全 文 ：应用与环境生物学报　 2006, 12(2):163～ 169 　 　
Chin J A pp lEnviron B io l=ISSN 1006-687X 　 2006-04-25
　
Chem ical Constituents from Gymnosporia varialilis Loes.
ZHANG X iuyun
1, 2, 3 , LIBogang1 , ZHOU M in1 , YUAN X iaohong1, 2＆ZHANG Guo lin1*
(1Chengdu Institute of B io logy , Ch inese Academ y of Sciences, Chengdu 610041, Ch ina)
(2GraduateUn iversity of Ch inese Academy of Sciences, Bei jing 100039, C hina)
(3Co llege of Life Science, Northwest S ci -TechUn iversity of Ag ricu lture and Forestry , Yangling 712100, Shaanxi, C hina)
Abstract　Tw en ty-seven com pounds w ere obtained from the 95% e thano lic ex tract o f ae rial par t ofGymnosporia varialilis Loe s,
and identified as prinsep io l(1), ( +) - pino resino l(2), ( -) - pinoresino l(3), ( - ) - sy ringare sino l(4), ( +) - cy-
cloo liv il(5), ( -) - oliv il(6), 1 - hydroxypino re sino l(7), ile latifo lD (8), scopo letin (9), β - am y rin aceta te (10), α
- am yrin aceta te (11), fupenzic acid(12), ( +) - ca techin(13), seco iso la riciresinol(14), pa lm ita te -1 -monog lyceride
(15), phy to l(16), ca ffe ic acid(17), 3, 4 - dim e thoxyc innam ic acid (18), ( -) -m assonire sino l(19), tanegoo l(20), β
- sitostero l(21), lupeo l(22), betulin (23), β - daucosterol(24), oleano lic ac id (25), urso lic acid(26) and ( -) -
oliv ilm onoaceta te (27). F ig 1, Tab 1, Re f 34
Keywords　Gymnosporia varia lilis Loes. ;ACE; lignan; triterpene;prinsepio l
CLC　Q949. 754. 706
刺茶美登木的化学成分研究
张秀云 1, 2, 3　李伯刚 1　周 敏 1　袁小红 1, 2　张国林 1*
(1中国科学院成都生物研究所　成都　 610041)
(2中国科学院研究生院　北京　 100039)
(3西北农林科技大学生命科学院　陕西杨陵　712100)
摘　要　从刺茶美登木地上部分的 95%乙醇提取物中分离并鉴定了 27个化合物:prinsep io l(1), ( +) -松脂醇(2),
( -) -松脂醇(3), ( -) -丁香树脂醇(4), ( +) - cyclooliv il(5), ( -) -橄榄树脂素 (6), 1 -羟基 -松脂醇 (7), ile-
la tifo l D (8),东莨菪素(9), β -香树素乙酸酯(10), α-香树素乙酸酯(11), fupenzic acid (12), (+) -儿茶素 (13),
secoiso laric ire sino l(14), 软脂酸 -1 -甘油单酯(15),植物醇(16), 咖啡酸 (17), 3, 4 -二甲氧基肉桂酸(18), ( -) -
m asson ire sino l(19), tanegoo l(20), β -谷甾醇(21), 羽扇豆醇(22), 白桦酯醇(23), β -胡萝卜甙 (24), 齐墩果酸(25),
熊果酸(26)和( -) -橄榄树脂素乙酸酯(27). 图 1表 1参 34
关键词　刺茶美登木;血管紧张素转化酶;木脂素;三萜;prinsep io l
CLC　Q949. 754. 706
　　The genusGymnosporia (orMay tenus) (Ce lastraceae) con-
sists o f abou t 300 species in thew or ld. About 20 species a re found
in Ch ina[ 1] . The plan ts o f th is genu s a re rich in trite rpenoids[ 2] ,
sesqu iterpeno ids[ 3] , alka loids[ 4 ～ 5] , flavonoid g lycosides[ 6～ 7] ,
pheno lics[ 8] and o ther com pounds. G. varialilism a in ly occu rs in
Hube i, S ichuan, Gu izhou and Yunnan prov inces[ 1] . The 95%
e thano lic ex trac t o f ae ria l part of G. varia lilis show ed ang io tensin
conve rting enzyme (ACE) inhibito ry activ ity in b io log ical sc reen-
ing. F rom this ex tract tw en ty - seven com poundsw e re isola ted and
identified as prinsepio l(1), ( +) - pino resino l(2), ( -) - pi-
nore sino l(3), ( - ) - syringa resino l (4), ( +) - cycloo liv il
(5), ( -) - oliv il(6), 1 - hydroxypino re sino l(7), ile latifol D
(8), scopo letin (9), β - amy rin aceta te (10), α- am y rin ace-
tate (11), fupenzic acid (12), ( +) - ca techin (13), seco iso-
laric iresino l(14), pa lm itate - 1 - m onog ly ce ride (15), phy to l
(16), caffeic acid (17), 3, 4 - d im ethoxycinnam ic ac id (18),
Received:2005-03-31　　A ccepted:2005-05-25
*C orresponding au thor(E-m ail:zhanggl@ cib. ac. cn)
( -) -m assoniresino l(19), tanegoo l(20), β - sitostero l(21),
lupeo l(22), be tu lin(23), β - dauco stero l(24), o leanolic acid
(25), urso lic acid(26) and ( -) - o liv il monoace tate (27).
1　M aterials＆M ethods
1. 1　Apparatus
M elting po ints we re dete rm ined on X - 6 m elting point appa-
ra tus and w ere uncorrec ted. Optica l rota tions we re m easured on a
Pe rkin E lm er 341 au tom atic po larim e te r. UV and IR spectra w ere
reco rded on Lam bda 35 spectrom e te r and a Perk in E lm er spectrum
one FT - IR spectrom eter (KBr), respective ly. M ass spec tra w ere
ob ta ined on a F inngan - LCQDECA mass spec trom eter (ESIMS).
NM R spectra we re reco rded on a B rukerAdvance 600 spectrom e te r
w ith TMS as in te rnal standa rd. Silica gel(80 ～ 100 m esh, 200 ～
300 m esh, Q ingdao H aiyang Chem ica l Co. L td. , China), silica
ge l 60(15 ～ 40 μm , M erck KGaA, Darm stad t, G erm any), RP -
C18(40 ～ 63 μm , M erck KG aA, Darm stad t, Germ any) and Seph-
adex LH - 20(Pha rmac ia Bio tech. Co. L td. , Sw eden) w ere used
for co lum n ch rom a tog raphy. Silica g el GF254 (Q ingdao H aiyang
Chem ical Co. L td. , China) w as used fo rTLC. A ll so lven ts inclu-
ding petro leum ethe r(60 ～ 90 ℃)w e re d istilled prio r to use. Sol-
vent sy stem s applied for TLC:S1:pe troleum e ther - acetone 15∶
1;S2∶ ch lo rofo rm -m e thano l 30 ∶ 1;S3:pe troleum ethe r- ac-
e tone 5 ∶ 1;S
4
:ch lo ro fo rm -m ethanol 10 ∶ 1;S
5
:pe tro leum
e the r- ace tone 10 ∶ 1;and S6:ch lo ro fo rm -m e thano l 20 ∶ 1.
1. 2　P lantm aterial
The aeria l pa rt of G. varialilis was co llected in April 2003
from Yanbian(盐边) Coun ty, S ichuan, China. The plan tm ateri-
a l wa s iden tified by P ro.f FU Fad ing at Chengdu Institute of B io lo-
gy, the Chine se Academy o f Sc ience s (CAS). A vouche r speci-
m en (A - 22) is deposited in the Chengdu Institu te o f B io logy,
CAS.
