{"id":2863,"date":"2015-05-02T09:40:49","date_gmt":"2015-05-02T09:40:49","guid":{"rendered":"http:\/\/biomedpharmajournal.org\/?p=2863"},"modified":"2016-09-03T08:30:53","modified_gmt":"2016-09-03T08:30:53","slug":"phytochemical-study-of-cynara-cadunculus-l-growing-in-libya","status":"publish","type":"post","link":"https:\/\/biomedpharmajournal.org\/staging\/vol7no1\/phytochemical-study-of-cynara-cadunculus-l-growing-in-libya\/","title":{"rendered":"Phytochemical Study of Cynara cadunculus L. Growing in Libya"},"content":{"rendered":"

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

Cynara cardunculus L<\/em>.is a wild plant widely growing\u00a0 in Libya .,it is a popular medicinal plants used in phytotherapy for its strong choleretic activity, it also used as hepatoprotective1<\/sup> and antioxidant2<\/sup>and hypoglycemic3<\/sup>, The obvious biological activities of this plant was a good motive to investigate it which is a wild Libyan plant.<\/p>\n

Result and Discssion\u00a0<\/strong><\/p>\n

The careful separation of the aerial part extract afforded in addition the \u03b2 sitosterol, stigmasterols, \u03b2 amyrin , \u03b2amyrin acetate, further 5 compounds, apigein1,Luteolin 2, cynaratriol3, B-sitosterol o-glycosides 4 and Luteolin 7-0- glucosides 5.<\/p>\n

The structures of these compounds could be easily deduced from Uv., IR., 1<\/sup>HNMR., MS. spectral data.<\/p>\n

Compound 1 the Uv. Spectral data showed that this compound is a flavenoid and by comparing the UV. Data with published data, we found out that this compounds.\u00a0Is apigrnin . The 1<\/sup>HNMR. and IR. data confirmed this result.\u00a0For compound 2 the UV, 1<\/sup>HNMR and IR data prove that this compound is luteolin.\u00a0The IR.data of compound 3 showed aband at 1780\u00a0cm-1<\/sup>which indicate that this compound has a lactone ring.<\/p>\n

Compound I\u00a0<\/strong><\/p>\n

IR Spectrum :- 3300 cm-1<\/sup>, 2890cm-1<\/sup>,2924cm-1<\/sup>,1652cm-1<\/sup>,1607cm -1<\/p>\n

UV.Spectrum data<\/strong><\/p>\n\n\n<\/colgroup>\n\n\n\n\n\n\n\n
Shift reagent<\/span><\/strong><\/td>\nmax<\/sub>\u05d2<\/span><\/span><\/strong><\/td>\n<\/tr>\n
Band I<\/span><\/strong><\/td>\nBand II<\/span><\/strong><\/td>\n<\/tr>\n
MeOH<\/span><\/td>\n265 cm-1<\/sup><\/span><\/span><\/td>\n338 cm-1<\/sup><\/span><\/span><\/td>\n<\/tr>\n
MeOH+ NaoMe<\/span><\/td>\n276 cm -1<\/sup><\/span><\/span><\/td>\n325,399 cm-1<\/sup><\/span><\/span><\/td>\n<\/tr>\n
MeOH+ALcL3<\/sub><\/span><\/span><\/td>\n276 cm-1<\/sup><\/span><\/span><\/td>\n240,345 cm-1<\/sup><\/span><\/span><\/td>\n<\/tr>\n
MeOH+ALcL3+<\/sub><\/span>HcL<\/span><\/span><\/td>\n277cm-1<\/sup><\/span><\/span><\/td>\n240,376cm-1<\/sup><\/span><\/span><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

