Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system

Chen Liang Zhao; Md. Shahid  Sarwar; Jiang Hai Ye; Chuen Fai  Ku; Wan Fei  Li; Guo Yong Luo; Jing Jie Zhang; Jun Xu; Zhao Feng Huang; Siu Wai  Tsang; Lu Tai  Pan; Hong Jie  Zhang

doi:10.1107/S2053229618005740

Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system

Chen Liang Zhao, Md. Shahid Sarwar, Jiang Hai Ye, Chuen Fai Ku, Wan Fei Li, Guo Yong Luo, Jing Jie Zhang, Jun Xu, Zhao Feng Huang, Siu Wai Tsang, Lu Tai Pan^*, Hong Jie Zhang^*

^*Corresponding author for this work

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

10 Citations (Scopus)

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Abstract

We report the isolation of a novel diterpene, designated as `amethane', from Isodon amethystoides (Lamiaceae). The diterpene [amethinol A; systematic name: (4aR,4bR,7R,10aS)-4b,7-dihydroxy-7-isopropyl-1,1-dimethyl-9-oxododecahydrobenzo[a]azulene-4a(2H)-carboxylic acid], possesses a unique skeleton containing a six/five/seven-membered tricyclic system. Intermolecular O—H…O close contacts were found to the carboxyl, carbonyl and hydroxy groups, connecting molecules into a two-dimensional structure. A possible biosynthetic pathway has been proposed. In addition, the compound was evaluated for its biological activities against different disease targets, and was found to significantly attenuate RORγt-dependent autoimmune responses.

Original language	English
Pages (from-to)	635-640
Number of pages	6
Journal	Acta Crystallographica Section C: Structural Chemistry
Volume	74
Issue number	5
DOIs	https://doi.org/10.1107/S2053229618005740
Publication status	Published - May 2018

Scopus Subject Areas

Condensed Matter Physics
Physical and Theoretical Chemistry
Inorganic Chemistry
Materials Chemistry

User-Defined Keywords

amethane diterpene
amethinol A
biosynthetic pathway
crystal structure
Isodon amethystoides
Lamiaceae
natural product
RORγt antagonist

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10.1107/S2053229618005740

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Zhao, C. L., Sarwar, M. S., Ye, J. H., Ku, C. F., Li, W. F., Luo, G. Y., Zhang, J. J., Xu, J., Huang, Z. F., Tsang, S. W., Pan, L. T., & Zhang, H. J. (2018). Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system. Acta Crystallographica Section C: Structural Chemistry, 74(5), 635-640. https://doi.org/10.1107/S2053229618005740

@article{c35c852e84c14ad9b87aad04531ecc5e,

title = "Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system",

abstract = "We report the isolation of a novel diterpene, designated as `amethane', from Isodon amethystoides (Lamiaceae). The diterpene [amethinol A; systematic name: (4aR,4bR,7R,10aS)-4b,7-dihydroxy-7-isopropyl-1,1-dimethyl-9-oxododecahydrobenzo[a]azulene-4a(2H)-carboxylic acid], possesses a unique skeleton containing a six/five/seven-membered tricyclic system. Intermolecular O—H…O close contacts were found to the carboxyl, carbonyl and hydroxy groups, connecting molecules into a two-dimensional structure. A possible biosynthetic pathway has been proposed. In addition, the compound was evaluated for its biological activities against different disease targets, and was found to significantly attenuate RORγt-dependent autoimmune responses.",

keywords = "amethane diterpene, amethinol A, biosynthetic pathway, crystal structure, Isodon amethystoides, Lamiaceae, natural product, RORγt antagonist",

author = "Zhao, {Chen Liang} and Sarwar, {Md. Shahid} and Ye, {Jiang Hai} and Ku, {Chuen Fai} and Li, {Wan Fei} and Luo, {Guo Yong} and Zhang, {Jing Jie} and Jun Xu and Huang, {Zhao Feng} and Tsang, {Siu Wai} and Pan, {Lu Tai} and Zhang, {Hong Jie}",

note = "Funding Information: Funding for this research was provided by: National Natural Science Foundation of China (grant No. 81760772); Domestic First-rate Fund of China [grant No. GNYL(2017)008]; Hong Kong Baptist University (HKBU) Interdisciplinary Research Matching Scheme (grant No. RC-IRMS/15-16/02); Science and Technology Department of Guangdong province (grant No. 2016A050503023). Publisher copyright: {\textcopyright} 2018 International Union of Crystallography",

