• Nghien ciru - Ky thuat
chromatography with ultraviolet detection". Biomedical Chromatography, 9(1), 36-41.
6 Raggi MA, Bugamelli F, Mandrioli R, De Ronchi D, Votterra V (1998), "Determination of clozapine in human plasma by solid-phase extraction and liquid chromatography with amperometric detection", Chromatographia, 47(1), 8-12.
7 Raggi MA, Bugamelli F, Sabbioni G, De Ronchi D, Pinzauti S, Votterra V (2000), "An improved HPLC- ED method for monitoring plasma levels of clozapine and its active metabolites in schizophrenic patients', Chromatographia, 51(3-4), 147-153
8. Rosland M, Szeto P, Procyshyn R. Barr AM, Wasan KM (2007), "Determination of clozapine and its metabolite, norclozapine in various bioiogical matrices
using high-performance liquid chromatography". Drug Development and Industrial Pharmacy. 33(10),1158- 66
9 Ulrich S, Baumann B, Wolf R, Lehmann D, Peters B, Bogerts B, Meyer FP (2003). "Therapeutic drug monitoring of clozapine and relapse—a retrospective study of routine clinical data'. International Joumal of Clinical PharmaccAogy and Therapeutics, ^^[y), 3-13.
10. Wohlferth A, Toepfner N, Hermanns-Clausen M, Auwarter V (2011), "Sensitive quantification of clozapine and its main metabolites norclozapine and clozapine-N-oxide in serum and unne using LC-MS/
MS after simple liquid-liquid extraction work-up".
Analytical and BioanalytJcal Chemistry, 400(3), 737- 746
{Ngdy nhdn bdi: 20/03/2015 - Ngdy duydt ddng: 04/05/2015)
^ Thanh phan hoa hoc
cua phan doan nirdc phan tren mat dat cay he mo (Psychotria prainii H. Lev.)
Nguyen Phi Hung', D6 Thi Ha\ Nguyin Tien Dat*, Nguyen Thj Thu^
Le Viet Dung^*, Nguyen Trong Thong''
'Benh vien Y hoc co truyen Trung uang -Vien Dugc Ueu
^Vien Hoa Sinh bien, 'TruongDgi hoc Y Ha \ai
*E-maiT [email protected]
Summary
Prom the aqueous factions of Psychotria prainii, 3 phytochemical compounds were isolated in high purity and structurally identified as roseoside, macarangioside F and 6-hydroxy-junipeionoloside by NMR and MS in reference to the literature. It is for the first time, the occurrence of these 3 compounds was revealed in the species Psychotria prainii in particular, and the genus Psychotria in generai
Keywords: Psychotria prainii, mseoside, macarangioside F, 6-hydroxy-junipeionoloside.
Dat vdn d6
He mg cd tfln khoa hge Id Psychotria prainii H. Lev., hg Cd phe (Rubiaceae), con dyge ggi Id lau long hoe, phdn bd fl- Cao Bdng, Lang Son^'i.
Theo Y hgc ed tmydn, cay efl vi ddng, tinh mat;
cfl tde dyng thanh nhi^t giai dflc, tan (y ehi huyet, trir thap, chi ly "'. Tuy nhifln, cho den nay cde cdng trinh nghien c(yu ve thdnh phdn hfla hge
eung nhy tdc dyng sinh hge ciia cdy he mg fl* Vi^t Nam cfln hgn ehe. Nghien eii'u ndy nhdm myc dieh byde dau tim hidu thdnh phan hfla hgc cua eay hd mg, ddt ndn mong eho cdc nghien ciru sau hon vd cd thdnh phan hda hgc vd tdc dyng sinh hgc eua lodi nay trong tyong lai