The 1<\/sup>Hmmr data showed signals at \u03b4-2.86(m, H-1) 1.85(dd, br, H-5) , 4.6 (dd-H-6) and 2.06( m-H7). Indicate that this compound has a gauaianolide structure.\u00a0The broad doublets at \u03b4 -3.95 (H-3) due to the proton under hydroxyl group the two broad singlets at \u03b4 -3.17 (H-14). Andat \u03b4- 4.99(H-14‘<\/sup>) indicate the presence isolated =CH2<\/sub> group.\u00a0The C13<\/sup>nmr confirm this assumption. Compound 5 ,the 1<\/sup>Hnmr signals are similar to compound 2 except the signals of sugar part which is glucose. The UV. data confirm this assumption.spectrum<\/p>\n

Compound 2<\/strong><\/p>\n

IR\u00a0 spectrum:- 3350 cm-1<\/sup>,2980-2890 cm-1<\/sup>, 1670 cm-1<\/sup>, 1620 cm-1<\/sup><\/p>\n

UV Spectrum<\/strong><\/p>\n\n\n\n\n\n\n\n\n
Shift reagent<\/strong><\/td>\nmax<\/sub>\u05d2<\/strong><\/td>\n<\/tr>\n
Band I<\/strong><\/td>\nBand II<\/strong><\/td>\n<\/tr>\n
MeOH<\/td>\n254 cm-1<\/sup><\/td>\n342 cm-1<\/sup><\/td>\n<\/tr>\n
MeOH+NaOMe<\/td>\n275 cm-1<\/sup><\/td>\n402 cm-1<\/sup><\/td>\n<\/tr>\n
MeOH+ALcL3<\/sub><\/td>\n274 cm-1<\/sup><\/td>\n338,425 cm-1<\/sup><\/td>\n<\/tr>\n
MeOH+ALcL3<\/sub>+HcL<\/td>\n266 cm-1<\/sup><\/td>\n296,354 cm-1<\/sup><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n

Exeperiment<\/strong><\/p>\n

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

material was collected from Musrata-libya. In March 2007, 1<\/sup>Hnmr spectra were recorded in (DCl3<\/sub> with Bruken wm400.<\/p>\n

Mass spectra were carried out in Shimadzu QP5050A, 70 e.v.<\/p>\n

-UV spectra were recorded by UV-1601 UV\/VIS Spectrophotometer<\/p>\n

-IR spectra were recorded by IR Spectrophotometer FT-IR Spectrometer<\/p>\n

MS spectrum: – 286(M+<\/sup>) ,( C15 <\/sub>\u00a0H10<\/sub> 06<\/sub>) ,279 (10), 168(29), 153(20), 149(100) ,137(52)<\/p>\n

Compound 3<\/strong><\/p>\n

IR spectrum :- 3520 cm-1<\/sup> 2990 -2890 cm-1<\/sup> , 1780 cm-1 <\/sup>, 1570 cm-1<\/sup><\/p>\n

1<\/sup>Hnmr spectrum:- \u03b4-2.88 m (H-1) , \u03b4-2.15m(H-2), \u03b4-1.1(m-H-a‘<\/sup>) , \u03b4-3.58 m (m, H-3), \u03b4-2.10 (m-H-4), \u03b4- 1.88( m-H-5), \u03b4-4.16 (t,H-6), \u03b4-2.2 (ddd-H-7) , \u03b4- 2.1 (m-H-8), \u03b4- 1.66(m-H-8′) , \u03b4-2.65 (tt,H-9), \u03b4-1.92(m-H-9′), \u03b4-3.69 (s-H-13), \u03b4- 3.17 (d-14), \u03b4- 4.9(d-H14′),\u00a0\u03b4-1.18( d-H-15)<\/p>\n

