全 文 ：Chemical Constituents of Impatiens pritzellii
ZHAO Xiao-Ya1 , ZHOU Xue-Feng1 , RUAN Han-Li1 , ZHANG Yong-Hui1 , PI Hui-Fang1 ,
SUN Han-Dong2 , WU Ji-Zhou1＊
1Faculty of Pharmaceutical Sciences , Tongji Medical College of Huazhong University of Science and Technology , Wuhan 430030;
2 State Key Laboratory of Phytochemistry and Plant Resources in West China , Kunming Institute of Botany , Kunming 650204 , China
【ABSTRACT】　AIM:To study the chemical constituents of Impatiens pritzellii Hook.f .var.hupehensis Hook.f.
METHOD:The constituents were repeatedly separated and purified on silica column.They were identified on the basis of
spectral analysis.RESULT:Five compounds were identified to be 2′-acetamido-3′-phenyl propyl 2-benzamido-3- phenyl pro-
pionate(1), spinasta-7 , 22(23)-dien-3β-O-paltimate(2), 3-O-[ 6′-O-palmitoyl-β-D-glucosyl] -spinasta-7 , 22(23)-diene
(3), di(2-ethy lhexyl)phthalate(4)and methyl docosanoate(5).CONCLUSION:All of them are isolated from Balsami-
naceae for the first time.
【KEY WORDS】　Impatiens pritzellii Hook.f .var.hupehensis Hook.f.;Alkaloid;Sterol;Ester
【CLC Number】　R284.1　　【Document code】　A　　【Ariticle ID】　1672-3651(2005)06-0354-03
【Received on】　2005-06-23
【Foundation Item】　This projectwas supported by National Natural Sci-
ence Foundation of China (No.30371733)
【＊Corresponding author】　Wu Ji-Zhou:Ph.D., Prof., Tel:027-
83692739 , E-mail:ywjz@mails.tjmu.edu.cn
　　 Impatiens pritzellii Hook.f.var.hupehensis
Hook.f.is a balsamin- aceous plant growing in the
northwestern part of Hubei Province , China.Folks use
the rhizomas to treat rheumatism , diarrhea and acute
bellyache
[ 1] .By far , chemical constituents of this herb
have not been reported.In our research , five com-
pounds were separated from cyclohexane fraction.The
structures of the compounds were identified by compara-
tive analysis of their spectral , chemical and physical
properties with those reported literatures.
1　Experimental
1.1　Plant Material and Apparatus
The rhizomas of Impatiens pritzellii Hook.f.var.
hupehensis Hook.f.were purchased from Enshi city of
Hubei province and identified by Prof.Dingrong Wang ,
Hubei Provincial Institute for Drug Control , China.
Melting points were determined on an XT4-100X
micro-melting point apparatus and were uncorrected.
Optical rotation was determined on a Perkin-Elmer digi-
tal polarimeter in CHCl3 solution.IR spectrum was ob-
tained on IR-460 spectrometer.1H NMR and 13C NMR
data were recorded on DRX-500 or Bruker AM-400
spectrometer , using TMS as an internal standard.MS
was measured on VG Auto Spec-3000 mass spectrome-
ter.Silica gel(100-200 mesh , Qingdao , China).
1.2　Extraction and Isolation
Crushed plant material (3.3 kg)was extracted
three times with MeOH.The MeOH extract was filtered
and concentrated under reduced pressure to give a vis-
cous residue(1 190 g).This residue was suspended in
H2O and partitioned with cyclohexane(14.5 g), EtOAc
(16 g)and n-BuOH (104.8 g)successively.The cy-
clohexane fraction was separated by repeated column
chromatography on silica gel eluting with P.e.-EtOAc-
MeOH to obtain 2′-acetamido-3′-phenyl propyl 2-
benzamido-3-phenyl propionate(1)(26 mg), spinasta-
7 , 22-dien-3β-O-paltimate (2)(6 mg), 3-O-[ 6′-O-
palmitoyl-β-D-glucosyl]- spinasta-7 , 22(23)-diene(3)
(64 mg), di (2-ethylhexyl)phthalate (4)(206 mg),
methyl docosanoate (5)(10 mg).The structures are
shown in Fig 1.
