Isolation and synthesis of a new bioactive ellagic acid derivative from Combretum yunnanensis.
A new ellagic acid derivative (1) was isolated from the branches of Combretum yunnanensis, and its structure was assigned as 4-(4' '-O-acetyl-alpha-rhamnopyranosyl)ellagic acid by analysis of its spectral data. Total synthesis of 1 was achieved by the glycosylation of 3,3'-di-O-benzylellagic acid (5) with 4-O-acetyl-2,3-di-O-benzyl-l-rhamnose (4) as a key reaction, and the absolute configuration of 1 was determined. Compound 1 showed weak inhibitory activity against the growth of various tumor cells and inhibited HIV-1 protease.
Asami
Yukihiro
Y
Department of Biosciences, School of Science and Technology, Teikyo University, 1-1 Toyosatodai, Utsunomiya 320-8551, Japan.
Ogura
Takashi
T
Otake
Noboru
N
Nishimura
Toshio
T
Xinsheng
Yao
Y
Sakurai
Takashi
T
Nagasawa
Hiromichi
H
Sakuda
Shohei
S
Tatsuta
Kuniaki
K
D000818:Animals; D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D029765:Combretum / Q000737:chemistry*; D004317:Doxorubicin / Q000494:pharmacology; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004610:Ellagic Acid / Q000031:analogs & derivatives / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D017320:HIV Protease Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D020128:Inhibitory Concentration 50; D007941:Leukemia P388; D051379:Mice; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular
C478195:4-(4''-O-acetyl-alpha-rhamnopyranosyl)ellagic acid; D000972:Antineoplastic Agents, Phytogenic; D004365:Drugs, Chinese Herbal; D017320:HIV Protease Inhibitors; D004610:Ellagic Acid; D004317:Doxorubicin