TAP CHi D i r a c HQC-5/2015 (S6 469 NAM 55)
• Nghien CIFU - Ky thuat
N g u y e n l i e u v a phu'O'ng p h a p n g h i e n c i > u
Nguyen liflu
Mau nghifln ciru id phan tren mgt dat ciia cdy he mg d y g c thu hai tai Son La. l\/lau eay dd d y g c xac djnh ten khoa hgd^' vd mau tieu ban d y g e lyu giir tgi phflng tieu ban cua Vign D y g c ligu (sd higu TB-9938), Phflng tieu ban cija Vifln Sinh thdi vd Tdi nguyen sinh vgt (sd hieu 1572013SL) vd phflng tieu bdn ciia Bg mfln T h y c vgt Tryfl'ng Ogi hgc D y g c Ha Nfli (sd hieu 18071/14)
P h y o n g phap nghifln eii'u Phuxmg phap phdn ldp cac h(}fp chit Phdn ldp cdc hgp chat tir phdn tren mat ddt hd mo bang sae k^ eflt va sde ky lop mdng (SKLM). Dung mdi, hda chat dimg de chidt xuat vd phan ldp gdm ethanol 96%, methanol (MeOH), dichloromethan (DOM) d y g e mua ciia cdc cflng ty hda chdt vd dat tiflu chudn cflng nghidp. Dung mfli dimg cho phan tich HPLC gdm aeetonitril (Merek), MeOH (Merck) vd n y d e cat hai lan dgt tiflu ehudn phan tich. Theo ddi cdc phdn doan sde ky bdng SKLM. Sdc ky cflt d y g c tidn hdnh vgi ehdt hdp phy Id diaion HP20, silica gel pha thyfl'ng (0,040-0,063 mm, Merck); YMC (Fuji Silysia Chemical Ltd.). SKLM d y g e t h y c hign tren ban mdng trdng san DC-Alufolien 60 F^^^
(Merck, silica gel, 0,25 mm) vd ban mflng pha dao RP-18 F^j^ (Merck, 0,25 mm). Phdt hign chat bdng den tir ngoai fl' hai byfl'c sflng 254 nm va 366 nm hodc dung thudc thir Id dung djeh H^SO^
10 % trong ethanol 96 % h o ndng dd phat hign vet chit
Phuxmg phdp xdc dinh ciu true hoa hgc cdc hgp chit
Xde djnh edu triic ede hgp ehat phan lap d y g c dya tren cdc thflng sd vgt ly va ede phyong phdp phd bao gdm: gflc quay cye, didm ehdy, phd khdi l y g n g , phd cgng hyfl'ng tir hat nhdn.
Didm chdy d y g e do tren mdy do dg ndng chay GALLENKAMP (Sanyo, Nhdt Bdn). Gflc quay eye d y g e do tren mdy do dg quay cye JASCO P-2000 digital polarimeter. Phd egng hyfl'ng tir hgt nhdn ghi bdng mdy Bruker AM 500 FT-NMR spectrometer voi ehdt chudn npi Id TMS. Phd khdl lygng phun mil dien t y (ESI-MS) do trfln
he may AGILENT 1200 series LC-MSD lon Trap.
He thdng mdy sac ky Idng hieu nang eao (HPLC) Shimadzu LC-20AD, detector PDA, cgt C l 8 (250 x 4 , 6 mm; 5 pm).
Chiet xuit va phan ldp cac hgp chit tinh khiit
10 kg d y g c lieu khfl Id phdn tren mat dat eua hd mg d y g c chiet hdi lyu vfl'i ethanol 96 % (3 Idn, moi lan 3 gio). Loe, ggp djeh chidt vd cfl djch chiet dyd'i dp suat gidm den eao dae (339,3 g). Cao ddc d y g c phdn tan trong 500 ml nyfl'c vd dem Ide Idn lygt ede dung moi cd do phdn cye tang dan gdm n-\\exan vd ethyl acetat Cat thu hdi dung mfli du'oi dp suat gidm thu d y g e cdc cao chiet phdn dogn t y o n g irng gdm eao n-hexan (113,0 g), ethyl acetat (83,3 g) vd egn nyfl'c (132,2 g).
Cgn n y o c d y g c dya Ifln cgt diaion HP20, rira giai bdng he dung mdi MeOH-H^O (0, 25 va 100%) thu d y g c 3 phan doan PPW1.3 - » PPW1.5.
