全 文 ：Studies on chemical constituents of Isodon eriocalyx var. laxif lora
NIU Xue-mei, LI Sheng-hong , NA Zhi, M EI Shuang-x i, ZHAO Qin-shi, SUN Han-dong
X
( State Key Labo rat or y o f Phyt ochemistr y and P lant Resources in West China , Kunming Institute
of Bot any , CAS, Kunming 650204, China )
Abstract: Object　To study the chem ical const ituents of the leaves of I sodon eriocaly x ( Dunn) Hara
var. lax if lora C. Y. Wu et H. W . Li. Methods　The leaves of I . eriocaly x var . lax if lor a were ex t racted
w ith 70% M e2CO, and separated and purif ied by column chromato graphies on silica g el or M CI gel . All
the compounds w ere identif ied on the basis of spectr al analy sis ( including 1D and 2D NMR and M S) o r di-
rect co-chromatographies w ith authent ic samples. Results　Fif teen compounds w ere iso lated fr om I . er io-
caly x var . lax if lora. Their st ructures w ere characterized as blumeno l A (Ⅰ ) , 2-formyl-5-hydrox-
ymethylfuran (Ⅱ) , 3, 4-dihydroxyphenacyl alcohol (Ⅲ) , caffeic acid (Ⅳ) , caf feic acid ethy lene ester
(Ⅴ ) , p -hydr oxybenzoic acid (Ⅵ ) , m-hydr oxybenzoic acid ( Ⅶ) , p -methylbenzoic acid (Ⅷ ) , 3, 4-
dimethoxypheno l (Ⅸ) , rosmanic acid (Ⅹ) , rosmanic acid methy l ester (Ⅺ) , cirsimar it in (ⅩⅡ) , 8-hy-
droxycirsimar it in (ⅩⅢ) , urso lic acid (ⅩⅣ) , and 2A-hydroxyursolic acid (ⅩⅤ) respect ively. Conclusion　
Compounds Ⅰ- Ⅴ, Ⅷ, Ⅸ and Ⅺ were isolated f rom this plant for the first t ime.
Key words: the leaves o f I sodon eriocaly x ( Dunn) Hara var. lax if lor a C. Y. Wu et H. W. Li; chemi-
cal const ituents; blumenol A
疏花毛萼香茶菜的化学成分研究
牛雪梅,黎胜红,纳　智,梅双喜,赵勤实,孙汉董
(中国科学院昆明植物研究所 植物化学与西部植物资源国家重点实验室,云南 昆明　650204)
摘　要: 目的　研究疏花毛萼香茶菜 I sodon er iocaly x var . lax if lora 叶的化学成分。方法　疏花毛萼香茶菜叶经
70%丙酮提取, 采用硅胶或 MCI 柱层析进行分离纯化,通过波谱分析(包括一维和二维核磁共振及质谱)或直接与
标准品对照进行结构鉴定。结果　从疏花毛萼香茶菜中分离得到 15 个化合物,分别鉴定为: 布卢姆醇 A(Ⅰ) , 2-醛
基-5-羟甲基呋喃(Ⅱ) , 3, 4-二羟基苯酰乙醇(Ⅲ) , 咖啡酸(Ⅳ) , 咖啡酸乙烯酯(Ⅴ) , 对-羟基苯甲酸(Ⅵ) ,间-羟基苯
甲酸(Ⅶ) , 对-甲基苯甲酸(Ⅷ) ; 3, 4-二甲氧基苯酚(Ⅸ) , 迷迭香酸(Ⅹ) ,迷迭香酸甲酯(Ⅺ ) , 滨蓟素(ⅩⅡ) , 8-羟基滨
蓟素(ⅩⅢ) , 乌苏酸(ⅩⅣ)和 2A-羟基乌苏酸(ⅩⅤ)。结论　化合物Ⅰ～Ⅴ, Ⅷ,Ⅸ和Ⅺ为首次从该植物中分离得到。
关键词: 疏花毛萼香茶菜叶;化学成分; 布卢姆醇 A
中图分类号: R284. 1　　　文献标识码: A　　　文章编号: 0253 2670( 2003) 04 0300 04
　　I sodon eriocaly x ( Dunn ) Hara var. lax if lora
C. Y. Wu et H. W. Li, a perennial shrub, be-