354　　Chin J Nat Med　Nov.2005　Vol.3　No.6
CJNM
中国天然药物 　2005年 11月　第 3卷　第 6期
Fig 1　Structures of compounds 1
2　Identification
2′-acetamido-3′-phenyl propyl 2-benzamido-3-phe-
nyl propionate (1)[ 2] , a colorless amorphous powder
(Pe.+ EtOAc), mp 185 ～ 186 ℃.[α] 20D -34°(c
0.5 , CHCl3).Its molecular formula(C27H28N 2O4)was
determined by HRFAB-MS (m z 467.1946 [ M +
Na] + , calcd.445.2049).FAB-MS m z:445[M +
H] +.The positive reaction with Dragendoff s reagent
was characteristic of alkaloids.IR absorption at 1726
cm
-1
and
13
C NMR(δ171.0)spectrum indicated that
compound 1 has one ester carbonyl group.IR absorption
at 3314 , 1661 , 1633 cm-1 and 13C NMR(δ170.8 ,
167.6)spectrum revealed that compound 1 had two
amido groups.In 1H and 13C NMR spectra , compound
1 showed the presence of three single substituted
benzene rings (δ133.3 , 136.3 , 136.8)and a acetyl
group.In addition , DEPT spectrum showed 2 tertiary
carbons , 3 secondary carbons including an oxymethylene
carbon atδ64.7.From HMBC spectrum , the 3′-H(δ
2.68 ,CH2)and 2′-H(δ4.23 ,CH)was correlated with
4′-C(δ136.8), 3-H(δ3.00 , CH2)and 2-H(δ4.68 ,
CH)were correlated with 4-C(δ136.3), 12 , 16-H(δ
7.66 , CH of phenyl)were correlated with 10-C(δ
167.6 ,C=O);the fragments at m z 105 , 91 in the
FAB-MS further confirmed the linkage.The sequence of
compound 1 was determined by the combination of
DEPT , HSQC , HMBC , 1H- 1H COSY experiments , its
structure was indentified as 2′-acetamido-3′-phenyl pro-
pyl 2-benzamido-3-phenyl propionate (1).Its 1H NMR
and
13
C NMR data were assigned in Table 1.
spinasta-7 , 22-dien-3β-O-paltimate(2)[ 3] .White
granular solid (EtOAc), mp 102 ～ 103℃.MF:
C45H78O2.FAB-MS m z:651[M +1] + , 607 , 395 ,
256.IR(KBr)cm-1:2916 , 2851 , 1741(C =O),
1631(C =C), 970 , 725. 1H NMR (500 MHz ,
CDCl3)of the paltimate moiety of 2 δ:0.88(3H , t ,
CH3), 1.25 [ brs , -(CH2)n-] , 1.63 (2H , m), 2.26
(2H , t ,-OCOCH2).13C NMR(125 MHz , CDCl3)of
paltimate moiety of 2 δ:14.2(CH3), 22.7 , 24.9 ,
29.4-29.7 , 31.9 , 34.3 , 173.5(C =O).1H NMR
(500 MHz , CDCl3)of the sterol moiety of 2δ:5.13-
5.18(2H , m , 7 , 22-H), 5.02 (1H , dd , 23-H),
4.71(1H , m , W1 2=15.9 Hz , 3-H), 1.02(3H , d ,
J =6.6 Hz , 21-H), 0.79 (3H , s , 19-H), 0.55
(3H , s , 18-H).13C NMR(125 MHz , CDCl3)of the
spinasterol moiety of 2:37.2 , 31.9 , 73.2 , 34.8 ,
40.1 , 29.7 , 117.3 , 139.5 , 49.3 , 34.4 , 21.5 ,
39.4 , 43.3 , 55.1 , 23.0 , 28.5 , 55.9 , 12.0 , 12.9 ,
40.9 , 21.1 , 138.1 , 129.5 , 51.3 , 31.9 , 21.5 ,
19.0 , 25.4 , 12.2.