Phdn doan PPW1.5 (11,0 g) d y g e d y a len cgt sdc ky pha t h y o n g . nya gidi bdng hfl dung mfli DCM-MeOH (100-0 %) thu du'gc 5 phdn dogn nhflPPW25.1 ->PPW25.5 Phan dogn PPW25.3 (708,8 mg) d y g c d y a len egt sdc ky pha dao YMC-PR18 rira gidi bdng he dung mdi MeOH- H^O (1:4) thu d y g e 3 phdn dogn PPW26.1 - * PPW26.3. Phdn doan PPW26.2 (38,0 mg) d y g e phdn tach tren cgt sac ky pha thyfl'ng, rira gidi bdng he dung mfli D C M - M e O H - H p (8:1:0,01), thu du-ge hgp chat 1 (7 mg). Hop ehat 2 (3,5 mg) d y g c phan lap tren egt sdc ky pha thyong ttr phdn doan PPW26.3 (30.4 mg) va rira gidi bdng hg dung mfli DCM-MeOH. Phan doan PPW25.4 (1,8 g) d y o c phdn tach tren egt sde ky pha dao YMC-PR18 vol he dung mfli M e O H - H p (1:3) thu d y g e 9 phdn doan PPW29.1^PPW29.9, Phdn doan PPW29.6 (134.6 mg) tidp tyc d y a len sac ky eflt pha thyfl'ng, rira giai bdng hg dung mfli D C M - M e O H - H p (6:1:0,01), thu d y g c hgp chdt 3 (4,3 mg).
K i t q u a v a b a n l u a n
Phan lgp vd xdc djnh cdu true cdc chdt Tir phdn doan n y o c eiia djeh ehiet EtOH 96
% phan tren mat dat he mg da phdn lap d y g e 3 hgp chdt Id roseosid (1), maearangiosid F (2) vd 6-hydroxy-junipeionolosid (3) (Hinh 1).
TAP CHi D i r a c H p c - 5/2015 (S6 469 NAM 55)
• Nghien CCFU - Ky thuat
Hinh 1 ; Cong thtic cau Ht/p chit 1:
Chat r i n mau t r l n g ; mp.: 155-156 °C; [a],,"
+9,0 (c 0,1, MeOH); •H-NMR (500 MHz, CD,OD);
8„ 1,04 C3H, s, H-11); 1,06 (3H, s, H-12); 1,31 (3H, d, J = 6,5 Hz, H-10); 1,96 (3H, d, J = 1,0 Hz, H-13); 2,18 ( I H , d, J = 17,0 Hz, H-2a); 2,64 (1H, d, J = 17,0 Hz, H-2b); 3,19 (1H, m, H-5');
3,24 (1H, m, H-2'); 3,27 (1H, m, H-4'); 3,30 (1H, m, H-3'); 3,66 (1H, dd, J = 6,0; 11,5 Hz, H-6a');
3.88 (1H, dd, J = 2,0; 11,5 Hz, H-6'b), 4,30 ( I H , d, J = 8,0 Hz, H-IO; 4,56 ( I H , dd, J = 6,0; 12,0 Hz, H-9); 5,76 ( I H , dd, J = 7,0; 15,5 Hz, H-7);
5.89 ( I H , d, J = 7,0 Hz, H-8), 6,00 (1H, d, J = 15,5 Hz, H-4); "C-NMR (125 MHz, CD,OD): 5^
42,5 (C-1); 50,7 (C-2); 201,2 (C-3); 127,2 (C-4);
167,3 (C-5); 80,0 (C-6); 131,5 (C-7), 133,7 (C-8);
78,1 (C-9); 23,4 (C-10); 23,5 (C-11); 24,7 (C-12);
19,5 (C-13); 101,2 (C-l'); 75,0 (C-2'); 78,3 (C- 30; 71,6 (C-4'); 78,2 (C-5'); 62,8 (C-6'); ESI-MS (negative): m/z 421 [M+CI]-
Tren pho •H-NMR cua hap chat 1 xuat hien tin hi^u dae tru'ng cua 4 nh6m methyl tai 5 1,04 (3H, s, H-11); 1,06 (3H, s, H-12); 1,31 (3H, d, J = 6,5 Hz, H-10) va 1,96 (3H, d, J = 1,0 Hz, H-13), mpt cap proton olefin cua lien l<et do) tai 5„ 5,76 (1H, dd, J = 7,0; 15,5 Hz, H-7) va 5,89 (1H, d, J