longs to I sodon Kudo, w hich is known for being
rich in ent-kaurane diter peno ids. A series of new
and known ent-kaurane diter peno ids f rom this
plant have been reported
[ 1, 2] . How ever , it w as
rarely r eported on other chemical const ituents ex-
cept diterpenoids. In this paper, w e describe the
isolat ion and str uctural elucidat ion of 15 non-diter-
penoids compounds ( including 12 pheno lic com-
pounds, 2 t riterpenoids and a caro tenoid-like com-
pound ) isolated from the leaves of I . eriocaly x
var. lax if lor a. T heir st ructures w er e identif ied as
blumeno l A ( Ⅰ ) [ 3] , 2-formyl-5-hydroxymethyl-
furan ( Ⅱ ) [ 4] , 3, 4-dihydroxyphenacyl alcohol
(Ⅲ) [ 5] , caf feic acid (Ⅳ) [ 6] , caffeic acid ethylene
·300· 中草药　Chinese T raditional and Herbal D rug s　第 34 卷第 4 期 2003年 4月
X 收稿日期: 2002-08-14作者简介:牛雪梅 ( 1973- ) ,女, 1993年毕业于广西师范大学化学化工系, 1996年获广西师范大学化学化工系硕士学位(有机合成专业) , 2001年获中国科学院昆明植物研究所博士学位(天然产物化学方面) ,现为中国科学院昆明植物研究所植物化学与西部植物资源国家重点实验室助理研究员,主要从事天然产物化学研究工作,在国内外核心期刊上发表相关研究论文 10 余篇。
* 通讯作者　　Tel: ( 0871) 5223251　　Fax : ( 0871) 5216434　　E-mail: h dsun@m ail . kib. ac. cn
ester (Ⅴ) [ 7] , p -hydr oxybenzoic acid (Ⅵ) , ( ident i-
cal with authent ic sample) , m-hydroxybenzoic acid
( Ⅶ ) , ( ident ical with authent ic sample ) ,
p -methylbenzo ic acid (Ⅷ) , ( ident ical w ith authen-
tic sample) , 3, 4-dimethoxyphenol (Ⅸ) [ 8] , ros-
manic acid ( Ⅹ ) , ( identical w ith authent ic
sample) , rosmanic acid methyl ester (Ⅺ) [ 6] , cirsi-
marit in (ⅩⅡ) [ 9] , 8-hydroxycirsimarit in (ⅩⅢ) [ 10] ,
ursol ic acid ( ⅩⅣ ) [ 11] , 2A-hydroxyurso lic acid
(ⅩⅤ) [ 12] . Among these 15 compounds, Ⅰ- Ⅴ,
Ⅷ, Ⅸ and Ⅺ wer e obtained from this plant for the
first t ime.
1　Experiment
1. 1　General. M S spect ra w ere recorded on a VG
Auto Spec-3000 spect rometer. NMR spect ra w ere
run on a Bruker AM-400 and DRX-500 inst ru-
ment .
1. 2　Plant mater ials. The leaves of I . er iocalyx
( Dunn) Har a var. lax if lor a C. Y. Wu et H. W.
Li w er e collected in Xishuangbanna Pr efectur e,
Yunnan Prov ince, Peoples Republic o f China , in
November 1999. It w as ident ified by Pro f. T ao G
D at Xishuangbanna Botanic Gar den. A voucher
specimen has been deposited in the Her barium of
Kunming Inst itute of Botany , the Chinese Acade-
my of Sciences.
