{"id":695,"date":"2015-02-15T06:20:49","date_gmt":"2015-02-15T06:20:49","guid":{"rendered":"http:\/\/biomedpharmajournal.org\/?p=695"},"modified":"2020-04-25T07:32:52","modified_gmt":"2020-04-25T07:32:52","slug":"a-new-glycoside-from-scutellaria-scandance-bark","status":"publish","type":"post","link":"https:\/\/biomedpharmajournal.org\/staging\/vol2no1\/a-new-glycoside-from-scutellaria-scandance-bark\/","title":{"rendered":"A New Glycoside from Scutellaria Scandance Bark"},"content":{"rendered":"

Introduction<\/strong><\/p>\n

Scutellaria scandens<\/em> belongs to the family Lamiaceae, is perennial erect shrub widely distributed in North Western Himalayas in India. Scutellaria species<\/em> have been used as antimicrobial medicine for a variety of purposes. (1).From leaves of S. scandans<\/em>. Pinosylvin -3-O-b-D glucopyranoside and 3,5-dihydroxy tras-stilbene-2-carboxylic acid, 2,4 dihydroxy-phenyl ethyl-6-O-sinapoly-b-D-glycopyranoside and 4-methoxy carbonyl methyl phenyl 6-sinapoly (2,3,) The chemical examination of Scutellaria species (4) has been reviewed. The present study has led to the isolation of a new \u03b1-D-Glycoside from an ethanolic extract of the bark of Scutellaria scandens<\/em>. The structure of compound has been elucidated through extensive FAB-mass, 1<\/sup>H and 13<\/sup>C NMR studies.<\/p>\n

Material and Methods<\/strong><\/p>\n

The bark of Scutellaria scandane<\/em> were collected from Ganglogaun, Dist. Chamoli,Garhwal,Uttrakhand and identifed from Department of Botany P.G. College. Gopeshwar where Vaucher specimen was deposited. The air dried barks of plant (3kg) was exhaustively extracted with 90% aqueous ethanol for 72 hours. The ethanolic extract was chromatographed over silica-gel on elution of coloum with Methanol-Chloroform (31:69) afforded compound purified by crystallization from methanol.<\/p>\n

Data<\/strong><\/p>\n

Colourless Crystalline Solid., FAB-m\/z 549 (M+H)+<\/sup>, 1<\/sup>H-NMR (400 MHz \u2013DMSO) (glycone \u2013hexose) \u03b4 3.80(s) , 4.75(d J=5.2Hz)), 4.85(t ,J=5.2 Hz), 4.90 (t, J=4.8 Hz) 4.25 (t, J=6.8Hz), 4.00 (dd, J=4.4,4.0 Hz), 4.60 (s), 4.45 (s), 4.50 (s). (aglycone) \u03b4 5.15 (s), 5.60 (s), 5.15 (s), 3.1 (s), 1.2 (s). (sinapic acid) \u03b4 5.3(s), 6.6 (d J=6.8 Hz), 6.25 (d, J=4.4 Hz), 3.6(s), 3.4(s). 13<\/sup>C-NMR (75 MHz, DMSO) (glycone-hexose) \u03b4 100.4(C1\u2019<\/sub>), 73.2(C2\u2019<\/sub>), 76.4(C3\u2019<\/sub>), 69.8(C4\u2019<\/sub>), 73.8(C5\u2019<\/sub>), 63.8(C6\u2019<\/sub>) (aglycone) \u03b4156.2(C1<\/sub>), 116.2(C2<\/sub>), 135.3(C3<\/sub>), 128.6(C4<\/sub>), 130.3(C5<\/sub>), 116.2(C6<\/sub>), 171.25(C7<\/sub>), 51.6(C8<\/sub>), 21.3(C9<\/sub>), (sinapic acid) \u03b4 124.4(C1\u201d<\/sub>), 106.2(C2\u201d<\/sub>), 148.2(C 3\u201d<\/sub>), 149.0(C4\u201d<\/sub>), 148(C5\u201d<\/sub>), 116.2(C6\u201d<\/sub>), 145.5(C7\u201d<\/sub>), 114.7(C8\u201d<\/sub>), 166.5(C9\u201d<\/sub>), 57.1(C10\u201d<\/sub>), 56.5(C11\u201d<\/sub>).<\/p>\n\n\n\n
\"Scheme<\/td>\nScheme 1:<\/strong><\/p>\n

 <\/p>\n

Click here to View Scheme<\/a><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

Result and Discussion<\/strong><\/p>\n

It was crystallized from methanol as colourless amorphous solid. It correspond the molecular ion peaks at m\/z 549 [M+H]+<\/sup>, their by indicating 548 amu. is the molecular weight of compound, other fragment ions was observed at m\/z 535, 429, 397,391, 369, 307 etc. in the positive ion FAB-MS. Elemental analysis of compound corresponded to the molecular formulae\u00a0 C27<\/sub> H32<\/sub> O12.<\/sub>\u00a0 The 1<\/sup>H-NMR spectrum of\u00a0 compound showed characteristic signals for anomeric proton (H-1′) at \u03b4 3.8 (s) indicate the presence of \u03b1 linkage. Acidic hydrolysis (7% MeOH-HCl, 10ml, 60 to 800<\/sup>C, 8hr) furnished aglycone (4-methoxycarbonyl-3-methyl phenol) identified by comparing its spectral data with that of literature (2) and\u00a0 D-glucose by co-TLC.<\/p>\n

