Anti-HIV-1 protease triterpenoid saponins from the seeds of Aesculus chinensis.
Eight bioactive triterpenoid saponins (1-8) were isolated from the seeds of Aesculus chinensis, four of which are novel compounds. The major saponins were identified as escin Ia (1), Ib (2), isoescin Ia (3) and Ib (4), while the new compounds were identified as 22alpha-tigloyl-28-acetylprotoaescigenin-3beta-O-¿beta -D-glucopyranos yl (1-2) ¿beta-D-glucopyranosyl (1-4)-beta-D-glucopyranosiduronic acid (escin IVc, 5), 22alpha-angeloyl-28-acetylprotoaescigenin-3beta-O-¿bet a-D-glucopyrano syl (1-2) ¿beta-D-glucopyranosyl (1-4)-beta-D-glucopyranosiduronic acid (escin IVd, 6), 28-tigloylprotoaescigenin-3beta-O-¿beta-D-glucopyranosyl (1-2) ¿beta-D-glucopyranosyl (1-4)-beta-D-glucopyranosiduronic acid (escin IVe, 7), and 28-angeloylprotoaescigenin-3beta-O-¿beta-D-glucopyranosyl (1-2) ¿beta-D-glucopyranosyl (1-4)-beta-D-glucopyranosiduronic acid (escin IVf, 8). The structures were determined by chemical and spectroscopic methods. All the above compounds were evaluated for their inhibitory activity against HIV-1 protease.
Yang
X W
XW
National Laboratory of Natural and Biomimetic Drugs, Beijing Medical University, Beijing 100083, People's Republic of China. xwyang@mail.bjmu.edu.cn
Zhao
J
J
Cui
Y X
YX
Liu
X H
XH
Ma
C M
CM
Hattori
M
M
Zhang
L H
LH
D002240:Carbohydrate Sequence; D002681:China; D018360:Crystallography, X-Ray; D017320:HIV Protease Inhibitors / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D010936:Plant Extracts / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*; D013055:Spectrophotometry, Infrared; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology*
D017320:HIV Protease Inhibitors; D010936:Plant Extracts; D012503:Saponins; D014315:Triterpenes