1. 3　Ex tract ion and isolat ion. T he dried and pow-
dered leaves ( 25 kg ) w ere ext racted w ith 70%
M e2CO at ro om temperature fo r three t imes and
filtered. The filt rate w as concentrated and ex tract-
ed w ith EtOAc. The EtOAc layer w as evapo rated
in vacuo to giv e the residue ( 1 000 g ) , w hich w as
subjected to silica g el column chr omatogr aphy, us-
ing CHCl3, CHCl 3-Me2CO ( 9∶1, 8∶2, 7∶3, 6∶
4, and 1∶1) and M e2CO as eluents to afford frac-
tions 1, 2, 3, 4, 5, 6 and 7, r espect ively . The
fr act ions w ere co llected and combined by monitor -
ing w ith TLC. Compounds ⅩⅣ ( 30 mg ) and ⅩⅤ
( 40 mg ) w er e obtained from fract ion 1. In the
same w ay , compoundsⅩⅡ ( 200 mg ) and ⅩⅢ ( 300
mg ) were af forded from fract ions 2 and 3, respec-
tiv ely . Fract ion 2 w as further purif ied on silica g el
CC elut ing w ith pet roleum-M e2CO ( 4∶1, 3∶1,
2∶1, 1∶1) to give Ⅱ ( 6 mg) , Ⅵ ( 11 mg ) , Ⅶ ( 9
mg ) and Ⅷ ( 7 mg ) . Fraction 4 w as repeatedly
t reated by middle-pressur e column chromato gra-
phy over silica gel developing w ith CHCl 3-M eOH
( 15∶1, 9∶1) and follow ed by recry stallizat ion to
y ield Ⅰ ( 16 mg ) . Fr act ion 5 w as subjected to mi-
ddle-pressure column chromatog raphy on silica gel
column using CHCl3-M eOH ( 9∶1 and 8∶2) as
eluents and the port ion elut ing by CHCl 3-M eOH
( 8∶2) w as purified by column chromatogr aphy
over MCI-gel CHP-20P developing w ith aqueous
M eOH ( 40% , 50% , 60%) to af for d compounds
Ⅲ ( 40 mg ) , Ⅳ ( 70 mg) , Ⅴ ( 13 mg ) , Ⅹ ( 100 g )
and Ⅺ( 20 mg) .
2　Identification
Compound Ⅰ ( blumeno l A) : C13H20O 3 , co lor-
less needles. EI-M S ( 70 eV ) m/ z ( %) : 224 [ M
+ ]
( 7) , 206 ( 29) , 191 ( 4) , 181 ( 9) , 168 ( 48) , 162
( 8) , 150 ( 40) , 135 ( 43) , 124 ( 100) , 111 ( 44) ,
107 ( 37) , 95 ( 37) , 79 ( 54) , 69 ( 42) , 55 ( 83) .
1
HNMR ( 400 MHz, C5D5N ) D: 2. 68 ( 1H, d, J =
16. 6 Hz, H-2a) , 2. 40 ( 1H, d, J = 16. 6 Hz, H-
2b) , 6. 25 ( 1H, d, J = 15. 6 Hz, H-7) , 6. 33 ( 1H,
dd, J= 5. 0, 15. 6 Hz, H-8) , 4. 70 ( 1H , m, H-9) ,
1. 45 ( 3H , d, J= 6. 6 Hz, M e-10) , 1. 12 ( 3H, s,
M e-11) , 1. 28 ( 3H, s, Me-12) , 2. 01 ( 3H, s, Me-
13) .
13
CNMR ( 100 MHz, C5D 5N ) D: 41. 5 s ( C-
1) , 50. 3 t ( C-2) , 197. 6 s ( C-3) , 126. 6 d ( C-4) ,
164. 3 s ( C-5) , 78. 9 s ( C-6 ) , 137. 2 d ( C-7) ,
129. 1 d ( C-8) , 67. 3 d ( C-9) , 24. 4 q ( C-10) ,
23. 4 q ( C-11) , 24. 4 q ( C-12) , 19. 3 q ( C-13) .
Compound Ⅱ ( 2-formyl-5-hydroxymethyl-
furan) : C6H6O 3, brow n powder. EI-M S ( 70 eV )
m / z ( % ) : 126 [ M
+
] ( 89) , 109 ( 50) , 97 ( 100) ,
81 ( 45) , 69 ( 80) , 59 ( 21) , 53 ( 54) . 1HNMR ( 400
MHz, CD 3OD) D: 9. 52 ( 1H, s, CHO ) , 7. 38
( 1H, d, J= 3. 5 Hz, H-3) , 6. 58 ( 1H , d, J = 3. 5
Hz, H-4) , 4. 60 ( 2H , s, CH2 ) ;
13
CNMR ( 100
MHz, CD 3OD) D: 179. 5 d ( CHO) , 163. 3 s ( C-
2) , 124. 7 d ( C-3) , 110. 9 d ( C-4) , 153. 9 s ( C-
5) , 57. 7 t ( CH 2) .
Compound Ⅲ ( 3, 4-dihydroxyphenacyl alco-
hol ) : C8 H8O 4, brow n needles. EI-M S ( 70 eV )
m / z ( % ) : 168 [ M
+
] ( 57) , 152 ( 5) , 149 ( 10) ,
137 ( 100) , 123 ( 4) , 109 ( 65) , 91 ( 10) , 81 ( 52) ,
·301·中草药　Chinese T raditional and Herbal D rug s　第 34 卷第 4 期 2003年 4月
63 ( 30) , 53 ( 51) .
