1896-77-1Relevant academic research and scientific papers
New cytotoxic spirostane saponin and biflavonoid glycoside from the leaves of Acacia saligna (Labill.) H.L. Wendl.
Gedara, Sahar R.,Galala, Amal A.
, p. 324 - 329 (2014)
New naturally occurring spirostane saponin (25S)-5β-spirostan-3β- yl-3-O-β-d-xylopyranosyl(1 → 3)-O-β-d-xylopyranosyl(1 → 4)-β-d-galactopyranoside (6) and biflavonoid glycoside myricetin-3-O- rhamnoside (C7-O-C7) myricetin-3-O-rhamnoside (4) along with a series of known compounds erythrodiol (1), 3β-O-trans-p-coumaroyl-erythrodiol (2), quercetin-3-O-α-l-rhamnoside (3) and myricetin-3-O-α-l-rhamnoside (5) were separated from the leaves of Acacia saligna (Labill.), H.L. Wendl. Compounds 1 and 2 were separated for the first time from genus Acacia. The structures of compounds 1-6 were established on the basis of extensive 1D and 2D NMR spectroscopic techniques in combination with EI-MS and HR-ESI-MS. These compounds were screened for their antioxidant and cytotoxic activities against HEPG2 (liver cancer) cell line and significant results were obtained. 2013
Practical Synthesis of α-Amyrin, β-Amyrin, and Lupeol: The Potential Natural Inhibitors of Human Oxidosqualene Cyclase
Chen, Dongyin,Xu, Fengguo,Zhang, Pu,Deng, Jie,Sun, Hongbin,Wen, Xiaoan,Liu, Jun
, (2017/10/20)
A practical synthesis of α-amyrin (1), β-amyrin (2), and lupeol (3) was accomplished in total yields of 32, 42, and 40% starting from easily available ursolic acid (4), oleanolic acid (5), and betulin (6), respectively. Remarkably, these three natural pentacyclic triterpenes exhibited potential inhibitory activity against human oxidosqualene cyclase.
Partial synthesis of C-ring derivatives from oleanolic and maslinic acids. Formation of several triene systems by chemical and photochemical isomerization processes
García-Granados, Andrés,López, Pilar E.,Melguizo, Enrique,Parra, Andrés,Simeó, Yolanda
, p. 1491 - 1503 (2007/10/03)
Some triterpenic compounds modified in C-ring were semi-synthesised from oleanolic acid contained in the solid waste of olive-oil pressing. The corresponding esters of oleanolic and maslinic acids rendered products with a diene system, which led to oleantrienes resembling previtamin D2 by an electrocyclic reaction. Chemical and photochemical isomerization of these compounds yielded two different trienes with similar structure to tachysterol and vitamin D2.
OXIDATIVE TRANSFORMATIONS OF TRITERPENOIDS OF THE URSANE AND OLEANANE SKELETA WITH HYDROGEN PEROXIDE. INTRODUCTION OF 11,12-DOUBLE BOND AND 13(28)OXIDE MOIETY IN THE URSANE SYSTEM
Majumder, P. L.,Bagchi, A.
, p. 649 - 656 (2007/10/02)
Treatment of oleanolic acid acetate (1b) with H2O2 in boiling HOAc gave the epoxy-γ-lactone 2b and the 12-hydroxy-γ-lactone 3b.The total absence of the 12-ketodihydro acid 4b among the oxidation products of 1b has been rationalised.The results of this reaction with several isomeric pairs of triterpenoids of the ursane and oleanane skeleta bearing functional groups at C-17 other than a carboxyl group show that for any appreciable oxidation involving the intermediacy of a 12β,13β-epoxide 6a or 6b, the 17-carboxyl group is an essential requirement.An intramolecular epoxidation of 12,13-double bond of 1a and 1b by 17-percarboxy acid formed in situ has been envisaged.The reactions aiming at introducing 11,12-double bond and 13(28)-oxide moiety in the ursane system are described.The desired compound 2c was obtained by treatment of the triol 1p with TsOH.With H2O2/TsOH, 1p, however, gave besides 2c, the rearranged product 8a.The difference in the chemical behaviour of 1p and 1q has been explained.Treatment of 2e with H2O2 in boiling HOAc gave the epoxide 2f.The mechanism of formation of 2a and 2b is discussed in the light of this observation.
BIARYLHEPTANOIDS AND OTHER CONSTITUENTS FROM WOOD OF ALNUS JAPONICA
Nomura, Masayasu,Tokoroyama, Takashi,Kubota, Takashi
, p. 1097 - 1104 (2007/10/02)
The wood of Alnus japonica has been shown to contain a number of biarylheptanoids as well as other phenolics, including secoisolariciresinol diferulate.The co-occurence of cyclized biarylheptanoids with their corresponding acyclic biarylheptanoids has been demonstrated and this fact may have biosynthetic significance.The possible chemotaxonomic importance of biarylheptanoids in members of the Betulaceae is discussed.The isolation and identification of several steroids and triterpenoids are also described.Key Word Index- Alnus japonica; Betulaceae; new biarylheptanoids; biosynthesis; chemotaxonomy; secoisolariciresinol diferulate; steroids; oleanan triterpenoids.