= 7,0 Hz, H-8) va mpt proton olefin trong noi doi Mt^c tai 6„ 6,00 (1H, s, H-4). Ngoai ra cac proton trong viing tir 5„ 3,19 - 4,30 du'O'c d y doan la cua phan tir du'dng. Tren pho "C-NMR va pho DEPT"
x u l t hi$n tin higu cua 19 nguyen tiJ' carbon, trong do CO 6 tin hieu carbon dae tru'ng cho phan tiJ' atrtmg glucose tai 6^ 101,2 (C-1'); 75,0 (C-2');
78,3 (C-3'); 71,6 (C-4'); 78,2 (C-5') va 62,8 (C-6');
13 nguyen tin carbon con lai trong do co 4 carton methyl, 1 carbon methilen, 4 carbon methin va 4 carbon bac bon (m6t nhom carboxyl tai 5^ 201,2 (C-3)). Hffp chat 1 chira hai lien ket doi, mot lien l^lt dang the 3 lan >C=CH- tai 6^ 127,2 (C- 4)/167,3 (C-5) va mpt dang the 2 lan - C H = C H -
tao Ccic hop ch^ 1-3
tai 5^ 131,5 (C-7)/133,7 (C-8) va v6i gia tn hing so lu'O'ng tac cao (J = 15,5 Hz) nSn n6i d6i nely c6 dang hinh hpc trans. Qua cac phSn tich trfin cho thay hep chat nay co khung megastigman gin vol mgt phan tu' dycrng glucose. Proton anome cua ph§n tLr dycrng co h i n g s6 tu'ong t^c cao (J
= 8,0 Hz) nen day la dycrng p-D-glucopyranosid.
Xet tren ph6 kh6i thay xuat hien tin hi^u m/z 421 [M+CI]- chirng to phan tir c6 khoi lu'p'ng M = 386.
So sanh voi cac dir lifiu pho lu'O'ng irng vifi hp'p chat roseosid thay co s y giong nhau a c^c vj tri.
Tir nhO'ng phan tich trfin cho phfip ket luan hpp chat 1 la roseosidi". Roseosid d§ du'O'c phSn ISp tir nhieu loai kh^c nhy Bauhinia varlegata i**', Alangium premnlfdliurrf^ v^ Junlperus phoneniceef^l Hp'p chat nSy d§ dyp'c chyng minh la co tac dyng tang ti^t insulin phg thuOc lieu trfin dong te bao INS-1, c6 t i l m n3ng trong irng dyng dieu tri tieu dyd'ng'^'.
H(?pchit2:
C h i t rSn mau trang; mp.: 221-292 °C; [a]„"
-3,0 (c 0,1, MeOH); 'H-NMR (500 MHz, CD,OD):
S„ 1,03 (3H, s, H-11); 1,28 (3H, s, H-13); 1,34 (3H, d, J = 6,5 Hz, H-10); 2,23 (1H, d, J = 17,0 Hz, H-2a); 2,32 (1H, d, J = 17,0 Hz, H-4a); 2,47 (1H, d, J = 10,0 Hz, H-6); 2,60 (1H, dd, J = 2,0, 17,0 Hz, H-2b); 2,67 ( I H , d, J = 17,0 Hz, H-4b);
3,20 ( I H , m, H-5'); 3,24 (1H, m, H-2'); 3,27 (IH, m, H-4'); 3,30 ( I H , m, H-3'); 3,62 ( I H , m, H-12a);
3,65 ( I H , m, H-6'a); 3,71 ( I H , d, J = 8,0 Hz, H-12b); 3,89 ( I H , dd, J = 2,0; 11,5 Hz, H-6'b);
4,34 ( I H , d, J = 7,5 Hz, H-10, 4,55 ( I H , t, H-9);
5,79 ( I H . dd. J = 2,0; 15,0 Hz, H-8); 6,00 (IH, dd, J = 9.5; 15,5 Hz, H-7); "C-NMR (125 MHz, CDjOD); 6^ 45,4 (C-1); 49,8 (C-2); 211,6 (C-3);
51,0 (C-4); 84,9 (C-5); 59,6 (C-6); 127,0 (C-7);
139,5 (C-8); 74,5 (C-9); 22,4 (C-10); 20,4 (C-11);
79,8 (C-12); 24,6 (C-13); 101,2 ( C - n ; 75,0 (C- 2'); 78,3 (C-3'); 71,7 (C-4'); 78,2 (C-50; 62,9 (C- 6'); ESI-MS (negative): m/z 421 [M+Clf.