1
HNMR ( 500 MHz, CD 3OD) D:
7. 38 ( 1H , d, J = 2. 0 Hz, H-2) , 6. 83 ( 1H, d,
J= 8. 0 Hz, H-5) , 7. 36 ( 1H, dd, J = 2. 0, 8. 0
Hz, H-6) , 4. 79 ( 2H , s, H 2-8) .
13
CNMR ( 125
MHz, CD 3OD) D: 127. 7 s ( C-1) , 115. 4 d ( C-2) ,
146. 7 s ( C-3) , 152. 6 s ( C-4) , 116. 0 d ( C-5) ,
122. 3 d ( C-6) , 198. 6 s ( C= O) , 65. 8 t ( C-8) .
Compound Ⅳ ( caf feic acid) : C9H8O 4 , brow n
needles. N egat ive FAB-M S ( 70 eV ) m / z ( %) :
179 [ M - H ]
-
( 100) .
1
HNMR ( 500 MHz, CD 3OD)
D: 7. 04 ( 1H, d, J= 2. 0 Hz, H-2) , 6. 77 ( 1H, d,
J= 8. 2 Hz, H-5) , 6. 93 ( 1H, dd, J = 2. 0, 8. 2
Hz, H-6) , 7. 54 ( 1H, d, J= 15. 8 Hz, H-7) , 6. 22
( 1H, d, J= 15. 8 Hz, H-8) .
13
CNMR ( 125 MHz,
CD3OD) D: 127. 8 s ( C-1) , 115. 5 d ( C-2) , 146. 7 s
( C-3) , 149. 4 s ( C-4) , 116. 5 d ( C-5) , 122. 9 d
( C-6) , 147. 1 d ( C-7) , 115. 1 s ( C-8) , 171. 1 s
( C-9) .
Compound Ⅴ ( caffeic acid ethylene ester ) :
C11H10O 4, yellow needles. EI-M S ( 70 eV ) m/ z
( % ) : 206 [ M + ] ( 45) , 163 ( 100) , 145 ( 40) , 135
( 63) , 117 ( 48) , 107 ( 18) , 105 ( 20) , 97 ( 20) , 89
( 67) , 77 ( 47) , 71 ( 37) , 63 ( 41) , 55 ( 58) .
1
HNMR ( 500 MHz, CD3OD) D: 7. 06 ( 1H , d, J=
2. 0 Hz, H-2) , 6. 78 ( 1H, d, J = 8. 2 Hz, H-5) ,
6. 97 ( 1H, dd, J= 2. 0, 8. 2 Hz, H-6) , 7. 64 ( 1H,
d, J = 15. 9 Hz, H-7) , 6. 27 ( 1H, d, J= 15. 9 Hz,
H-8) , 7. 38 ( 1H, dd, J = 6. 3, 14. 0 Hz, H-10) ,
4. 93 ( 1H, d, J= 14. 0 Hz, H-11a) , 4. 60 ( 1H, d,
J = 6. 3 Hz, H-11b) .
13
CNMR ( 125 MHz,
CD3OD) D: 127. 5 s ( C-1) , 115. 3 d ( C-2) , 146. 9 s
( C-3) , 150. 1 s ( C-4) , 116. 6 d ( C-5) , 123. 4 d
( C-6) , 148. 7 d ( C-7) , 113. 6 s ( C-8) , 165. 9 s ( C-
9) , 142. 5 d ( C-10) , 97. 7 t ( C-11) .
Compound Ⅵ ( p-hydr oxybenzoic acid ) :
C7H6O3 , white plates. EI-M S ( 70 eV ) m/ z ( %) :
138 [ M+ ] ( 95) , 121 ( 100) , 110 ( 22) , 93 ( 75) ,
81 ( 40) , 74 ( 28) , 65 ( 86) , 53 ( 84) .
1
HNMR ( 400
MHz, acetone-d6 ) D: 7. 92 ( 2H, d, J= 8. 6 Hz, H-
2 and H-6) , 6. 92 ( 2H, d, J= 8. 6 Hz, H-3 and H-
5) .
