• N g h i e n CLPU - Ky thugt r
Cac hop chat megastigman va lignan phan lap tu* la cay bum bup bong to Mallotus macrostachyus (Miq.) Muell.-Arg
Nguyen Hodi Nam, Nguyen Phu-tfng Thdo, Phan T h j Thanh Hu-ffng, Nguyin Xufin Cu-dng, Ninh T h j Ngpc, V u Anh T u , L6 Ddc Dat, ChSu Ng^c D i f p , Phan VSn Ki^m, Chau V a n M i n h Vi^n Hoa sinh Bien, Vi^n Khoa hgc va Cong ngh^ Vi^t Nam
Dat van de
Chi ba bdt {Matlotus) Id mdt chl Idn thudc hp thdu dau (Euphorbiaeeae). Ddn nay, da ed khoang 150 lodi Mallotus d u y e ghi nhgn trdn thd gidi, phan bd chu yeu d cae khu v y c t d An Op, Sri Lanka ddn Thai Lan, Lao, Campuchia, Viet Nam va khdp vijng Malesian. Ve phia Nam, ehung phan bd tdi midn Ddng Fiji, mien Bdc va Bdng Australia. Len phia Bdc, cd the bdt ggp khd nhieu lodi phan bd tai Trung Qudc, Trieu Tien va Nhat Ban. Rat nhidu lodi Mallotus da d u a c s d dyng Idm thude de chua nhieu loai bdnh khac nhau n h u : cay bye nui cao M.
japonicus dup'c s u dung trong y hpe ddn toe Tnjng Qudc de ehua bdnh viem lodt dg day, ta trang va dieu hda cdc chue phan cua bp may tieu hda ndi chung; d nudc ta loai bai bai M.
, contubemalis dup'c dung lam thude chua cae benh thdp khdp, u phong, mijn nhpt, ngda; loai buc trudn M. repandus d u g c s d dung tai Thai Lan de ehua benh viem da day, viem dau gan, viem dau khdp va ehua rdn doe cdn...'^' ^'.
Bum bup bdng to ed ten khoa hoc Id Mallotus macrostachyus (Miq.) Muell.-Arg, thudc ho thau dau (Euphorbiaeeae). Day la loai cay gd, cao den 10 m. 0 nude ta, eay mpc d trong cac lum bui va ven rdng den dp eao 400 m d Ninh Binh, Lang S a n , Thda Thien - Hue, Lao Cai, Hda Binh... Trong dan gian, la non dup'c gia ddp cam mau vet thuang. Nudc sdc la dung rua sach vdt thuang va la h a ndng diJng lam thude dap vet thuang va mun nhpt '^'. Trong khudn khd dd tai hap tac theo nghj dinh t h u Viet Nam - Bi tap trung nghien edu vd thanh phan hda hpe vd hoat ttnh sinh hpe eija cac loai Mallotus va
TAP CHi Dl/OC HQC - 08/2012 (SO 436 NAM 52)
Phyllanthus cCia Vidt Nam, bdi bdo ndy cdng bd kdt qud phdn ldp vd xdc djnh eau true cOa ba h y p chdt megastigman vd hai h y p chdt lignan t d edn chidt methanol eua Id cdy bijm byp bdng to M. macrostachyus. Cau true hda hpe eua cac hyp chdt d u y e xdc dinh bdng cdc phuang phdp phd bao gdm: phd khdi luyng (ESl-MS) vd phd edng hudng t u hgt nhan ( I D and 2D-NMR).
Vat lieu va phu'cng phap nghien ciru
Phu'O'ng phdp chung
PhuKmg phap phan lap cic hop chit sic ky lop mong (TLC)
Sdc ky Idp mdng d u a c thyc hipn tren ban mdng trang sdn DC-Alufolien 60 F254 (Merck 1,05715), RP,8 F2S4S (Merck). Phat hipn ehat bdng den t d ngoai d hai budc sdng 254 nm va 368 nm hoge dung thudc t h u la dung dich H2S04 10% d u a c phun deu len ban mdng, say khd rdi ha ndng t d t d den kht hien mau,
Sdc/cycp(('CCj
Sdc ky cdt d u y c tien hanh vdi ehat hap phy la Silica gel pha thudng vd pha dao. Silica get pha thudng cd c d hat la 0,040-0,063 mm (240- 430 mesh). Silica gel pha dao CDS hoae YMC RP-18 (30-50 nm, FuJislllsa Chemical Ltd.).
