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GP PHN KHO ST THNH PHN HA HC CA V R BN (SONNERATIA CASEOLARIS L.)

L Thanh Phc v T Minh T 1

ABSTRACT
From the petroleum ether extracts of the roots of Sonneratia caseolaris L., collected in Tra On district, Vinh Long province, two compounds have been isolated: lupeol (C30H50O) and betulinaldehyde (C30H50O2). The structures of these compounds have been elucidated by modern spectroscopic methods: 1H-NMR, 13C-NMR, DEPT NMR. Keywords: Sonneratia caseolaris L. root, chemical components, lupeol, betulinaldehyde Title: Contribution to the study on the chemical components of Sonneratia caseolaris L. root

TM TT
T dch chit petroleum ether ca r cy Bn trng ti huyn Tr n, tnh Vnh Long, c lp c hai hp cht l: lupeol (C30H50O) v betulinaldehide (C30H50O2). Cu trc ha hc ca cc hp cht ny c xc nh bng cc phng php ph hin i 1H-NMR, 13C-NMR, DEPT NMR. T kha: R Bn Sonneratia caseolaris L., thnh phn ha hc, lupeol, betulinaldehyde

1 T VN Cy Bn c tn khoa hc l Sonneratia caseolaris L. thuc h Bn (Sonneratiaceae) ( Huy Bch et al., 2004) nay i sang h Lythraceae. Bn l loi cy c trng nhiu ven cc con sng, ca bin, trn cc bi t bi v l mt qun th khng th thiu ca rng ngp mn ven bin nc ta. Vi h thng r pht trin cy Bn c kh nng chn sng, chng xi mn v gi; theo dn gian Bn chng nhng c dng to thm hng v cho cc mn n m cn c th to ra nhng bi thuc c gi tr nh: cm mu, vim ty, gii nhit ( Huy Bch et al., 2004). Trn th gii Bn c s dng nh cht khng oxi ha v cc t bo c hi. Hn na dn gian s dng nh cht lm se vt thng, cha bong gn, cha bnh tr, ngn cn xut huyt (Jiny Varghese K et al., 2010). Vit Nam, thnh phn ha hc cy Bn cha c nghin cu. Tuy nhin, trn th gii c mt s bi bo nghin cu v loi cy ny nhng cha ch nghin cu n b phn r. Do lm sng t thm c s khoa hc cho nhng bi thuc dn gian v gp phn vo nhng nghin cu mi, chng ti phn lp v xc nh cu trc ha hc cc hp cht ca r Bn (Sonneratia caseolaris L.) trng ti huyn Tr n, tnh Vnh Long.

