Parviflorenes B-F, novel cytotoxic unsymmetrical sesquiterpene-dimers with three backbone skeletons from Curcuma parviflora

Kazufumi Toume; Masae Takahashi; Kentaro Yamaguchi; Takashi Koyano; Thaworn Kowithayakorn; Masahiko Hayashi; Kanki Komiyama; Masami Ishibashi

doi:10.1016/j.tet.2004.09.043

Parviflorenes B-F, novel cytotoxic unsymmetrical sesquiterpene-dimers with three backbone skeletons from Curcuma parviflora

Kazufumi Toume, Masae Takahashi, Kentaro Yamaguchi, Takashi Koyano, Thaworn Kowithayakorn, Masahiko Hayashi, Kanki Komiyama, Masami Ishibashi^*

^*Corresponding author for this work

Department of Medicinal Resources Management, Institute of Natural Medicine

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

29 Scopus citations

Abstract

Five novel natural products classified as dimeric sesquiterpenes, named parviflorenes B-F (2-6), possessing three types of novel backbone frameworks, have been isolated from Curcuma parviflora (Zingiberaceae). The structures of 2-6 were elucidated by means of spectroscopic studies, and the structure of 2 was further unambiguously established by X-ray crystallographic analysis. Compounds 2, 4, and 6 have an unsymmetrical bis-cadinane skeleton, while compound 3 is a dimer of cadinane and iso-cadinane, and compound 5 possesses another novel carbon framework consisting of two cadinanes with different bond-connection. These new compounds with novel carbon skeletons showed cytotoxicity against tumor cell lines.

Original language	English
Pages (from-to)	10817-10824
Number of pages	8
Journal	Tetrahedron
Volume	60
Issue number	48
DOIs	https://doi.org/10.1016/j.tet.2004.09.043
State	Published - 2004/11/22

Keywords

Curcuma parviflora
Cytotoxicity
Dimeric sesquiterpene
X-ray analysis
Zingiberaceae

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2004.09.043

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@article{e7317a915b094ea3b1ee7c3496fdda11,

title = "Parviflorenes B-F, novel cytotoxic unsymmetrical sesquiterpene-dimers with three backbone skeletons from Curcuma parviflora",

abstract = "Five novel natural products classified as dimeric sesquiterpenes, named parviflorenes B-F (2-6), possessing three types of novel backbone frameworks, have been isolated from Curcuma parviflora (Zingiberaceae). The structures of 2-6 were elucidated by means of spectroscopic studies, and the structure of 2 was further unambiguously established by X-ray crystallographic analysis. Compounds 2, 4, and 6 have an unsymmetrical bis-cadinane skeleton, while compound 3 is a dimer of cadinane and iso-cadinane, and compound 5 possesses another novel carbon framework consisting of two cadinanes with different bond-connection. These new compounds with novel carbon skeletons showed cytotoxicity against tumor cell lines.",

keywords = "Curcuma parviflora, Cytotoxicity, Dimeric sesquiterpene, X-ray analysis, Zingiberaceae",

author = "Kazufumi Toume and Masae Takahashi and Kentaro Yamaguchi and Takashi Koyano and Thaworn Kowithayakorn and Masahiko Hayashi and Kanki Komiyama 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. ",

year = "2004",

month = nov,

day = "22",

doi = "10.1016/j.tet.2004.09.043",

language = "英語",

volume = "60",

pages = "10817--10824",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

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T1 - Parviflorenes B-F, novel cytotoxic unsymmetrical sesquiterpene-dimers with three backbone skeletons from Curcuma parviflora

AU - Toume, Kazufumi

AU - Takahashi, Masae

AU - Yamaguchi, Kentaro

AU - Koyano, Takashi

AU - Kowithayakorn, Thaworn

AU - Hayashi, Masahiko

AU - Komiyama, Kanki

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.

PY - 2004/11/22

Y1 - 2004/11/22

N2 - Five novel natural products classified as dimeric sesquiterpenes, named parviflorenes B-F (2-6), possessing three types of novel backbone frameworks, have been isolated from Curcuma parviflora (Zingiberaceae). The structures of 2-6 were elucidated by means of spectroscopic studies, and the structure of 2 was further unambiguously established by X-ray crystallographic analysis. Compounds 2, 4, and 6 have an unsymmetrical bis-cadinane skeleton, while compound 3 is a dimer of cadinane and iso-cadinane, and compound 5 possesses another novel carbon framework consisting of two cadinanes with different bond-connection. These new compounds with novel carbon skeletons showed cytotoxicity against tumor cell lines.

AB - Five novel natural products classified as dimeric sesquiterpenes, named parviflorenes B-F (2-6), possessing three types of novel backbone frameworks, have been isolated from Curcuma parviflora (Zingiberaceae). The structures of 2-6 were elucidated by means of spectroscopic studies, and the structure of 2 was further unambiguously established by X-ray crystallographic analysis. Compounds 2, 4, and 6 have an unsymmetrical bis-cadinane skeleton, while compound 3 is a dimer of cadinane and iso-cadinane, and compound 5 possesses another novel carbon framework consisting of two cadinanes with different bond-connection. These new compounds with novel carbon skeletons showed cytotoxicity against tumor cell lines.

KW - Curcuma parviflora

KW - Cytotoxicity

KW - Dimeric sesquiterpene

KW - X-ray analysis

KW - Zingiberaceae

UR - http://www.scopus.com/inward/record.url?scp=14344261355&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2004.09.043

DO - 10.1016/j.tet.2004.09.043

M3 - 学術論文

AN - SCOPUS:14344261355

SN - 0040-4020

VL - 60

SP - 10817

EP - 10824

JO - Tetrahedron

JF - Tetrahedron

IS - 48

ER -

Parviflorenes B-F, novel cytotoxic unsymmetrical sesquiterpene-dimers with three backbone skeletons from Curcuma parviflora

Abstract

Keywords

ASJC Scopus subject areas

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