Sesquiterpene lactone glycosides, eudesmanolides, and other constituents from Carpesium macrocephalum

Chao Yang; Yan Ping Shi; Zhong Jian Jia

doi:10.1055/s-2002-32899

Sesquiterpene lactone glycosides, eudesmanolides, and other constituents from Carpesium macrocephalum

Chao Yang
, Yan Ping Shi
, Zhong Jian Jia^*

^*Corresponding author for this work

Lanzhou University
CAS - Lanzhou Institute of Chemical Physics

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

58 Scopus citations

Abstract

Two new sesquiterpene lactone glycosides and two new eudesmanolides, along with twelve known compounds were isolated from seeds of Carpesium macrocephalum. The structures of these new compounds were elucidated as 2α-O-β-D-glucopyranosyl-5α, 11αH-eudesma-4(15)-en-12,8β-olide (1), 2α-O-β-D-glucopyranosyl-5αH-eudesma-4(15),11(13)-dien-12, 8β-olide (2), 2α-acetoxy-5α-hydroxy-11αH-eudesma-4(15)-en-12,8β- olide (3) and 2α,5α-dihydroxy-11αH-eudesma-4(15)-en-12,8β-olide (4) by spectroscopic methods including 2D NMR techniques (¹H-¹H COSY, ¹H-¹H NOESY, HMQC, HMBC) and chemical transformations. Compounds 1, 6, 8, 9 and 10 exhibited moderate antibacterial activity, while compound 4 showed appreciable cytotoxic activity against cultured SMMC-7721 (human hepatoma cell).

Original language	English
Pages (from-to)	626-630
Number of pages	5
Journal	Planta Medica
Volume	68
Issue number	7
DOIs	https://doi.org/10.1055/s-2002-32899
State	Published - 2002
Externally published	Yes

Keywords

Antibacterial activity
Carpesium macrocephalum
Compositae
Cytotoxic activity
Eudesmanolide
Sesquiterpene lactone glycosides

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title = "Sesquiterpene lactone glycosides, eudesmanolides, and other constituents from Carpesium macrocephalum",

abstract = "Two new sesquiterpene lactone glycosides and two new eudesmanolides, along with twelve known compounds were isolated from seeds of Carpesium macrocephalum. The structures of these new compounds were elucidated as 2α-O-β-D-glucopyranosyl-5α, 11αH-eudesma-4(15)-en-12,8β-olide (1), 2α-O-β-D-glucopyranosyl-5αH-eudesma-4(15),11(13)-dien-12, 8β-olide (2), 2α-acetoxy-5α-hydroxy-11αH-eudesma-4(15)-en-12,8β- olide (3) and 2α,5α-dihydroxy-11αH-eudesma-4(15)-en-12,8β-olide (4) by spectroscopic methods including 2D NMR techniques (1H-1H COSY, 1H-1H NOESY, HMQC, HMBC) and chemical transformations. Compounds 1, 6, 8, 9 and 10 exhibited moderate antibacterial activity, while compound 4 showed appreciable cytotoxic activity against cultured SMMC-7721 (human hepatoma cell).",

keywords = "Antibacterial activity, Carpesium macrocephalum, Compositae, Cytotoxic activity, Eudesmanolide, Sesquiterpene lactone glycosides",

author = "Chao Yang and Shi, \{Yan Ping\} and Jia, \{Zhong Jian\}",

year = "2002",

doi = "10.1055/s-2002-32899",

language = "英语",

volume = "68",

pages = "626--630",

journal = "Planta Medica",

issn = "0032-0943",

publisher = "Georg Thieme Verlag",

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}

TY - JOUR

T1 - Sesquiterpene lactone glycosides, eudesmanolides, and other constituents from Carpesium macrocephalum

AU - Yang, Chao

AU - Shi, Yan Ping

AU - Jia, Zhong Jian

PY - 2002

Y1 - 2002

N2 - Two new sesquiterpene lactone glycosides and two new eudesmanolides, along with twelve known compounds were isolated from seeds of Carpesium macrocephalum. The structures of these new compounds were elucidated as 2α-O-β-D-glucopyranosyl-5α, 11αH-eudesma-4(15)-en-12,8β-olide (1), 2α-O-β-D-glucopyranosyl-5αH-eudesma-4(15),11(13)-dien-12, 8β-olide (2), 2α-acetoxy-5α-hydroxy-11αH-eudesma-4(15)-en-12,8β- olide (3) and 2α,5α-dihydroxy-11αH-eudesma-4(15)-en-12,8β-olide (4) by spectroscopic methods including 2D NMR techniques (1H-1H COSY, 1H-1H NOESY, HMQC, HMBC) and chemical transformations. Compounds 1, 6, 8, 9 and 10 exhibited moderate antibacterial activity, while compound 4 showed appreciable cytotoxic activity against cultured SMMC-7721 (human hepatoma cell).

AB - Two new sesquiterpene lactone glycosides and two new eudesmanolides, along with twelve known compounds were isolated from seeds of Carpesium macrocephalum. The structures of these new compounds were elucidated as 2α-O-β-D-glucopyranosyl-5α, 11αH-eudesma-4(15)-en-12,8β-olide (1), 2α-O-β-D-glucopyranosyl-5αH-eudesma-4(15),11(13)-dien-12, 8β-olide (2), 2α-acetoxy-5α-hydroxy-11αH-eudesma-4(15)-en-12,8β- olide (3) and 2α,5α-dihydroxy-11αH-eudesma-4(15)-en-12,8β-olide (4) by spectroscopic methods including 2D NMR techniques (1H-1H COSY, 1H-1H NOESY, HMQC, HMBC) and chemical transformations. Compounds 1, 6, 8, 9 and 10 exhibited moderate antibacterial activity, while compound 4 showed appreciable cytotoxic activity against cultured SMMC-7721 (human hepatoma cell).

KW - Antibacterial activity

KW - Carpesium macrocephalum

KW - Compositae

KW - Cytotoxic activity

KW - Eudesmanolide

KW - Sesquiterpene lactone glycosides

UR - https://www.scopus.com/pages/publications/0036311958

U2 - 10.1055/s-2002-32899

DO - 10.1055/s-2002-32899

M3 - 文章

C2 - 12142997

AN - SCOPUS:0036311958

SN - 0032-0943

VL - 68

SP - 626

EP - 630

JO - Planta Medica

JF - Planta Medica

IS - 7

ER -

Sesquiterpene lactone glycosides, eudesmanolides, and other constituents from Carpesium macrocephalum

Abstract

Keywords

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