Khoa Khoa hc T Nhin, Trng i hc Cn Th

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2 PHNG TIN V PHNG PHP Nguyn liu: R cy Bn c thu hi (phn pha trn mt t) ti x Lc S Thnh huyn Tr n, tnh Vnh Long, sau ra sch, tch ly phn v, ct nh, phi kh. Phng php: Chit hot cht: V r Bn c ngm trong cn 96, phn dch chit c quay loi dung mi thu c cao cn. Sau ly cao cn chit vi dung mi petroleum ether (PE) c quay loi dung mi thu c cao PE. Phn lp cht t cao PE: thc hin qu trnh sc k ct, cht hp ph l silica gel, theo di qu trnh sc k ct bng sc k lp mng thin layer chromatography (TLC), gii ly ct bt u t PE sau tng phn cc bng dung dch PE vi ethyl acetate (EtOAc) theo t l thch hp. Thuc th hin vt l dung dch vanillin/ sulfuric acid 10% trong methanol. Cc phn on th hin Rf ging nhau trn TLC c gp li. Tin hnh sc k ct tip tc vi cc phn on ging nhau phn lp c cht sch. Xc nh cu trc ca cht phn lp c: s dng cc phng php ph nghim: 1H-NMR, 13C-NMR, DEPT NMR v cc ti liu lin quan xc nh cu trc cc cht phn lp c. Ph NMR c o trn my Bruker Advance 500 MHz (Vin Cng Ngh, s 18 Hong Quc Vit, Cu Giy, H Ni). Silica gel dng cho sc k ct pha thng c ht 0.040-0.063 mm. Sc k lp mng c thc hin trn bn mng trng sn silica gel KG 60 F254. Cc ha cht tinh khit khc c xut x t Trung Quc. 3 KT QU THO LUN 3.1 Kt qu sc k ct T 2.012 g cao petroleum ether tin hnh sc k ct thng vi h dung mi gii ly PE:EtOAc v EtOAc:MeOH c phn cc tng dn. Kt qu phn on PE:EtOAc = 90:10 thu c 25 mg mt hp cht tinh khit c dng tinh th mu trng, hin vt trn TLC cho mt vt trn mu hng tm vi Rf = 0.29 (PE:EtOAc = 90:10). Nhit nng chy 188-190C. K hiu hp cht ny l PHUOC-TO01. phn on PE:EtOAc = 95:5 kt qu thu c 34 mg mt hp cht tinh khit, c dng tinh th hnh kim mu trng c trn TLC xut hin vt mu tm c Rf = 0.36 (PE:EtOAc = 80:20). K hiu hp cht ny l PHUOC-TO-02. 3.2 Kt qu d liu ph Hp cht PHUOC-TO-01: Ph 1H NMR (500 MHz, CDCl3) (ppm), J (Hz): 0.74 (3H, s, CH3-24), 0.81(3H, s, CH3-25), 0.91 (3H, s, CH3-27), 0.95 (3H, s, CH3-23), 0.97 (3H, s, CH3-26), 1.69 (3H, s, CH3-30), 2.85 (1H, m, H-19), 3.18 (1H, dd, J= 11.5, 5.0 Hz, H-3), 4.62 (1H, br. s, H-29), 4.74 (1H, br. s, H-29), 9.67 (1H, s, CHO). Ph 13C NMR (125.8 MHz, CDCl3), (ppm): 15.1 (C-27), 15.3 (C-24), 15.8 (C25), 16.1 (C-26), 18.3 (C-6), 19.0 (C-30), 20.8 (C-11), 25.6 (C-12), 27.4 (C-2), 28.0 (C-23), 28.8 (C-16), 29.3 (C-15), 29.9 (C-21), 33.3 (C-22), 34.4 (C-7), 37.2

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(C-10), 38.8 (C-1), 38.8 (C-13), 38.9 (C-4), 40.9 (C-8), 42.6 (C-14), 47.6 (C-19), 48.1 (C-18), 50.5 (C-9), 55.4 (C-5), 59.3 (C-17), 79.0 (C-3), 110.2 (C-29), 149.7 (C-20), 206.7 (C-28). T cc d kin trn nhn danh c PHUOC-TO-01 l betulinaldehyde (Hnh 1). Kt qu ny cng ph hp vi kt qu ca Most. Nazma Parvin et al., 2009.
29 20 30 17 18 25 1 2 HO 3 23 4 10 5 6 24 9 8 27 7 26 16 15 11 12 14 13 19 21 22 28 CHO

Hnh 1: Cng thc cu to ca betulinaldehyde

Betulinaldehyde l mt triterpen c tm thy trong cc loi thc vt, c kh nng khng mt s loi vi trng nh: Basillus subtilis, Escherichia coli, Pseudomonas (M. Shoeb et al., 2005), gy c i vi t bo trn mng bng ca chut (Manuel Jess Chan-Bacab et al., 2001). Ngoi ra n l hp cht quan trng tng hp betulinic acid v cc dn xut ca betulin mt trong nhng hp cht c th dng iu tr cc bnh kh cha tr nh: ung th, HIV (Perumal Yogeeswari et al., 2005). Hp cht PHUOC-TO-02 Ph 1H-NMR (500 MHz, CDCl3), (ppm), J (Hz): 0.68 (d, 1H, J = 9.5 Hz, H-5), 0.76 (s, 3H, CH3-24), 0.79 (s, 3H, CH3-28), 0.83 (s, 3H, CH3-25), 0.95 (s, 3H, CH3-27), 0.97 (s, 3H, CH3-23), 1.03 (s, 3H, CH3-26), 1.66 (s, 3H, CH3-30), 1.87 1.96 (m, H-21), 2.35 (dt, 1H, J = 11, 5.5 Hz, H-19), 3.18 (dd, 1H, J = 11, 5 Hz, H3), 4.57 (br s, 1H, H-29), 4.69 (br s, 1H, H-29). Ph 13C-NMR (125.8 MHz, CDCl3), (ppm): 14.6 (C-27), 15.4 (C-24), 16.0 (C25), 16.1 (C-26), 18.0 (C-28), 18.3 (C-6), 19.3 (C-30), 21.0 (C-11), 25.2 (C-12), 27.5 (C-2, C-15), 28.0 (C-23), 29.7 (C-21), 34.3 (C-7), 35.6 (C-16), 37.2 (C-10), 38.1 (C-13), 38.7 (C-1), 38.9 (C-4), 40.0 (C-22), 40.9 (C-8), 42.9 (C-14), 43.0 (C17), 48.0 (C-18), 48.3 (C-19), 50.4 (C-9), 55.3 (C-5), 79.0 (C-3), 109.3 (C-29), 150.9 (C-20). T nhng d kin trn PHUOC-TO-02 c nhn danh l lupeol (Hnh 2). Kt qu ny cng ph hp vi kt qu ca Tian Minqing et al., 2009.

