Two new bioactive diterpenes identified from Isodon interruptus

Qi Ji Li; Chen Liang Zhao; Chuen Fai Ku; Yu Zhu; Xun Jin Zhu; Jing Jie Zhang; Stephen T. Deyrup; Lu Tai Pan; Hong Jie Zhang

doi:10.1016/j.bioorg.2019.103512

Two new bioactive diterpenes identified from Isodon interruptus

Qi Ji Li, Chen Liang Zhao, Chuen Fai Ku, Yu Zhu, Xun Jin Zhu, Jing Jie Zhang, Stephen T. Deyrup, Lu Tai Pan^*, Hong Jie Zhang^*

^*Corresponding author for this work

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

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Abstract

In the course of our ongoing studies to discover bioactive chemical constituents from plants in the genus Isodon, two new diterpenes, kunminolide A (1) and rabdokunmin F (2) were isolated from the leaves of the medicinal plant Isodon interruptus. Kunminolide A (1) is a novel abietane-like diterpene with a novel skeleton, herein designated as 9, 10-seco-neoabietane. Rabdokunmin F (2) is an ent-kaurene diterpene with C-18 oxidized to a carboxylic acid group. The structures were determined by spectroscopic means including analysis of 1D- and 2D-NMR spectral data. Crystals of 1 obtained from methanol were suitable for X-ray analysis, which confirmed the chemical structure. Kunminolide A (1) demonstrated chemopreventive potential by inducing QR1 activity with a CD value of 14.3 µM, and rabdokunmin F (2) was found to have cytotoxic activities with IC₅₀ values in the range of 1.1–3.0 µM.

Original language	English
Article number	103512
Journal	Bioorganic Chemistry
Volume	95
DOIs	https://doi.org/10.1016/j.bioorg.2019.103512
Publication status	Published - Jan 2020

User-Defined Keywords

Antimicrobial activity
Cytotoxicity
Isodon interruptus
Kunminolide A
Plant natural products
QR1 activity
Rabdokunmin F

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10.1016/j.bioorg.2019.103512

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@article{2fcf2daa1c9247f0902d8782d5bcb09d,

title = "Two new bioactive diterpenes identified from Isodon interruptus",

abstract = "In the course of our ongoing studies to discover bioactive chemical constituents from plants in the genus Isodon, two new diterpenes, kunminolide A (1) and rabdokunmin F (2) were isolated from the leaves of the medicinal plant Isodon interruptus. Kunminolide A (1) is a novel abietane-like diterpene with a novel skeleton, herein designated as 9, 10-seco-neoabietane. Rabdokunmin F (2) is an ent-kaurene diterpene with C-18 oxidized to a carboxylic acid group. The structures were determined by spectroscopic means including analysis of 1D- and 2D-NMR spectral data. Crystals of 1 obtained from methanol were suitable for X-ray analysis, which confirmed the chemical structure. Kunminolide A (1) demonstrated chemopreventive potential by inducing QR1 activity with a CD value of 14.3 µM, and rabdokunmin F (2) was found to have cytotoxic activities with IC50 values in the range of 1.1–3.0 µM.",

keywords = "Antimicrobial activity, Cytotoxicity, Isodon interruptus, Kunminolide A, Plant natural products, QR1 activity, Rabdokunmin F",

author = "Li, {Qi Ji} and Zhao, {Chen Liang} and Ku, {Chuen Fai} and Yu Zhu and Zhu, {Xun Jin} and Zhang, {Jing Jie} and Deyrup, {Stephen T.} and Pan, {Lu Tai} and Zhang, {Hong Jie}",

note = "Funding Information: This work was funded by Domestic First-rate Fund of China, China [No. GNYL (2017)008], the International Cooperation Project of Guizhou Province, China (No. 2009-700122), the Research Grants Council of the Hong Kong Special Administrative Region, China (Project No. 12102219), Hong Kong Baptist University, Research Committee, Initiation Grant – Faculty Niche Research Areas, Hong Kong (RC-IG-FNRA/17-18/12), Faculty Research Grant, Hong Kong Baptist University, Hong Kong (FRG2/17-18/103), and the Hong Kong Baptist University, Hong Kong (HKBU) Interdisciplinary Research Matching Scheme under Grants, Hong Kong (RC-IRMS/15-16/02 and RC-IRMS/16-17/02). Publisher copyright: {\textcopyright} 2019 Elsevier Inc. All rights reserved.",

year = "2020",

month = jan,

doi = "10.1016/j.bioorg.2019.103512",

language = "English",

volume = "95",

journal = "Bioorganic Chemistry",

issn = "0045-2068",

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T1 - Two new bioactive diterpenes identified from Isodon interruptus

