Chemical constituents of Adinandra glischroloma Hand.–Mazz. and their chemotaxonomic significance

• Published in: Biochemical systematics and ecology 2024-04, Vol.113, p.104803, Article 104803
• Main Authors: Hang, Pho Thi Thuy, Nga, Nguyen Thi Thu, Thuong, Sy Danh, Thanh, Le Nguyen, Van Phuong, Nguyen, Mau, Chu Hoang, Quan, Nguyen Huu
• Format: Article
• Language: English
• Subjects: Adinandra glischroloma; betulinic acid; chemotaxonomy; diterpenoids; ecology; family; Flavonoids; genus; Lignan; lignans; Megastigmane; oleanolic acid; Pentacyclic triterpenes; Pentaphylacaceae; species; spectroscopy; sterols; ursolic acid; Vietnam
• ISSN: 0305-1978; 1873-2925
• DOI: 10.1016/j.bse.2024.104803

The phytochemical investigation of the leaves of Adinandra glischroloma Hand.–Mazz. resulted in the isolation of fourteen known compounds including nine triterpenoids: 28-nor-urs-12-ene-3β,17β-diol (1), micromeric acid (2), 23-hydroxy ursolic acid (3), euscaphic acid (4), pomolic acid (5), 3,13-dihydroxy ursolic acid 28,13-olide (6), ursolic acid (7), betulinic acid (8), and oleanolic acid (9); one diterpene: ent-kaur-16-en-19-oic-acid (10); one megastigmane: (3S, 5R, 6S, 9R)-megastigmane-3,9-diol (11), one flavonoid: isoquercetin (12); one lignan: syringaresinol (13), and one sterol: β-sitosterol (14). The chemical structures were determined by NMR, MS spectroscopic analyses and comparison with literature values. All of these compounds were isolated from A. glischroloma for the first time. Furthermore, this is the first report on the isolation of compounds 1–3, 10, and 11 from the genus Adinandra and the Pentaphylacaceae family. Compounds 1–3, 10, and 11 may be used as chemotaxonomic markers to differentiate between A. glischromola from other species of the Adinandra genus. Our results showed that A. glischroloma plant is rich in pentacyclic triterpenes and possessed a strong relationship with other Adinandra species in Vietnam. [Display omitted] •Fourteen compounds 1–14 were identified from the leaves of Adinandra glischroloma.•Compounds 1–3, 10, and 11 are reported for the first time from the Pentaphylacaceae family.•The chemical composition of A. glischroloma plant is rich in pentacyclic triterpenes.