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.
Duc Viet Ho  1 ,  Takeshi Kodama  2 ,  Hien Thi Bich Le  1 ,  Kiem Van Phan  3 ,  Thao Thi Do  4 ,  Tai Huu Bui  5 ,  Anh Tuan Le  6 ,  Nwet Nwet Win  2 ,  Hiroshi Imagawa  7 ,  Takuya Ito  8 ,  Hiroyuki Morita  9 ,  Hoai Thi Nguyen  10
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: [email protected].
  • 9. Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan. Electronic address: [email protected].
  • 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: [email protected].
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.
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