• Nghien ciru - Ky thuat
dup'C GB.Bu^)1 Id: 3-O^-t>fllucopyranosyf-20-O- [p-D-glucopyranosyl(1-.6)-ct-L-arabinopyranQsyl]- 3^, 12p,20p-bihydroxydammar-24-en.
Day la cong bo dIu tien ve dammaran saponin phdn Idp Kf loar Gynostemma bunnanicum King ex Chakrav. (giao co lam Miin Dien) thu hdi a Viet Nam.
Tai lieu tham khao 1. Pham Thanh K^, Vu Di>c Canh, Phgm Thanh Hucng, Nguyen Kim Phirong (2007), "Nghign cmj tac dgng ha diolesterol mau cua duoc ttSu giao c6 lam - Gynostemma pentaphyllum (Thunb.) Makino," Tap chi Du^hQC. so 373, thang 5/2007 tr 9-10
2. Phgm Thanh Ky, Phan Thj Phi Phi, P. T. T. Anh (2007), "Nghien ci>u tec dyng tang dap irng mien djch cua duOT li#u giao co lam [Gynostemma pentaphyllum (Thunb.) IMakino)." T^p chi Thdng tin YDuoc 5 tr 35- 38.
3. Phgm TTianh K^', Phgm T. Huwng, T. L. V. Hien (2007), "Nghien oHi tdc dyng i>c che kh6i u cua saponin chiet ti> gido c6 lam [Gynostemma pentaphyllum (Thunb.) Makino)." Tap chi Thong tin YDu^. 11.
4. Pham Thanh Ky (2006), TTiuc tSp Duoc lieu (phan hoa hgc).
5. Cho. Lee., et al. (2010). 'Physicochemical charactenzatran and NMR assignments of ginsenosldes Rb1, Rb2, Re, and Rd isolated from Panax ginsend' J Ginseng Res., Vo\ 34, No. 2, pp. 113-121 (Ngay nh$n bai: 06/07/2016 - Ngay duyet dSng: 01/09/2016)
Cac hop chit triterpenoid tu- cay buc nau (Mallotus mollissimus (Geisel.) Airy-Shaw)
Phan Minh Giang", Ngo Th| Thu Huyin, Phan T6ng S m Khoa Hoa hoc, Truang Dai hgc Khoa hQc Tu nhirn. D^l hoc QuSc gia Ha Npi E-mail: phanmiiibgiang@yahoo. com
Summary
Keymwtfs: Ma/tote mollissimus, Euphorbiaoeae, Hiteipenad. tamxerane Datvan de
Chi Malhtus (hp Euphorblaceae) c(S si^ 6a dang sinh hoc vi d u tnJc hba hoc. Pham HoSng H« (nam 1999) da IhSng ke 33 ioii Mallotus cOa Vl^t Nam m. Cic nghiSn o i u trong khoSrg 30 n^m cho thay dc toil Malbtus sinh t6ng hyp cac chit chuyen hda thi> c4p thupc cSc nh6m terpenoid steroid, flavonoid, benzopyran. coumahnolignold vi phioraglucinol; cac chat nSy cho mot pho tong do hoat tinh sinh hoc hCru ich nhu- chong ung thir. b i o ve gan, chong oxy hoa ... K. Nhieu loai MalkXus la cac cay thu6c co tniy4n do dd cac hyp chit trong cSc cSy Mallohis ciia Viet Nam rat duwc cltCi y nghien a j u nhu' c i c loai ba bet tiing (M apelta), ba bit nhin (M. glabriusculus), bum bup nau (M paniculatus). ba bst dd (M. metcamanus) m6i khS (M. p«ca(us). cSnh kiln (M. philippensis) ba b i t liin (M. nanus), bum bgp gal (M. barbatus) vi bilm bup bdng to (M. macmstachyus) i«!.
TAP CHi Dir(?C HQC - 9/2016 (S6 485 NAM 56)
cay buc nau (M. mollissimus (Geisel.) Alry,^haw syn. M. riclnokles (Pers.) Miill-Arg.) ciJa Viot Nam chua d u ^ nghien ciXi ve thinh phan hda hpc nhung da co mot s4 cdng bo ve hoat tinh chdng oxy hda va khang ky sinh triing Leismania cCIa M.
mollissimus " i . Bai bao nay lin 6hu Sen cdng b6 cac ket qua phin lap va xac dlnh cau tnic cda 4 chat triterpenoid va p-sitosterol tir ia cay bgc nSu.
