A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides

Lai King Sy; Geoffrey D. Brown; Richard Haynes

doi:10.1016/S0040-4020(98)00148-3

A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides

Lai King Sy
, Geoffrey D. Brown
, Richard Haynes

University of Hong Kong

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

75 Citations (Scopus)

Abstract

Seven novel cadinane sesquiterpenes, including the seven-membered endoperoxide lactone arteannuin H (1), two six-membered lactones arteannuins I (4) and J (5), three five-membered lactones arteannuins K-M (6-8) and a keto acid arteannuin N (9) have been isolated from the dried leaves of Artemisia annua in addition to the known compounds dihydroartemisinic acid (27), dihydroarteannuin B (24) and dihydro-epi-deoxyarteannuin B (22). It is proposed that these novel sesquiterpenes are biogenetically related to dihydroartemisinic acid via intermediate secondary and tertiary allylic hydroperoxides.

Original language	English
Pages (from-to)	4345-4356
Number of pages	12
Journal	Tetrahedron
Volume	54
Issue number	17
DOIs	https://doi.org/10.1016/S0040-4020(98)00148-3
Publication status	Published - 23 Apr 1998

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@article{cc903d23a01e486ea68b3c7245643128,

title = "A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides",

abstract = "Seven novel cadinane sesquiterpenes, including the seven-membered endoperoxide lactone arteannuin H (1), two six-membered lactones arteannuins I (4) and J (5), three five-membered lactones arteannuins K-M (6-8) and a keto acid arteannuin N (9) have been isolated from the dried leaves of Artemisia annua in addition to the known compounds dihydroartemisinic acid (27), dihydroarteannuin B (24) and dihydro-epi-deoxyarteannuin B (22). It is proposed that these novel sesquiterpenes are biogenetically related to dihydroartemisinic acid via intermediate secondary and tertiary allylic hydroperoxides.",

author = "Sy, \{Lai King\} and Brown, \{Geoffrey D.\} and Richard Haynes",

note = "Funding Information: We would like to thank Professor Li Xian-Jun of the Chemistry Department, Sichuan Union University, Chengdu, PRC for kindly providing the A. annua plant material used in this study. This research was funded by a grant from the Bioteehnology Research Institute of Hong Kong.",

year = "1998",

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doi = "10.1016/S0040-4020(98)00148-3",

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T1 - A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides

AU - Sy, Lai King

AU - Brown, Geoffrey D.

AU - Haynes, Richard

N1 - Funding Information: We would like to thank Professor Li Xian-Jun of the Chemistry Department, Sichuan Union University, Chengdu, PRC for kindly providing the A. annua plant material used in this study. This research was funded by a grant from the Bioteehnology Research Institute of Hong Kong.

PY - 1998/4/23

Y1 - 1998/4/23

N2 - Seven novel cadinane sesquiterpenes, including the seven-membered endoperoxide lactone arteannuin H (1), two six-membered lactones arteannuins I (4) and J (5), three five-membered lactones arteannuins K-M (6-8) and a keto acid arteannuin N (9) have been isolated from the dried leaves of Artemisia annua in addition to the known compounds dihydroartemisinic acid (27), dihydroarteannuin B (24) and dihydro-epi-deoxyarteannuin B (22). It is proposed that these novel sesquiterpenes are biogenetically related to dihydroartemisinic acid via intermediate secondary and tertiary allylic hydroperoxides.

AB - Seven novel cadinane sesquiterpenes, including the seven-membered endoperoxide lactone arteannuin H (1), two six-membered lactones arteannuins I (4) and J (5), three five-membered lactones arteannuins K-M (6-8) and a keto acid arteannuin N (9) have been isolated from the dried leaves of Artemisia annua in addition to the known compounds dihydroartemisinic acid (27), dihydroarteannuin B (24) and dihydro-epi-deoxyarteannuin B (22). It is proposed that these novel sesquiterpenes are biogenetically related to dihydroartemisinic acid via intermediate secondary and tertiary allylic hydroperoxides.

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DO - 10.1016/S0040-4020(98)00148-3

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SN - 0040-4020

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JO - Tetrahedron

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IS - 17

ER -

A novel endoperoxide and related sesquiterpenes from Artemisia annua which are possibly derived from allylic hydroperoxides

Abstract

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