Table 1　1H NMR and 13C NMR data of compound 1
Position δH δC HMBC correlations
1 170.8 , s H2 , H3 ,H1′
2 4.68(1H , dd , J =7.4, 15.1) 54.7 , d H3
3 3.00(2H , d, J =7.4) 38.2 , t H2 , H5 ,H9
4 136.3 , s H2 , H3 ,H5 , H9
5 7.05(d, J=7.5) 128.9 , d H6 , H7 ,H3
6 7.08(t , J =7.5) 128.4 , d H5 , H7
7 7.02(t , J =7.5) 126.4 , d H6 , H8
8 7.08(t , J =7.5) 128.4 , d H7 , H9
9 7.05(d, J=7.5) 128.9 , d H8 , H7 ,H3
10 167.6 , s H12 , H16 , H2
11 133.3 , s H13 , H15
12 7.66(1H , d, J =7.3) 127.0 , d H13 , H14
13 7.36(1H , t , J =7.3) 128.3 , d H12 , H14
14 7.44(1H , t , J =7.3) 131.8 , d H12 , H16 , H13 , H15
15 7.36(1H , t , J =7.3) 128.3 , d H14 , H16
16 7.66(1H , t , J =7.3) 127.0 , d H15 , H14
1′ 3.79(2H , qd) 64.7 , t H2′,H3′
2′ 4.23(1H ,m) 49.3 , d H1′,H3′
3′ 2.68(2H , d, J =7.3) 37.1 , t H2′,H1′, H5′, H9′
4′ 136.8 , s H5′,H9′, H3′, H2′
5′ 7.16(d, J=7.2) 129.1 , d H6′,H7′, H3′
6′ 7.19(t , J =7.2) 128.4 , d H5′,H7′
7′ 7.13(t , J =7.2) 126.8 , d H6′,H8′, H5′, H9′
8′ 7.19(t , J =7.2) 128.4 , d H7′,H9′
9′ 7.16(d, J=7.2) 129.1 , d H8′,H7′, H3′
10′ 171.0 , s H2′,H11′
11′ 1.99(3H , s) 20.6 , q
　　3-O-[ 6′-O-palmitoyl-β-D-glucosyl ]-spinasta-7 ,
22(23)-diene(3)[ 4-6] .White sheet crystals(EtOAc),
mp 168 ～ 169 ℃.MF:C51H88O7.IR(KBr)cm-1:
中国天然药物 　2005年 11月　第 3卷　第 6期
CJNM
Chin J Nat Med　Nov.2005　Vol.3　No.6　355　
2957 , 2851 , 1735(C =O), 1632(C =C), 1468 ,
1379 , 1300-1150(C-O-C), 971 , 722 [ -(CH2)n-, n
>4] .1H NMR(500 MHz , CDCl3)of the paltimate
moiety of 3δ:0.88 (3H , t , CH3), 1.25 [ brs , -
(CH2)n-] , 1.63 (2H , m), 2.34 (2H , t , -OCO-
CH2).13C NMR (125 MHz , CDCl3)of the paltimate
moiety of 3δ:14.1(CH3), 22.7 , 24.9 , 29.4-29.8 ,
31.9 , 34.3 , 174.4(C =O);1H NMR (500 MHz ,
CDCl3)of the steroid glycoside moiety of 3δ:5.16-
5.12(2H , m , 7 , 22-H), 5.03 (1H , dd , 23-H),
4.71(1H , m , 3-H), 4.35(1 H , d , J =7.3Hz),
1.02(3H , d , J =6.6 Hz , 21-H), 0.85 (3H , d , J
=6.9Hz , 26-H)0.80(3H , t , J =2.8 Hz , 29-H),
0.80(3H , d , J =2.8Hz , 27-H), 0.79(3H , s , 19-
H), 0.54 (3H , s , 18-H).13C NMR (125 MHz ,
CDCl3)of the steroid glycoside moiety of 3:37.2 ,
30.1 , 79.2 , 34.5 , 40.3 , 30.1 , 117.4 , 139.5 ,
49.4 , 34.5 , 21.5 , 39.4 , 43.2 , 55.1 , 23.0 , 28.5 ,
56.0 , 12.0 , 13.0 , 40.9 , 21.4 , 138.1 , 129.5 ,
51.3 , 31.9 , 21.1 , 19.0 , 25.4 , 12.2 , 101.2 (C-
1′), 73.8(C-2′), 76.1(C-3′), 70.3(C-4′), 73.8
(C-5′), 63.5(C-6′).
Di(2-ethylhexyl)phthalate(4)[ 7] .Colorless oil.