Nguyen ll$u va p h u o n g phap n g h B n c i n j Phuomg p h i p va thiet bj
Pho h4ng ngoai (IR) dm?c ghi tren thilt bi Impact^lO-Nicolet FT-IR spectrometer. Pho kh6i lu^ng phun diSn tit (ESI-MS) diryc ghi trdn hs thong LC/MSD Trap Agilen Senes 1100. Cdc ph6 cpng hird'ng ti> hat nhan prpton ('H-NMR 500 MHz) duprc ghi tren thilt bi Bruker Avance 500 v»i tetrametylsilan (TMS) la chit ChuIn nSi zero (5 = 0). Dp chuyln dich hod hoc 6 duyc b i l u thl bang ppm, J tinh theo Hz. S i c ky I6p mdng
33
• Nghien ciJu - Ky thuat
du'p'c thijc hlon trdn t a n mdng trang san DC- Alufollen 60 Fjj, (Merck, Dannstadt, CHLB Di>c) vd'i Idp silica gel day 0,2 mm tren nen nhdm.
Phat hien v^t chit bang thulc thi> vanliin/H^SO^
dac 1%. S i c ky c6t (CC, FC va Minl-C) du'oc thyc hi§n tren chit h i p phu silica gel (Merck, Dannstadt, CHLB Di>c) v6i cac co' hat 63-200.
40-63 va 15-40 pm.
Nguyen lieu thin: v | t
Nguyen lieu thuK: vat la Id c i y buc nau (M. mollissknus (Geisel.) Airy-Shaw) diroc thu thap vao thang 7 nam 2013 a xa Klm Linh, huypn Vi Xuyen, tfnh Ha Glang. giam dinh bdi nha thvc vat hoc Sa Nhat Tam (Sd Khoa hoc va Cdng ngh?
tinh Ha Glang).
Chilt va phan l|p
La ducrc phoi khd trong bdng ram. sau dd diryc s l y tiep trong tu s l y d nhlpt do 40-50
"C. M i u khd duyc nghien thanh bot mjn. Bdt la khd cay bye nSu (2 kg) duvc ngam chilt trong methanol d- nhidt 66 phdng 5 Ian. m i l l l n 3 ngay.
Djch chilt methanol duyc d t loai dung mdi dudi ap suit giam thu 6vac phln chilt methanol.
Phln chilt nay dup-c hda trang nude d t va chilt Ian lup't vol cac dung mdi cd dp phan eye tang d i n tu n-hexan va diclomethan thu dyye cae djch chilt tuyng ijng. Sau khi duyc lam khan bang Na^SO^. cac djch ndy dyye d t loai dung mdi dudi dp suit giam eho cae d n chilt n-hexan (157,9 g) va diclomethan (40 g).
^ 40 g d n chiet /^hexan duyc phdn tach bing sac ky cOt thudng (CC) tr«n silica gel, n>a giai vyi h0 dung mdi gradient rt-hexan-aceton 90-1 49 1 19:1. 15:1, 12:1. 9:1. 6:1. 3:1. 1:1. cho 15 nhdrri phan dean. Nhdm phan doan 3 (0,23 g) duyc phSn tach bing sic k:> cpt Snh ehe (Minl-C) tren silica gei vol h$ dung mdi gradient n-hexan-ethyl acetat 19:1, 3:1 cho chat 1 (2,9 mg). Nhdm phdn doan 4 (0.34 g) duyc phan tdch bang MInl-C trdn silica gel vdi he dung mdi n-hexan-aceton 19:1.
9:1 va tinh ohi tiep bang Mini-C tr§n silica gel vol he dung mdi n-hexan-ethyl acetat eho ehit 2 (4.8 mg). Nhdm phdn doan 10 (1.8 g) duyc phan tach noi tiep bang CC va Minl-C tren silica gel vyi hp dung mdi n-hexan-ethyl acetat 30:1 cho chit 3 (5 mg). 40 g phan chilt diclomethan duyc phdn tach CC tren silica gel, n>a giai vyi hp dung mdi gradient r^hexan-aceton 29:1,19:1, 9:1. 6:1. 3:1, 1:1 cho 12 nhdm phan doan. Nhdm phdn doan 1 (0,8 g) duyc phdn tach Mini-C trdn silica gel' vyi h# dung mdi gradient n-hexan-ethyl acetat 99-1 50:1,19:1 cho chat 4 (7 mg). Nhdm phan doan 3
duyc k i t tinh trang dung mdi chay cOt d nhi$t dO phdng eho chit 5 (5 mg).