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29 20 30 17 18 25 1 2 HO 3 23 4 10 5 6 24 9 8 27 7 26 16 15 11 12 14 13 19 21 22 28

Hnh 2: Cng thc cu to ha hc lupeol

Lupeol l mt triterpen c tm thy rt nhiu trong cc thc phm rau, qu, cy tri. Nhng nghin cu trong khong ba thp k tr li y cho thy lupeol c hot tnh dc l quan trng. Nghin cu in vitro v cn lm sng i vi ng vt cho thy lupeol c kh nng khng vim, khng vi trng, c ch sinh trng ca t bo ung th u v c, lm h cholesterol. Lupeol cng c th nghim trn c th sng, nh mt phng thuc iu tr cho thy c th cha lnh vt thng, tiu ng, tim mch, thn, vim khp. ng ch l lupeol c kh nng tr bnh chn lc t gy nh hng i vi t bo lnh bnh (Hifzur Rahman Siddique et al., 2010). 4 KT LUN phn lp v xc nh cu trc ca hai hp cht: betulinaldehyde v lupeol t dch chit petroleum ether ca r cy Bn. Trong hp cht betulinaldehyde ln u c phn lp trn cy Sonneratia caseolaris L., hp cht lupeol c pht hin trn cy ny nhng c trng ti cc vng khc khng phi Vit Nam. y l nhng hp cht c nghin cu u c hot tnh sinh hc cao do phn no gii thch c s khoa hc ca cc bi thuc tr liu dn gian nh nu trn. TI LIU THAM KHO
Huy Bch, 2004. Cy thuc v ng vt lm thuc Vit Nam, NXB Khoa hc v K thut, H Ni. (I), tr. 187-188. Jiny Varghese K , Belzik N, Nisha A R ,Resiya S, Resmi S,Silvipriya KS 2010. Pharmacognostical and phytochemical studies of a Mangrove ( Sonneratia caseolaris ) from Kochi of Kerala state in India, Journal of Pharmacy Research 3 (11), 2625-2627. Hifzur Rahman Siddique, Mohammad Saleem, 2010. Beneficial health effects of lupeol triterpene: A review of preclinical studies, Volume 88, Issues 7-8, 14 February 2011, Pages 285-293 Life Sciences. Manuel Jess Chan-Bacab and Luis Manuel Pea-Rodrguez, 2001. Plant natural products with leishmanicidal activity, The Royal Society of Chemistry Journal 18, 674688. Margareth B. C. Gallo. Miranda J. Sarachine 2009. Biological Activities of Lupeol, International Journal of Biomedical and Pharmaceutical Sciences. Most. Nazma Parvin, Mohammad S. Rahman, Mohammad S. Islam and Mohammad A. Rashid 2 2009. Chemical and biological investigations of Dillenia indica Linn, Bangladesh Journal Pharmacol 4: 122-125. 132

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M. Shoeb, M. I. R. Mamun, N. Nahar and M. Mosihuzzaman, 2005. Biological Screening of Zizyphus rugosa and Zizyphus oenoplia extractives, Dhaka Univ. J. Pharm. Sci. 4(2): 131-134. Perumal Yogeeswari and Dharmarajan Sriram 2005. Betulinic Acid and Its Derivatives: A Review on their Biological Properties, Current Medicinal Chemistry 12, 657-666. Tian Minqing, Dai Haofu, Li Xiaoming, Wang Bingui, 2009. Chemical constituents of marine medicinal mangrove plant Sonneratia caseolaris, Chinese Journal of Oceanology and Limnology Vol. 27 No. 2, P. 288-296.

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