\u00a01<\/sup>H-NMR spectrum of the compound showed singlet at \u03b4 5.3 for tetra-substituted benzene two sharp singlet at \u03b4 3.6 and 3.4 for two\u00a0 methoxy groups respectively. The signals for two \u03b1-\u03b2-methine was observed at \u03b4 6.6 (d, J=6.8 Hz) and \u03b4 6.25 (d, J=4.4 Hz) for sinapic acid (6′-O-4”-methoxy-sinapoyl). Two singlet at \u03b4 5.6 and 5.15 for trisubstituted benzene and sharp singlet at \u03b4 3.1 and 1.2 for one methoxy of ester group and one methyl group respectively assigned for aglycone (4-methoxy carbonyl-3-methyl-phenyl). For sugar moiety, six peaks were observed at \u03b4 3.8 (s), 4.75 (d, 4.4Hz). 4.85(t, 5.2 Hz) 4.9 (t, 4.8Hz) 4.0(dd, 7.2 & 10.4 Hz) and three singlet beak at \u03b4 4.6(s),\u00a0 4.45(s), 4.50(s) for hydroxy groups (2).<\/p>\n

13<\/sup>C-NMR spectrum\u00a0 of the compound showed chemical shifts of the carbon signals at \u03b4 100.4 (C-1′), 73.2 (C-2′), 76.4(C-3′), 69.8(C-4′), 73.8(C-5′), 63.3 (C-6′) which corresponding with analogous data of the glucose (2). The signals for aglycone part \u03b4 156.2 (C-1) aromatic carbons, 116.2, 135.3, 128.6, 130.3, 116.2 for C-2, 3, 4, 5, 6 respectively. The signals at \u03b4 171.25 (C-7) for\u2013CO-O group \u03b4 51.6 for methoxy carbon, \u03b4 21.3 for methyl group. The signals for sinapic acid at \u03b4 124.4 (C-1”), 106.2 (C-2”), 148.2 (C-3”), 149.2(C-4”), 148.0 (C-5”), 116.2 (C-6”) were reported for aromatic carbons and the signal for -CH=CH- were reported at \u03b4 145.5 and 114.7 and \u03b4 166.5 (C-9” -CO-O). Two signals were observed at for d 57.1 (C-10”) and 56.5 (C-11”) for methoxy groups. These data correlate with the reported data of sinapic acid (4).<\/p>\n

\u00a0<\/strong>Antibacterial activities<\/strong><\/p>\n

The ethanotic extract of Scutellaria\u00a0 scandans<\/em> moderately active against two bacterial cultures as klebsiella pneumniae and Mycobacterium\u00a0 smegmatis by use Agar well diffusion method (5).<\/p>\n

Acknowledgement<\/strong><\/p>\n

A authors express their thanks to Principal, Govt. P.G. College Gopeshwar Chamoli, for availing lab facility and SAIF, CDRI, Locknow for recording spectra, and SBSPG institute of Biomedical Dehradun for antibacterial activities.<\/p>\n

Reference<\/strong><\/p>\n

    \n
  1. Gaur; R.D. \u201cFlora of District Garhwal\u201d Trans Media, Srinagar Garhwal 1999.<\/li>\n
  2. Miyaichi \u2013Y Imoto-Y., Kizu-H., Shoyakugaku Zasshi 1988, 42:3, 204.<\/li>\n
  3. Ishiura-A.,Kizu-H., Tomimori-T., Shoyakugaku Zasshi 1993, 47:3, 287.<\/li>\n
  4. Malikov\u00a0 V.M. Yuldashev\u00a0 M.P. Yuldashev, Khiin Prir Soedin, 2002, 5, 385.<\/li>\n
  5. Cony, C.H., Lyne, M.P. and Grange, M.J. (1995) Microbiological Methods, 7th<\/sup> ed, Butter \u00a0worth-Heinemann. Ltd, Great Britain<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"

    Introduction Scutellaria scandens belongs to the family Lamiaceae, is perennial […]<\/p>\n","protected":false},"author":2,"featured_media":0,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[6],"tags":[],"class_list":["post-695","post","type-post","status-publish","format-standard","hentry","category-vol2no1"],"_links":{"self":[{"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/posts\/695","targetHints":{"allow":["GET"]}}],"collection":[{"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/users\/2"}],"replies":[{"embeddable":true,"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/comments?post=695"}],"version-history":[{"count":4,"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/posts\/695\/revisions"}],"predecessor-version":[{"id":32989,"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/posts\/695\/revisions\/32989"}],"wp:attachment":[{"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/media?parent=695"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/categories?post=695"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/biomedpharmajournal.org\/staging\/wp-json\/wp\/v2\/tags?post=695"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}