Tap
chi
Hoa hgc, T. 47 (6), Tr. 716 - 719, 2009
CAC HOP CHAT ISOFLAVON VA DIHYDROPHENANTHREN TLf
CAY
Sl/A
BAC BO {DALBERGIA TONKINENSIS)
Den Tda soan 5-12-2008
TRAN ANH
TU^',
NGUYEN TIEN DAT', NGUYEN HOAI NAM', NGUYEN QUANG
HUNG',
TRAN MINH HOP, TRAN HUY
THAI',
CHAU VAN MINH', PHAN
VAN
KIEM'
'Vien
Hoa hgc cdc Hgp chdt Thien nhien,
Vien
Khoa hgc vd Cdng nghe Viet
Nam
Vien Sinh thdi vd Tdi nguyen sinh vat, Vien Khoa hgc vd Cong nghe Viet Nam
ABSTRACT
The plants of the Dalbergia genus have been used for a long time in Vietnamese traditional
medicine. In our continuing study on the chemical constituent and biological activities of
medicinal plants, a phytochemical investigation of the methanol extract of Dalbergia tonkinensis
led to the isolation of
two isoflavones
(1, 2) and a dihydrophenanthrene (3). Their structures were
identified hy spectroscopic methods including

lie
ehi
su sin sinh NO. Tuy nhien, hiu nhu ehua cd
nghien
ciiu
nao vl thanh phin hda hgc
cQng
nhu
boat tfnh sinh hgc
ciia cay
sua Bic bg tai Viet
Nam cung nhu tren
thi
gidi. Bii bio nay thdng
bao nhiing
kit
qua nghien
ciiu
ban diu ve thanh
phin hda hgc
ciia cay
sua Bic bg. Bing cac
phuang phap sic ky ket hgp, cac hgp chit
genistein (I), lanceolarin (2) va
9,\Q-threo-3-[l-
(3,10-dihydroxy-9-hydroxymetyl-2,5-
dimethoxy)-9,10-
dihydrophenanthrenyl]propenal (3) da dugc
phan lap. Ciu triic hda hgc
ciia

Fujisilisa-
Nhat Ban).
2.
Cac
phuong
phap phd
- Phd khdi lugng phun mil dien tir (ESI-MS)
dugc do tren may AGILENT 1200 LC-MSD
716
Trap
ciia
Vien Hda hgc cac hgp chit thien nhien,
Vien Khoa hgc vi Cdng nghe Viet Nam.
- Phd cdng hudng tir nhan (NMR) dugc do
tren may Bruker AM500 FT-NMR Spectrometer,
Vien Hda hgc, Vien Khoa hgc va Cdng nghe
Viet Nam.
3.
Miu thuc vat
Miu
cay
sua Bic bd dugc thu hai vao thang
8 nam 2008 tai Ha Ndi va dugc TS Trin Thi
Phuang Anh, Vien Sinh thii va Tai nguyen sinh
vat giam dinh. Miu tieu ban dugc luu giir tai
Vien sinh thai vi Tii nguyen sinh vat.
4.
Phan lap cac chat
Miu
cay

tir phan doan F2 va F3 tuong ting bing sic ky
cdt pha thudng va pha dio vdi he dung mdi
thich hgp.
Genistein (1):
CISHIQOJ.
Chat rin mau nau
nhat; ESI-MS
m/z:
271
[M-i-H]^
'H-NMR
(CDfiD,
500 MHz)
5„:
6,22
(IH,
br s, H-8),
6,32
(IH,
br s, H-6), 6,86 (2H, br d,
/
= 8,0 Hz,
H-3',
H-5'), 7,37 (2H, br d, / = 8,0 Hz,
H-2',
H-6'),
8,00
(IH,
br s, H-2);
"C-NMR

/ =
2,0 Hz, H-8), 6,74
(IH,
d,
/
= 2,0 Hz, H-6), 7,00 (2H, br d,
7
= 8,0 Hz,
H-3',
H-5'), 7,50 (2H, br d, / = 8,0 Hz, H-2', H-
6'), 8,15
(IH,
br s, H-2); Glucose: 5,00
(IH,
d,
/
= 7,5 Hz,
H-1"),
3,50
(IH,
m, H-2"), 3,69
(IH,
m, H-3'), 3,36
(IH,
m, H-4'), 3,51
(IH,
m, H-
5"), 3,65
(IH,
m,

