Journal of Natural Sciences Research ISSN 2224-3186 (Pa er! ISSN 222"-#$21 (%nline! &ol.3' No.

11' 2#13

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Isolation and Characterization of Estra–2ll–en –17–ol, 3yl benzoate from Mucuna pruriens ( Utilis).
Rose(ar) I*unwanne +cheg,u 1- an. John/ull %n)e0achi 1che(e 2 -1. 2e art(ent of 3he(istr)' 4l5an I0o0u 6e.eral 3ollege of 1.ucation' P. %. /o7 1#33' %werri. I(o State. Nigeria. 2. 2e art(ent of 3he(istr)' 8ichael %0 ara +ni5ersit) of 4griculture +(u.i0e. +(uahia . 4,ia State . Nigeria. -3orres on.ing author' (rsriu9)ahoo.co(. Abstract 3he(ical in5estigation of the ,ioacti5e constituents of the see.s of Mucuna pruriens (utilis) resulte. in the isolation of a new steroi.' 1stra:2ll:en :1;:ol' 3)l ,en*oate. <he structure was eluci.ate. using N8R s ectrosco ) in co(,ination with IR an. 8S s ectra .ata. Keywords: 8ucuna' anti-(icro,ial' anti-o7i.ant' anti-infla((ator)' anti-h) ertensi5e. 1 Introd!ction Plants ha5e ,een 0nown to ,e useful to (an= as source of foo. an. .rug. <he) are of ara(ount i( ortance in the treat(ent of .iseases for (an. Nigeria is ,lesse. with (an) of such lants an. the) are use. as foo. an. in her,al (e.icine to cure .iseases an. heal in>uries. So(e of these lants e7hi,it anti-(icro,ial' anti-o7i.ant' antiinfla((ator) an. anti-h) ertensi5e acti5ities. Such (e.icinal lants inclu.e Mucuna pruriens (utilis!. M. pruriens is e7tensi5el) use. in her,al (e.icine an. as foo.. <he see.s ha5e ,een foun. to contain high le5els of rotein an. car,oh).rate an. thus the flour has ,een reco((en.e. to ,e incor orate. into cereals an. root?tu,er foo. ro.ucts to i( ro5e their nutritional @ualit) (+.ensi an. 10e' 2###!. <he flour is use. in sou as sou thic0ener an. to enhance the fla5our of the sou . M. pruriens is grown wi.el) as a green 5egeta,le' ,oth the green o.s an. the (ature ,eans are ,oile. an. eaten as foo. (/ur0ill' (1$$"!= 2u0e' (1$81!!. <he see.s are also roaste. an. groun. to (a0e a coffee su,stitute. 17tracts fro( the see.s ha5e ,een reco((en.e. as one of the ,est tonics to i( ro5e 5italit) (8an)a( et al' 2##4!. M. pruriens is highl) 5alue. ,ecause of its (e.icinal use. It is use. in her,al (e.icine as a owerful ner5ine tonic an. an effecti5e a hro.isiac in the treat(ent of .isor.ers of the (ale an. fe(ale re ro.ucti5e s)ste(s (Nu(i.a' 2##$= 1*ueh' 1$$;= 4(in et al' 1$$6!. <he see.s are effecti5e in the treat(ent of ar0inson .iseases (8an)a( et al' 2##4= Aat*enschlager et al' 2##4!. 17tracts fro( the see.s ha5e ,een use. to enhance se7ual sta(ina' sensation an. li,i.os in ,oth (en an. wo(en .ue to its .o a(ine in.ucing ro erties (4(in et al' 1$$6= Biuliano an. 4llar.'2##1!. Mucuna pruriens see.s ha5e also ,een foun. to ha5e anti.e ressant ro erties when consu(e.. It is a 5er) ,eneficial su le(ent for ,o.) ,uil.ers as it increases the ,o.)Cs a,ilit) to ,uil. lean (uscle' ,rea0.own fat' an. is highl) reco((en.e. to s orts(en (Ra) Sahelian' 8.2!. 6ro( literature' it is o,5ious that Mucuna pruriens see.s contain so(e hor(ones since it is use. to ,uil. lean (uscles an. as a hro.isiac ,) the nati5es' ,ut isolation has not ,een (a.e to that effect' thus this stu.) was un.erta0en to isolate an. characteri*e ,ioacti5e constituents of Mucuna pruriens see.s. 2 "aterials and "ethod 2 1 #lant "aterials D <he see.s of M. pruriens were har5este. fro( the fiel. of National Root 3ro s Research Institute +(u.i0e '4,ia state' Nigeria. 4uthentication of lant (aterials was .one ,) 2r 4. N(eregini of <a7ono() section' 6orestr) 2e art(ent' 8icheal %0 ara +ni5ersit) of 4griculture' +(u.i0e' Nigeria. 2 2 E$traction and Isolation of #lant "aterials D <he see.s were crac0e.' the testa were re(o5e. an. the see.s were (ille. into fine ow.er with <ho(as Eille) (illing (achine an. then store. in air tight ,ottles for anal)sis. 20g of the sa( le was ercolate. in $8F ethanol for 48hrs' this was then filtere.. <he filtrate was concentrate. with Rotar) e5a orator at 4#o3 to a .ar0 ,rown cru.e e7tract (44.3g!. <he cru.e e7tract was artitione. ,etween 3G3l3 an. water an. a 3G3l3 - solu,le fraction (1;."g! was o,taine.. 1#.#g of the 3G3l3 fraction was then artitione. ,etween etroleu( ether (6# : 8##3! an. a@ueous (ethanol. ".#g of the 3G3l3 fraction was then su,>ecte. to colu(n chro(atogra h) o5er silica gel (2## (esh! an. elute. gra.uall) with 1##(l etroleu( ether' then etroleu( ether D 3G3l3 ($#D1#= 8#D2#= ;#D3#= 6#D4#= "#D"#= 4#D6#= 3#D;#= 2#D8#= 1#D$#=!' an. 1##(l 3G3l3= then 3G3l3 D 8ethanol ($#D1#= 8#D2#= ;#D3#= 6#D4#= "#D"#= 4#D6#= 3#D;#= 2#D8#= 1#D$#! an. 1##(l (ethanol to )iel. ten (a>or fractions la,ele. D B ()ellow oil' #.3g!' I ( )ellow oil'#.4g!' , (,rown oil' #.3g! c1 ()ellow oil'#.6g!' sc2()ellow oil' #.6#g!'. (,rown oil #.32g! f2 (,rown soli.' #.3g!' g2 (,rown oil' #."g!' h (.ar0 ,rown oil' #.4g!' i (light )ellow oil' #.3g! an. i2 (light )ellow oil' #.4g!. 84