Phwong phap xac dmh cau true hoa hoc cac hgp chat
Pho cong hwong tir nhan (NMH) Phd cdng hudng t d nhan (NMR) ' H - N M R (500 MHz) va "C-NMR (125 MHz) duac do tren may Bruker AM500 FT-NMR Spectrometer, Vien Hoa hoc, Vten Khoa hoc va Cdng nghe Viet Nam.
33
Nghidn CCFU - Ky thu j t
Mdu thvpc v$t
Mdu Id cdy bum bgp bdng to Mallotus macrostachyus (Mlq.) Muell. -Arg (Euphorbiaeeae) dup'c thu hdl vdo thdng 8 ndm 2010 tgi v a n Bdn, Ldo Gal. Tdn khoa hpe d u v c GS. TS. Nguydn NghTa Thin. Dgi hpe Khoa hpe T y nhifln, Dgi hgc Qudc gia Hd Ndl vd ThS.
N g u y i n Thd C u d n g , Vidn Sinh thdi vd Tdi nguydn Sinh v$t gidm djnh. Mdu tidu bdn d u y c luu t r u tgi phdng mdu eua Vidn Hda sinh bidn.
Phfln l$p cdc hp'p chdt
Ld bCim bgp bdng to khd (2,5 kg) d u y c nghidn thdnh bdt vd chidt 3 ldn bdng methanol (MeOH) (3 X 5 lit) d nhidt dd 50°C trdn thidt bj chidt sidu dm thu d u y c 21,6 g edn chidt. Cdn chidt ndy d u y c hda tan vdo 2 lit nudc cdt vd tidn hdnh chidt phdn phdn bd Idn l u p l vdi doroform ( 3 x 2 lit) vd ethyl
acetat ( 3 x 2 lit) thu d u y c cdc c$n chidt tuong dng: doroform (MMc, 12,7 g), e t h ^ acetat (MMe, 6,1 g) vd cdn n u d c (MMw, 2,2 g).
Phdn dogn MMe vd MMw d u y c gom Igi vd tdch thdnh bdn phdn dogn, MMw1-MMw4, bdng sdc ky cOt silica gel pha t h u d n g n>a gidi bdng dorcfomi/MeOH (20/1. 10/1. 5/1 vd 1/1). T i ^ tgc phdn tdch phdn dogn MMw2 (1,3 g) bdng sdc k^ cdt silica gel pha t h u d n g s u dgng h$
dung mdi rua gidi clorofonTi/MeOH 7/1 thu duyc edc h y p chdt 1 (15 mg) vd 2 (10 mg). H y p chdt 3 (7 mg) d u y c tinh ehd t d phdn dogn MMw3 (5,2 g) bdng sdc ky cdt silica gel pha thudng rua gidi bdng doroform/MeOH 3 / 1 . Phdn dogn MMw4 (0,8 g) d u y c tinh chd bdng sdc ky eOt silica gel pha t h u d n g s u dgng h$ dung mdi n>a gidi eloroform/MeOH 2,3/1 thu d u y c cdc hyp c h d t 4 ( 1 4 m g ) v d 5 ( 2 1 m g )
V
O HO /1 A 2
UM
c-
Hinh 1: Ciu true hoi Corchoionosid C (1)
Ch^t bOt mau tr^ng. DO quay ci^c [a^ +25°
(MeOH, c 0,5). ESl-MS: m/z 409 [ M ' N a ] * , cSng thitc phan ti> CijHjoOa, M = 386, 'H-NMR (500 MHz, CDjOD) v4 "C-NMR (125 MHz, CD3OD) xem bang 1
Icarisid 85 (2)
Ch^t bOt mau trSng. Dg quay c v c [a^ - 1 3 ° (MeOH. c 0,5). ESl-MS: m/z 389 [M+H]*, cong Ihiic phan ti> C19H32O,, M= 388 'H-NMR (500 MHz, CD3OD) v4 "C-NMR (125 MHz, CD3OD) xem bang 1.
Macaranglosid F (3)
Chat bpt mau trang. Do quay c y c [ a ] " - 6 ° (MeOH, c 0,6). ESl-MS: m/z 389 [M+H]*, cong IhLHC phan tie C,9H320,, M= 388. 'H-NMR (500
OMe hQC cua cic hgrp chit 1-5
MHz. CD3OD) va "C-NMR (125 MHz, CD3OD) xem bang 1.
