae)

Tung Pin Su, Tsu Jen Kuo, San Nan Yang, Gene Hsiang Lee, Yen Tung Lee, Yi Chen Wang, Jih Jung Chen, Zhi Hong Wen, Tsong Long Hwang^*, Ping Jyun Sung

^*Corresponding author for this work

School of Traditional Chinese Medicine

Research output: Contribution to journal › Journal Article › peer-review

2 Scopus citations

Abstract

Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane 2 was established on the basis of spectroscopic analysis and compared with that of model compound 1. One aspect of the stereochemistry of the known compound 1 was revised. Briarane 2 was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells.

Original language	English
Article number	18040183
Journal	Marine Drugs
Volume	18
Issue number	4
DOIs	https://doi.org/10.3390/md18040183
State	Published - 2020

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Publisher Copyright:
© 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

Keywords

Briarane
COX-2
Fragilide
INOS
Junceella fragilis
Juncenolide
X-ray

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title = "11β,20β-Epoxybriaranes from the gorgonian coral Junceella fragilis (Ellisellidae)",

abstract = "Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane 2 was established on the basis of spectroscopic analysis and compared with that of model compound 1. One aspect of the stereochemistry of the known compound 1 was revised. Briarane 2 was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells.",

keywords = "Briarane, COX-2, Fragilide, INOS, Junceella fragilis, Juncenolide, X-ray",

author = "Su, {Tung Pin} and Kuo, {Tsu Jen} and Yang, {San Nan} and Lee, {Gene Hsiang} and Lee, {Yen Tung} and Wang, {Yi Chen} and Chen, {Jih Jung} and Wen, {Zhi Hong} and Hwang, {Tsong Long} and Sung, {Ping Jyun}",

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year = "2020",

doi = "10.3390/md18040183",

language = "英语",

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AU - Su, Tung Pin

AU - Kuo, Tsu Jen

AU - Yang, San Nan

AU - Lee, Gene Hsiang

AU - Lee, Yen Tung

AU - Wang, Yi Chen

AU - Chen, Jih Jung

AU - Wen, Zhi Hong

AU - Hwang, Tsong Long

AU - Sung, Ping Jyun

N1 - Publisher Copyright: © 2020 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).

PY - 2020

Y1 - 2020

N2 - Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane 2 was established on the basis of spectroscopic analysis and compared with that of model compound 1. One aspect of the stereochemistry of the known compound 1 was revised. Briarane 2 was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells.

AB - Two 11,20-epoxybriaranes, including a known compound, juncenolide K (1), as well as a new metabolite, fragilide X (2), have been isolated from gorgonian Junceella fragilis collected off the waters of Taiwan. The absolute configuration of juncenolide K (1) was determined by single-crystal X-ray diffraction analysis for the first time in this study and the structure, including the absolute configuration of briarane 2 was established on the basis of spectroscopic analysis and compared with that of model compound 1. One aspect of the stereochemistry of the known compound 1 was revised. Briarane 2 was found to enhance the generation of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) release from RAW 264.7 cells.

KW - Briarane

KW - COX-2

KW - Fragilide

KW - INOS

KW - Junceella fragilis

KW - Juncenolide

KW - X-ray

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U2 - 10.3390/md18040183

DO - 10.3390/md18040183

M3 - 文章

C2 - 32244363

AN - SCOPUS:85083042280

SN - 1660-3397

VL - 18

JO - Marine Drugs

JF - Marine Drugs

IS - 4

M1 - 18040183

ER -

11β,20β-Epoxybriaranes from the gorgonian coral Junceella fragilis (Ellisellidae)

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