Ket qua va ^ao luan
_ Phln chilt methanol la eSy bye ndu duyc phdn bd l i n luvt glQia HjO va n-hexan, CH^CIj d l cho cae phan ehilt tuyng ung. Cae phan chilt ndy duyc phan tdch bang s i c ki cpt gradient (CC vd Mini-C) eho 4 chit triterpenoid 1,3-5vap-sltosterol (2). p-Sltosteral (2) duyc nhan dang bang each so sanh TLC phan tich va p h i IR vyi chit ehuln. Cdc hyp chit triterpenoid duyc xac djnh d u tnje bang p h i khol luyng (ESI-MS) vi pho cpng huong Hi i hat nhan (NMR) vi so sanh cac gia tri pho vdi cua 3
cac chit duyc cdng bo. I Taraxerol (1): Bdt vd (Inh hlnh mdu trjng.
R, = 0.35 (TLC. silica gel. n-hexan-EtOAc 9:1.
v/v). ESI-MS (che dd duyng): m * 427.3 (IMtHf) (C3.H„0), 409.2 ([M+H-+l,On 'H-HMR (CDCL):
6 (ppm) 0.8 (3H. s. 23-CH,). 0.82 (3H. s. 28-CHJ 0.91 (6H. s. 27-CH,. 30-CH,). 0.93 (3H. s. 24-CH ) 0.95 (3H. s. 29-CH,). 0.98 (3H. s, 25-CH,). 1.09 (3H. s, 26-CH3), 3.19 (1H. dd J = 11.5 Hz. 4.5 Hz H-3), 5.53 (1H. dd. J = 8.0 Hz. 3.0 Hz. H-15).
P-Sitosterol (2): Tinh t h l hlnh klm mau tilng.
R, = 0,44 (TLC, silica gel, n-hexan-EtOAc 4:1. v/v). ' ' " • (^™,. "^ri"') 3433. 1644, 1464,1378, 1057.
Acid oleanollc (3): B6t vd djnh hinh miu trlng. R, = 0,28 (TLC, silica gel, n-hexan- EtOAe 9.1, v/v). ESI-MS (che dO duyng): n»t 457,2 ([M+H]-) ( C „ H „ 0 , ) , 439,2 ([M+H-+l,Or).
'H-NMR (CDCy: 5 (ppm) 0,76 (3H, s, 26-CH,), 0,78 (3H. s. 23-CH,), 0.9 (3H, s, 25-CH,). 0.91 (3H, s, 29-CHJ. 0,93 (3H. s. 30-CH,). 0.99 (3H, s, 24-CH,), 1.14 (3H. s. 27-CH,). 2.83 (1H. dd. J
= 13,5 Hz, 4,0 Hz, H-18), 3.22 (1H. dd. J = 11.0 Hz. 4.5 Hz. H-3). 5.27 (1H. t. J = 3.5 Hz, H-12).
Taraxeron (4): Bpt v6 djnh hlnh mau trlng. R, I
= 0.32 (TLC. silica gel. n-hexan-EtOAo 9:1. v^). \ ESI-MS (che dp duyng): m/z 425.2 ([M+H]*) 1)
<f=joH„0). 407.2 ([M+H-H,0]*). <H-NMR (CDCIJ:
5 (ppm) 0.83 (3H. s. 28-CH,). 0,91 (3H, s. 30- CH,). 0.92 (3H, s. 27-CH,). 0,96 (3H. s. 29-CHJ.
1.07 (3H. s. 26-CH,), 1,08 (3H, s, 24-CH,). 1,09 (3H, s, 25-CH,), 1.14 (3H. s. 23-CH,). 2.37 (IN.
ddd. m. H-2a). 2.57 (1H. ddd. m. H-2b), 5.56 (1H.
d d . J = 8 . 5 H z . 3.0 Hz. H-15).
Epitaraxerol (5): Bpt vd djnh hinh mdu trlng.
