Triterpenoid saponins and others glycosides from the stem barks of Pancovia turbinata Radlk. (October 2021)

• Record Type: Journal Article
• Authors: Moffi Biang, Armand Emmanuel; Messi, Lin Marcellin; Le Doux Kamto, Eutrophe; Simo, Line Made; Lavedan, Pierre; Vedrenne, Marc; Mbing, Josephine Ngo; Pegnyemb, Dieudonné Emmanuel; Haddad, Mohamed; Noté, Olivier Placide
• Is Part Of: Carbohydrate research. Volume 508(2021)
• Publication Date: 2021-10
• Subjects: Sapindaceae -- Pancovia turbinata -- Triterpenoid saponins -- Farnesyl glycoside -- NMR; Carbohydrates -- Periodicals; Chemistry, Organic -- Periodicals; Biochemistry -- Periodicals; Carbohydrates -- Periodicals; Chimie organique -- Périodiques; Glucides -- Périodiques; Biochemistry; Carbohydrates; Chemistry, Organic; Periodicals; Electronic journals; 507.78
• DOI: 10.1016/j.carres.2021.108393
• Languages: English
• ISSNs: 0008-6215

Abstract

Abstract: In our continuing search of saponins from the plant of Sapindaceae family, phytochemical investigation of the stem barks of Pancovia turbinata Radlk., led to the isolation and structural characterization of two new triterpenoid saponins, named turbinatosides A-B (1 –2 ), one new farnesyl glycoside, named turbinoside A (3 ), one new coumarin glucoside, named panturboside A (4 ), together with a known saponin (5 ). The structures of the new compounds were established, using extensive analysis of NMR techniques, mainly 1D NMR ( 1 H, 13 C, and DEPT) and 2D NMR (COSY, NOESY, HSQC, HSQC-TOCSY and HMBC) experiments, HRESIMS and by comparison with the literature data, as 3- O - β -d -xylopyranosyl-(1 → 3)- α -l -arabinopyranosyl-(1 → 4)- β -d -glucopyranosyl-(1 → 3)- α -l -rhamnopyranosyl-(1 → 2)- α -l -arabinopyranosylhederagenin 28- O - β -d -glucopyranosyl ester (1 ), 3- O-α -l -arabinopyranosyl-(1 → 4)- β -d -glucopyranosyl-(1 → 3)- α -l -rhamnopyranosyl-(1 → 2)- α -l -arabinopyranosylhederagenin 28- O - β -d -xylopyranosyl-(1 → 4)- β -d -glucopyranosyl ester (2 ), 1- O -{ β -d -glucopyranosyl-(1 → 3)- α -l -rhamnopyranosyl-(1 → 2)-[ α -l -rhamnopyranosyl-(1 → 6)]- β -d -glucopyranosyl}-( 2E, 6E )-farnes-1, 12-diol (3 ), and 5- O - β -d -glucopyranosyl-5, 6, 7-trihydroxy-8-methoxycoumarin (4 ), respectively. Our findings highlight the presence of - 3 Rha- 2 Ara- 3 hederagenin oligosaccharidic sequence usually described in saponins from Sapindoideae subfamily of Sapindaceae family, as well as farnesol glycosides, and represent therefore a valuable contribution to the chemotaxonomy of the Sapindoideae subfamily. Graphical abstract: Image 1 Highlights: Glycosides of triterpenoid, farnesyl, and coumarin were isolated. Their structures were deduced from chemical methods and spectroscopic analysis. The presence of - 3 Rha- 2 Ara- 3 hederagenin oligosaccharidic sequence is highlighted.