TAP CHi D i r p c HOC - s/2015 (S6 469 NAM 55)
Nghien CLFU - Ky thuat
lap tir Psychotria yunnanensis i^l Vomifoliol. dang aglyeon cua roseosid va6-hydroxy-junipeionolosid dygc phan lap tir cac lodi Psychotria cadigensis va Psychotria gitingensis trong cae nghien eii'u eflng bo nam 2012 ""i vd 2014 i^l Cae dCr lieu nay eo y nghta khoa hgc nhdt djnh dflng gflp cho viec nghifln ciru moi lien he ve thdnh phdn hfla hoc ciia cde lodi thuge c^i Psychotria.
K i t luSn
Tir phan doan nyde eua phan tren mat dat cay he mg thu hdi tai tinh Son La, ba hgp ehat roseosid (1), maearangiosid F (2) vd 6-hydroxy- junipeionolosid (3) lan ddu tifln dyoe phan lap tir chi Psychotria.
Tai lieu tham khao 1. V6 Van Chi (2012), Twdiin cay thudc Viet Nam (bo moi). tap 1, NXB Y hoc, 1307-1308
2. Trdn Phi Hiing, Nguyin Quynh Nga, Pham Tha- nh Huyin, Le Viet Dung, Nguyin Vilt Than (2014),
"Dae dilm hinh thai va giai phlu cua cay thulc h i mo", Tsip chlDwocheu. 19 (6), 319-324
3 Nguyin Hoai Nam, Nguyin Phu'ong Thao, Phan Th] Thanh Hu-ong, Nguyin Xuan Cu'dng, Ninh Thi Ngoc, Vu Anh Tii, Lg Diic Dgt, Chau Ngoc Diep, Phan Van Kiem, Chau Van Minh (2012), "Cac hap chdt me- gastigman va lignan phan lap tCf la cSy bCim bup bong to Mallotus macrostachyus (Miq ) Muell.-Arg", Tap chl Dwac hoc, th^ng 8, 33-37
4 Champavier Y, Comte G., Vercauteren J., Allais D. P, Chulia A. J (1999). "Norterpenid and sesquiter- penoid glucosides from Juniperus phonenicea and Ga- lega officinalis". Phytochemistry, 50, 1219-1223.
5 Prankish N . de Sousa Menezes R, Mills C, Sheridan H (2010), "Enhancement of insulin release from the beta-celi line iNS-1 by an ethanolic extract of Bauhinia vanegata and its major constituent roseoside". Planta Medica, 76(10), 995-997
6 Matsunami K, Otsuka H., Kondo K, Shinzato T, Kawahata M , Yamaguchi K, Takeda Y (2009),
"Absolute configuration of (+-) pmoresiol 4-0-[6"-0- galloyl]-/3-D-glucopyranoside, macarangiosides E, and F isolated from the leaves of Macaranga tananus", Phytochemistry. 70, 1277-1285
7. Otsuka H , Yao M., Kamada K-, Takeda Y (1995),
"Alangionoside G-M Glycoside of megastigmane de- rivatives from the leaves of Alangium premnifolium", Chemical and Pharmaceutical Bulletin, 43(5), 754-759.
8. Qinpei L, Junsong \N, Ungyi K, (2014),
"Chemical constituents from Psychotria yunnanensis and its chemotaxonomic study", Biochemical Systematics and Ecology. 52(0), 20-22,
9- Tan M. A , Eusebio J. A , Alejandro G J D.
(2012), "Chemotaxonomic implications of the absence of alkaloids in Psychotria gitingensis". Biochemical Systematics and Ecology, 45(0), 20-22
10 Tan M A , Panghulan G F M, Uy M M, Takayama H. (2014), "Chemical Constituents from Psychotna cadigensis and their chemotaxonomic relevance", Amencan Journal of Essential Oils and Natural Products, 1(4), 18-19.
(Ngdy nhdn bdi: 05/02/2015 - Ngdy duydt ddng: 04/05/2015)
jDanh gia tac dung u*c che enzym alpha glucosidase in vitro cua 4 loai Gymnema R. Br.