(*).Prnorvslnol dl-O-fi-D-glucopyranosId (t) Chat bOI mau t r l n g . DO quay a/o [a]J - 2 ? (MeOH, c 0,5) ESI-f/IS: m/z 681 [ M - H ] , cdng thl>c phan tu- C32H.20,e, M = 682. 'H-NMR (500 MHz, DMSO-tf,) 5 (ppm): 3,05 (2H, m, H-1, H- 5), 4,68 (2H, d, J= 4,0 Hz, H-2, H-6), 3,79 (2H, dd, J= 3,0, 9,0 Hz, H..4, H,-8), 4,15 (2H, dd, J' 7,0, 9,0 Hz, Ho-4, Ht-S), 6,95 (2H, d, J= 2,0 Hz, H-2\ H-2"), 7,04 (2H, d, J= 8,5 Hz, H-5', H-5"), 6,85 (2H, dd, > 2,0, 8,5 Hz, H-6', H-6"), 3,77 (6H, s. -OMe), 4,86 (2H, d, J= 7,0 Hz, H-1"', H- 1'"'), 3,23 (2H, H-2"', H-2""), 3,27 (2H. H-3'", H- 3'"'), 3,15 (2H, t, J= 9,0 Hz, H-4"', H-4""), 3,26 (2H, H-6"', H-5""), 3,44 (2H, dd, > 5,5, 12,0 Hz, H,-6"', H.-6"") va 3,65 (2H, dd, J= 2,5, 12,0 Hz,
TAP CHI DU'PC HQC - 08/2012 (SO 436 NAMjJH
• Ngnien CIFU - Ky tnugt
Hb-6'", H[,-6""); "C-NMR (125 MHz. DMSO-ds) 6 (ppm): 53,63 (C-1. C-5), 84,79 (C-2, C-6), 71,00 (C-4, C-8), 135,16 ( C - r , 0-1"), 110,52 ( 0 - 2 , 0 - 2"), 145,85 (C-3', C-3"). 148,96 (C-4', C-4"), 115,24 (C-5', C-5"), 118,17 (C-6', C-6"), 56,70 (- OMe), 100,16 (C-V", C-1'"'), 73,18 (C-2'", C- 2""), 76,80 (C-3'", C-3'"'), 69,67 (C-4'", C-4""), 76,98 (C-5'",C-5"") t i 60,66 (C-6"', C-6'"').
Syringaresinol di-O-p-D-glucopyrBnosid (5) Chat bpt mau trang. DO quay c y c [ a j p - 1 8 ° (MeOH, c 0,5). ESl-MS: m/z 765 [M+Na]*, cOng thipc phan tir C S J H M O , , , M = 742. 'H-NMR (500 MHz. DMSO-dj) 5 (ppm): 3,06 (2H, m, H-1, H- 6), 4,67 (2H, d, J= 3,5 Hz, H-2, H-6), 3,82 (2H, dd, J= 3,0, 9,0 Hz, H.-4, H.-8), 4,22 (2H, dd, J=
7,0, 9,0 Hz, Hb-4, Ht-8), 6,66 (4H, s, H-2', H-2", H-6', H-6"), 3,76 (12H, s, -OMe), 4,87 (2H, d, J=
7,0 Hz, H-1'". H-1""), 3,12 (2H, H-2'". H-2'"'), 3,20 (2H, H-3'", H-3""), 3,09 (2H, H-4'", H-4""), 3,19 (2H, m. H-5"', H-5""), 3,42 (2H, dd, J= 5,0, 12,0 Hz, H.-6'", H.-6"") va 3,60 (2H. dd, J= 2,0, 12,0 Hz, HB-6'", H J - 6 " " ) : "C-NMR (126 MHz, DMSO-ds) 5 (ppm). 53,63 (C-1, C-5), 84,79 (C- 2, C-6), 71,00 (C-4, C-8), 135,16 (C-1', C-1"), 110,52 (C-2', C-2"), 145,86 (C-3', C-3"), 148,96 (C-4', C-4"), 115,24 (C-5, C-5"), 118,17 (C-6', C-6"), 56,70 (-OMe), 102,68 (C-1'", C-l'"'), 74,13 (C-2"', C-2""), 76,48 (C-3'", C-3'"'), 69,92 (C-4'", C-4""), 77,14 (C-5"',C-5"") va 60,90 (C- 6'", C-6'"').
