Oleanane triterpenoids from Rubia philippinensis and their inhibitory effect on 20-HETE synthesis

• Published in: Natural product research Vol. 35; no. 8; pp. 1267 - 1273
• Main Authors: Quan, Khong Trong, Min, Byung Gu, Hwang, In Hyun, Choi, Yeon Jung, Kim, Sang Kyum, Na, MinKyun
• Format: Journal Article
• Language: English
• Published: England Taylor & Francis 01-04-2021; Taylor & Francis Ltd
• Subjects: 16β-hydroxyrubiprasin B; 20-HETE; Humans; Hydroxyeicosatetraenoic Acids - biosynthesis; Magnetic Resonance Spectroscopy; Microsomes - drug effects; Microsomes - metabolism; Molecular Structure; NMR; Nuclear magnetic resonance; Oleanane triterpenoids; Oleanolic acid; Oleanolic Acid - analogs & derivatives; Oleanolic Acid - chemistry; Plant Roots - chemistry; Rubia - chemistry; Rubia philippinensis; Structure-Activity Relationship; Synthesis; Triterpenes - chemistry; Triterpenes - pharmacology; Triterpenoids; 20-HETE; Rubia philippinensis; 16β-hydroxyrubiprasin B; Oleanane triterpenoids
• ISSN: 1478-6419; 1478-6427
• DOI: 10.1080/14786419.2019.1645656

A new oleanane triterpenoid (2) was isolated from the roots of Rubia philippinensis. The structure of 2 was determined by analysis of HRMS and NMR data and identified as a rubiprasin analogue, 16β-hydroxyrubiprasin B. Four related known compounds were also encountered which include rubiprasin B (1), maslinic acid (3), 4-epi-hederagenin (4) and oleanolic acid (5). The compounds 3-5 displayed moderate inhibitory activity against the synthesis of the eicosanoid 20-HETE.