2014Chemistry & BiodiversityRequires access

Triterpene Saponins from the Roots of Ilex asprella

Lei Yu, Shepo Shi, Yuelin Song, Dan Bi, Peng‐Fei Tu

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Abstract

Six new triterpene saponins, ilexasprellanosides A-F (1-6, resp.), together with eleven known compounds were isolated from the roots of Ilex asprella. The new saponins were characterized as ursa-12,18-dien-28-oic acid 3-O-β-D-xylopyranoside (1), 19α-hydroxyursolic acid 3-O-β-D-(2'-O-acetylxylopyranoside) (2), 19α-hydroxyursolic acid 3-O-β-D-glucuronopyranoside (3), 3β,19α-dihydroxyolean-12-en-23,28-dioic acid 28-O-β-D-glucopyranoside (4), 19α-hydroxyoleanolic acid 3-O-β-D-(2'-O-acetylxylopyranoside) (5), 19α-hydroxyoleanolic acid 3-O-β-D-glucuronopyranoside (6). The structures of the new compounds were elucidated by analysis of their spectroscopic data and chemical degradation. Compounds 2, 4, oleanolic acid 3-O-β-D-glucuronopyranoside, 3-β-acetoxy-28-hydroxyurs-12-ene, and pomolic acid showed significant cytotoxic activities against human tumor cell line A549 (IC50 values of 1.87, 2.51, 1.41, 3.24, and 5.63 μM, resp.).

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What this paper is about

Six new triterpene saponins, ilexasprellanosides A-F (1-6, resp.), together with eleven known compounds were isolated from the roots of Ilex asprella. The new saponins were characterized as ursa-12,18-dien-28-oic acid 3-O-β-D-xylopyranoside (1), 19α-hydroxyursolic acid 3-O-β-D-(2'-O-acetylxylopyranoside) (2), 19α-hydroxyursolic acid 3-O-β-D-glucuronopyranoside (3), 3β,19α-dihydroxyolean-12-en-23,28-dioic acid 28-O-β-D-glucopyranoside (4), 19α-hydroxyoleanolic acid 3-O-β-D-(2'-O-acetylxylopyranoside) (5), 19α-hydroxyoleanolic acid 3-O-β-D-glucuronopyranoside (6). The structures of the new compounds were elucidated by analysis of their spectroscopic data and chemical degradation. Compounds 2, 4, oleanolic acid 3-O-β-D-glucuronopyranoside, 3-β-acetoxy-28-hydroxyurs-12-ene, and pomolic acid showed significant cytotoxic activities against human tumor cell line A549 (IC50 values of 1.87, 2.51, 1.41, 3.24, and 5.63 μM, resp.).

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Available abstract

Six new triterpene saponins, ilexasprellanosides A-F (1-6, resp.), together with eleven known compounds were isolated from the roots of Ilex asprella. The new saponins were characterized as ursa-12,18-dien-28-oic acid 3-O-β-D-xylopyranoside (1), 19α-hydroxyursolic acid 3-O-β-D-(2'-O-acetylxylopyranoside) (2), 19α-hydroxyursolic acid 3-O-β-D-glucuronopyranoside (3), 3β,19α-dihydroxyolean-12-en-23,28-dioic acid 28-O-β-D-glucopyranoside (4), 19α-hydroxyoleanolic acid 3-O-β-D-(2'-O-acetylxylopyranoside) (5), 19α-hydroxyoleanolic acid 3-O-β-D-glucuronopyranoside (6). The structures of the new compounds were elucidated by analysis of their spectroscopic data and chemical degradation. Compounds 2, 4, oleanolic acid 3-O-β-D-glucuronopyranoside, 3-β-acetoxy-28-hydroxyurs-12-ene, and pomolic acid showed significant cytotoxic activities against human tumor cell line A549 (IC50 values of 1.87, 2.51, 1.41, 3.24, and 5.63 μM, resp.).

Key concepts: Triterpene, Oleanolic acid, Chemistry, Stereochemistry, Terpene, Saponin, Triterpenoid, Alternative medicine

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