13
CNMR ( 100 MHz, acetone-d6 ) D: 169. 0 s
( COOH) , 122. 3 s ( C-1) , 132. 8 d ( 2C, C-2 and
C-6) , 116. 0 d ( 2C, C-3 and C-5) , 162. 7 s ( C-4) .
Rf values on TLC are consistent w ith tho se o f au-
thent ic sample.
Compound Ⅶ ( m-hydroxybenzoic acid ) :
C7H6O 3, colorless needles. EI-MS ( 70 eV )
m / z ( %) : 138 [ M + ] ( 68) , 120 ( 100) , 92 ( 96) ,
84 ( 32) , 64 ( 38) , 53 ( 13) .
1
HNMR ( 400 MHz,
C5D5N ) D: 10. 88 ( 1H , brs, COOH) , 6. 95 ( 1H,
brs, H-2) , 7. 18 ( 1H, d, J = 8. 4 Hz, H-4) , 7. 49
( 1H, m, H-5) , 8. 26 ( 1H, d, J= 8. 0 Hz, H-6) .
13CNMR ( 100 MHz, C5D 5N) D: 174. 5 s ( COOH) ,
115. 4 s ( C-1) , 117. 8 d ( C-2) , 163. 0 s ( C-3) ,
119. 2 d ( C-4) , 131. 4 d ( C-5) , 135. 4 d ( C-6) . Rf
v alues on TLC are consistent with tho se of authen-
t ic sample.
Compound Ⅷ ( p -methylbenzoic acid ) :
C8H8O 2, colorless needles. EI-M S ( 70 eV ) m/ z
( %) : 136 [ M
+ ] ( 80) , 121 ( 100) , 107 ( 8) , 93
( 63) , 77 ( 13) , 65 ( 65) , 53 ( 16) .
1
HNMR ( 400
MHz, C5D5N ) D: 12. 67 ( 1H, br s, COOH) , 8. 08
( 2H, m, H-2 and H-6) , 7. 18( 2H , m, H-3 and H-
5) , 2. 51 ( 3H, s, CH3 ) .
13
CNMR ( 100 MHz,
C5D5N ) D: 193. 1 s ( COOH) , 129. 8 s ( C-1 ) ,
131. 5 d ( 2C, C-2 and C-6) , 116. 2 D ( 2C, C-3 and
C-5) , 162. 7 s ( C-4) , 26. 3 q ( CH 3) . Rf values on
T LC ar e consistent w ith those of authent ic sample.
Compound Ⅸ ( 3, 4-dimethoxyphenol ) :
C8H10O 3, br ow n powder . EI-MS ( 70 eV ) m/ z
( %) : 154 [ M + ] ( 60) , 136 ( 100) , 108 ( 40) , 97
( 5) , 80 ( 37) , 69 ( 7) , 63 ( 12) , 55 ( 64) .
1
HNMR
( 400 MHz, CD3OD) D: 7. 24 ( 1H, d, J = 3. 0 Hz,
H-2) , 6. 77 ( 1H, d, J= 8. 8 Hz, H-5) , 6. 93 ( 1H,
dd, J= 3. 0, 8. 8 Hz, H-6) , 3. 31 and 3. 28 ( each
3H, s, OCH3 ) .
Compound Ⅹ ( rosmanic acid ) : C18 H16 O8 ,
brow n amorphous solid. EI-M S ( 70 eV) data and
Rf values on T LC are consistent w ith those of au-
thent ic sample.
Compound Ⅺ ( rosmanic acid methyl ester ) :
C19 H18O 8, brow n powder . EI-MS ( 70 eV ) m/ z
( %) : 374 [ M
+ ] ( 3) , 314 ( 23) , 208 ( 3) , 194
( 100) , 180 ( 41) , 163 ( 79) , 153 ( 7) , 136 ( 28) ,
123 ( 57) , 89 ( 28) , 77 ( 18) , 63 ( 11) .
