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Wednesday 20 January 2016

Four antibacterial monoterpenoid derivatives from the herba of Senecio Cannabifolius less




The plant material was dipped into water overnight (1:10) and then extracted for three times after the material had been boiled for 2 h. Filtration and rotary evaporation of the resulting extract gave a residue (780 g), which was dissolved in water and extracted with chloroform, ethyl acetate, and n-butanol. The n-butanol layer was passed through a lowbar ODS column (1.873 g) eluted with MeOH-H 2 O (5:95, 1:9 v/v) and by HPLC with 15%MeOH-H 2 O-1%THF to furnish 1 (31.5 mg, [Figure - 1], 2 (16.3 mg,[Figure - 2]), 3 (11.6 mg, [Figure - 3]), and 4 (11.5 mg, [Figure - 4]).

Compound 1:Elution of the column with MeOH-H 2 O (5:95) afforded yellow liquid 1. IR umax (KBr): 3396, 2928, 1710, 1669, 1365, 1242, 1157, 1077 cm -1sub . HRESIMS (positive) m/z : 403.1959[M+H]+ (calcd. for C 19 H 31 O 9 , 403.1963). 1sub H-NMR (400 MHz, DMSO- d 6 ): d5.76 (1H, s, H-1), 2.11 (3H, s, CH 3 -4), 2.25 (1H, dd, J=2.0; 12.8 Hz, H 2 -3'a), 1.26 (1H, m, H 2 -3'b), 4.16 (1H, m, H-4'), 1.97 (1H, dd, J=2.4; 12.4 Hz, H 2 -5'a), 1.35 (1H, m, H 2 -5'b), 1.28 (3H, s, CH 3 -7'), 1.31 (3H, s, CH 3 -8'), 1.07 (3H, s, CH 3 -9'), 5.09 (1H, s, OH-2'), 4.24 (1H, d, J=8.0 Hz, H-1''), 2.89 (1H, dt, J=8.0; 4.4 Hz, H-2''), 3.07 (1H, m, H-3''), 3.13 (1H, m, H-4''), 3.10 (1H, m, H-5''), 3.66 (1H, ddd, J=2.0; 5.2; 10.4 Hz, H 2 -6''a), 3.45 (1H, ddd, J=5.2; 5.2; 10.4 Hz, H 2 -6''b), 4.88 (1H, d, J=4.4 Hz, OH-2''), 4.88 (1H, m, OH-3''), 4.91 (1H, m, OH-4''), 4.46 (1H, t, J=5.2 Hz, OH-6'').13sub C-NMR (100 MHz, DMSO- d 6 ): d99.6 (C-1), 208.9 (C-2), 197.6 (C-3), 26.2 (C-4), 118.4 (C-1'), 70.4 (C-2'), 46.0 (C-3'), 70.6 (C-4'), 46.9 (C-5'), 35.5 (C-6'), 30.3 (C-7'), 28.7 (C-8'), 31.6 (C-9'), 101.2 (C-1''), 73.4 (C-2''), 76.7 (C-3''), 70.0 (C-4''), 76.7 (C-5''), 61.0 (C-6'').

Indian Journal of Pharmaceutical Sciences
http://www.ijpsonline.com/article.asp?issn=0250-474X;year=2006;volume=68;issue=3;spage=332;epage=336;aulast=Wu

RESEARCH PAPER
Year : 2006  |  Volume : 68  |  Issue : 3  |  Page : 332-336
Four antibacterial monoterpenoid derivatives from the herba of Senecio Cannabifolius less

1 School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China-110 016,
2 School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, China-110 016,
3 Faculty of Agriculture, Kochi University, Nankoku, Japan-783-8502, 

Correspondence Address:
L J Wu
School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China-110 016 





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