AU - Li, Qi Ji

AU - Zhao, Chen Liang

AU - Ku, Chuen Fai

AU - Zhu, Yu

AU - Zhu, Xun Jin

AU - Zhang, Jing Jie

AU - Deyrup, Stephen T.

AU - Pan, Lu Tai

AU - Zhang, Hong Jie

N1 - Funding Information: This work was funded by Domestic First-rate Fund of China, China [No. GNYL (2017)008], the International Cooperation Project of Guizhou Province, China (No. 2009-700122), the Research Grants Council of the Hong Kong Special Administrative Region, China (Project No. 12102219), Hong Kong Baptist University, Research Committee, Initiation Grant – Faculty Niche Research Areas, Hong Kong (RC-IG-FNRA/17-18/12), Faculty Research Grant, Hong Kong Baptist University, Hong Kong (FRG2/17-18/103), and the Hong Kong Baptist University, Hong Kong (HKBU) Interdisciplinary Research Matching Scheme under Grants, Hong Kong (RC-IRMS/15-16/02 and RC-IRMS/16-17/02). Publisher copyright: © 2019 Elsevier Inc. All rights reserved.

PY - 2020/1

Y1 - 2020/1

N2 - In the course of our ongoing studies to discover bioactive chemical constituents from plants in the genus Isodon, two new diterpenes, kunminolide A (1) and rabdokunmin F (2) were isolated from the leaves of the medicinal plant Isodon interruptus. Kunminolide A (1) is a novel abietane-like diterpene with a novel skeleton, herein designated as 9, 10-seco-neoabietane. Rabdokunmin F (2) is an ent-kaurene diterpene with C-18 oxidized to a carboxylic acid group. The structures were determined by spectroscopic means including analysis of 1D- and 2D-NMR spectral data. Crystals of 1 obtained from methanol were suitable for X-ray analysis, which confirmed the chemical structure. Kunminolide A (1) demonstrated chemopreventive potential by inducing QR1 activity with a CD value of 14.3 µM, and rabdokunmin F (2) was found to have cytotoxic activities with IC50 values in the range of 1.1–3.0 µM.

AB - In the course of our ongoing studies to discover bioactive chemical constituents from plants in the genus Isodon, two new diterpenes, kunminolide A (1) and rabdokunmin F (2) were isolated from the leaves of the medicinal plant Isodon interruptus. Kunminolide A (1) is a novel abietane-like diterpene with a novel skeleton, herein designated as 9, 10-seco-neoabietane. Rabdokunmin F (2) is an ent-kaurene diterpene with C-18 oxidized to a carboxylic acid group. The structures were determined by spectroscopic means including analysis of 1D- and 2D-NMR spectral data. Crystals of 1 obtained from methanol were suitable for X-ray analysis, which confirmed the chemical structure. Kunminolide A (1) demonstrated chemopreventive potential by inducing QR1 activity with a CD value of 14.3 µM, and rabdokunmin F (2) was found to have cytotoxic activities with IC50 values in the range of 1.1–3.0 µM.

KW - Antimicrobial activity

KW - Cytotoxicity

KW - Isodon interruptus

KW - Kunminolide A

KW - Plant natural products

KW - QR1 activity

KW - Rabdokunmin F

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U2 - 10.1016/j.bioorg.2019.103512

DO - 10.1016/j.bioorg.2019.103512

M3 - Journal article

C2 - 31901752

AN - SCOPUS:85077226837

SN - 0045-2068

VL - 95

JO - Bioorganic Chemistry

JF - Bioorganic Chemistry

M1 - 103512

ER -

Two new bioactive diterpenes identified from Isodon interruptus

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