1. 3　Methods
1. 3. 1　Extrac tion and iso lation　　A ir - dried and pow de red
ae rial part ofG. varia lilis(50 kg) w as ex tracted w ith 95% EtOH
(150 L×3, each 7 day s) at 25 ℃. A fte r remova l of the so lvents
under reduced pressure, 2 000 g residuew as obtained. Par t o f the
re sidue (1 000 g) w as suspended in H2O (1. 5 L) and then ex-
tracted successive ly w ith pe tro leum e ther (1. 5 L×5) and E tOA c
(1. 5 L ×5) to g ive co rrespond ing frac tions A (petroleum ethe r
phase, 320 g), B (E tOAc phase, 400 g) and C (w a te r phase,
280 g).
F rac tion B (400 g) w as disso lved in me thano l(1. 5 L) and
ex tracted w ith pe tro leum e ther(1. 5 L×2) to affo rd corre sponding
fractions BA (pe tro leum e ther phase, 276 g) and BB (m e thano l
phase, 124 g).
F rac tion BA w as subjected to silica gel co lum n(ф 17×L 45
cm , 1. 5 kg) g radien tly e luted w ith petro leum e ther- ace tone (80
∶ 1, 50 ∶ 1, 20∶ 1, 5 ∶ 1, each 5 000 m L) to y ie ld sub frac-
tions BA
1
(84 g), BA
2
(96 g), BA
3
(38 g), BA
4
(15 g) and BA
5
(43 g). Com pound 1 (15 g) was obtained by re crysta llizing BA2
from ace tone. Them othe r liquid was separated on silica ge l co lum n
(ф 7×L 30 cm , 350 g) g radien tly e luted w ith pe tro leum ethe r-
ace tone(50∶ 1, 20∶ 1, 5∶ 1, each 1 000 mL) to y ield com-
pound 16(16 m g). Compounds 21 (600 mg), 22 (80 m g) and
23 (15 mg) we re obta ined from fraction BA 3 by silica ge l co lum n
(ф 7×L 30 cm , 350 g, pe tro leum e ther - ace tone 10∶ 1). BA4
w as separated ove r silica gel co lum n (ф 6×L 20 cm , 300 g, pe-
troleum ethe r- EtOAc 4∶ 1 and then ф 3×L 20 cm, 150 g, pe-
troleum ethe r- ace tone 8 ∶ 1) to g ive com pounds 10 (12 mg),
11 (15 m g), 25 (20 mg) and 26 (50 m g). Com pound 15 (10
m g) w as iso la ted from fraction BA5 by silica g el co lum n (ф 9 ×L
30 cm, 450 g, ch lo ro fo rm -E tOAc 4∶ 1). The remnan t of BA5
w as separated by reve rse - phase silica ge l co lum n (RP - 18, 90
g, M eOH -H2O 3 ∶ 2, V /V) to affo rd a m ixture. The m ixture
w as fu rther purified by HPLC (RP - 18, CH3CN -H2O 1 ∶ 4,
V /V) to give com pounds 19 (9 m g) and 20 (8 m g).
F rac tion BB (124 g) was d iv ided into six subfractions BBA
(19 g), BBB (15 g), BBC (22 g), BBD (13 g), BBE (10 g)
and BBF (45 g) by silica ge l co lum n(ф 17×L 45 cm , 1. 0 kg)
g radiently e lu ted w ith chloro form -me thano l(50 ∶ 1, 20 ∶ 1,
10 ∶ 1, 2∶ 1, each 3 000 mL). Compounds 3 (5 m g) and 2
(11 m g) w ere obta ined from BBA by silica ge l co lum n(pe tro leum
e the r- ace tone 5∶ 1). The rem nant o f BBA was sepa ra ted by re-
ve rse - pha se silica ge l co lum n (RP - 18, 40 g, M eOH - H2O 3
∶ 2, V /V) to give com pounds 4(6 mg) and 14(15 m g). BBB
w as subjected to silica g el co lum n eluted w ith ch lo rofo rm -m etha-
no l(20 ∶ 1) and then reverse - pha se silica ge l column (RP -
18, M eOH -H2O 3∶ 2) to give compound 12(8 mg). BBC w as
d iv ided into two fractions BBC1(15 g) and BBC2(8 g) by silica
ge l co lum n(chloroform -m ethano l 15 ∶ 1). Com pounds 6 (20
m g) and 7(5 mg) we re obtained from BBC
1
by silica ge l co lum n
(ch lo ro fo rm -m e thano l - E tOAc 10 ∶ 1 ∶ 0. 5). C om pound 8
(10 m g) w as y ie lded from BBC2 by silica ge l column eluted w ith
ch lo rofo rm - ace tone (5 ∶ 1) and then purified by Sephadex LH
- 20. BBD w as divided in to two fractions BBD1(6 g) and BBD2
(7 g) by silica ge l co lum n(ch lo rofo rm -m e thano l- EtOAc 6∶ 1
∶ 0. 5). Com pounds 18 (5 m g) and 17(15 mg) w ere ob ta ined
from BBD1 by silica gel co lum n(chloro form -me thano l -E tOAc 8
∶ 1 ∶ 0. 5). Compounds 9(60 m g) and 7(3 m g) w ere y ie lded
from BBD2 by silica ge l co lumn e luted w ith chloro form - ace tone
(3 ∶ 1). Compound 24 (125 m g) w as separa ted from BBE by
silica ge l co lumn (chloro form -me thano l 5 ∶ 1). The rem nant of
BBE w as subjec ted to reverse - phase silica ge l column (RP - 18,
M eOH -H2O 40∶ 60) to yie ld com pounds 5 (3 m g) and 13 (6
m g).
1. 3. 2　Angioten sin conver ting enzym e assay　　ACE inh ibi-
tory activ ity w as de term ined by the m ethod of C arm el[ 9] .
95% E tOH extract o fG. varia lili d isplayed ACE inh ibitory
activ ity. F rac tion B show ed ACE inhib itory activ ity of 115. 19% a t
a concen tra tion o f 100 μg /m L tak ing catopril a t a concentration of
10 μg /m L as re ference.
2　Results＆ D iscussions
2. 1　Physica l and spectral data
P rinsep iol(1):Wh ite needle c rystal, m. p. 122. 2 ～
123. 4℃ (CHC l3), [ α] 25D -13. 0°(c 0. 10, E tOA c), UV λMeOHm ax
( logε) nm:234 (1. 87), 280 (2. 05), IR νKB rm ax cm - 1:3 460,
1 904, 1 699, ESIMS m /z (%):391 ([ M +H] +, 20), 389
([M -H] - , 100), 1H -NMR (600MH z, DMSO -d6)δ:6. 94
(2H , d, J = 1. 4 H z, H - 2′, H - 2″), 6. 74 (2H , dd, J =
8. 1 H z, 1. 4 H z, H - 6′, H - 6″), 6. 69 (2H, d, J = 8. 0 H z,
H - 5′, H - 5″), 4. 86(2H, s, H - 2, H - 6), 3. 96(2H, d, J
=9. 2 H z, H -4α, H - 8α), 3. 78 (2H , d, J =9. 2 H z, H -
4β, H - 8β), 3. 73 (6H, s, 3′, 3″- OCH3), 13C -NM R (150
MH z, DMSO -d6) data are shown in Tab le 1. The optica l ro ta-
tion, IR, UV and 1H - NMR da ta w ere consistent w ith those of
prinsepiol[ 10] .