K^t qud vi thdo lu|ln
Hqip chJit 1 du'p'c phdn l$p dU'O'i d^ng chcit bOt mau t r i n g . TrOn ph6 'H-NMR ciia 1 xuSt hiOn cac tin hiOu d$c trung cua ba proton olefin [SH 5,89 ( I H , br s, H-4), 6,98 ( I H , d, J = 15,5 Hz, H-7) va 6,76 (1H, dd, J = 7,0, 15,5 Hz, H-8)], mOt proton oximetin [5H 4,55 ( I H , m, H-9)], mOt proton anome t6„ 4,30 ( I H , d. J = 7,5 Hz, H-1')] va hai proton ciia mOt nhOm oximetilen [5H 3,65 ( I H , dd, J = 6,0, 12,0 Hz, H,-6' vS 3,87 ( I H , dd, J = 2,0, 12,0 Hz, Hb-6')]. Xem xit h i n g s6 tuwng tac ciia cac proton olefin ciing vd'i s y xuSt hiOn ci^a b6n carbon olefin tai 6c 127,12 (CH, C J | ) / 1 6 7 , 1 0 ( C , C-6) va 133,72 (CH, C-7)/133,70 (CH, C-8) cho ph^p xac d|nh s y cd mat cua mOt Win k^t ddi bj the ba vi trf va mpt lign ket dOi ngoai vong bj t h i hai vj Iri c6 c^u hinh trans. Gia trj hang so tuxyng tac id-n ciia proton anome ciing vdi cac tfn hieu cacbon ciia don vj d u i m g tai 8c 101,25 (CH, C- 1'), 74,94 (CH, C-2), 78,34 (CH, C-3'), 71,66 (CH, C^t'), 78,16 (CH, C-5') va 62,82 (CH2, C-6'), dac tarng cho mpt goc d u ^ n g /?-D-glucose.
Ngoai ra, tren pho 'H-NMR ciia 1 con xuat hien cac tin hieu dac tru-ng cua mgt nhdm metyl bgc hai tgi 5H 1,22 (3H, d, J = 6,5 Hz, H-10) va ba nhom methyl bac ba (tu^ng irng mdi tin hipu 3H, s) tai 6„ 1,06 (H-11), 1,03 (H-12)va 1,96 (H-13).
Tin hieu proton methyl H-13 bj djch chuydn rat manh vh phia viing tru'ong thap che phep d y doan nhom methyl nay gan vao lien ket doi
Bang 1 : Sd lieu phd NMR cua 1 - 3va cac hgp chit tham khao
SH''(J'H2) SC Aglycon
SH''(J = H2) & ' & ' • SH"'(J-HZ)
2 50,8 50,72 2,61 d (17,0) 51,2 50,92 2,53 d (17,0) 2,12 d (17,0) 2,12 d (17,0)
49,85 2,56 d (17,0) 2,18 d (17,0) 212,28 '- 4
5 6 7 8 9 10
127,1 127,12
167,1 167,10 80,0 80,01 133,8 133,72
5,89 br s
6,98 d (15,5)
-
133,7 133,70 5,75 dd (7,0, 15,5) 74,6 74,67
22,2 21,99 4,55 m 1,22 d (6,5)
126,8
171,8 79,5 34,8 33,1 77,9 22,2
126,53
171,58 79,23 34,56 32,84 77,67 21,99
5,80 br s
1 82 m/2 05 m 1 4em/1.75m
3.78 m 1,22 d (6,5)
50,7
85,6 54,9 22,2 37,8 76,0 20,1
50,03
85,56 55.03 21,73 37,41 77,71 20,80
2,62 d (17,0) 2,23 d (17,0)
1,73*
1,6971,70*
1,74m/1,70' 3,90 m 1,30 d (6,5)
TAP CHI DUOC HOC - 08/2012 (SO 436 NAM 52)
• Nghien ci^u - Ky thujtt
13 19.5 19,56 9-O.GIucopyranose
V 2' 3 4' 5 6
101.3 75,0 78,2 71,7 78.4 62,8
101.25 74,94 78,34 71,66 78,16 62,82
C 1 Sc' Sc" SH''''(J-HZ) SC' 12 24,7 24,69 1,03 brs
1.96 brs
4,3Cl"dT7^5J^
3722- 3,32- T,29*"
3,18 m"
62,82 3,65 dd(6,07l 2,0) 62,9 62,67 3,e7dd(2fl,12,0)
'Sc cue corchoionosid d*', "125 MHz, "do trong mecerengiosid F^', ' tin hi^u bj chdng lip.
