Dammarane-Type Triterpenoids from Gentianella azurea

• Published in: Journal of natural products (Washington, D.C.) Vol. 77; no. 5; pp. 1201 - 1209
• Main Authors: Huang, Yu-jie, Lu, Hui, Yu, Xue-li, Zhang, Shu-wei, Wang, Wen-qiong, Fen, Lin-yin, Xuan, Li-jiang
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society and American Society of Pharmacognosy 23.05.2014; Amer Chemical Soc
• Subjects: Animals; Chemistry, Medicinal; Dammaranes; Drugs, Chinese Herbal - chemistry; Drugs, Chinese Herbal - isolation & purification; Drugs, Chinese Herbal - pharmacology; Gentianella - chemistry; Life Sciences & Biomedicine; Lipopolysaccharides - pharmacology; Macrophages - drug effects; Mice; Molecular Structure; Nitric Oxide - biosynthesis; Nuclear Magnetic Resonance, Biomolecular; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; Triterpenes - chemistry; Triterpenes - isolation & purification; Triterpenes - pharmacology; GLYCOSIDES; NITRIC-OXIDE; INFLAMMATION; CONSTITUENTS
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np500077z

Thirteen new dammarane-type triterpenoids (1–13) and four known analogues, gentirigenic acid (14) and the gentirigeosides A, B, and E (15–17), were isolated from Gentianella azurea. Their structures were elucidated by detailed analysis of the NMR, MS, and X-ray crystallographic data. This is the first report of dammarane-type triterpenoids in the Gentianella genus. In addition, the known structures of gentirigenic acid (14) and the gentirigeosides A, B, and E (15–17) were revised based on the X-ray diffraction analysis. Gentirigeoside A (15) was found to inhibit nitric oxide production in RAW 264.7 macrophages with an IC50 value of 6.6 ± 2.1 μM.