Details

Autor(en) / Beteiligte

• Pailee, Phanruethai
• Prachyawarakorn, Vilailak
• Mahidol, Chulabhorn
• Ruchirawat, Somsak
• Kittakoop, Prasat

Titel

Protoberberine Alkaloids and Cancer Chemopreventive Properties of Compounds from Alangium salviifolium

Ist Teil von

• European Journal of Organic Chemistry, 2011-07, Vol.2011 (20-21), p.3809-3814

Ort / Verlag

Weinheim: WILEY-VCH Verlag

Erscheinungsjahr

2011

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• New protoberberine alkaloids, namely alangiumkaloids A (1) and B (2), 27‐O‐trans‐caffeoylcylicodiscic acid (3), and β‐D‐glucopyranos‐1‐yl N‐methylpyrrole‐2‐carboxylate (5) together with myriceric acid B (4), isoalangiside (6), alangiside (7), 3‐O‐demethyl‐2‐O‐methylalangiside (8), and demethylalangiside (9) have been isolated from Alangium salviifolium. The cancer chemopreventive properties and cytotoxic activities of the isolated compounds were evaluated. Compounds 3, 4, and 9 scavenged DPPH free radicals with IC50 values of 21.4, 21.8, and 24.0 μM, respectively. Alangisides 7 and 9 inhibited superoxide anion radical formation in the xanthine/xanthine oxidase (XXO) assay with IC50 values of 19.4 and 5.3 μM, respectively. Compounds 6–9 showed excellent antioxidant activity in the oxygen radical absorbance capacity (ORAC) assay with 12.8–24.9 ORAC units. Compounds 3 and 4 inhibited aromatase activity with IC50 values of 4.7 and 6.8 μM, respectively. Although the isolated compounds showed only weak cytotoxicity or were inactive, compounds 3 and 4 exhibited cytotoxic activity towards the MOLT‐3 cell line with IC50 values of 5.6 and 3.9 μM, respectively, and compound 8 selectively inhibited the growth of the HepG2 cancer cell line with an IC50 value of 7.1 μM. Protoberberine alkaloids 1 and 2, triterpene caffeate 3, and β‐D‐glucopyranos‐1‐yl N‐methylpyrrole‐2‐carboxylate (5) have been isolated from Alangium salviifolium. Radical scavenging, antioxidant, and aromatase inhibitory activities imply that the isolated compounds might be useful for cancer chemoprevention.