Tr«n phA "C-NMR ciia 1 xu4t hiOn cao tin hi$u ciia 19 carbon trong dd c6 13 fin hiOu cua aglycon va 6 tin hiOu cua mOt dan vj duHi^ng glucose. Di6u nay cho ph6p d y doan hp'p c h i t 1 c6 t h i la mOt d i n s u i t megastigman. Cf p h i n aglycon, ngoai c i c tin hiOu cua hai Ii4n k i t dOi, mOf nhdm oximetin [Sc 74,67 (C-9)] va 4 nhdm metyl [Sc 21,99 (C-10), 23,48 (C-11), 24,69 (C- 12) va 19,56 (C-13)] nhy da nSu, cdn x u l t hiOn cac tin hipu d$c tryng ciia mpt nhdm ceton [6c 201,28 (C-3)] va mOt carbon bSc b i n g i n tnyc t i l p v * i nguyen tir oxi [6c 80,01 (C-6)] Trdn c a s d cdc phan tich nSu tren, s i li#u p h i "c-NMR ciia 1 d u a c so sanh vd'i cac s6 liOu t y a n g irng da d y g c cdng b l cho hap c h i t ccrchoionosid C ' " va n h j n d u a c s y phii hap hpan toan d t i t ca cac VI tri tu'ang irng (bang 1). Ngpai ra, c i u true hda hoc cua 1 d y a c k h i n g dfnh b i n g k i t qua php HMBC. Tu'ang tac HMBC giOa cdc prpton H-2 (6„ 2,12 va 2,61) va C-3 (Sc 201,28) cho phdp xac dinh v| tri ciia nhdm ceton tgi C-3. Vj tri cua nhdm OH tgi C-6 d u v c xdc djnh b i n g t y a n g tac HMBC giu'a cac proton methyl H-11 (S„ 1,06)/H-12 (5„ 1,03)/H-13 (6„ 1,96) va C-6 (Sc 80,01). Proton anome H-1' (6H 4,30) c6 tu'ang tac HMBC vdi C-9 (Sc 74,67) chirng minh vi tri lien k i t ciia don vj d u o n g glucose tgi carbon nay. Nhy v§y, hap c h i t 1 d y a c xdc djnh la corchoionosid C.
cac pho NMR cua hpp chat 2 tyang t y nhy cac pho tu'ang irng ciia 1 cho phep xdc djnh hai hap chat cd cau tnjc r i t giong nhau. Sy khdc bipt dd nhan thay n h i t la sy mat di cac tin hipu cua lien kel doi ngogi vong cau hinh trans vd thay vac dd Id tin hieu ciia hai nhdm metilen [Sc 34,56 (C-7)
Sc' 24,4
22,0
104,4 75,4 78,4 71,8 78,4
Sc"
24,30
21,87"
104713"
75,15 78,18 71,50 78,10
2 Ar^rJ-Hz;
0,99 b r s
2,02 b r s
4,30 d (75) 3,13 dd (7,5. 9,0)
3,30- 3,24*
3,24*
79,5
*'
"2572"
102.4 75,3 78,3 72,0 78,0
*'••
79,37
25,24
104,28 75,33 78,24 71,68 77,87
J Sn'^iJ'Hz) 3,57 dd (2,5, 7,0)
3.60 d (7,0) 1.33 brs
4.30 d (7,6) 3,18 dd (7,5, 9,0)
3,33*
3,30*
3,30*
3,63dd(6,0,12,0) 63,1 62.83 3,67 dd (6,0,12.0) 3,80dd(20, 12,0) 3,87 dd (2,0, 12,0) CDsOD, '500 MHz, 'So cie icensid Bs™, ' * Clis
va 32,84 (C-8)] tnSn cdc p h i ciia 2 so vdi cac phi tyang irng ciia 1. S y phii hap hoan toan v l s i l i | u p h i ' C-NMR cua 2 so vdi cdc sA liOu tyang irng dd d y d c cdng b l trong tai li$u tham khdo (bdng 1) cho phdp xdc djnh hop c h i t 2 chinh Id icansid Bs'".
