559-70-6Relevant articles and documents
Purification and properties of squalene-2,3-epoxide cyclases from pea seedlings
Abe,Sankawa,Ebizuka
, p. 1755 - 1760 (1992)
Dramatic changes in the activities of squalene-2,3-epoxide: cycloartenol cyclase and β-amyrin cyclase were observed in germinating pea seeds. By taking advantage of this phenomenon, the two cyclases were purified from pea seedlings. The cyclases were purified to homogeneity by solubilization with Triton X-100, chromatography on hydroxylapatite and diethylaminoethyl (DEAE)-cellulose, isoelectric focusing and gel filtration. Cycloartenol cyclase was purified 471-fold to a specific activity of 167 pkat/mg protein, while β-amyrin cyclase was purified 4290-fold to a specific activity of 28 pkat/mg protein. They each showed a single band on sodium dodecyl sulfate polyacrylamide gel electrophoresis with a molecular mass of 55 and 35 kilodaltons (kDa), respectively. The apparent K(m) values for (3S)-squalene-2,3-epoxide were estimated to be 25 and 50 μm, respectively. The cyclases required Triton X-100 or deoxycholate for their highest activity and each showed a broad pH optimum within the range of pH 6.5-7.5. Inhibition by p-chloromercuribenzene sulfonic acid and N-ethylmaleimide suggested involvement of an SH group at the active site of each enzyme.
An improved scalable synthesis of α- and β-amyrin
Serbian, Immo,Csuk, René
, (2018/07/13)
The synthesis of α- and β-amyrin was accomplished starting from easily accessible starting materials, oleanolic, and ursolic acid. The procedures allow the preparation of β-amyrin in an exceptionally short scalable manner via selective iodation and reduction. For α-amyrin, a different synthetic approach had to be chosen providing access to α-amyrin in medium-to-large scale.
COMPOSITIONS COMPRISING TRITERPENOIDS AND USES THEREOF FOR TREATING OPTIC NEUROPATHY
-
, (2018/03/28)
The invention relates to compositions and formulations comprising at least one triterpenoic acid and at least one neutral triterpenoid and uses thereof for treating optic neuropathy conditions.
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.
COMPOSITIONS COMPRISING TRITERPENOIDS
-
Page/Page column 88; 89; 90, (2017/04/11)
The invention relates to compositions and formulations comprising at least one triterpenoic acid and at least one neutral triterpenoid and uses thereof for treating for use in treating a condition selected from Alzheimer's disease (AD), Parkinson's Diseases (PD) and vascular dementia (VD).
β-Amyrin Biosynthesis: Promiscuity for Steric Bulk at Position 23 in the Oxidosqualene Substrate and the Significance of Hydrophobic Interaction between the Methyl Group at Position 30 and the Binding Site
Kaneko, Ikki,Hoshino, Tsutomu
, p. 6657 - 6671 (2016/08/16)
To examine how the sterics at the 23 position of (3S)-2,3-oxidosqualene 1 influence the polycyclization cascade in β-amyrin biosynthesis, substrate analogues substituted with an ethyl group (10, 11), a hydrogen atom (12, 13), or a propyl residue (14) at the 23 position were incubated with β-amyrin synthase. The bulkier ethyl group was accepted as a substrate, leading to formation of the β-amyrin skeleton (42, 43) without truncation of the multiple cyclization reactions. Analogue 13, possessing a hydrogen atom and an ethyl group at the 23E and 23Z positions, respectively, was also converted into the β-amyrin skeleton 45. However, the analogue lacking an ethyl group at the 23Z position (12) underwent almost no conversion, strongly indicating that an alkyl group must exist at the Z position. The cyclization of the analogue with a propyl substituent at the Z position (14) was poor. Analogue 15 possessing CH2OH at the 23E position afforded a new compound 47 in a high yield as a result of trapping of the final oleanyl cation. Conversely, 16 with 23Z-CH2OH afforded novel compounds 48-50 in low yields, which resulted from the intermediary dammarenyl and baccharenyl cations. Therefore, the hydrophobic interaction between the 23Z-alkyl group and its binding site (possibly via CH/π interaction) is critical for adopting the correct chair-chair-chair-boat-boat conformation and for the full cyclization cascade.
Triterpene esters: Natural products from dorstenia arifolia (moraceae)
Fingolo, Catharina E.,De S. Santos, Thabata,Filho, Marcelo D.M. Vianna,Kaplan, Maria Auxiliadora C.
