A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora

Duc Viet Ho; Takeshi Kodama; Hien Thi Bich Le; Kiem Van Phan; Thao Thi Do; Tai Huu Bui; Anh Tuan Le; Nwet Nwet Win; Hiroshi Imagawa; Takuya Ito; Hiroyuki Morita; Hoai Thi Nguyen

doi:10.1016/j.bmcl.2015.05.066

A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora

Duc Viet Ho, Takeshi Kodama, Hien Thi Bich Le, Kiem Van Phan, Thao Thi Do, Tai Huu Bui, Anh Tuan Le, Nwet Nwet Win, Hiroshi Imagawa, Takuya Ito^*, Hiroyuki Morita, Hoai Thi Nguyen

^*Corresponding author for this work

Section of Natural Products & Drug Discovery, Division of Medicinal Resources, Institute of Natural Medicine

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

21 Scopus citations

Abstract

Abstract A new polyoxygenated cyclohexene, (-)-3-O-debenzoylzeylenone (1), and a new megastigmane glycoside, grandionoside A (2), were isolated from the aerial parts of Uvaria grandiflora collected in Vietnam, together with ten known compounds including polyoxygenated cyclohexenes (3-6), a triterpenoid (7), an alkaloid (8), a long chain alcohol (9), hexenyl glycopyranoside (10), and saponins (11-12). Their chemical structures were elucidated by a combination of extensive NMR spectroscopy with X-ray crystallographic analysis for 1, and chemical conversion for 2. Compound 1 exhibited significant cytotoxicity against the LU-1 and SK-Mel-2 cell lines with IC₅₀ values of 4.68 and 3.63 μM, respectively. Remarkably, the cytotoxicity of 12 against the LU-1, KB, Hep-G2, MKN-7, and SW-480 cell lines was comparable to that of ellipticine, the positive control, with IC₅₀ values ranging from 1.24 to 1.60 μM.

Original language	English
Article number	22756
Pages (from-to)	3246-3250
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	25
Issue number	16
DOIs	https://doi.org/10.1016/j.bmcl.2015.05.066
State	Published - 2015/07/03

Keywords

Cytotoxicity
Megastigmane glycoside
Polyoxygenated cyclohexene
Uvaria grandiflora

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2015.05.066

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title = "A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora",

abstract = "Abstract A new polyoxygenated cyclohexene, (-)-3-O-debenzoylzeylenone (1), and a new megastigmane glycoside, grandionoside A (2), were isolated from the aerial parts of Uvaria grandiflora collected in Vietnam, together with ten known compounds including polyoxygenated cyclohexenes (3-6), a triterpenoid (7), an alkaloid (8), a long chain alcohol (9), hexenyl glycopyranoside (10), and saponins (11-12). Their chemical structures were elucidated by a combination of extensive NMR spectroscopy with X-ray crystallographic analysis for 1, and chemical conversion for 2. Compound 1 exhibited significant cytotoxicity against the LU-1 and SK-Mel-2 cell lines with IC50 values of 4.68 and 3.63 μM, respectively. Remarkably, the cytotoxicity of 12 against the LU-1, KB, Hep-G2, MKN-7, and SW-480 cell lines was comparable to that of ellipticine, the positive control, with IC50 values ranging from 1.24 to 1.60 μM.",

keywords = "Cytotoxicity, Megastigmane glycoside, Polyoxygenated cyclohexene, Uvaria grandiflora",

author = "Ho, {Duc Viet} and Takeshi Kodama and Le, {Hien Thi Bich} and Phan, {Kiem Van} and Do, {Thao Thi} and Bui, {Tai Huu} and Le, {Anh Tuan} and Win, {Nwet Nwet} and Hiroshi Imagawa and Takuya Ito and Hiroyuki Morita and Nguyen, {Hoai Thi}",

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doi = "10.1016/j.bmcl.2015.05.066",

language = "英語",

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T1 - A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora

AU - Ho, Duc Viet

AU - Kodama, Takeshi

AU - Le, Hien Thi Bich

AU - Phan, Kiem Van

AU - Do, Thao Thi

AU - Bui, Tai Huu

AU - Le, Anh Tuan

AU - Win, Nwet Nwet

AU - Imagawa, Hiroshi

AU - Ito, Takuya

AU - Morita, Hiroyuki

AU - Nguyen, Hoai Thi

PY - 2015/7/3

Y1 - 2015/7/3

N2 - Abstract A new polyoxygenated cyclohexene, (-)-3-O-debenzoylzeylenone (1), and a new megastigmane glycoside, grandionoside A (2), were isolated from the aerial parts of Uvaria grandiflora collected in Vietnam, together with ten known compounds including polyoxygenated cyclohexenes (3-6), a triterpenoid (7), an alkaloid (8), a long chain alcohol (9), hexenyl glycopyranoside (10), and saponins (11-12). Their chemical structures were elucidated by a combination of extensive NMR spectroscopy with X-ray crystallographic analysis for 1, and chemical conversion for 2. Compound 1 exhibited significant cytotoxicity against the LU-1 and SK-Mel-2 cell lines with IC50 values of 4.68 and 3.63 μM, respectively. Remarkably, the cytotoxicity of 12 against the LU-1, KB, Hep-G2, MKN-7, and SW-480 cell lines was comparable to that of ellipticine, the positive control, with IC50 values ranging from 1.24 to 1.60 μM.

AB - Abstract A new polyoxygenated cyclohexene, (-)-3-O-debenzoylzeylenone (1), and a new megastigmane glycoside, grandionoside A (2), were isolated from the aerial parts of Uvaria grandiflora collected in Vietnam, together with ten known compounds including polyoxygenated cyclohexenes (3-6), a triterpenoid (7), an alkaloid (8), a long chain alcohol (9), hexenyl glycopyranoside (10), and saponins (11-12). Their chemical structures were elucidated by a combination of extensive NMR spectroscopy with X-ray crystallographic analysis for 1, and chemical conversion for 2. Compound 1 exhibited significant cytotoxicity against the LU-1 and SK-Mel-2 cell lines with IC50 values of 4.68 and 3.63 μM, respectively. Remarkably, the cytotoxicity of 12 against the LU-1, KB, Hep-G2, MKN-7, and SW-480 cell lines was comparable to that of ellipticine, the positive control, with IC50 values ranging from 1.24 to 1.60 μM.

KW - Cytotoxicity

KW - Megastigmane glycoside

KW - Polyoxygenated cyclohexene

KW - Uvaria grandiflora

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A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora

Abstract

Keywords

ASJC Scopus subject areas

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