Lobocrassins A-E: New cembrane-type diterpenoids from the soft coral Lobophytum crassum

Chia Ying Kao; Jui Hsin Su; Mei Chin Lu; Tsong Long Hwang; Wei Hsien Wang; Jih Jung Chen; Jyh Horng Sheu; Yueh Hsiung Kuo; Ching Feng Weng; Lee Shing Fang; Zhi Hong Wen; Ping Jyun Sung

doi:10.3390/md9081319

Lobocrassins A-E: New cembrane-type diterpenoids from the soft coral Lobophytum crassum

Chia Ying Kao, Jui Hsin Su, Mei Chin Lu, Tsong Long Hwang, Wei Hsien Wang, Jih Jung Chen, Jyh Horng Sheu, Yueh Hsiung Kuo, Ching Feng Weng, Lee Shing Fang, Zhi Hong Wen, Ping Jyun Sung^*

^*Corresponding author for this work

School of Traditional Chinese Medicine

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

37 Scopus citations

Abstract

Five new cembrane-type diterpenoids, lobocrassins A-E (1-5), were isolated from the soft coral Lobophytum crassum. The structures of cembranes 1-5 were established by spectroscopic and chemical methods and by comparison of the spectral data with those of known cembrane analogues. Lobocrassin A (1) is the first cembranoid possessing an α-chloromethyl-α-hydroxy-γ- lactone functionality and is the first chlorinated cembranoid from soft corals belonging to the genus Lobophytum. Lobocrassins B (2) and C (3) were found to be the stereoisomers of the known cembranes, 14-deoxycrassin (6) and pseudoplexaurol (7), respectively. Lobocrassin B (2) exhibited modest cytotoxicity toward K562, CCRF-CEM, Molt4, and HepG2 tumor cells and displayed significant inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.

Original language	English
Pages (from-to)	1319-1331
Number of pages	13
Journal	Marine Drugs
Volume	9
Issue number	8
DOIs	https://doi.org/10.3390/md9081319
State	Published - 08 2011

Keywords

Cembrane
Cytotoxicity
Elastase
Lobocrassin
Lobophytum crassum
Superoxide anion

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10.3390/md9081319

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title = "Lobocrassins A-E: New cembrane-type diterpenoids from the soft coral Lobophytum crassum",

abstract = "Five new cembrane-type diterpenoids, lobocrassins A-E (1-5), were isolated from the soft coral Lobophytum crassum. The structures of cembranes 1-5 were established by spectroscopic and chemical methods and by comparison of the spectral data with those of known cembrane analogues. Lobocrassin A (1) is the first cembranoid possessing an α-chloromethyl-α-hydroxy-γ- lactone functionality and is the first chlorinated cembranoid from soft corals belonging to the genus Lobophytum. Lobocrassins B (2) and C (3) were found to be the stereoisomers of the known cembranes, 14-deoxycrassin (6) and pseudoplexaurol (7), respectively. Lobocrassin B (2) exhibited modest cytotoxicity toward K562, CCRF-CEM, Molt4, and HepG2 tumor cells and displayed significant inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.",

keywords = "Cembrane, Cytotoxicity, Elastase, Lobocrassin, Lobophytum crassum, Superoxide anion",

author = "Kao, {Chia Ying} and Su, {Jui Hsin} and Lu, {Mei Chin} and Hwang, {Tsong Long} and Wang, {Wei Hsien} and Chen, {Jih Jung} and Sheu, {Jyh Horng} and Kuo, {Yueh Hsiung} and Weng, {Ching Feng} and Fang, {Lee Shing} and Wen, {Zhi Hong} and Sung, {Ping Jyun}",

year = "2011",

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AU - Su, Jui Hsin

AU - Lu, Mei Chin

AU - Hwang, Tsong Long

AU - Wang, Wei Hsien

AU - Chen, Jih Jung

AU - Sheu, Jyh Horng

AU - Kuo, Yueh Hsiung

AU - Weng, Ching Feng

AU - Fang, Lee Shing

AU - Wen, Zhi Hong

AU - Sung, Ping Jyun

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N2 - Five new cembrane-type diterpenoids, lobocrassins A-E (1-5), were isolated from the soft coral Lobophytum crassum. The structures of cembranes 1-5 were established by spectroscopic and chemical methods and by comparison of the spectral data with those of known cembrane analogues. Lobocrassin A (1) is the first cembranoid possessing an α-chloromethyl-α-hydroxy-γ- lactone functionality and is the first chlorinated cembranoid from soft corals belonging to the genus Lobophytum. Lobocrassins B (2) and C (3) were found to be the stereoisomers of the known cembranes, 14-deoxycrassin (6) and pseudoplexaurol (7), respectively. Lobocrassin B (2) exhibited modest cytotoxicity toward K562, CCRF-CEM, Molt4, and HepG2 tumor cells and displayed significant inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.

AB - Five new cembrane-type diterpenoids, lobocrassins A-E (1-5), were isolated from the soft coral Lobophytum crassum. The structures of cembranes 1-5 were established by spectroscopic and chemical methods and by comparison of the spectral data with those of known cembrane analogues. Lobocrassin A (1) is the first cembranoid possessing an α-chloromethyl-α-hydroxy-γ- lactone functionality and is the first chlorinated cembranoid from soft corals belonging to the genus Lobophytum. Lobocrassins B (2) and C (3) were found to be the stereoisomers of the known cembranes, 14-deoxycrassin (6) and pseudoplexaurol (7), respectively. Lobocrassin B (2) exhibited modest cytotoxicity toward K562, CCRF-CEM, Molt4, and HepG2 tumor cells and displayed significant inhibitory effects on the generation of superoxide anion and the release of elastase by human neutrophils.

KW - Cembrane

KW - Cytotoxicity

KW - Elastase

KW - Lobocrassin

KW - Lobophytum crassum

KW - Superoxide anion

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Lobocrassins A-E: New cembrane-type diterpenoids from the soft coral Lobophytum crassum

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