Triterpenoid saponins and others glycosides from the stem barks of Pancovia turbinata Radlk

被引:3
作者
Biang, Armand Emmanuel Moffi [1 ,2 ]
Messi, Lin Marcellin [1 ,3 ,4 ]
Kamto, Eutrophe Le Doux [1 ]
Simo, Line Made [1 ]
Lavedan, Pierre [5 ]
Vedrenne, Marc [5 ]
Mbing, Josephine Ngo [1 ]
Pegnyemb, Dieudonne Emmanuel [1 ]
Haddad, Mohamed [4 ]
Note, Olivier Placide [1 ,4 ]
机构
[1] Univ Yaounde I, Fac Sci, Dept Chim Organ, Lab Pharmacochim Subst Nat, BP 812,POB 812, Yaounde, Cameroon
[2] Inst Rech Med & Etud Plantes Med Cameroun IMPM, BP 13033, Yaounde, Cameroon
[3] Inst Rech Agr Dev IRAD, BP 2067, Yaounde, Cameroon
[4] Univ Toulouse, IRD, UPS, UMR Pharma Dev 152, Toulouse, France
[5] UPS, Inst Chim Toulouse, Toulouse, France
关键词
Sapindaceae; Pancovia turbinata; Triterpenoid saponins; Farnesyl glycoside; NMR; ACYCLIC SESQUITERPENE OLIGOGLYCOSIDES; CONSTITUENTS; CONFIGURATION; PERICARPS; ROOTS; HUSKS;
D O I
10.1016/j.carres.2021.108393
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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 (H-1, C-13, and DEPT) and 2D NMR (COSY, NOESY, HSQC, HSQC-TOCSY and HMBC) experiments, HRESIMS and by comparison with the literature data, as 3-O-beta-D-xylopyranosyl-(1 -> 3)-alpha-L-arabinopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyranosylhederagenin 28-O-beta-D-glucopyranosyl ester (1), 3-O-alpha-L- arabinopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-alpha-L-arabinopyr-anosylhederagenin 28-O-beta-D-xylopyranosyl-(1 -> 4)-beta-D-glucopyranosyl ester (2), 1-O-{beta-D-glucopyranosyl-(1 -> 3)-alpha-L-rhamnopyranosyl-(1 -> 2)-[alpha-L-rhamnopyranosyl-(1 -> 6)]-beta-D-glucopyranosyl}-(2E,6E)-farnes-1,12-diol (3), and 5-O-beta-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.
引用
收藏
页数:8
相关论文
共 30 条
[1]  
Adeyemi T. O., 2012, International Journal of Biodiversity and Conservation, V4, P358
[2]  
[Anonymous], [No title captured]
[3]  
APG I.V., 2016, BOT J LINN SOC
[4]  
Aubreville A., 1973, MUSEUM NATL HIST NAT, V1
[5]   Triterpenoid saponins from the stem barks of Chytranthus klaineanus Radlk. ex Engl [J].
Biang, Armand Emmanuel Moffi ;
Kamto, Eutrophe Le Doux ;
Simo, Line Made ;
Antheaume, Cyril ;
Lavedan, Pierre ;
Vedrenne, Marc ;
Note, Olivier Placide ;
Pegnyemb, Dieudonne Emmanuel ;
Mbing, Josephine Ngo ;
Haddad, Mohamed .
PHYTOCHEMISTRY LETTERS, 2020, 37 :37-41
[6]  
Burkhill H.M, 2000, ROYAL BOT GARDEN
[7]   Characterization of chemopreventive agents from the dichloromethane extract of Eurycorymbus cavaleriei by liquid chromatography-ion trap mass spectrometry [J].
Cheng, Lin ;
Zhang, Xiaoyu ;
Zhang, Min ;
Zhang, Peng ;
Song, Zhihang ;
Ma, Zhongjun ;
Cheng, Yiyu ;
Qu, Haibin .
JOURNAL OF CHROMATOGRAPHY A, 2009, 1216 (24) :4859-4867
[8]   Triterpene saponins from Billia rosea [J].
De Freitas, Luis ;
Jimenez, Doris ;
Pimentel, Sherley ;
Mitaine-Offer, Anne -Claire ;
Pouysegu, Laurent ;
Quideau, Stephane ;
Paululat, Thomas ;
Gonzalez-Mujica, Freddy ;
Rojas, Luis B. ;
Rodriguez, Maria ;
Lacaille-Dubois, Marie-Aleth .
PHYTOCHEMISTRY, 2017, 141 :105-113
[9]   Triterpenoid saponins from the pulp of Sapindus mukorossi and their antifungal activities [J].
Hu, Qingwen ;
Chen, Ying-Ying ;
Jiao, Qi-Yang ;
Khan, Afsar ;
Li, Feng ;
Han, De-Feng ;
Cao, Gui-Dong ;
Lou, Hong-Xiang .
PHYTOCHEMISTRY, 2018, 147 :1-8
[10]   THE CONFIGURATION AND CONFORMATION OF THE ARABINOSE MOIETY IN PLATYCODINS, SAPONINS ISOLATED FROM PLATYCODON-GRANDIFLORUM, AND MI-SAPONINS FROM MADHUCA-LONGIFOLIA BASED ON C-13 AND H-1-NMR SPECTROSCOPIC EVIDENCE - THE TOTAL STRUCTURES OF THE SAPONINS [J].
ISHII, H ;
KITAGAWA, I ;
MATSUSHITA, K ;
SHIRAKAWA, K ;
TORI, K ;
TOZYO, T ;
YOSHIKAWA, M ;
YOSHIMURA, Y .
TETRAHEDRON LETTERS, 1981, 22 (16) :1529-1532