title: A new polyoxygenated cyclohexene and a new megastigmane glycoside from Uvaria grandiflora.
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.
authors.affiliation: Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, 06 Ngo Quyen, Hue City, Viet Nam.
authors.forename: Duc Viet
authors.initials: DV
authors.lastname: Ho
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
authors.forename: Takeshi
authors.initials: T
authors.lastname: Kodama
authors.affiliation: Faculty of Pharmacy, Hue University of Medicine and Pharmacy, Hue University, 06 Ngo Quyen, Hue City, Viet Nam.
authors.forename: Hien Thi Bich
authors.initials: HT
authors.lastname: Le
authors.affiliation: Institute of Marine Biochemistry, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Kiem Van
authors.initials: KV
authors.lastname: Phan
authors.affiliation: Institute of Biotechnology, VAST, 18 Hoang Quoc Viet, Caugiay, Hanoi, Viet Nam.
authors.forename: Thao Thi
authors.initials: TT
authors.lastname: Do
authors.affiliation: 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.
authors.forename: Tai Huu
authors.initials: TH
authors.lastname: Bui
authors.affiliation: Quang Tri Center of Science and Technology, Mientrung Inst. for Scientific Research, 121 Ly Thuong Kiet, Dong Ha, Quang Tri, Viet Nam.
authors.forename: Anh Tuan
authors.initials: AT
authors.lastname: Le
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
authors.forename: Nwet Nwet
authors.initials: NN
authors.lastname: Win
authors.affiliation: Faculty of Pharmaceutical Sciences, Tokushima Bunri University, Yamashiro-cho, Tokushima 770-8514, Japan.
authors.forename: Hiroshi
authors.initials: H
authors.lastname: Imagawa
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan. Electronic address: itot@inm.u-toyama.ac.jp.
authors.forename: Takuya
authors.initials: T
authors.lastname: Ito
authors.affiliation: Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan. Electronic address: hmorita@inm.u-toyama.ac.jp.
authors.forename: Hiroyuki
authors.initials: H
authors.lastname: Morita
authors.affiliation: 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.
authors.forename: Hoai Thi
authors.initials: HT
authors.lastname: Nguyen
mesh_terms: D000972:Antineoplastic Agents, Phytogenic / Q000302:isolation & purification* / Q000494:pharmacology*; D002240:Carbohydrate Sequence; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D003512:Cyclohexanones / Q000302:isolation & purification* / Q000494:pharmacology*; D053138:Cyclohexenes / Q000302:isolation & purification* / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D004611:Ellipticines / Q000494:pharmacology; D005960:Glucosides / Q000302:isolation & purification* / Q000494:pharmacology*; D006027:Glycosides; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D008969:Molecular Sequence Data; D045792:Norisoprenoids / Q000302:isolation & purification* / Q000494:pharmacology*; D031046:Uvaria / Q000737:chemistry*; D014961:X-Ray Diffraction
chemical_list: D000972:Antineoplastic Agents, Phytogenic; D003512:Cyclohexanones; D053138:Cyclohexenes; D004611:Ellipticines; D005960:Glucosides; D006027:Glycosides; D045792:Norisoprenoids; C413264:megastigmane; C034192:ellipticine
keywords: Cytotoxicity; Megastigmane glycoside; Polyoxygenated cyclohexene; Uvaria grandiflora