Compound 5<\/strong><\/p>\n

IR spectrum<\/strong><\/p>\n

3340 cm-1<\/sup>, 2990-2800cm-1<\/sup>, 1660cm-1<\/sup> ,1610 cm-1<\/sup><\/p>\n

U.V. spectrum<\/strong><\/p>\n\n\n<\/colgroup>\n\n\n\n\n\n\n\n
Shift reagent<\/span><\/strong><\/td>\nmax<\/sub>\u05d2<\/span><\/span><\/strong><\/td>\n<\/tr>\n
Band I<\/span><\/strong><\/td>\nBand II<\/span><\/strong><\/td>\n<\/tr>\n
MeOH<\/span><\/td>\n256 cm-1<\/sup><\/span><\/span><\/td>\n345 cm-1<\/sup><\/span><\/span><\/td>\n<\/tr>\n
MeOH+NaOMe<\/span><\/td>\n266 cm-1<\/sup><\/span><\/span><\/td>\n305 cm-1<\/sup><\/span><\/span><\/td>\n<\/tr>\n
MeOH+ALcL3<\/sub><\/span><\/span><\/td>\n278 cm-1<\/sup><\/span><\/span><\/td>\n338,420 cm-1<\/sup><\/span><\/span><\/td>\n<\/tr>\n
MeOH+ALcL3<\/sub><\/span>+HcL<\/span><\/span><\/td>\n258 cm-1<\/sup><\/span><\/span><\/td>\n356,388 cm-1<\/sup><\/span><\/span><\/td>\n<\/tr>\n<\/tbody>\n<\/table>\n

 <\/p>\n

M.S spectrum<\/strong><\/p>\n

286 (M+<\/sup>– glucose), 256 (10), 156(20),60(80), 44(100)<\/p>\n

Extraction and isolation<\/strong><\/p>\n

The air dried material (1kg) was extracted with methanol- ether-pot.ether(1:1:1) affording after deffaling with methanol 14 g. extract.Column chromatography. (SiO2<\/sub>) of the obtained extract furnished 7 fractions .known compounds were usually identified by comparing their data with those\u00a0authentic data .The pet.- ether fraction gave by TLC (SiO2<\/sub>,PF245,pet.ether:ETAC 9:1) B-amyrin acetate, B-amy rine, fraction 4( ET2<\/sub>O- pet.toether 1:1)gave \u03b2-sitosterol and stigmasterols.\u00a0Fraction 5 (ET2<\/sub>O) gave by TLC ( SiO2<\/sub>, CHCL3<\/sub>-MeoH (9:1)\u00a020 mg\u00a0 apigein and 39 mg of Luteolin and 10 mg of cynaratriol.\u00a0Fraction 6( ET2<\/sub>O:MeOH 1:1) give a12 mg of lutealin-7-0-glucoside.) after using PTLC ( Sio2,<\/sub> CHCL3,<\/sub>MeOH- 1:2).<\/p>\n

Refereces<\/strong><\/p>\n

    \n
  1. Evans,W.C,2002 ” Treas and Evans pharmacognosy”15th<\/sup> Ed.,w.B.saunders co LTD. Landon,Toronto,Tokyo.,p. 12<\/li>\n
  2. Alavi S.A. (1983) Flora ofLiby(Asteraceac)Faculty of science, Tripoli university;Tripoli. Vol(107), p.63<\/li>\n
  3. Kelly,M,and Alan,p.(1996) controlling cynara cardunculus, California exotic pestcouncul ) .\u00a0p.2S-32-<\/li>\n
  4. Heimgartner,M.;Pietrzak,R.;geertsen,p.; and Pais, M(1990)\u00a0 phytochemistry,15,p.651<\/li>\n
  5. Nie,R.L,Morito,T.,Kasai, R.; Wu,J.Z.and Tanaka.0(1984) planta Medica. 32,p.3906.<\/li>\n
  6. Hidaka K., IIO,M., Matsuda,y.;Kohda, H.,Yamahara,J.(1987) phytochemistry26,p.2032<\/li>\n
  7. Delgado,M.C.C,Das,Lva.,M.s., and Fo,R.B.(1984) Phytochemistry17,p.1349.<\/li>\n<\/ol>\n","protected":false},"excerpt":{"rendered":"

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