164 　　　　　　　　应 用与 环 境生 物学 报　　Chin J App lEnviron B io l　　　　　　　　　　　　　　 　　　12卷
(+) - P inoresino l(2):Wh ite am o rphous pow de r, m. p.
125. 1～ 126. 3 ℃ (CHC l
3
), [ α] 25
D
+70. 2°(c 0. 23, CHC l
3
),
UV λMeOHm ax ( log ε) nm:233 (2. 75), 280 (2. 06), IR νKB rm ax:
3 550, 1 615, 1 511 cm - 1 , ESIM S m /z (%):358 ([ M ] +,
10), 341 ([ M -OH] - , 100), 1H -NM R (600 MH z, CDC l3)
δ:6. 91 (2H, s, H - 2′, H -2″), 6. 90 (2H , d, J =8. 2 H z,
H -5′, H - 5″), 6. 83 (2H , d, J =8. 4 H z, H - 6′, H - 6″),
5. 65 (2H , s, 4′- , 4″-OH), 4. 74 (2H , d, J = 3. 8 H z, H
- 2, H -6), 4. 25(2H , dd, J = 8. 7, 6. 5 H z, H - 4α, H -
8α), 3. 91(6H , s, 3′- , 3″- OCH3), 3. 89 (2H , dd, J =
9. 2, 3. 0H z, H - 4β, H - 8β), 3. 11 (2H , s, H - 1, H -5),
13C -NMR (150MH z, CDC l3) da ta are in Tab le 1. The optica l
ro tation, IR, UV and NMR da ta we re in agreem en t w ith those of
(+) - pino resino l[ 11] .
( -) - P inoresino l(3):W hite amo rph ism pow de r, m. p.
125. 5～ 127. 1 ℃ (CHC l3), [ α] 25D - 40. 6°(c 0. 80, CHC l3),
UV λMeOHm ax ( log ε) nm:233 (2. 82), 280 (2. 14), IR νKB rm ax:
3 551, 1 611, 1 514 cm - 1 , ESIM S m /z (%):358 ([ M ] +,
10), 341 ([ M -OH] - , 100), 1H -NM R (600 MH z, CDC l3)
δ:6. 91 (2H, s, H - 2′, H -2″), 6. 90 (2H , d, J =8. 2 H z,
H -5′, H - 5″), 6. 83 (2H , d, J =8. 4 H z, H - 6′, H - 6″),
5. 65 (2H , s, 4′- , 4″-OH), 4. 74 (2H , d, J = 3. 8 H z, H
- 2, H -6), 4. 25(2H , dd, J = 8. 7, 6. 5 H z, H - 4α, H -
8α), 3. 91(6H , s, 3′- , 3″- OCH3), 3. 89 (2H , dd, J =
9. 2, 3. 0 H z, H - 4β, H - 8β), 3. 11 (2H, s, H - 1, H - 5),
13C -NMR (150MH z, CDC l3) da ta are in Tab le 1. The optica l
ro tation, UV and NM R da tawe re in accordance w ith those of( -)
- p inore sino l[ 12] .
(+) - Syr ingaresinol (4):Pale ye llow need les, m. p.
166. 5～ 168. 7 ℃ (CHC l3), [ α] 25D +10. 1°(c 0. 13, M eOH),
UV λMeOH
m ax
( logε) nm:272 (1. 24), 215(2. 95), IR νKB r
m ax
3 437,
1 633, 1 456 cm - 1 , ESIMS m /z (%):875 ([ 2M +K ] +,
100), 1H -NMR (600MH z, CDC l
3
) δ:6. 58 (4H , s, H - 2′,
H -2″, H - 6′, H - 6″), 5. 52 (2H , s, 4′- , 4″- OH), 4. 73
(2H , d, J = 4. 0 H z, H - 2, H -6), 4. 28 (2H , dd, J = 8.
9, 6. 5 H z, H - 4α, H - 8α), 3. 92 (2H , d, J =3. 1 H z, H -
4β, H - 8β), 3. 91 (12H , s, 3′- , 5′- , 3″- , 5″-OCH
3
),
3. 10 (2H , m , H - 1, H -5), 13C -NMR (150MH z, CDC l3)
data a re in Table 1. The optica l ro ta tion and 13C -NMR da ta w ere
in acco rdance w ith those o f(+) - syringare sino l[ 13] .
(+) - Cyc loolivil (5):Wh ite am o rphous powder, m. p.
167. 5 ～ 169. 1 ℃ (CHC l3), [ α] 25D + 55. 1°(c 0. 11, CH3
OH), ESIM Sm /z (%):375([M -H] - , 100), UVλMeOHm ax ( log
ε) nm:365(2. 57), 282(2. 45), IRνKB r
max
3 465, 2 933, 1 605,
1 518, 1 266 cm - 1 , 1H -NMR (600MH z, DM SO -d6)δ:8. 82
(1H , s, 4 -OH), 8. 40(1H , s, 4′-OH), 6. 71 (1H , d, J =
8. 0 H z, H - 5), 6. 65(1H, s, H -2), 6. 55 (1H , s, H - 2′),
6. 53 (1H , d, J = 8. 0 H z, H - 6), 6. 06 (1H , s, H - 5′),
4. 97 (1H, s, 9 -OH), 4. 74(1H, s, 9′-OH), 4. 33(1H , s,
8′-OH), 3. 85(1H , d, J =11. 6 H z, H - 7), 3. 69 (6H , s,
3, 3′-OCH3), 3. 60 (2H, m, 9α, 9′α-H), 3. 37 (2H , m ,
9β and 9′β -H), 3. 08 (1H , d, J = 16. 5 H z, 7′α-H), 2. 43
(1H , d, J =16. 5H z, H - 5), 1. 88(1H , d, J =11. 2 H z, H
- 8), 13C -NMR (150MH z, DMSO - d6) δ:147. 9 (C - 3),
146. 2(C - 3′), 145. 2(C - 4), 144. 4(C - 4′), 137. 4 (C -
1), 132. 6(C - 1′), 125. 6 (C - 6′), 122. 3 (C - 6), 116. 6
(C - 5′), 115. 8 (C - 5), 113. 9 (C - 2), 112. 9 (C - 2′),
73. 5 (C - 8′), 68. 5 (C - 9′), 59. 5 (C - 9), 56. 2 (3 -
OCH3), 56. 0 (3′-OCH3), 46. 1 (C - 8), 43. 6 (C - 7),
39. 3 (H - 7′). The IR, UV and NMR da ta we re in acco rdance
w ith those o f(+) - cycloo liv il[ 14] .
( -) -O livil(6):Wh ite am orphous powder, m. p. 116. 2 ～
118. 1℃ (CHC l
3
), [ α] 20
D
- 51. 5°(c 0. 12, CH
3
OH), UV
λMeOHm ax ( logε) nm:227 (2. 05), 282 (3. 12), IR νKB rm ax:3 410,
1 605, 1 518, 1 455 cm - 1 , ESIMSm /z(%):375([ M -H] - ,
100), 751([ 2M -H] - , 80), 1H - NMR (600MH z, CDC l3)
δ:7. 02(1H , s, H - 6″), 6. 89(1H, d, J =8. 0H z, H - 5′),
6. 87 (2H , s, H - 2″, H -5″), 6. 81 (1H , d, J =1. 5 H z, H
- 2′), 6. 78 (1H, dd, J =8. 1, 1. 5 H z, H - 6′), 5. 63, 5. 59
(each 1H , s, 4′, 4″-OH), 4. 70(1H, d, J=8. 0H z, H - 2),
3. 96, 3. 83 (each 1H , dd, J = 10. 7, 5. 6 H z, H - 8), 3. 91
(1H , d, J =8. 2 H z, H -4), 3. 68(1H , d, J =9. 1 H z, H -
4), 3. 89, 3. 90 (each 3H , s, 3′, 3″- OCH3), 3. 06, 2. 95
(each 1H , d, J = 13. 7 H z, H - 6), 2. 50 (1H , m , H - 1),
13C -NMR (150MH z, CDC l3) da ta are in Tab le 1. The optica l
ro tation UV, IR and NMR da ta we re in accordance w ith those of
( -) - o livil[ 15] .
