The Structure and Absolute Configuration of Cyclotirucanenol, a New Triterpene from Euphorbia tirucalli Linn

Abstract

The structure and absolute configuration of “cyclotirucanenol” a new triterpene isolated from Euphorbia tirucalli has been established as 24β-methyl-9β-19-cyclolanost-20-en-3β-ol through chemical and spectroscopic studies including 2D-NMR.

Cycloartane-Type Triterpenes from Amberboa ramosa

“…Five protons were exchangeable with D20 in base in the 'H-nmr spectrum of the diketone of 1. In a 'H-'H homonuclear chemical shift correlation spectrum (COSY-45) of 1 the comparatively upfield carbinol methine proton at [3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20] showed cross peaks with two other protons and hence could be assigned to C-3. The large coupling (_/ax,ax = 9.8 and Vax.eq = 4.11 Hz) allowed us to assign ß and equatorial orientation to the hydroxyl group at C-3.…”

“…[M]+ 442.3866 (C30H,0O2) (30), [M-H20]+ 424.3728 (C30H48O) (45), (M -H20 -Me]+ 409-3481 (C29H4,0) (36), [M -2HzO]+ 409.3481 (C29H450) (36), [M -2H2OJ+ 406.3666 (C30H46) ( 12), [M -2H20 -Me]+ 391.3311 (C29H43) (10), [M-H20-C3H7}+ 381.3129 (C27H41) ( 6), [M-H20-C5H9]+ 355.3062 (C2,H390) (1), [M -C8Hi50]+ 315.2701 (C22H3sO) (17), (M-C9H160]+ 302.2650 (C21H340) (40), [M -C8H150 -H20]+ 297.2573 (C22H33) (11), [M-C9H160-H20]+ 284.2524 (C21H32) (13), [M-C9H16Q-C8H150] + 175.1483 (C13H19) (55); 'H-nmr (CDC13) 4.70 and 4.60 (br s, H2-21), 3.20 (dd, 7 = 9.9, 4.5 Hz, H-3), 2.14 (m, H2-22), 1.33 and 1.31 (s, H3-26 and H3-27), 0.98 (s, H3-30), 0.96 (s, H3-18), 0.88 (s, H3-28), 0.86 18.23 (q, C-18), 29.90 (t, C-19), 156.49 (s, C-20), 106.69 (t, C-21), 33-04 (t, C-22), 34.29 (t, C-23), 39.19 (t, C-24), 70.97 (s, C-25), 29.39 (q, C-26), 29.46 (q, C-27), 19.30 (q, C-28), 25.31 (q, C-29), 14.89 (q, C-30). The assignments were made with the help of hetero-COSY as well as comparison with related triterpenes (15,16). Reduction of 2.-Compound 2 (18 mg) in HOAc (1.5 ml) was hydrogenated over PtOa (10 mg).…”

Antibacterial and Antioxidant Activities of Triterpenoids Isolated from Endemic Euphorbia arbuscula Stem Latex

“…For instance, compounds such as 24-methyl-9,19-cyclolanost-24-en-3-ol and 19-norlanosta-5,24-dien-3-ol,9-methyl-,(3β, 9β,10α) were discovered in E. caducifolia latex extract [5]. In addition, cyclotirucanenol and cycloeuphordenol were isolated from E. tirucalli [6,7] latex, while 9,19-cyclolanost-22(22′),24-diene-3-ol (nerifoliene) and euphol were obtained from fresh latex of latex E. nerifolia [8]. Tese compounds play a crucial role in the identifcation and classifcation of Euphorbia species.…”

Chemical Constituents From Phalaenopsis Hybrids and Their Bioactivities

“…24 The successive purification by a combination of conventional chromatographic techniques characterized one new compound apigenin 6-C-β-d-ribopyranosyl-7- O- β-d-glucopyranoside ( 1 ) (Figure 1). In addition, 11 known compounds including saponarin ( 2 ) 25 (3',7-di- O -sinapyl-glucosyl)-3-glucosyl cyanidin ( 3 ) 15 mixtures of β-sitosteryl acetate ( 4 ) and stigmasteryl acetate ( 5 , 26 mixtures of β-sitosterol ( 6 ) and stigmasterol ( 7 ) 27 cyclotirucanenol ( 8 ) 28 vanillic acid ( 9 ) 27 p -methoxybenzaldehyde ( 10 ) 29 canthin-6-one ( 11 ) 27 and methyl 4-β-d-glucopyranosyloxy- trans -cinnamate ( 12 ) 30 were also identified by spectroscopic data in comparison with the published values reported in the literature.…”