^ Viet Nam
Nguyin Thi Hiroiig, Phiing Thanh Hiromg, Bao Thi Mai Anh
Tnc&ng Dgi hqc Duac Ha Ndi
*E-mad: [email protected]
Summary
Regarding that the Gymnema R Br sp. in general and G. sylvestre in particular is well-known for hypoglycemic effects, following our recent studies on hypoglycemic activity of Vietnamese Gymnema sp.
samples at various levels on streptozocine-induced hyperglycemic mice, in this study the mechanism responsible for the hypoglycemic activity was clarified. The alpha glucosidase inhibitory activity of 20 Vietnamese Gymnema sp. ecotypes of 4 species (G. sylvestre, G. latifolium, G. yunnanense and
TAP CHI DirOC HOC - 5/2015 (S6 469 NAM 55)
• Nghien CLFU - Ky thuat
Tren phd 'H-NMR eOa hgp chat 2 xuat hign tin dae tryng eiia 3 nhflm methyl tgi 5„ 1,03 (3H, s, H-11); 1.28 (3H, s, H-13) va 1,34 (3H, d, J = 6,5 Hz, H-10), mgt edp proton olefin tgi 5^ 5,79 ( I H , dd, J = 2,0; 15,0 Hz, H-8) vd 6,00 ( I H . dd. J = 9,5;
15,5 Hz, H-7) vd cde tin hieu proton trong viing 5„
3,20 - 4,34 d y doan 2 ehya mflt phdn tir d y d n g . Trfln phd '^C-NMR va phd DEPT xudt hifln tin hiflu eiia 19 nguyfln tu' carbon, trong do efl 6 carbon eiia phdn tir d y o n g glucose [5^ 101,2 (C-
^y, 75,0 (C-2'); 78,3 {C-Zy, 71,7 (C-4'); 78,2 (C- 5") va 62,9 (C-6')l vd 13 nguyen tir carbon cfln lai trong do eo 3 carbon methyl, 3 carbon methilen (mflt carbon gan tn^c tiep vol nguyfln tir oxy nfln cfl dfl chuyen djeh eao 5^ 79,8), 4 carbon methin vd 3 carbon bge bon (mgt nhflm carboxyl tgi 5^
211,6 (C-3)). Phd khdi xuat hien pie ion phdn tii' tgi m/z 421 [M+CI]- t y o n g irng vfl'i cflng thire phdn t y C^JH^p^ (M = 386). Vfl'i du' ligu phdn tich tren ket hop so sanh v&'\ tdi lieu tham khdo'^i cho phflp xdc djnh hgp ehat 2 la maearangiosid F. Maearangiosid F da d y g e phdn ldp tir nhidu lodi khdc nhau nhy Mallotus macrostachyus (eay biim byp bflng) i^', Macaranga tanariif^\...
H^pchitS:
Chat rdn mdu trdng, mp. 145-147°C; ^H-NMR (500 MHz, CD3OD): 5^ 1,09 (3H, s, H-12); 1,27 (3H, d, J = 6,5 Hz. H-10); 1.94 (3H, s, H-13); 2,42 ( I H , d, J = 1 7 , 5 H z , H-2a);2.67(1H. d. J = 1 7 . 5 Hz. H-2b); 3.18 ( I H . t, H-2'); 3,26 ( I H , m, H-3', 5*); 3,30 ( I H , m, H-4'); 3,62 ( I H . d, J = 10,0 Hz, H - l l a ) ; 3,69 ( I H , m, H -6'a); 3,88 ( I H , d, J = 2,0 Hz. H-6'b); 3.98 ( I H , d, J = 10,0 Hz, H - l l b ) ; 4,18 ( I H , d, J = 8.0 Hz, H-I*); 4.35 ( I H . t, H-9); 5,78 ( I H . d, J = 1 5 , 5 H z . H - 7 ) ; 5 , 8 5 ( 1 H , dd, J = 5,5, 15.5 Hz. H-8); 5,94 ( I H , s, H-4); ''C-NMR (125 MHz. CD3OD): 5p 46,2 (C-1); 44,5 (C-2); 201.2 (C-3); 127,7 (C-4); 167,4 (C-5); 79,4 (C-6); 129,6 (C-7); 137,2 (C-8), 68.6 (C-9); 23,7 (C-10); 74,6 (C-11); 20,1 (C-12); 19,5 (C-13); 104.5 (C-1');
75,0 (C-2'); 77,8 (C-3'); 71,4 (C-4'); 78,0 (C-S");
62.6 (C-6'); ESi-MS (negative): m/z 437 [M+CI]-.