1 -Hydroxyp inoresinol(7):W hite am o rphous pow de r, m.
p. 112. 1 ～ 114. 5 ℃ (CHC l3 ), UV λM eOHmax ( log ε) nm:338
(3. 61), 282 (3. 94), IR νKB rm ax:3 415, 2 940, 1 650, 1 605,
1 522 cm - 1 , ESIM Sm /z (%):375 ([ M +H] +, 100), 1H -
NM R (600MH z, CDC l
3
)δ:7. 01(1H, s, H -6″), 6. 99 (1H ,
d, J =1. 7 H z, H -2′), 6. 96(H , d, J = 8. 1 H z, H - 5′),
6. 91 (2H , s, H - 2″, H - 5″), 6. 88 (1H, dd, J = 8. 1, 1. 7
H z, H - 6′), 5. 69 and 5. 54(2H , s, 4′, 3″-OH), 4. 87 (1H ,
d, J =5. 0 H z, H -2), 4. 86(1H , s, H -6), 4. 55 and 3. 85
(2H , t, J =8. 8 H z, H - 8), 4. 06 and 3. 91(2H , d, J =9. 4
H z, H - 4), 3. 93 and 3. 91 (6H , s, 3′, 5″- OCH3), 3. 13
(1H , m , H - 1), 13C -NM R (150MH z, CDC l3) data are in Ta-
b le 1. The UV and NM R data we re in agreem en tw ith those repo r-
ted[ 16] .
Ilelatifo lD (8):W hite am orphous powder, m. p. 152. 1 ～
154. 6℃ (CHC l3), [ α] 25D +18. 3°(c 0. 12, MeOH), [ α] 25D +
11. 3°(c 0. 08, C5 H5N), 1H - NMR (600 MH z, CDC l3) δ:
0. 83 (3H , s, 24 -H), 0. 94 (3H , d, J = 6. 4 H z, 29 -H),
0. 99 (3H , s, 25 -H), 1. 00 (3H , d, J = 6. 3 H z, 30 -H),
1. 04 (3H , s, 27 -H), 1. 06(3H , s, 26 -H). 1. 17 (3H , s,
23 -H), 3. 02 (1H , dd, J =7. 9 H z, H - 3), 3. 77(1H , m),
5. 57 (1H , dd, J =10. 0, 3. 0 H z, H -11), 5. 98(1H , dd, J
=8. 8, 4. 5 H z, H - 12), 13C - NMR (150MH z, CDC l3) δ:
165　 2期 ZHANG X iuyun, et a l. :Chem icalC on stituents from Gym nosporia varia lilis Loes. 　　
179. 7(C - 28), 133. 0(C - 11), 129. 2 (C -12), 89. 5(C -
13), 83. 9(C - 3), 69. 0 (C - 2), 60. 6 (C - 18), 54. 9(C -
9), 53. 0 (C - 5), 46. 2 (C -14), 45. 1 (C -17), 42. 0 (C -
1), 41. 8 (C - 8), 40. 3 (C - 20), 39. 2 (C - 4), 38. 1 (C -
19), 37. 6(C - 10), 31. 3(C - 7), 31. 2 (C - 22), 30. 8 (C
- 21), 28. 2(C -23), 25. 5 (C - 15), 22. 8 (C - 16), 19. 1
(C - 25), 19. 1(C - 26), 19. 0 (C -30), 17. 8(C - 6), 17. 6
(C - 29), 16. 1 (C - 24), 16. 1 (C - 27). The optica l ro ta tion
and NMR da ta we re in accordance w ith tho se of ile latifo lD[ 17] .
Tab le 1　 13C -NMR data of compounds 1 ～ 4, 6, 7, 19, 20 and 27 in CDC l
3
at 150MHz
C - atom 1 2 3 4 6 7 19 20 27
1 88. 2 54. 2 54. 2 54. 4 60. 7 91. 7 85. 1 56. 0 62. 4
2 87. 7 85. 9 85. 9 86. 1 83. 1 85. 8 80. 7 85. 8 84. 2
4 75. 2 71. 7 71. 7 71. 8 76. 6 74. 8 74. 3 71. 2 77. 7
5 88. 2 54. 2 54. 2 54. 4 81. 2 60. 2 81. 2 53. 0 81. 2
6 87. 7 85. 9 85. 9 86. 1 39. 2 87. 8 39. 1 77. 6 39. 4
8 75. 2 71. 7 71. 7 71. 8 59. 0 71. 7 64. 5 63. 3 56. 3
1′ 129. 1 132. 9 132. 9 132. 1 133. 8 132. 4 127. 9 134. 0 133. 3
2′ 112. 9 108. 6 108. 6 102. 7 108. 7 109. 1 110. 0 111. 2 108. 8
3′ 146. 6 145. 2 145. 2 147. 2 145. 4 146. 2 146. 4 149. 1 145. 8
4′ 147. 6 146. 7 146. 7 134. 3 146. 5 146. 8 144. 7 147. 4 146. 5
5′ 115. 2 114. 3 114. 3 147. 2 114. 1 114. 3 114. 2 116. 0 114. 1
6′ 120. 8 119. 0 119. 0 102. 7 119. 5 119. 6 120. 2 120. 7 119. 6
1 129. 1 132. 9 132. 9 132. 1 128. 2 127. 1 129. 3 136. 2 127. 8
2 112. 9 108. 6 108. 6 102. 7 112. 8 109. 4 113. 0 111. 4 112. 6
3 146. 6 145. 2 145. 2 147. 2 146. 8 146. 9 146. 7 149. 1 146. 7
4 147. 6 146. 7 146. 7 134. 3 144. 8 145. 5 145. 7 147. 5 144. 8
5 115. 2 114. 3 114. 3 147. 2 114. 5 114. 7 114. 3 116. 0 114. 5
6 120. 8 119. 0 119. 0 102. 7 122. 9 120. 0 123. 1 120. 8 122. 7
-O CH 3 56. 2 56. 0 56. 0 56. 4 56. 0
55. 9
56. 0
55. 9
56. 0
55. 9
56. 4 56. 0
55. 9
　　Scopoletin (9):W hite amo rphous powder, m. p. 177. 1 ～
178. 8 ℃ (CHC l3). UV λMeOHm ax ( log ε) nm:344 (3. 13), 228
(3. 24), IR νKB rm ax 3 447, 1 628 cm - 1 , ES IM S m /z (%):193
([M +H] +, 100), 191 ([ M -H] - , 100), 1H -NMR (600
MH z, CDC l3) δ:7. 61 (1H , d, J = 9. 5 H z, H - 4), 6. 91
(1H , s, H - 5), 6. 85(1H, s, H - 8), 6. 28(1H, d, J =9. 5
H z, H - 3), 3. 96 (3H , s, -OCH3), 13C - NMR (150MH z,
CDC l3)δ:161. 4 (C - 2), 150. 3 (C - 7), 149. 7 (C - 6),
144. 0(C - 9), 143. 2 (C - 4), 113. 4 (C - 5), 111. 5 (C -
10), 107. 5 (C - 3), 103. 2 (C - 8), 56. 4 ( - OCH
3
). The
spec tra l da taw ere iden tical to tho se reported[ 18] .