Journal of Natural Sciences Research ISSN 2224-3186 (Pa er! ISSN 222"-#$21 (%nline! &ol.3' No.11' 2#13

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3hro(atogra hic ( artition chro(atogra h)' colu(n chro(atogra h)' an. <H3! an. s ectrosco ic (IR' 1GN8R' 13 3N8R an. 8S! techni@ues were e( lo)e. to isolate' characteri*e an. i.entif) acti5e constituents fro( 3G3l3 e7tracts of the see.s. 3 % &es!lts and 'isc!ssions: 3o( oun. I1J was elute. with (ethanol an. chlorofor( at the ratio of ;#D3#. It was isolate. as )ellow oil (#.6g!. /ase. on co(,ine. anal)sis of GR1I8S ((?* 44".41!' 1GN8R' 133N8R an. IR s ectra' co( oun. I1J was ro ose. as 1stra:2 ll :en :1;:ol' 3)l ,en*oate with the (olecular for(ula 32$G34%4' (?* 446 calculate.. 4nal)sis of the IR is shown in <a,le 1 an. the anal)sis of 1GN8R an. 133N8R are shown in <a,le 2. <he IR s ectru( re5eale. the resence of h).ro7)l' ali hatic' car,on)l' aro(atic an. ether ,an.s at (34;#."2c(-1' 2$24.$;c(-1' 1;41.#c(-1' 3##8."$c(-1 an. 116$.8$c(-1! res ecti5el).

12 11 1 9 2 5l 4l 3l 2l *1+ Estra)2ll)en)17)ol, 3yl benzoate 6l 1l % 7
l

18 3G3 13 14

%G

O
17 16 15 1ll

2ll 3ll

4ll 3G3

10 5

8 7 6

3 % 4

(able 1: Infra)red Analysis of Estra–2ll–en –17–ol, 3yl benzoate *1+ from M. pruriens I& Absor,tion -cm)1. /!nctional 0ro!, Com,o!nd 34;#."2 %G 4lcohol 3##;.8$ 3K3 4ro(atic 2$2".44 : 3G2 4li hatic 28"".3" : 3G2 4li hatic 1;42.;3 3K% 3ar,on)l 116;.;6 3:% 1ther