(C-3"),
71,7 (C-4"), 77,3 (C-5"), 69,0 (C-6");
Apiose: 111,2 (C-1'"), 78,3 (C-2'"), 80,4 (C-3"'),
75,1 (C-4"') vi 66,0 (C-5'").
1:
R' =
R^
=
H
2:
R' = Me,
R^
=
-/9-D-aplofuranosyl-(l->6)-/J-D-glucopyranoside
OHC
OMe
OMe OH
Hinh 1: Ciu tnic hda hgc cua cac hap chit 1-3
9,10-/;zreo-3-[7-(3,10-dihydroxy-9-
hydroxymethyl-2,5-dimethoxy)-9,10-
dihydrophenanthrenyl]propenal (3):
C20H20O6
Chit rin mau vang. ESI-MS
m/z:
357
[M-i-H]*;
'H-NMR
(CDCI3,
500 MHz)
5„:

H-l')
va 9,63
(IH,
d,
/ =
7,5 Hz, H-3');
"C-
NMR
(CDCL,
125 MHz)
5^:
53,0 (C-9), 56,0
(2-OMe),
56,1
(5-OMe),
63,9
(C-11),
88,9 (C-
10),
108,7 (C-4), 112,3 (C-6), 118,1 (C-8),
119,4(0-1), 126,4(0-2'),
128,1 (C-7), 129,1 (C-
8a),
132,2 (C-4a,
C-lOa),
144,5 (C-5), 145,9 (C-
3),
146,7 (C-2), 151,5 (C-4b), 153,0 (C-1') va
193,5 (C-3').
Ill

6,22
(IH,
br s,
H-8) va 6,32
(IH,
br s, H-6)] va mdt tfn hieu
singlet d trudng tha'p
5„
8,00
(IH,
br s, H-2) ggi
y 1 cd dang khung
isoPavone.
Phd
'^C-NMR
khing dinh 1 la mot isoflavone vdi
sir
xuit hien
ciia
13 pic (trong dd cd hai pic chap vdi cudng
id cao ban) vdi mdt tin hieu cacbon bac 3 tai
trudng tha'p
5^-
154,5 la do lien hgp vdi mot
nhdm cacbonyl d
vi
tri beta.
Kit
hgp cic dir
kien nay vi so sanh vdi tai lieu tham khao cho

apiose gin vao vi trf niy. Phd HMBC cua 1 cho
tha'y tucmg tac
ciia
proton
ciia
nhdm metoxy vdi
C-4
(5c
159,2), proton anome H-1"
(5„
5,00)
ciia
glucose tuang tic vdi C-7
(5^
164,8) vi
proton anome H-l'"
(S,y
4,99)
eiia
apiose tuang
tac vdi C-6"
(5^
69,0)
ciia
glucose. Cac dir kien
phd
ciia
2 hoin loan
phii
hgp vdi cac dir kien da

193,5 (C-3'). Hing sd tucmg tic
/ =
15,5 Hz
giira hai proton H-l' vi H-2' chirng td ndi ddi
nay cd cau hinh trans. Cae tfn hieu singlet
ciia
4
proton tren hai vdng tham ciing vdi su cc mat
ciia
mot nhdm medn tai
5,-
53,0 (C-9), mot
nhdm oximetin tai
5^
88,9 (C-10) vi mot nhdm
oximetilen
5c
63,9 (C-11) cho thiy 3 cd dang
khung dihydrophenanthene [5, 6]. Cau hinh
tuang ddi d hai vi trf H-9 va
H-10
dugc xac dinh
cd dang threo- do hai proton nay cd hing sd
tucmg tic
/
= 7,0 Hz. Phd hai chilu HMBC
ciia
3 cho thiy tuang tac giiia H-2' (5,., 6,60) vdi C-7
(5c
128,1), giira H-l'

phd ESI-MS hoan toan
phii
hgp
cdng thiic phan tir la
C2oH2oO(;.
Kit
hgp cac dir
kien nay va so sanh vai tai lieu tham khao [5],
hgp chat 3 dugc xac dinh la
9,10-r/;rc'o-3-[7-
(3,10-dihydroxy-9-hydroxymethyl-2,5-
dimethoxy)-9,10-dihydrophenanthrenyl]-
propenal. Day li lin diu tien khung
dihydrophenanthren dugc tim thay trong chi
Dalbergia.
TAI
LIEU THAM KHAO
1.
Vo Van Chi. Tir
diin
cay thud'c Viet Nam,
Nha xuat ban Y hgc, 1252- 1255(1999).
2.
P. K. Agrawal.
Carbon-13
NMR of
Flavonoids, Elsevier, the Netherlands, trang
196(1989).
718
3.