β -Amyr in acetate(10):W hite am o rphous powder, m. p.
224. 5 ～ 227. 1 ℃ (CHC l3), IR νKB rm ax 3 441, 1 734, 1 637,
1 367, 1 244 cm - 1 , ES IM Sm /z (%):467([ M -H] - , 100),
1H -NM R (600MH z, CDC l3)δ:5. 15(1H , t, J =3. 6 H z, H
- 12), 4. 53(1H , t, J = 8. 4 H z, H -3), 2. 20 (3H , s, -
COOCH3), 1. 62 (3H , s), 1. 09 (3H , s), 1. 03 (3H , s),
1. 00 (3H , s), 0. 94 (3H , s), 0. 90(3H , s), 0. 89 (3H , s),
0. 82 (3H , s), 13C -NMR (150MH z, CDC l3) δ:171. 0 ( -
COOCH3), 145. 2 (C - 13), 121. 7 (C - 12), 81. 0 (C - 3),
23. 4, 23. 2, 21. 3, 18. 3, 17. 5, 16. 9, 16. 7, 15. 7 ( -CH3).
The spectral data we re in ag reem ent w ith those of β - am y rin ace-
tate[ 19] .
α-Amyr in acetate(11):W hite am o rphous powder, m. p.
238. 1 ～ 240. 3 ℃ (CHC l3). IR νKB rm ax 3 446, 1 735, 1 636,
1 367, 1 245 cm - 1 , ES IM Sm /z (%):467([ M -H] - , 100),
1H -NM R (600 MH z, CDC l3) δ:5. 15 (1H, t, H - 12, J =
3. 5 H z), 4. 53 (1H , t, H - 3), 2. 20 (3H , s, - COOCH3),
1. 62 (3H , s), 1. 09 (3H , s), 1. 03 (3H , s), 1. 00(3H , s),
0. 94 (3H , s), 0. 90(3H , s), 0. 89 (3H, s), 0. 82 (3H , s),
13C -NMR (150MH z, CDC l3) δ:171. 0 ( -COOCH3), 139. 6
(C - 13), 124. 3 (C -12), 81. 0 (C - 3), 23. 4, 23. 2, 21. 4,
18. 3, 17. 5, 16. 9, 16. 7, 15. 7 ( - CH3). The spec tra l da ta
w ere in ag reement w ith those o fα- am y rin aceta te[ 19] .
Fupenzic ac id (12):W hite amo rphou s pow de r, m. p.
191. 2～ 192. 8 ℃ (ace tone). [ α] 25
D
+50. 1°(c 0. 12, M eOH).
UV λMeOHm ax ( logε) nm:270 (2. 08), IRνKB rm ax 3 434, 1 687, 1 636
cm - 1 , 1H -NMR (600 MH z, CD
3
OD) δ:0. 88 (3H, s, H -
26), 0. 94(3H , d, J = 6. 6 H z, H - 30), 1. 11(3H , s, H -
24), 1. 18 (3H, s, H - 23), 1. 21 (3H , s, H - 29), 1. 23
(3H , s, H - 25), 1. 35(3H, s, H - 27), 2. 00 (1H , dd, J =
11. 8, 6. 7 H z, H -20), 2. 12 (1H , m, H - 11a), 2. 24 (1H ,
m , H -11b), 2. 53 (1H , s, H - 18), 5. 35 (1H , br s, H -
12), 6. 29(1H , s, H - 1). 13C -NMR (150MH z, CD3OD)δ:
201. 0(C - 3), 180. 8(C - 28), 144. 6 (C -2), 139. 0 (C -
13), 128. 8 (C -1), 127. 6 (C - 12), 72 (C - 19), 53. 8 (C
- 18), 53. 7(C - 5), 48. 2 (C - 17), 44. 1 (C - 4), 42. 7 (C
- 9), 41. 7 (C - 20), 41. 6 (C - 10), 40. 3 (C - 14), 38. 0
(C - 8), 37. 5 (C - 22), 32. 6(C - 7), 28. 2 (C -15), 26. 7
(C - 23), 25. 9(C - 21), 25. 7 (C -29), 25. 1(C - 16), 23.
4 (C -27), 23. 2 (C - 11), 20. 8 (C - 24), 18. 8 (C - 25),
18. 6 (C - 6), 16. 5(C - 26), 15. 2(C - 30). The op tica l ro ta-
tion, UV, IR and NMR da ta w ere iden tical w ith those repo r-
ted[ 20] .
166 　　　　　　　　应 用与 环 境生 物学 报　　Chin J App lEnviron B io l　　　　　　　　　　　　　　 　　　12卷
(+) - Ca tech in (13):W hite am orphous pow de r, m. p.
138. 9 ～ 141. 1 ℃, [ α] 25D +2. 2°(c 0. 51, M eOH), UV λMeOHm ax
( logε) nm:280 (3. 92), 216(4. 62), ES IMS m /z (%):579
([ 2M -H ] - , 50), 289 ([ M - H ] - , 100), 603 ([ 2M +
Na] +, 100), 291 ([M +H] +, 20). Itw as identified by com pa-
ring its NMR and IR spec tra l data w ith those o f ( +) - ca te-
chin[ 21] .
( -) - Secoisolar iciresinol (14):W hite am orphous pow-
der, m. p. 125. 1 ～ 126. 9 ℃ (acetone), [ α] 25D - 25. 5°(c
0. 11, Me2 CO), UV λM eOHmax ( log ε) nm:272 (1. 52), 208
(1. 29), IR νKB r
m ax
3 438, 1 635, 1 455 cm - 1 , ESIM Sm /z (%):
385([M +Na] +, 100), 361 ([ M -H] - , 100), 1H -NM R
(600MH z, CDC l3)δ:6. 81 (2H , d, J =7. 9 H z, H - 5′, H -
5″), 6. 63 (2H , dd, J = 8. 0, 1. 5 H z, H - 6′, H - 6″), 6. 59
(2H , d, J =1. 5 H z, H - 2′, H - 2″), 4. 65 (4H , br s, 4×-
OH), 3. 82 (6H , s, 2×-OCH
3
), 3. 83 (2H , dd, J = 11. 3,
4. 3 H z, H - 9′α, H - 9″α), 3. 56 (2H , dd, J = 11. 3, 4. 3
H z, H - 9′β, H - 9″β), 2. 75(2H , dd, J = 13. 7, 8. 0 H z, H
- 7′α, H - 7″α), 2. 65 (2H , dd, J =13. 7, 7. 8 H z, H - 7′β,
H -7″β), 2. 05 (2H , s, H - 8′, H - 8″), 13C - NM R (150
MH z, CDC l3) δ:146. 4 (C -4′, C - 4″), 143. 8 (C - 3′, C -
3″), 132. 4 (C - 1′, C - 1″), 121. 7 (C - 6′, C - 6″), 114. 1
(C - 5′, C -5″), 111. 4 (C - 2′, C - 2″), 61. 1 (C - 9′, C -
9″), 55. 8 ( -OCH3), 43. 9 (C -8′, C - 8″), 35. 9(C - 7′, C
- 7″). Its op tical rota tion and 13C -NM R spectral da tawe re in ac-
co rdancew ith those reported[ 22] .