R, = 0.37 (TLC. silica gel. n-hexan-(CH,),CO 4:1. v/v). ESI-MS: m/z 427,2 ([M+H]-) (C,„H„0), 409,2 ([M+H-H,0)*). 'H-NMR (CDCi,): 5 (ppm) 0,82 (3H. s. 24-CH,). 0.86 (3H. s, 28-CH,).
TAP cut DirOC HOC - 9/2016 (S(i 485 NAM 56)
• Nghien cOu - Ky thuat
0,92 (6H, s, 27-CH,, 30-CH,), 0,94 (3H, s, 23-
CH,), 0.95 (6H, s, 25-CH,. 29-CH,), 1.09 (3H. s. 26-CH,). 3.39 (1H. s br. H-3). 5.52 (1H. dd. J = 8.5 Hz. 3.0 Hz. H-15).
P h i EShMS eiJa 1 eho pic Ion gia phan tu y m/^
427,3 ([M+H]') va pic y m t 409,2 ([M+H-H,0]*) gia thilt mat cdng thiic phan tft C„H O d a rndt hyp chit triterpenoid. Tinh todn sy thieu hyt hydro cho thiy 1 cd the la mdt triterpenoid nam vdng ed mOt n i l ddi trong phdn tu. Pho 'H-NMR (CDCI,) d a 1 xdc djnh cdc tin hipu cdng hudng tu proton cua 8 nhdm methyl b$c ba d' 6„ 0,8 (3H, s). 0.82 (3H s) 0,91 (6H, s). 0.93 (3H, s), 0.95 (3H. s), 0,98 (3H, s) va 1,09 (3H, s), mdt nhdm oxymethin d 6„ 3,19 (1H. dd. J = 11.5 Hz. 4.5 Hz) va mdt proton oleiinie cda mOt n i l ddi the ba lin d' 5„ 5,53 (1H. dd, J = 8.0 Hz. 3,0 Hz). Nhdm hydroxy duyc gid thilt Id y vj tri C-3 xult phat tu dU ki#n p h i 'H-NMR (8„ 3,19. dd) va sy phdt sinh sinh vat d a eac triterpenoid dl ti>
squalen-2,3K)xid. Cdc du kidn p h i 'H-NMR d a 1 hoan toan phii hyp vdi pho d a taraxerol tu Myrica njbra «. Hod lap t h l 3p ciJa nhdm hydroxy da duyc xdc djnh nhd hang so tuyng tac Idn diaxlal ciJaH-3(J=11.5Hz).
Cdng two phdn t u C„H.jO, cua 3 duyc gia thilt tir p h i ESI-MS qua pic ion gid phdn tu 6 m t 457.2 (IM + H]*) va pic 6 m/z 439.2 ([M+H-H O]*) Phi 'H-NMR (CDCI,) cOa 3 ehi ra sy d mat cua 7 nhdm methyl bac ba o' dang singlet 6 5 0 76 (3H). 0.78 (3H), 0,9 (3H), 0.91 (3H). 0.93™ (SH).
0.98 (3H) va 1,14 (3H), mdt nhdm oxymethin 6 6„
3,22 (1H, m) va mdt proton olefinie d 5„ 5,27 (1H, t, J = 3,5 Hz). Cdc tin hieu ndy phu hyp vyi mpt ehit oleanan C^ d mdt nhdm methyl bj oxy hda thdnh nhdm acid eartxjxylic. Nhdm hydroxy duyc gid thilt lidn k i t vdo C-3 tu sy phat sinh sinh vat cda cac d i t oleanan tu squalen qua squalen oxid.
Nhdm ndy duyc dlnh hudng 3p do hang so tuyng tde J = 11,0 Hz ciJa hai proton diaxlal H-2/H-3. So sdnh p h i d a 3 vdi p h i d a d e chit oleanen-12- en trong d e tai lidu tham khao da xac djnh duyc d u tnJc d a chit nay la add oleanollc PI.