year = "2018",

month = may,

doi = "10.1107/S2053229618005740",

language = "English",

volume = "74",

pages = "635--640",

journal = "Acta Crystallographica Section C: Structural Chemistry",

issn = "2053-2296",

publisher = "John Wiley & Sons Ltd.",

number = "5",

}

Zhao, CL, Sarwar, MS, Ye, JH, Ku, CF, Li, WF, Luo, GY, Zhang, JJ, Xu, J, Huang, ZF, Tsang, SW, Pan, LT & Zhang, HJ 2018, 'Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system', Acta Crystallographica Section C: Structural Chemistry, vol. 74, no. 5, pp. 635-640. https://doi.org/10.1107/S2053229618005740

Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system. / Zhao, Chen Liang; Sarwar, Md. Shahid ; Ye, Jiang Hai et al.
In: Acta Crystallographica Section C: Structural Chemistry, Vol. 74, No. 5, 05.2018, p. 635-640.

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

TY - JOUR

T1 - Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system

AU - Zhao, Chen Liang

AU - Sarwar, Md. Shahid

AU - Ye, Jiang Hai

AU - Ku, Chuen Fai

AU - Li, Wan Fei

AU - Luo, Guo Yong

AU - Zhang, Jing Jie

AU - Xu, Jun

AU - Huang, Zhao Feng

AU - Tsang, Siu Wai

AU - Pan, Lu Tai

AU - Zhang, Hong Jie

N1 - Funding Information: Funding for this research was provided by: National Natural Science Foundation of China (grant No. 81760772); Domestic First-rate Fund of China [grant No. GNYL(2017)008]; Hong Kong Baptist University (HKBU) Interdisciplinary Research Matching Scheme (grant No. RC-IRMS/15-16/02); Science and Technology Department of Guangdong province (grant No. 2016A050503023). Publisher copyright: © 2018 International Union of Crystallography

PY - 2018/5

Y1 - 2018/5

N2 - We report the isolation of a novel diterpene, designated as `amethane', from Isodon amethystoides (Lamiaceae). The diterpene [amethinol A; systematic name: (4aR,4bR,7R,10aS)-4b,7-dihydroxy-7-isopropyl-1,1-dimethyl-9-oxododecahydrobenzo[a]azulene-4a(2H)-carboxylic acid], possesses a unique skeleton containing a six/five/seven-membered tricyclic system. Intermolecular O—H…O close contacts were found to the carboxyl, carbonyl and hydroxy groups, connecting molecules into a two-dimensional structure. A possible biosynthetic pathway has been proposed. In addition, the compound was evaluated for its biological activities against different disease targets, and was found to significantly attenuate RORγt-dependent autoimmune responses.

AB - We report the isolation of a novel diterpene, designated as `amethane', from Isodon amethystoides (Lamiaceae). The diterpene [amethinol A; systematic name: (4aR,4bR,7R,10aS)-4b,7-dihydroxy-7-isopropyl-1,1-dimethyl-9-oxododecahydrobenzo[a]azulene-4a(2H)-carboxylic acid], possesses a unique skeleton containing a six/five/seven-membered tricyclic system. Intermolecular O—H…O close contacts were found to the carboxyl, carbonyl and hydroxy groups, connecting molecules into a two-dimensional structure. A possible biosynthetic pathway has been proposed. In addition, the compound was evaluated for its biological activities against different disease targets, and was found to significantly attenuate RORγt-dependent autoimmune responses.

KW - amethane diterpene

KW - amethinol A

KW - biosynthetic pathway

KW - crystal structure

KW - Isodon amethystoides

KW - Lamiaceae

KW - natural product

KW - RORγt antagonist

UR - http://www.scopus.com/inward/record.url?scp=85046533633&partnerID=8YFLogxK

U2 - 10.1107/S2053229618005740

DO - 10.1107/S2053229618005740

M3 - Journal article

C2 - 29726475

AN - SCOPUS:85046533633

SN - 2053-2296

VL - 74

SP - 635

EP - 640

JO - Acta Crystallographica Section C: Structural Chemistry

JF - Acta Crystallographica Section C: Structural Chemistry

IS - 5

ER -

Isolation, evaluation of bioactivity and structure determination of amethinol A, a prototypic amethane diterpene from Isodon amethystoides bearing a six/five/seven-membered carbon-ring system

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