Trfln pho 'H-NMR eiia hgp ehat 3 xudt hifln tin hiflu dgc tryng cua 3 nhflm methyl tai 5„ 1,09 (3H, s, H-12); 1,27 (3H. d. J = 6,5 Hz. H-10) vd 1.94 (3H. s, H-13), mflt cap proton olefin eua lifln kdt dfli tgi 5„ 5,78 ( I H . d, J = 15,5 Hz, H-7) vd 5,85 (1H, dd, J = 5,5; 15,5 Hz, H-8) vd mflt proton olefin trong ndi doi khdc tai S^ 5,94 ( I H , s, H-4). Ngodi
ra, cdc proton trong viing tir 5„ 3,18-4,18 d y g e d y doan Id eua phdn tir d y o n g . Tren pho "C-NMR vd phd D E P T xuat hien tin hiflu eua 19 nguyen tir carbon, trong do co 6 earbon eua phdn t y dyfl'ng glucose [5^ 104,5 {C-^y, 75,0 (C-2'); 77,8 (C-3');
71.4 (C-4'); 78,0 (C-S') vd 62,6 (C-6'),13 nguyfln t y earbon trong do efl 3 earbon methyl, 2 earbon methilen (mgt nhom gdn trye tidp vfl'i nguyen tir oxy tai 5^, 74,6). 4 carbon methin vd 4 carbon bdc bdn (mflt nhflm carboxyl tai 5^ 199,6 (C-3)). Hgp chat ndy chira hai lien ket dfli, mgt lien kdt dgng thd 3 Idn >C=CH- tgi 5^ 127,7 (C-4) vd 167.4 (C- 5); mgt dang the hai Idn - C H = C H - tai 5^, 129,6 (C-7) vd 137,2 (C-8) vfl'i gia tn hdng sd t y o n g tdc eao (J = 15,5 H z ) , nfln ndi dfli ndy cfl dang trans.
Qua phdn tich tren eho d y dodn hgp ehat tren co khung megastigman gdn v ^ i mflt phdn tii' d y d n g glucose. Proton anome eua phdn til' d y d n g cfl hang sd t y o n g tac cao (J = 8,0 Hz) nfln ddy la dyfl'ng p-D-glucopyranosld. Phd HMBC cho thay efl s y t y o n g tdc giira proton H-2 vdi carbon C-1, 3, 6 vd 11; H-4 vdi C-2 vd 6; H-7 vdi C-6, 8 vd 9; H-10 vdi C-8 va 9; H-12 vdi C-1, 6 vd 11, H-11 vdi C-1, 6, 12 va 1' va H-13 vdl C-4. 5 vd 6. T y o n g tdc giira proton H-11 vdi carbon C-1' khdng dmh phan t y d y d n g gdn vdo vj tri C-11 trfln khung megastigman Phd khdi xudt hifln pie ion phdn tir tai m^ 437 [M+CI] t y o n g irng vdi eflng thirc phdn tir C^J^^p^ (M = 402). So sdnh ede dir lieu phd cua 3 vdi hgp chdt 6-hydroxy- junipeionolosidi^i thay efl s y triing hgp d cdc vj tri, do dfl hgp chat 3 d y g c xdc djnh Id 6-hydroxy- Junipeionolosid. Hgp ehat ndy d y g e phdn lgp lan dau tien tir todi Juniperus phoneniceaf'^
B a n l u a n
Ba hgp chdt monoterpen glycosid: roseosid (1).
maearangiosid F (2) va 6-hydroxy-junipeionolosid (3) lan dau tien d y g c phdn lgp tir phan tren mdt ddt eua cay hd mg (Psychotria prainii) Cae hgp chat nay eung d y g e eong bo lan dau tidn trong chl Psychotria. Nghien ciru ndy cung chi ra moi lifln hfl vd thdnh phdn hfla hgc eua lodi Psychotria prainii vd eae loai thugc ehi Psychotria do s y eo mat eua ede hgp ehat ehiet tdch d y g c co eau true khung co ban (aglyeon) gidng vdi cdc hgp ehat da d y g c phdn ldp tir cae lodi khdc thuflc chi ndy tarde day '* - ' " l Aglyeon eua maearangiosid F efl cau true khung t y o n g t y vdi drummondol phdn
TAP CHI Du'gc HOC - 5/2015 (S6 469 NAM 55)