Palm itate - 1 - m onoglyceride (15):White am o rphous
pow de r, m. p. 82. 2 ～ 84. 4 ℃, ESIMS m /z (%):353 ([ M +
Na] +, 100), 1H -NMR (600MH z, CDC l3)δ:4. 20 (1H , dd,
J =11. 6 H z, 4. 6 H z, H -1), 4. 15 (1H, dd, J = 11. 6 H z,
6. 1 H z, H - 1), 3. 93 (1H , p, J = 4. 6 H z, H - 2), 3. 69
(1H , dd, J =11. 3, 3. 6 H z, H -3), 3. 60(1H , dd, J =11.
3, 5. 8 H z, H - 3), 2. 35 (2H , t, J = 7. 6 H z, H - 2′), 1. 63
(2H , t, J = 7. 2 H z, H - 3′), 1. 25 (24H , m, H - 4′-H -
15′), 0. 88(3H , t, J = 7. 1 H z, H - 16′), 13C -NM R (150
MH z, CDC l3) δ:174. 3 (C - 1′), 70. 3 (C - 2), 65. 2 (C -
3), 63. 3 (C - 1), 34. 2 (C - 2′), 31. 9 (C - 14′), 29. 1 -
29. 7 (C -4′- 13′), 24. 9 (C - 3′), 22. 7 (C -15′), 14. 1 (C
- 16′). The spec tra l data w ere in ag reem ent w ith tho se repo r-
ted[ 23] .
Phytol (16):Co lo rless cry sta l, m. p. 81. 5 ～ 86. 7 ℃
(ch lo ro form), ESIM Sm /z(%):295([M -H] - , 100), 1H -
NMR (600MH z, CDC l3)δ:5. 41(1H, m , H -2), 4. 16 (2H ,
d, J =7. 0 H z, H - 1), 2. 00 (2H , m , H - 4), 1. 68 (3H , s,
H -17), 0. 88 - 0. 84(12H , H - 16, 18, 19, 20). 13C -NM R
(150MH z, CDC l3)δ:140. 3(C -3), 123. 1(C - 2), 59. 4(C
- 1), 39. 9 (C - 4), 39. 4 (C - 14), 37. 4 (C - 6), 37. 4 (C
- 8), 37. 3 (C - 10), 36. 7 (C -12), 32. 8(C -7), 32. 7(C
- 11), 27. 9(C - 15), 25. 1(C - 5), 24. 8 (C - 9), 24. 5(C
- 13), 22. 7 (C - 16), 22. 6(C - 20), 19. 8 (C - 19), 19. 7
(C - 18), 16. 2 (C - 17). The IR, 1H -NM R and 13C -NMR
da ta w ere in ag reem ent w ith those of phy to l[ 24] .
Caffe ic ac id (17):Wh ite amo rphous pow de r, m. p. 111. 3
～ 113. 5℃, UV λM eOHmax ( log ε) nm:229 (2. 59), 290 (3. 04),
318(3. 51), IR νKB rm ax:3 435, 3 235, 1 644, 1 620 cm - 1 , 1H -
NM R (600MH z, CDC l3) δ:10. 07 (1H , s, - COOH), 8. 32
(1H , d, H -7, J =8. 7 H z), 7. 86 (1H , d, H - 2, J = 3. 2
H z), 7. 45 (1H , d, H - 8, J =8. 5 H z), 7. 34(1H, dd, H -
6, J =7. 4, 3. 2 H z), 7. 33 (1H , 5, H -5, J =7. 4 H z), 13C
-NM R (150MH z, CDC l3)δ:185. 1 ( -COOH), 136. 7(C -
3), 135. 3(C - 4), 124. 5(C - 8), 124. 4(C - 1), 123. 0(C
- 5), 122. 0 (C - 7), 119. 8 (C - 6), 111. 5 (C - 2). The
spec tra l da taw ere in acco rdance w ith tho se of ca ffeic ac id[ 25] .
3, 4 -D im ethoxyc innam ic acid (18):Pa le yellow powder,
m. p. 108. 7 ～ 109. 8 ℃, UV λMeOHm ax ( log ε) nm:229 (2. 81),
280(2. 26), 320(2. 50), IR νKB rmax:3 435, 1 640, 1 619 cm -1 ,
1H -NM R (600MH z, CDC l3)δ:7. 62 (1H , d, J =15. 8 H z,
H - 7), 7. 08 (1H , dd, J =8. 1, 1. 6 H z, H - 6), 7. 03 (1H ,
d, J =1. 6 H z, H -2), 6. 92 (1H , d, J = 8. 1 H z, H - 5),
6. 29 (1H , d, J = 15. 8 H z, H - 8), 3. 93 (3H, d, 3 -
OCH3), 3. 80 (3H , d, 4 - OCH3), 13C - NM R (150 MH z,
CDC l3)δ:167. 7 ( -COOH), 148. 0(C - 3), 146. 8(C - 4),
145. 0(C - 8), 127. 0 (C - 1), 123. 0 (C - 5), 115. 2 (C -
7), 114. 7(C - 6), 109. 3 (C - 2). The spec tra l data w ere in
acco rdance w ith those o f 3, 4 - dim e thoxycinnam ic ac id[ 26] .
( -) -M asson iresinol(19):Wh ite am orphous powder, m.
p. 91. 5 ～ 93. 5 ℃ (chloroform), [ α] 25D - 28. 5°(c 0. 11,
M eOH), UV λMeOHm ax ( logε) nm:228 (2. 15), 280 (3. 01), IR
νKB rm ax:3 411, 1 610, 1 520, 1 450 cm -1 , ES IMSm /z (%):391
([M - H] - , 15), 1H - NMR (600 MH z, CDC l3) δ:6. 96
(1H , d, J = 1. 5 H z, H -2), 6. 90(1H, d, J = 8. 1 H z, H
- 5), 6. 87 (1H, d, J = 7. 9 H z, H - 5), 6. 82 (1H , d, J
=1. 6 H z, H - 2′), 6. 82 (1H, dd, J = 8. 1, 1. 5 H z, H -
6′), 6. 77 (1H , dd, J =8. 0, 1. 6 H z, H - 6), 5. 67, 5. 59
(2H , s, 4′-, 4-OH), 4. 98 (1H, s, H - 2), 3. 95, 3. 77
(2H , m , H - 8), 3. 94, 3. 78(2H, d, J =9. 4 H z, H -4), 3.
89 (6H , s, 3′- , 3-OCH3), 2. 99, 2. 83 (2H , d, J =13. 7
H z), 2. 72, 2. 71 (2H , s, 1 -OH , 5 -OH), 2. 00 (1H , m , 8
-OH), 13C -NMR (150MH z, CDC l3) data are in Table 1. The
op tical ro ta tion and NMR data w ere consistent w ith tho se o f( -)
-m assoniresino l[ 27] .