MF:C24H38O4.FAB-MS m z:391[M+1] + , 279(M
+1-C8 H17), 167(279-C8 H17 +1), 149 , 113 (C8
H17).1H NMR(500MHz , Pyr)δ:0.88 ～ 0.94(12H ,
m , 4×CH3), 1.27 ～ 1.44 (16H , m , 8 , 9 , 10 , 12-
H), 1.68 (2H , m , 7-H), 4.22 (4H , qd , 6-H),
7.53(2H , dd , J =6.0 , 3.0 Hz), 7.71(2H , dd , J
=6.0 , 3.0 Hz).13C NMR(125 MHz , Acetone)δ:
10.9(C-13), 14.0(C-11), 22.9(C-10), 23.7(C-
12), 28.8 (C-9), 30.3 (C-8), 38.7 (C-7), 68.1
(C-6), 128.8 (C-2), 130.8(C-3), 132.4 (C-1),
167.7(C-4).
Methyl docosanoate(5)[ 8] .White power.MF:C23
H46O2.IR(KBr)cm-1:2924 , 2853 , 1744 (C=O),
1467.FAB-MS m z:355([M+1] + , 26), 299(37),
271(100), 111(28), 97(15), 73(39).1H NMR
(500 MHz , CDCl3)δ:0.88 (3H , t , CH3), 1.25
[ brs , -(CH2)n-] , 1.63 (2H , m , β-CH2 of C =O),
2.30 (2H , t , -CH2 CO), 3.67 (3H , s , CH3O).
13
C NMR(125 MHz , CDCl3)δ:14.1 , 22.7 , 25.0 ,
29.2-29.7 , 31.9 , 34.1 , 51.4 , 173.5.
References
[ 1] Wan DR , Li AJ , Feng HL.Pharmacognostical studies on Lengshuiqi
[ J] .J Chin Med Mater , 1989 , 12(4):18.
[ 2] 　Gu ZB, Yang GJ , Liu WY , et al.A new alkaloid from Patrinia
scabra[ J] .Chin Chem Letters.2002, 13(10):957-958.
[ 3] 　He L , Cheng DL , Pan X.Chemical constituents of Aster albescens
[ J] .China J Chin Mater Med , 1996 , 21(8):483-484.
[ 4] 　Du J , Xu JW.Chemical constituents of Impatiens siculifer Hook.f.
[ J] .China J Chin Mater Med , 1995 , 20(4):232-233.
[ 5] 　Gomes DdCF , Alegrio LV.Acyl steryl glycosides from Pithecello-
bium cauliflorum[ J] .Phytochemistry , 1998 , 49(5):1365-1367.
[ 6] 　Jiang Y , Liu L , Tu PF.Study on chemical constituents of Polygala
tenuifolia[ J] .Chin J Nat Med , 2003 , 1(3):142- 145.
[ 7] 　Zhang XR, Peng SL , Xiao SC , et al.Chemical Constituents of Ly-
simachia candida[ J] .Chin J Appl EnvironBiol , 1998 , 4(2):145-
147.
[ 8] 　WuR , YeQ , Cheng NY , et al.Study on the chemical constituents
of Aspidopterys obcordata hemsl[ J] .Nat Prod Res Dev , 2001 , 13
(1):14-16.
冷水七的化学成分
赵晓亚1 ,周雪峰1 ,阮汉利1 ,张勇慧1 ,皮慧芳1 ,孙汉董2 ,吴继洲1＊
1华中科技大学同济药学院 , 湖北 武汉 430030;
2中国科学院昆明植物研究所 植物化学与西部植物资源持续利用国家重点实验室 ,云南 昆明 650204
　　【摘　要】　目的:研究凤仙花属植物冷水七 Impatiens pritzellii Hook.f .var.hupehensis Hook.f.的化学成分。方法:用
柱色谱分离得到化学成分 ,用光谱法测定其结构。结果:分离鉴定了 5个化合物 , 分别为:2′-乙酰胺基-3′-苯基苯丙醇基2-
苯酰胺基-3-苯基苯丙酯(1),豆甾-Δ7 , 22-双烯-3β-棕榈酸酯(2),豆甾-Δ7 , 22-双烯-3-O-β-D-葡萄糖苷-6′-O-棕榈酸酯(3), 邻
苯二甲酸二(2-乙基己基)酯(4)和二十二烷酸甲酯(5)。结论:这 5 个成分均为首次从该属植物中分得。
【关键词】　冷水七;生物碱;甾体;酯
　　【基金项目】　国家自然科学基金资助项目(30371733)
356　　Chin J Nat Med　Nov.2005　Vol.3　No.6
CJNM
中国天然药物 　2005年 11月　第 3卷　第 6期