, p. 4247 - 4256 (2013/06/05)
The phytochemical study of Dorstenia arifolia Lam. (Moraceae) has led to the identification of 18 triterpenes esterified by fatty acids, five triterpenes without esterification, 12 triterpenes esterified by acetic acid, together with a known furanocoumarin: α-amyrin (1), β-amyrin (2) α-amyrin acetate (3) β-amyrin acetate (4), α-amyrin octanoate (5), β-amyrin octanoate (6), α-amyrin decanoate (7), β-amyrin decanoate (8), α-amyrin dodecanoate (9), β-amyrin dodecanoate (10), α-amyrin tetradecanoate (11), β-amyrin tetradecanoate (12), α-amyrin hexadecanoate (13), β-amyrin hexadecanoate (14), glutinol (15), glutinyl acetate (16), 11-oxo-α-amyrin (17), 11-oxo-β-amyrin (18), 11-oxo-α-amyrin acetate (19), 11-oxo- β-amyrin acetate (20) 11-oxo-α-amyrin octanoate (21) 11-oxo-β-amyrin octanoate (22), 11-oxo-α-amyrin decanoate (23), 11-oxo-β-amyrin decanoate (24) 11-oxo-α-amyrin dodecanoate (25) 11-oxo-β-amyrin dodecanoate (26), ursa-9(11),12-dien-3-yl acetate (27), oleana-9(11),12-dien-3-yl acetate (28), ursa-9(11),12-dien-3-yl decanoate (29), oleana- 9(11),12-dien-3-yl decanoate (30), 12,13-epoxyolean-3-yl acetate (31), 12,13-epoxyolean- 9(11)en-3-yl acetate (32), taraxeryl acetate (33), lupenyl acetate (34), lanosta-8,24-dien-3- yl acetate (35) and psoralen (36). The identification of the triterpene compounds isolated as isomeric mixtures obtained from the hexane extract was based mainly in mass spectra and 13C-NMR data. The long-chain alkanoic acid esters of the triterpenes α- and β-amyrin; 11-oxo-α- and 11-oxo-β-amyrin; ursa- and olean-9(11),12-dien-3-yl; have not been reported before in the literature as constituents of the Dorstenia genus.
TRITERPENE OXIDASE DERIVED FROM PLANT BELONGING TO GENUS GLYCYRRHIZA, GENE ENCODING THE SAME, AND METHOD OF USING THE SAME
-
, (2012/10/08)
Identification of a protein having an activity of oxidizing oleanane-type triterpene, and a gene encoding the protein, the protein and the gene, and use thereof are provided. For example, a protein having an activity of oxidizing oleanane-type triterpene obtained from a plant in the family Fabaceae, a gene encoding the protein and use thereof are provided. The protein is shown in, for example, SEQ ID NO: 4, 14 or 18, and the gene encoding the protein is shown in, for example, SEQ ID NO: 3, 13 or 17. A transformant into which the gene is introduced can be produced, and thereby a triterpene oxidase can be obtained.
Ethylenediamine: An effective reagent for deacetylation of natural products
Mohankumar, Ramasamy,Ilango, Kaliappan,Santhanakrishnan, Vichangal Pridiuldi,Radhakrishnan, Viswanathan,Narasimhan, Srinivasan
experimental part, p. 851 - 858 (2010/12/25)
The use of ethylenediamine in methanol is described for the selective cleavage of the acetate group in nimbin (1) to 6-deacetyl nimbin (1a) under microwave irradiation. This method enables to deacetylate without affecting other functional groups such as ,α,β-unsaturated ketone, ester, ether, etc. in certain tetranortriterpenoids and other acetate-containing natural compounds.
New triterpenoids and other constituents from a special microbial-fermented tea - Fuzhuan brick tea
Ling, Tie-Jun,Wan, Xiao-Chun,Ling, Wei-Wei,Zhang, Zheng-Zhu,Xia, Tao,Li, Da-Xiang,Hou, Ru-Yan
experimental part, p. 4945 - 4950 (2011/08/03)
Fuzhuan brick tea, a special microbial-fermented tea prepared from the leaves of Camellia sinensis var. sinensis, is a traditional beverage used in China throughout history. Phytochemical investigation of this material led to the identification of three new triterpenoids, 3 ,6α,13β- trihydroxyolean-7-one (1), 3β-acetoxy-6α,13β-dihydroxyolean-7- one (2), and 3β-O-(8-hydroxyoctanoyl)-12-oleanene (3), together with 11 known compounds, friedelin (4), β-amyrone (5), β-amyrin (6), α-spinasterone (7), α-spinasterol (8), 22,23-dihydro-α- spinasterone (9), 22,23-dihydro-α-spinasterol (10), α-phytol (11), α-tocopherol (12), α-tocoquinone (13), and caffeine (14). The structures of 1-13 were determined by spectroscopic and chemical methods. Compounds 1 and 2 are the first two examples of triterpenoids possessing a 6-hydroxy-7-one function. All of the compounds, except 6, 8, 10, 11, and 14, were isolated from tea and Camellia spp. for the first time. The antibacterial activities of 1 were assessed against some enteric pathogenic microbes. Compound 1 showed no cytotoxic activity against A-549, Bel-7402, and HCT-8 cell lines.