Tanegoo l(20):W hite am o rphous pow de r, m. p. 138. 2 ～
140. 1℃ (ch lo ro fo rm), [ α] 25D +58. 2°(c 0. 10, M eOH), UV
λMeOHm ax ( logε) nm:227 (2. 11), 285 (2. 89), IR νKB rm ax:3 415,
1 610, 1 520 cm - 1 , ES IM Sm /z (%):375([ M -H] - , 100),
1H -NMR (600MH z, CDC l3)δ:7. 00(1H , d, J =1. 6 H z, H
- 2), 6. 92(1H , d, J =1. 3 H z, H - 2′), 6. 83 (1H , dd, J
=8. 1, 1. 6 H z, H - 6), 6. 80(1H , dd, J =8. 1, 1. 6 H z, H
- 6′), 6. 77 (1H, d, J = 7. 9 H z, H - 5), 6. 76 (1H , d, J
=8. 1 H z, H - 5′), 4. 96 (2H, dd, J = 14. 5, 9. 0 H z, H -
167　 2期 ZHANG X iuyun, et a l. :Chem icalC on stituents from Gym nosporia varia lilis Loes. 　　
4), 3. 88, 3. 86 (each 3H , s, 3′- , 3-OCH3), 3. 73 (1H ,
dd, J =9. 0, 6. 6 H z, H - 8), 3. 64 (1H , m, H - 8), 3. 66
(1H , m, H -2), 3. 60 (1H, m, H - 6), 2. 63 (1H , m , H -
1), 2. 27 (1H , m , H - 5), 13C -NM R (150MH z, CDC l
3
) δ:
149. 1(C - 3), 149. 1 (C - 3′), 147. 5 (C - 4), 147. 4 (C
- 4′), 136. 2 (C - 1), 134. 0 (C - 1′), 120. 8 (C - 6),
120. 7(C - 6′), 116. 0(C - 5), 116. 0 (C -5′), 111. 4(C -
2), 111. 2 (C -2′), 85. 8(C - 2), 77. 6 (C - 6), 71. 2 (C
- 4), 63. 3(C - 8), 56. 4 (3-OCH3), 56. 4 (3′-OCH3),
56. 0(C - 1), 53. 0 (C - 5). It w as identified as tanegoo l by
comparing its spectroscopic da taw ith those reported[ 28] .
β - S itosterol(21):Co lorless needles (acetone), m. p.
137. 2～ 139. 5 ℃. I tw as determ ined by com pa ring w ith au then tic
sam ple on TLC ( so lven t sy stem:S1 , S2).
Lupeol(22):Co lo rless need le s(ace tone), m. p. 214. 8 ～
216. 3℃. It wa s identified by compa ring w ith au thentic samp le on
TLC (so lven t system:S1 , S2).
Betu lin (23):Co lo rless need le s(ace tone), m. p. 201. 5 ～
202. 8 ℃. It was identified by comparing its TLC behav ior w ith
tha t of authentic sam ple ( solvent system:S1 , S2).
β -Daucosterol(24):W hite am o rphous powder, m. p. >
300℃. Itw as dete rm ined by com pa ring w ith authentic sam ple on
TLC (so lven t system:S3 , S4).
O leanolic ac id (25):Co lo rle ss need les ( ace tone), m. p.
210. 2～ 212. 1 ℃. I tw as determ ined by com pa ring w ith au then tic
sam ple on TLC ( so lven t sy stem:S5 , S6).
Ursolic ac id (26):Co lo rless need le s (ace tone), m. p.
206. 1～ 208. 0 ℃. I tw as determ ined by com pa ring w ith au then tic
sam ple on TLC ( so lven t sy stem:S5 , S6).
( -) - O liv il monoace tate (27):W hite am orphous pow-
der, m. p. 125. 1 ～ 126. 4 ℃. UV λMeOHmax ( log ε) nm:228
(2. 16), 280 (3. 45), IR νKB rm ax:3 415, 1 610, 1 515, 1 455
cm - 1 , [ α] 20D - 40. 7°(c 0. 10, CH3 OH), ES IMS m /z (%):
431([M +Na] +, 100), 1H - NMR (600 MH z, CDC l3) δ:
7. 04 (1H , s, H - 6″), 6. 91 (1H , d, J = 8. 2 H z, H - 5′),
6. 90 (2H , s, H - 2″, H - 5″), 6. 81 (1H, s, H - 2′), 6. 77
(1H , d, J =8. 1 H z, H -6′), 5. 63, 5. 60(each 1H , s, 4′- ,
4″-OH), 4. 70 (1H , d, J = 7. 0 H z, H - 2), 4. 39, 4. 23
(each 1H , dd, J =11. 6, 6. 6 H z, H - 8), 3. 91(1H , m , H -
4), 3. 72 (1H , d, J = 9. 5 H z, H -4), 3. 92 (6H , s, 3′, 3″
-OCH3), 2. 98, 2. 87 (each 1H , d, J = 13. 7 H z, H - 6),
2. 60 (1H , m , H - 1), 2. 07(3H , s, -OCOCH
3
), 13C -NMR
(150MH z, CDC l3) data are in Tab le 1. Itw as iden tified as( -)
- o livil m onoace ta te by comparing the spectro scop ic da ta w ith
tho se reported[ 29] .
2. 2　D iscussion
P rinsepio l(1), the m ost abundant compound in this p lant,
d isp layed 29. 3% vaso re laxant ac tivity a t a concentra tion o f 100
μm ol /L[ 30] . (+) - ca techin(13) show ed m ode ra te ACE inh ibi-
tory activ ity [ 31～ 33]. C affe ic acid(17) show ed ACE inhibito ry ac-
tiv ity w ith inh ibitory ra tio o f 65% at a concentration of 500μm ol /
L[ 34] . H ow ever, ( +) - ca te chin (13) and ca ffeic acid (17)
w ere no t responsib le fo r the ACE inh ibito ry ac tivity o f the ex trac t
considering the ir contents. Neverthe less, in v iew of theACE activ-
ity o f the crude ex trac t and the content of prinsepio l(1), it cou ld
be expec ted that this plan tm ight be a po ten tia lm edicina l he rb fo r
the treatm ent o f cardiovascular diseases.
3　Conclusion
The twenty - seven com pounds w ere obta ined from the 95%
e thano lic ex trac t of the ae rial par t ofG. varialilis. TheACE inh ibi-
tory active components need to be furthe r stud ied.
Fig. 1　S tructu res of compound s 1, 13 and 17
R eferences
1　Delectis F lorae Reipub licae Popu laris S inicae Agendae A cadem iae S in i-
cae E dita (中国植物志编辑委员会). F loR eip Pop S in. Bei jing (北
京):Science Press (科学出版社), 1999, 45:136
2　Gon za lezAG , A lvarenga NL, Bazzocch i IL, Ravelo AG, Mou jir L.
T ri terpene trim ers fromMay tenus scu tioid es:cycloadd ition compound s. J
Na t Prod, 1999, 62 (8):1185～ 1187
3　Gon za lez AG , T in cusi BM , B azzocch i IL, Tokuda H , N ish ino H ,
Konoshim a T, J im enez IA, Ravelo AG. A nti - tum or p romot ing ef fects
of sesqu iterpenes from Maytenus cuzcoina (Celas traceae). B ioorg M ed
Chem , 2000, 8:1773～ 1778
4　 Schan eberg BT, G reen DK, Sneden AT. D ihydroagarofu ran sesqu itr-
pene alkaloids f rom Maytenus pu tter lickoid es. J Nat P rod, 2001, 64
(5):624 ～ 626
5　O rab iKY, A l -Qasoum iS I, E l-O lemy MM , M ossa JS, Muhamm ad I.
D ihyd roagarofu ran alkaloid and triterpen es f rom Maytenu s heterophylla
andMaytenus arbutifolia. Phytoch em istry , 2001, 58 (3):475～ 480
6　Leite JPV , Rastrelli L, Rom uss iG , O liveira AB, V ilegas JHY, V ilegas
W , P izza C. Iso lation andH PLC qu an titative ana lysis of flavonoid g lyco-
s ides f rom Brazi lian beverages(Maytenu s ilicifolia andM. aqu ifo lium).