P h i ESI-MS cda 4 cho mdt pic ion gia phan t u
* m/z 426.2 ([M+H]') va pic d 407,2 (IM+H-H,0]')
T * P CHl DirtJC HQC - 9/2016 ( S 6 485 NAM 56)
cho gia thilt ve cdng thuc phan t u C,„H.„0 cua mpt tnterpenoid. Pho 'H-NMR (CDCI,) cda 4 cho thay su d mat d a d c tin hieu cpng huyng ti>
proton d a 8 nhdm methyl singlet y 5,^ 0,83 (3H s) 0,91 (3H, s), 0,92 (3H. s). 0.96 (3H. s). 1.07 (3H.
s). 1.08 (3H.S). 1,09 (3H.s)va 1.14 (3H,s)va mdt proton olefinie d a mdt n i l ddl t h l ba Ian 6 3 5,56 (1H, dd, J = 8,5 Hz. 3,0 Hz). Tinh toan sy thieu hyt hydro chothlydayiamdttnterpenoldnamvdngd mpt n i l ddi t h l ba lln vd mOt nhdm eart)onyi trong phdn ti>. Hal proton it 5 2,37 (1H, m) va 2,57 (1H.
m) d n g huyng 6 cac tan s6 d a cae proton y cac vi^tri llln k l vol mdt nhdm cartjonyi. do dd manh d u tnJe -CO-CH,-CH,- da duyc thilt Idp Trdn cy sy d e du klpn pho MS va NMR 4 da duyc xac
^ n h la taraxeron R
Pho ESI-MS eua chit 5 cho mdt pic Ion gia phan tir a m/z 427.2 ([M+H]*) vd pic * m/z 409,2 ([M+H-H,or) gia thilt d n g thuc phan ti> C,.H O cua mot triterpenoid. Pho 'H-NMR (CDCI,) eCia 5 xac anh cac tin hi$u d n g hucmg ti> proton cua 8 nhdm methyl bdc 3 y S„ 0,82 (3H, s), 0,86 (3H s) 0,92 (6H. s), 0,94 (3H. s), 0,95 (6H, s) vd 1,09 ( 3 H ! s). mdt nhdm oxymetin d 6„ 3.39 (1H. s br) va mot proton olefinie d a mdt noi ddl t h l ba l i n i> 5 5 52 (1H. dd. J = 8.5 Hz. 3.0 Hz), cac du' kipn ph'i riay tuyng ty nhu cua chit 1. tuy nhidn sy khdc biet y hang so tuyng tac nhd giua H-2 va H-3 (s br).
eho thIy H-3 d^ vl tri equatorial. Cae da kidn p h i 'H-NMR ciia 5 phu hyp vol pho cda epitaraxerol duyc phan Idp tir la d y Mallotus apelta ^'"i.
Ket luan
Da phdn lap va xac djnh duyc d u tnJe cua 4 hyp chit triterpenoid ia taraxerol. acid oleanollc.
taraxeron, epitaraxerol va |3-sltosteroi Kr Id d y bye ndu (Maltotus mollissimus (Geisel.) /\iry-Shaw).
Sy phat hidn cac d i t taraxeran ddc blpt la d p epime taraxerol/epitaraxerol d the dang chii y v l sy phan loai thyc vat theo hda hoe d a d c loai
• Nghien CIPU - Ky thuat
Mallohjs; c a p e p i m e n a y m o i c h i dipcrc p h a t h i # n d & i g t t i o i t r o n g M. apelta v a M. maaostachyus.
C a c terpenrad-steroid n a y Ja c a c t h a n h p h a n c h i n h v a CO t h e x a c d j n h h o a t t f n h s i n h h o c c u e n h o m c h i t lipid it p h a n asc t r o n g la c a y b u c n a u .
Loi cam cm: N g h i e n c u u n a y d u w c t a i trcr b o i Q u y p h a t trien K h o a h o c v a c o n g n g h $ q u 6 c g i a { N A F O S T E D ) t r o n g d e tai m a s 6 1 0 4 . 0 1 - 2 0 1 2 . 1 0 .
Tai lieu ttiam Ithao 1. Phgm Hoang H5 (1999), Cay cd Viet Nam, Nha xu^t ban Tre, Thanh pho H 6 Chf Minh.
2. C. Riviere. V. N. T. Hong, Q. T. Hong, G.
Chataigne", N. N. Hoai, B. D^aegher, C . Tisteert, T.
N. T. KJm. Y. V. Heyden, M. C . \fein. J . Quetfn-Ledercq (2010), "Ma/fofas ^)ecies from Wetnamese mountainous areas: phirtochemistry and phannacolOQical activities*, Phytochem. Rev., 9, 217-253.
3. M. G. Phan, M. T. \Aj. T. S. R i a n (2013),
"Riytochemical studies « i Malk^us barbabjs'. Chenvstry of Natural Compounds. 49,129-130.
