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

Bioorg Med Chem Lett. 2015 Aug 15;25(16):3246-50. doi: 10.1016/j.bmcl.2015.05.066. Epub 2015 May 30.

Authors

Duc Viet Ho¹, Takeshi Kodama², Hien Thi Bich Le¹, Kiem Van Phan³, Thao Thi Do⁴, Tai Huu Bui⁵, Anh Tuan Le⁶, Nwet Nwet Win², Hiroshi Imagawa⁷, Takuya Ito⁸, Hiroyuki Morita⁹, Hoai Thi Nguyen¹⁰

Affiliations

¹ Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, 06 Ngo Quyen, Hue City, Viet Nam.
² Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
³ Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
⁴ Institute of Biotechnology, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
⁵ Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam; College of Pharmacy, Chungnam National University, Daejeon 305-764, Republic of Korea.
⁶ Quang Tri Center of Science and Technology, Mientrung Inst. for Scientific Research, 121 Ly Thuong Kiet, Dong Ha, Quang Tri, Viet Nam.
⁷ Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
⁸ Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan. Electronic address: itot@inm.u-toyama.ac.jp.
⁹ Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan. Electronic address: hmorita@inm.u-toyama.ac.jp.
¹⁰ Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, 06 Ngo Quyen, Hue City, Viet Nam; Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan. Electronic address: hoai77@gmail.com.

PMID: 26077495
DOI: 10.1016/j.bmcl.2015.05.066

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.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / isolation & purification*
Antineoplastic Agents, Phytogenic / pharmacology*
Carbohydrate Sequence
Cell Line, Tumor
Cell Survival / drug effects
Cyclohexanones / isolation & purification*
Cyclohexanones / pharmacology*
Cyclohexenes / isolation & purification*
Cyclohexenes / pharmacology*
Drug Screening Assays, Antitumor
Ellipticines / pharmacology
Glucosides / isolation & purification*
Glucosides / pharmacology*
Glycosides
Humans
Magnetic Resonance Spectroscopy
Models, Molecular
Molecular Sequence Data
Norisoprenoids / isolation & purification*
Norisoprenoids / pharmacology*
Uvaria / chemistry*
X-Ray Diffraction

Substances

Antineoplastic Agents, Phytogenic
Cyclohexanones
Cyclohexenes
Ellipticines
Glucosides
Glycosides
Norisoprenoids
megastigmane
ellipticine