A monocarbocyclic sesterterpenoid biosynthetic precursor of leucosceptroids from Leucosceptrum canum and its metabolic isomerization by a specialist insect

被引：9

作者：

Guo, Kai ^{[1
,2
]}

Luo, Shi-Hong ^{[3
]}

Guo, Da-Le ^{[1
,2
]}

Li, De-Sen ^{[4
,5
]}

Hua, Juan ^{[3
]}

Liu, Yan Chun ^{[4
,5
]}

Liu, Yan ^{[1
,2
,4
,5
]}

Li, Sheng-Hong ^{[1
,2
,4
,5
]}

机构：

[1] Chengdu Univ Tradit Chinese Med, State Key Lab Southwestern Chinese Med Resources, Chengdu 611137, Peoples R China

[2] Chengdu Univ Tradit Chinese Med, Innovat Inst Chinese Med & Pharm, Chengdu 611137, Peoples R China

[3] Shenyang Agr Univ, Coll Biosci & Biotechnol, Shenyang 110866, Peoples R China

[4] Chinese Acad Sci, State Key Lab Phytochem & Plant Resources West Ch, Kunming 650201, Yunnan, Peoples R China

[5] Chinese Acad Sci, Kunming Inst Bot, Yunnan Key Lab Nat Med Chem, Kunming 650201, Yunnan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2022年 / 9卷 / 08期

基金：

中国国家自然科学基金; 中国博士后科学基金;

关键词：

GLANDULAR TRICHOMES; DETOXIFICATION; DITERPENOIDS; DEFENSE;

D O I：

10.1039/d2qo00138a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Pre-leucosceptroid (1), a rare monocarbocyclic sesterterpenoid featuring a cyclopentane ring with a terminal furan moiety, was isolated from the leaves of Leucosceptrum canum. Discovery of 1 suggested a two-step cyclization in the formation of the skeleton of leucosceptroids in plants, indicating its important role as a biosynthetic precursor of leucosceptroids. Its isomer, isopre-leucosceptroid (2), was isolated from the excrement of Nacna malachitis larvae, a specialist insect feeding on L. canum, suggesting that metabolic isomerization of alpha-hydroxyl keto from 1 to 2 might be a new insect detoxification mechanism. Their structures including the absolute configurations were determined by extensive spectroscopic analysis and quantum chemical calculations.

引用

页码：2209 / 2214

页数：6

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