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Journal of Natural Sciences Research ISSN 2224-3186 (Pa er! ISSN 222"-#$21 (%nline! &ol.3' No.11' 2#13

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(able 2: 11 and 13C2"& Analysis of Estra – 2ll – en ) 17) ol) 3yl benzoate 31 δC 1 12;.$" 3G ".323 IG. 2 128.12 3G ".342 IG. 3 13#.#6 3 L L 4 12$.;6 3G ".3"# 1Gs " 13#.2; 3 L L 6 31."$ 3G2 1.231 2Gt ; 31.;2 3G2 1.2"4 2Gt 8 33.66 3G 1.6#; IG. $ 33.$$ 3G 1.62$ IG. 1# 12$.;6 3 : : 1.2;8 2G@ 11 31.;" 3G2 12 31.84 3G2 1.28" 2Gt 13 34.11 3 : : 14 34.14 3G 1.3;6 IGt 1.3#2 2Gt 1" 31.$$ 3G2 16 34.;" 3G 2.#8# 1G. 1; ;;.11 3:%G ;.26" 1Gs 18 14.13 3G3 #.8"; 3Gs 12;.$" 3 L L 1l 2l 128.12 3G ".36# IG. 3l 13#.#6 3G ".3;# IGt 4l 12$.;6 3G ".323 1Gt "l 13#.2; 3G ".342 IGt 6l 12$.;6 3G ".3"# IG. ;l 1;3.38 3K% L L 1ll ;6.6$ 3G2 ".386 2Gt 2ll 1;2.$2 3G 2.34; IG@ 3ll 1;3.34 3G 2.3;3 IG( 4ll 14.18 3G3 #.8"; 3G.

3G 3G L 3G L 3G2 3G2 3G 3G : 3G2 3G2 : 3G 3G2 3G %G 3G3 L 3G 3G 3G 3G 3G L 3G2 3G 3G 3G3

4 5 sin6let, d 5 do!blet, t 5 tri,let, 7 5 7!artet, m 5 m!lti,let <he (ass s ectru( of co( oun. I1J showe. (?* 44".41 which was calculate. for 32$G34%4 ((?* 446! an. ,ase ea0 (?* "".18 calculate. for 34G; ((?* ""!. <he 1GN8R s ectru( of co( oun. I1J showe. resence of (eth)lene rotons o,ser5e. at MG1.231' MG1.2"4' MG1.2;8' MG1.28"' (ethine rotons at MG 1.6#; - MG 2.3;3 an. aro(atic rotons which showe. their signals at MG ".232 : MG ".3;#. <he s ectru( in.icate. resence of h).ro7)l roton at MG ;.26". <he 133N8R s ectru( .e icte. the resence of aro(atic car,on ato(s' their che(ical shifts were o,ser5e. at M12;.$" - M13#.2;. <he car,on)l che(ical shifts a eare. at M1;3.38. <he (eth)l car,ons showe. their signals at M14.13 an. M14.18. <he signals of the (eth)lene car,ons were o,ser5e. at M31."$ : M31.$$ while the che(ical shifts of the (ethine car,ons a eare. at M 33.66 : M 34.2". 6rag(entation attern of co( oun. I1J is shown in fig (1!. 2etach(ent of 34G; ion fro( the co( oun. affor.e. the ,ase ea0 (?* "".18 calculate. for (?* "". <he clea5age ,etween the two o7)gen ato(s in the ,en*oate ga5e the ea0 at (?* 1#". 4lso .etach(ent of 3"G"% ion fro( the co( oun. affor.e. another ro(inent ea0 (?* 81.2# calculate. for (?* 81. <he isolate. co( oun. has the s0eleton of 1stra.iol' a se7 hor(one. <he roton in the secon. h).ro7)l is re lace. ,) hen)l o7i.e. 1stra.iol rotects against ,rain in>ur)' neuro.egeneration an. cogniti5e .ecline. It rotects against stro0e in>ur) (2u,al et al' 2###! <hus' this co( oun. isolate. fro( M. pruriens has ,iological an. h)siological acti5ities. <he resence of this co( oun. in Mucuna pruriens see. (a) ,e the reason wh) the nati5es use this lant in the treat(ent of .isor.ers of the (ale an. fe(ale re ro.ucti5e s)ste(s' ar0inson .isease an. increase li,i.o in ,oth (en an. wo(en (Nu(i.a' 2##$= 1*ueh' 1$$;= 4(in et al' 1$$6!. 1stra.iol has ,een foun. to re.uce an7iet) an. .e ression : li0e ,eha5ior of age. fe(ale (ice (Ealf an. 6r)e' 2##"!. <he isolate. co( oun. (a) also ,e the reason mucuna pruriens see.s are use. ,) the her,alists as anti- .e ressant. Concl!sion <he results resente. here showe. that M. pruriens lant can ser5e as a har(aco.)na(ic agent. <he lant can ,e seen as a otential source of useful .rugs an. can ser5e as source of @ualit) raw (aterial for har(aceutical

