Resveratrol Derivatives from Vatica albiramis

被引:17
作者
Abe, Naohito [1 ]
Ito, Tetsuro [1 ]
Oyama, Masayoshi [1 ]
Sawa, Ryuichi [2 ]
Takahashi, Yoshikazu [2 ]
Iinuma, Munekazu [1 ]
机构
[1] Gifu Pharmaceut Univ, Lab Pharmacognosy, Gifu 5011196, Japan
[2] Inst Microbial Chem, Shinagawa Ku, Tokyo 1410021, Japan
关键词
Vatica albiramis; Dipterocarpaceae; resveratrol oligomer; structure elucidation; albiraminol; UPUNA-BORNEENSIS; STEM BARK; OLIGOMERS; PLANTS; TETRAMERS;
D O I
10.1248/cpb.59.452
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Three new stilbene derivatives, albiraminols A (1) (resveratrol hexamer), B (2) (resveratrol dimer), and vatalbinoside F (3) (mono-glucoside of resveratrol dimer), along with malibatol were isolated from acetone soluble portions of the stem of Vatica albiramis. The structures of the isolates were established on the basis of spectroscopic analyses, including a detailed NMR spectroscopic investigation. The biosynthetic aspects of the isolates are discussed in this paper. Compound 1 is composed of tetrameric resveratrol (vaticanol B (1A)) and dimeric resveratrol (1B) and is the first instance of the resveratrol derivative bearing a 5,6,11,12-tetrahydro-5,11-epoxydibenzo[a,e][8]annulene ring system. Compound 2 possesses a novel 4,5-dihydro-13-oxabenzo[3,4]azuleno[7,8,1-jkl]phenanthrene skeleton in the framework.
引用
收藏
页码:452 / 457
页数:6
相关论文
共 19 条
[11]   Antibacterial activity of extracts prepared from tropical and subtropical plants on methicillin-resistant Staphylococcus aureus [J].
Nitta, T ;
Arai, T ;
Takamatsu, H ;
Inatomi, Y ;
Murata, H ;
Iinuma, M ;
Tanaka, T ;
Ito, T ;
Asai, F ;
Ibrahim, I ;
Nakanishi, T ;
Watabe, K .
JOURNAL OF HEALTH SCIENCE, 2002, 48 (03) :273-276
[12]   AMPELOPSIN-A, AMPELOPSIN-B AND AMPELOPSIN-C, NEW OLIGOSTILBENES OF AMPELOPSIS-BREVIPEDUNCULATA VAR HANCEI [J].
OSHIMA, Y ;
UENO, Y ;
HIKINO, H ;
YANG, LL ;
YEN, KY .
TETRAHEDRON, 1990, 46 (15) :5121-5126
[13]   Resveratrol tetramers from Vatica diospyroides [J].
Seo, EK ;
Chai, HB ;
Constant, HL ;
Santisuk, T ;
Reutrakul, V ;
Beecher, CWW ;
Farnsworth, NR ;
Cordell, GA ;
Pezzuto, JM ;
Kinghorn, AD .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :6976-6983
[14]  
*SER SOFTW, PCMODEL V9 0
[15]   Vaticanol C, a novel resveratrol tetramer, reduces lymph node and lung metastases of mouse mammary carcinoma carrying p53 mutation [J].
Shibata, Masa-Aki ;
Akao, Yukihiro ;
Shibata, Eiko ;
Nozawa, Yoshinori ;
Ito, Tetsuro ;
Mishima, Satoshi ;
Morimoto, Junji ;
Otsuki, Yoshinori .
CANCER CHEMOTHERAPY AND PHARMACOLOGY, 2007, 60 (05) :681-691
[16]   DISTRIBUTION OF RESVERATROL OLIGOMERS IN PLANTS [J].
SOTHEESWARAN, S ;
PASUPATHY, V .
PHYTOCHEMISTRY, 1993, 32 (05) :1083-1092
[17]   Vaticanol B, a resveratrol tetramer, regulates endoplasmic reticulum stress and inflammation [J].
Tabata, Yoshiyuki ;
Takano, Katsura ;
Ito, Tetsuro ;
Iinuma, Munekazu ;
Yoshimoto, Tanihiro ;
Miura, Hikari ;
Kitao, Yasuko ;
Ogawa, Satoshi ;
Hori, Osamu .
AMERICAN JOURNAL OF PHYSIOLOGY-CELL PHYSIOLOGY, 2007, 293 (01) :C411-C418
[18]  
TSUKAMOTO T, NUTR METAB, V7
[19]   Antimicrobial resveratrol tetramers from the stem bark of Vatica oblongifolia ssp oblongifolia [J].
Zgoda-Pols, JR ;
Freyer, AJ ;
Killmer, LB ;
Porter, JR .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (11) :1554-1559