. ° < ^ ! ^ o r
Hinh 2: Md( sd tu'ang tic (H -> C) chinh Iren phd HMBC cua 1
Hap c h i t 3 cung du'ac phdn ldp dirdi dgng bOt mdu t r i n g . Cdc p h i NMR cua 3 tifong ty n h y cdc p h i tirong irng ciJa 2. Diem khac nhau giya hai h y p c h i t la s y m l t di cdc tin higu ciia mdt nhdm methyl bdc ba vd l i l n k i t dSi b| t h i ba vj tri vd thay vdo dd Id cdc tin hiOu ciia mOt nhdm pximetiien [Sc 79,37 (C-12)], mOt nhom metin [6c 55,03 (C-6)] vd mOt nhdm metilen [5c 50,03 (C-4)] trdn cdc p h i ciia 3 so vdi cac phi t y d n g irng ciia 2. H a p c h i t 3 d y a c xac (^nh Id macarangiosid F '^' b i n g s y phu hap ve so lieu pho "C-NMR so vdi cac s i llOu da du'ac cdng b l trong tai ligu tham khdo (bang 1).
Hai hap c h i t cdn Igi d u v c xac djnh Id (+)- pinoresinol di-0-/)-D-glucopyranosid (4)'", syringaresinol di-O-^D-glucopyranosid (5) ^^\ tren c a sd phan tich chi t i l t cac k i t qua php I D , 2D- NMR vd ESl-MS k i t hap so sdnh vdi cdc so ligu php da d u v c cdng bo trong tdi ll$u tham khdo.
TAP CHI DU'qC HQC - 08/2012 (S6 436 NAM 52)
• Nghien CIFU - Ky thugt
Ket luan
Nghidn CLPU thdnh ph^n hda hpe cdy bum byp bdng to Mallotus macrostachyus (Mlq.) Muell.-Arg da phdn l^p dup'c ba hp'p eh^t megatigman, corchoionosid C (1), icarisid Bg (2) va macarangiosid F (3) vd hai hp'p eh^t lignan, (+)-pinoresinol di-0-/?-D-glucopyranosid (4) vd syringaresinol di-0-;8-D-glueopyranosid (5). C6u trCie hda hpe eCia eac hp'p ch6t du'p'c xdc i^nh bang cdc phuong phdp ph6 bao g6m ph6 edng hu-d-ng tu" hgt nhdn mpt ehi^u vd hai chl^u (1D- and 2D-NMR) vd ph6 kh6i lu(?ng (ESl-MS), k^t hep so sdnh vd'i ede s6 li$u ph6 da du'p'c edng bo. Bdy la lan dSu tidn cdc hp'p chlit ndy du'p'c phan l$p tCr cdy M. macrostachyus.
Summary
Three megatigmans - corchoionoside C (1), icariside 65 (2), and macarangioside F (3) and two lignans - (•*-)-pinoresinol di-0-fi-D-glucopyranoside (4) and syhngaresind di-O-0-D-giueopyranoside (5) were isolated from the methanol extracts of Mallotus macrostachyus (Miq.) Muell.-Arg leaves.
Their chemical stnjctures were elucidated by 1D- NMR, 2D-NMR and ESI mass spectral experiments in companson with the literature values. This is the first report of these compounds from M. macrostachyus.
Lo-i cam a n ; Cdng trinh du'p'e hoan thanh voi sir tai trp' kinh phi eua de tdi hp'p tae quoc te theo Nghi djnh thu- Viet Nam - Bi.
Tdi li^u tham khdo 1. La Dinh Mdi, Tr^n Minh H<?\, Duong D(tc Huy6n, Tr^n Huy ThSi, Ninh Khfc Bdn (2005). Tdi nguyin thuc v$t Viit Nam - NhOng dy chiia c6c hop chit cd tioet tinh sinh h<?c. t$p I, NXB Ndng nghiOp, tr. 47-57.
2. NguySn NghTa Thin (2007), Taxonomy of Euphorbiaeeae in Vietnam, Vietnam National University Publishers, pp. 179-202.
3. ve van Chl (1999), TO- (Jl4n ciy thu6c Vi$t Nam, Nhd xuSt bdn Y hpe, trang 135.
4. Yoshlkawa M,, Shimada H., Saka M., Yoshizumi S, Yamahara J.. Matsuda H. (1997),
"Medicinal foodstuffs. V. Moroheiya. (1): Absolute stereostructures of corcholonosides A, B, and C, histamine release inhibitors from the leaves of Vietnamese Corchonis olitonus L. (Tiliaceae)", Chemical & Pharmaceutical Bulletin. 45, pp 464-469.
5. Matsunami K., Otsuka H., Takeda Y., Miyase T.
(2010), "Reinvestigation of the absolute stereochemistry of megastigmane giucoside, icanside Bs", Chemical &
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