86

Journal of Natural Sciences Research ISSN 2224-3186 (Pa er! ISSN 222"-#$21 (%nline! &ol.3' No.11' 2#13

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in.ustries. <hus this contri,utes to the scientific e5i.ence for the use of this (e.icinal lant in tra.itional (e.icine for the treat(ent of .iseases li0e ains' .e ressions' erectile .)sfunction' ar0inson .isease' e.t.c.

Ac8nowled6ement Ee are grateful to 2r N0echi I,isi of 3he(istr) .e art(ent' 8icheal %0 ara +ni5ersit) of 4griculture' +(u.i0e' Nigeria for running our s ectra in 3hina an. to 2r 4. N(eregini of <a7ono() section' 6orestr) .e art(ent' 8icheal %0 ara +ni5ersit) of 4griculture' +(u.i0e' Nigeria for authenticating our sa( le. &eferences 4(in' A.8.N' Ahan' 8.N an. Oillur-Reh(an S' (1$$6! PSe7ual function i( ro5ing effect of Mucuna pruriens in se7uall) nor(al (ale ratsP. /ur0ill' G.8 (1$$"!.<he useful Plants of Eest <ro ical 4frica.(5ol 3!.Ro)al /otanic Bar.ens'Hon.on .P 1#1. 2u0e J.4. (1$81!. Gan.,oo0 of legu(es of worl. econo(ic i( ortance. Plenu( ress. New Nor0. 2u,al' 2./' Ohu' G. Nu' J.' Rau' S.E.' Shughrue' P.J.' 8erchenthaler'I.' Ain.)'8.S.an. Eise' P.8.'(2###!.Q1strogen rece tor a' not ,' is a critical lin0 in estra.iol-(e.iate. rotection against ,rain in>ur)R.Proc. Natl. Acad. Sci. USA, 10,1073. 1*ueh' 8.I (1$$;! 3ulti5ation an. +tili*ation of 8inor 6oo. Hegu(es in Nigeria. <ro ical Brain legu(e Infor(ation 3enter' II<4' I,a.an' Nigeria Biuliano' 6. an. 4llar.' J.(2##1!. 2o a(ine an. se7ual function. Int J Impot es 13 Suppl 3D18-28 Aat*enschlager R' 15ans 4' an. 8anson' 4 (2##4!. 8ucuna ruriens in Par0insonSs .iseaseD a .ou,le ,lin. clinical an. har(acological stu.). J Neurol Neurosur! Ps"c#iatr" ;"D16;2-16;; 8an)a('/.+.'2hanase0aran'8. an. Gare'<.4 (2##4!.Neuro rotecti5e effects of the anti ar0inson .rug 8ucuna Pruriens. P#"tot#er es 18D$;-1#1. Nu(i.a'8.H(2##$!. Q<he effects of Raw an. Processe. Mucuna pruriens see. /ase. 2iets on the growth ara(eters an. (eat characteristics of /enin Hocal Buinea 6owlR. International $ournal o% Poultr" sciences 8($!. Ra) Sahelian' 8.2. 4ccesse. at www.ra)sahelian.co(?(ucuna ruriens.ht(l. +.ensi' 1.4 an. 10e' %. (2###!. Pro7i(ate 3o( osition an. 6unctional Pro erties of 6lour Pro.uce. fro( Mucuna coc#inc#inensis an. Mucuna utilis. 6oo. an. 6i,er ro.uction in Nigeria in the 21st centur). Pg 1;# : 1;3. Ealf'4.4 an. 6r)e' 3.4. (2##"!. 4n7iet) an. anti- .e ressi5e ,eha5ior ro.uce. ,) Ph)siological estra.iol regi(en (a) ,e (o.ulate. ,) h) othala(ic : ituitar) a.renal a7is acti5it). Neurops"c#op#armmacolo!" 3#(;!D 1288 : 13#1.

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