J AgriF ood Chem , 2001, 49 (8):3796～ 3801
7　W ilegasW , S anomm iyaM , Rastrel liL, Pizza C. Isolation and structu re
168 　　　　　　　　应 用与 环 境生 物学 报　　Chin J App lEnviron B io l　　　　　　　　　　　　　　 　　　12卷
elu cidation of tw o new flavonoid g lycos ides from the infusion ofM aytenus
aquifolium Leaves. evalu ation of the antiu lcer acivity of the in fu sion. J
Ag riF ood Chem , 1999, 47 (2):403～ 406
8　Hussein G, N akamu ra N, M eselhy MR, H attori M. Phenolics from
Maytenus senega lensis. Phytochem istry, 1999, 50 (4):689 ～ 694
9　C arm e lS, YaronA. An in tram olecu larly quenched fluorescen t tripep tide
as a fluorogen ic substrate of angiotensin - i - converting enzym e and of
bacterial d ipep tidy l carboxypep tidase. Euro J B iochem , 1978, 87:265
～ 273
10　K ilidhar SB, Parthasarathy MR, Sharm a P. Prinsep iol, a lignan from
stem s ofPrinsepia U ti lis. Phytoch em istry , 1982, 21 (3):796～ 797
11　Tsukam oto H , H isada S, N ish ibe S. L ignans from bark of Fra xinus
m and shurica var. japon ica andF. japon ic. Chem Pharm B u ll, 1984,
32 (11):4482 ～ 4489
12　Zhuang LG , S eligm ann O, Ju rcic K, W agner H. Inhaltsstoffe von
Daphne Tangu tica. P lan taM ed , 1982, 45:172 ～ 176
13　Abe F, Yam au chi R. 9α- hyd roxypinores inol, 9α- hyd roxym ediores-
inol and related lignans f rom Al lam anda neriifolia. Phy tochem istry,
1988, 27 (2):575～ 577
14　Zheng XH (郑训海), Kong LY (孔令义). S tudies on chem ica l con-
sti tuen ts ofEp im ed ium koreanum. Ch in Trad itHerbD rugs (中草药),
2002, 33 (11):964～ 967
15　Kadow ak i E, Yosh ida Y, N itoda T, Bab a N , Nakajim a S. ( - ) -
olivil and (+) - 1 - acetoxyp inoresinol from the o live tree (O lea euro-
pa ea L inne;O lea ceae) as feed ing stim u lants of the olive w eevil(D ys-
ceru s perfora tus). B iosci B iotechnol B iochem , 2003, 67 (2):415 ～
419
16　C ow an S, S tew artM , Abb iw DK, LatifZ , S ark er SD, N ash R J. Lig-
nans from S trophan thu sg ra tus. F itoterapia, 2001, 72 (1):80～ 82
17　N ish imu ra K , M iyase T, Noguch iH , ChenXM. A cyl- CoA:cho les-
terol acyltran sferase (ACAT) inh ib itros from Ilex spp. Nat M ed,
2000, 54 (6):297～ 305
18　Abyshev MF, Zm eikov VP. 13C - NMR spectra and structu re of
bungeid io l and its transform ation p roducts. Chem Na t Compd , 1982,
18:270～ 276
19　Zhong H J (钟海军), Lu o SD (罗士德), W ang HY (王惠英 ),
Chen JJ(陈纪军), LiXQ (李雪琼). Chem ical cons tituen ts ofCrepis
phoenix. Acta B otYunnan (云南植物研究), 1999, 21 (4):531～
534
20　H attoriM , Kuo KP, Shu YZ , Tezuka Y, K ikuch iT , N amba T. A trit-
erpene from the fru its of R ubus ch ing ii. P hytoch em istry , 1988, 27
(12):3975～ 3976
21　Zhou ZH (周志宏), Yang CR (杨崇仁). C hem ical consti tuen ts of
crude green tea, the m aterial of Pu - er Tea inYunnan. Acta Bo tYun-
nan (云南植物研究), 2000, 22 (3):343～ 350
22　Fonseca SF, C ampe llo JP, Barata LES, Ruveda EA. 13C -NM R spec-
t ral analysis of lignan s from Araucaria angu st ifolia. Phy tochem istry,
1978, 17:499～ 502
23　Y in F (尹锋 ), H u LH (胡立宏), Lou FC (楼凤昌). Chem ical
s tudies on the herb ofO cimum basilicum L. Ch in J NatM ed (中国天
然药物), 2004, 2 (1):20 ～ 24
24　Wu SH (吴少华), M a YB (马云保), Lu o XD (罗晓东 ), W u DG
(吴大刚), Liu JK (刘吉开). The chem ical con stituents from Toricel-
lia angu lata. Acta B ot Yunnan (云南植物研究 ), 2000, 22 (2):
214 ～ 218
25　W u ZJ (吴志军), Ouyang MA (欧阳明安), Yang CR (杨崇仁 ).
Polyphenolic const ituen ts ofSa lvia sonch ifolia. ActaB otYunnan (云南
植物研究), 1999, 21 (3):393～ 398
26　Yang XD (羊晓东), Zhao JF (赵静峰), M ei SX (梅双喜 ), Li L
(李良 ). S tudy on the chem ical con stituents of Lagotis yunnanesis
(Ⅰ ). J Yunnan Un iv (云南大学学报), 2003, 25 (2):141 ～ 143
27　Shen ZB, Th eander O. ( - ) - m asson iresinol, a lignan from P inus
m asson iana. Phytochem istry, 1985, 24 (2):364 ～ 365
28　Abe F, Yam auch i T. Tanegosides A , B and C, Lignan G lycosides
f rom Tra chelospermum liukiuense. Chem Pharm B u ll, 1990, 38 (8):
2143 ～ 2145
29　Tokuoka Y , Daigo K, Takem oto T. Con stituen ts of epimedium Ⅲ .
ligno ids ofEpim ed ium g rand if lorum. Yakugu Za ssh i, 1975, 95 (5):
557 ～ 563
30　Piccinel liAL, A rana S, C aceresA , Bianca REV , Sorren tino R, Ras-
t relli L. New lignans f rom the roo ts of Va leriana prionoph ylla w ith an-
t iox idative and vasorelaxan t activi ties. J Na t P rod , 2004, 67 (8):
1135 ～ 1140
31　ActisGL, O ttavian i JI, K een CL, Fraga CG. Inh ib ition of angiotens in
converting enzym e (ACE) activity by f lavan - 3 - ols and p rocyan i-
dins. FEB S Let, 2003, 555 (3):597～ 600
32　T su tsum iY, Sh im ada A, M iyano A, N ish id a T, M itsugnaga T. In vitro
screen ing of angiotensin I - converting enzym e inhibitors from Japanese
C edar(Cryp tom eria japon ica). J Wood S ci, 1998, 44:463～ 468
33　M eun ierMT , V illie F , JonadetM , Bastide J, B as tide P. Inh ib ition of
angiotension I converting enzyme by flavano lic compound s:in vitro and
in vivo S tud ies. P lan ta Med, 1987, 53 (1):12 ～ 15
34　Borm annH , M elzigM F. Inhibi tion of m etallopep tid ases by flavonoids
and related com pounds. Pha rmaz ie, 2000, 55 (2):129 ～ 132
169　 2期 ZHANG X iuyun, et a l. :Chem icalC on stituents from Gym nosporia varia lilis Loes.