4. VQ Minh Trang, D o Thj Kim Hu&. Phan T & i g S o n , Phan Mtnti Giang (2012), ' N ^ « e n cCw thanh frfian h6a hpc cSy bCim bgp gai [MaBotus barbalus) vd cay bCim b y p
bong to [Mallobjs macrostechyos). h p Ei,5)hort)iac8ae"
Tap eft/Hoa ftpc, 50,466-470.
5. M. G . Phan, M. T V u . T. S. Phan. K. Matsunami HKteaki Oteuka (2013), T h e firet occurence of a Maftjftis 3.4-sea>taraxerane tritejpenoid from Malotus barbatus: Records of Nabjral F^oducts. 7,157-1M,
6. I. W. Kusuma, N . M. Sari. H. Kuspradini (2015),
"Search for antimicrobial and antioxidant a<aivities from plants used by Bentian tnbe in East Kalimantan". UNEJ Open conference system. Internationa conference on Ibod, ^ricultuiB, and natural resources.
7. L Monzote. A . Pincin. W . N. Setzer (2014), -Antileishmanial potential o f trt^xcal rainforest plant e x t i a d s " , Medicines, 1.32-55.
8. N. Sakurai, Y Yaguchi, T inoue (1987), Triterpenoids from Myrica rubra', Phytochemisbv 26.
217-219.
9. Z . Guvenalp, H. Ozbek. A . Kuruuajm-Uz. C.
Kazaz, L O. Demirezer (2009), •Seawidary metetroTites from Wepete heliotropifolia', Turk. J. Chem., 33,667-675.
10. V. K. Phan. V. M. Chau. T. H. Hoang, H. N Nguyen. J . J . Lee. Y H. Kim (2004), -pentacydk:
triteipenoids from Mallobjs apelte', AnOi. Phann R M L 27.1109-1113.
{Ngay nh§n bai: 08/06/2016 - Ngay duy&t dSng: 01/09/2016}
Mot so hop chSt phan lap tir re cay ba kich {Morinda officinalis How.) trong ff tinh Quang Nmh
Vu BiTc Lffi'*, Nguyin Tien Vihig% Nguyin Thi Thiiy An^
'Khoa YDuac. DH Quoc gia Ha NQI - Vien Phap y Quoc gia
^Hgcvi^n Quany 'E-mail: [email protected]
Summary
t h , 2 Z Z S ^ J ' ! ^ ^ r i " " ^ ^ * * ^ ' "'•^•l " * ^ I" Ouang m,h province,
S S S Z ^ r / ^ "^f'^fi^'d'onBlosrapft/c-nelhodsand/tfenlWas.- 12a-l^roxyevodol (1).
S ^ ^ S ^ S i a t ^ l ^ S ^ ' S . ^ S f ^ ' ^ ' ^ ' ^ ^ " * ^ ' ^ ' ' ' ' ' ' ' ' ^SandNMR TlS^cZbunds(
<^ (^/'""^leelatedlrom mots of MonndarMckialis (How.) for the nrsl time Keymrds: 12a-Hydmxyevodol, Inedelarh3-cne, daucosterol.
Cac cong tiinh nghien cyu hoa hoc v^ d y Jfi . " ' " ^ ^ ' * ' * ^^"^ '*y " ' • * P*K" hay say ' ^ ''''^^ (Morinda omdnalis How.) d u yeu dyye Wi6 cua cay lia kich. V] thu6e nay duorc dung d i t i * " hanh y Tmng Qufic, d c k i t qud nghiSn d u S . " ! l . ' S ? _ ' ' ! ' ' ? • ' ^ ' ^ P '^"^ 1*1. san aa phan lap d y y e mpt s6 thinh phSn trong d y cot yau mem, lung g6i moi dau. La mpt vi thuSc b6
fri nao va Snh l<hi. ba k i d d n d i > a cac benh llet dyyng, » ^ t tinh d m , dl mong Bnh, phu n y kinh nguyot kh6ng dSu, benh phong thap I'-^i.
chu y^u la cac anthraquinon b i n g phu-crng ph^p s i c ky hi#n dgi '^ i . MOt s6 nghien ci>u v6 hogt tinh sinh hpc cung da duvc tien hdnh vd k^t quS chf ra djch c^iet ba kich cd t ^ dyng ch6ng vi6m.
TAP C H i DlXqfC HQC - 9/2016 ( S 6 4S5 NAM 56)
