Cytotoxic dimeric sesquiterpenoids from Curcuma parviflora: Isolation of three new parviflorenes and absolute stereochemistry of parviflorenes A, B, D, F, and G

Kazufumi Toume; Masaaki Sato; Takashi Koyano; Thaworn Kowithayakorn; Takao Yamori; Masami Ishibashi

doi:10.1016/j.tet.2005.05.016

Cytotoxic dimeric sesquiterpenoids from Curcuma parviflora: Isolation of three new parviflorenes and absolute stereochemistry of parviflorenes A, B, D, F, and G

Kazufumi Toume, Masaaki Sato, Takashi Koyano, Thaworn Kowithayakorn, Takao Yamori, Masami Ishibashi^*

^*Corresponding author for this work

Department of Medicinal Resources Management, Institute of Natural Medicine

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

17 Scopus citations

Abstract

Three novel dimeric sesquiterpenoids, named parviflorenes G-I (1-3), have been isolated from Curcuma parviflora (Zingiberaceae), and their structures were elucidated by means of spectroscopic studies. Absolute stereochemistry of parviflorene G (1) as well as previously isolated related compounds, parviflorenes A (4), B (5), D (6), and F (7), was revealed by CD spectral data and chemical means. Parviflorenes G (1) and I (3) were cytotoxic against HeLa cells, while parviflorenes A (4) and F (7) were cytotoxic against all tested tumor cell lines in the human cancer cell line panel assay.

Original language	English
Pages (from-to)	6700-6706
Number of pages	7
Journal	Tetrahedron
Volume	61
Issue number	28
DOIs	https://doi.org/10.1016/j.tet.2005.05.016
State	Published - 2005/07/11

Keywords

Absolute stereochemistry
Curcuma parviflora
Cytotoxicity
Dimeric sesquiterpene
Zingiberaceae

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tet.2005.05.016

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title = "Cytotoxic dimeric sesquiterpenoids from Curcuma parviflora: Isolation of three new parviflorenes and absolute stereochemistry of parviflorenes A, B, D, F, and G",

abstract = "Three novel dimeric sesquiterpenoids, named parviflorenes G-I (1-3), have been isolated from Curcuma parviflora (Zingiberaceae), and their structures were elucidated by means of spectroscopic studies. Absolute stereochemistry of parviflorene G (1) as well as previously isolated related compounds, parviflorenes A (4), B (5), D (6), and F (7), was revealed by CD spectral data and chemical means. Parviflorenes G (1) and I (3) were cytotoxic against HeLa cells, while parviflorenes A (4) and F (7) were cytotoxic against all tested tumor cell lines in the human cancer cell line panel assay.",

keywords = "Absolute stereochemistry, Curcuma parviflora, Cytotoxicity, Dimeric sesquiterpene, Zingiberaceae",

author = "Kazufumi Toume and Masaaki Sato and Takashi Koyano and Thaworn Kowithayakorn and Takao Yamori and Masami Ishibashi",

note = "Funding Information: This work was partly supported by a Grant-in-Aid from the Ministry of Education, Culture, Sports, Science, and Technology of Japan and by a Grant-in-Aid from the Keimeikai Foundation.",

year = "2005",

month = jul,

day = "11",

doi = "10.1016/j.tet.2005.05.016",

language = "英語",

volume = "61",

pages = "6700--6706",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "28",

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TY - JOUR

T1 - Cytotoxic dimeric sesquiterpenoids from Curcuma parviflora

T2 - Isolation of three new parviflorenes and absolute stereochemistry of parviflorenes A, B, D, F, and G

AU - Toume, Kazufumi

AU - Sato, Masaaki

AU - Koyano, Takashi

AU - Kowithayakorn, Thaworn

AU - Yamori, Takao

AU - Ishibashi, Masami

N1 - Funding Information: This work was partly supported by a Grant-in-Aid from the Ministry of Education, Culture, Sports, Science, and Technology of Japan and by a Grant-in-Aid from the Keimeikai Foundation.

PY - 2005/7/11

Y1 - 2005/7/11

N2 - Three novel dimeric sesquiterpenoids, named parviflorenes G-I (1-3), have been isolated from Curcuma parviflora (Zingiberaceae), and their structures were elucidated by means of spectroscopic studies. Absolute stereochemistry of parviflorene G (1) as well as previously isolated related compounds, parviflorenes A (4), B (5), D (6), and F (7), was revealed by CD spectral data and chemical means. Parviflorenes G (1) and I (3) were cytotoxic against HeLa cells, while parviflorenes A (4) and F (7) were cytotoxic against all tested tumor cell lines in the human cancer cell line panel assay.

AB - Three novel dimeric sesquiterpenoids, named parviflorenes G-I (1-3), have been isolated from Curcuma parviflora (Zingiberaceae), and their structures were elucidated by means of spectroscopic studies. Absolute stereochemistry of parviflorene G (1) as well as previously isolated related compounds, parviflorenes A (4), B (5), D (6), and F (7), was revealed by CD spectral data and chemical means. Parviflorenes G (1) and I (3) were cytotoxic against HeLa cells, while parviflorenes A (4) and F (7) were cytotoxic against all tested tumor cell lines in the human cancer cell line panel assay.

KW - Absolute stereochemistry

KW - Curcuma parviflora

KW - Cytotoxicity

KW - Dimeric sesquiterpene

KW - Zingiberaceae

UR - http://www.scopus.com/inward/record.url?scp=20444466851&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2005.05.016

DO - 10.1016/j.tet.2005.05.016

M3 - 学術論文

AN - SCOPUS:20444466851

SN - 0040-4020

VL - 61

SP - 6700

EP - 6706

JO - Tetrahedron

JF - Tetrahedron

IS - 28

ER -

Cytotoxic dimeric sesquiterpenoids from Curcuma parviflora: Isolation of three new parviflorenes and absolute stereochemistry of parviflorenes A, B, D, F, and G

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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