1
HNMR
( 400 MHz, CD 3OH) D: 7. 04 ( 1H, d, J = 2. 0 Hz,
H-2) , 6. 77 ( 1H, d, J = 8. 0 Hz, H-5) , 6. 94 ( 1H,
dd, J = 2. 0, 8. 0 Hz, H-6) , 7. 55 ( 1H , d, J =
·302· 中草药　Chinese T raditional and Herbal D rug s　第 34 卷第 4 期 2003年 4月
16. 0 Hz, H-7) , 6. 25 ( 1H, d, J= 16. 0 Hz, H-8) ,
6. 71 ( 1H, d, J = 2. 0 Hz, H-2′) , 6. 56 ( 1H, d,
J= 8. 4 Hz, H-5′) , 6. 66 ( 1H , dd, J = 2. 0, 8. 4
Hz, H-6′) , 2. 97 ( 2H, m, H-7′) , 5. 19 ( 1H, dd,
J = 7. 3, 5. 4 Hz, H-8′) , 3. 68 ( 3H, s, OCH3 ) .
13
CNMR ( 100 MHz, CD 3OD) D: 127. 7 s ( C-1) ,
114. 3 d ( C-2) , 146. 8 s ( C-3) , 149. 8 s ( C-4) ,
116. 6 d ( C-5) , 123. 2 d ( C-6) , 147. 9 d ( C-7) ,
116. 4 d ( C-8) , 169. 3 s ( C-9) , 128. 9 s ( C-1′) ,
115. 8 d ( C-2′) , 145. 4 s ( C-3′) , 146. 2 s ( C-4′) ,
117. 6 d ( C-5′) , 121. 9 d ( C-6′) , 37. 9 t ( C-7′) ,
74. 7 d ( C-8′) , 172. 2 s ( C-9′) , 52. 9 q ( OCH3 ) .
Compound ⅩⅡ ( cirsimaritin ) : C17H14O 6, y el-
low crystal . EI-M S ( 70 eV) m/ z ( %) : 314 [ M
+ ]
( 100) , 299 ( 94) , 285 ( 60) , 271 ( 65) , 254 ( 21) ,
239 ( 8) , 208 ( 3) , 200 ( 14) , 181 ( 52) , 167 ( 13) ,
153 ( 74) , 119 ( 47) , 69 ( 75) .
1
HNMR ( 400 MHz,
C5D 5N) D: 6. 79 ( 1H, s, H-3) , 13. 63 ( 1H , brs,
5-OH) , 3. 88 ( 3H, s, 6-OCH3) , 6. 93 ( 1H, s, H-
8) , 7. 94 ( 2H, d, J = 8. 4 Hz, H-2′and H-6′) ,
7. 27 ( 2H, d, J = 8. 4 Hz, H-3′and H-5′) .
13CNMR ( 100 MHz, C5D 5N ) D: 164. 6 s ( C-2) ,
103. 4 d ( C-3) , 182. 8 s ( C-4) , 153. 4 s ( C-5) ,
132. 9 s ( C-6) , 159. 0 s ( C-7) , 91. 3 d ( C-8) ,
153. 2 s ( C-9) , 106. 1 s ( C-10) , 122. 0 s ( C-1′) ,
128. 6 d ( 2C, C-2′and C-6′) , 162. 5 s ( C-4′) ,
116. 8 d ( 2C, C-3′and C-5′) , 56. 1 q ( 6-OCH3 ) ,
60. 3 q ( 7-OCH3 ) .
Compound ⅩⅢ ( 8-hydr oxycirsimarit in ) :
C17H14O7 , o range crystal . EI-M S ( 70 eV ) m/ z
( % ) : 330 [ M + ] ( 95) , 329 ( 16) , 315 ( 100) , 297
( 36) , 287 ( 8) , 212 ( 2) , 197 ( 58) , 169 ( 45) , 119
( 38) , 118 [ B1
+ ] ( 54) , 77 ( 4) . 1HNMR ( 500
MHz, DM SO-d6 ) D: 6. 80 ( 1H , s, H-3) , 12. 43
( 1H, s, 5-OH ) , 3. 81 ( 3H , s, 6-OCH3 ) , 3. 92
( 3H , s, 7-OCH3 ) , 9. 26 ( 1H, br s, 8-OH) , 10. 39
( 1H, br s, 4′-OH) , 8. 00 ( 2H , dd, J = 2. 0, 8. 3
Hz, H-2′and H-6′) , 6. 93 ( 2H , dd, J = 2. 0, 8. 3
Hz, H-3′and H-5′) . 13CNMR ( 125 MHz, DM SO-
d6 ) D: 164. 2 s ( C-2) , 102. 5 d ( C-3) , 182. 8 s ( C-
4) , 144. 7 s ( C-5) , 136. 2 s ( C-6) , 148. 0 s ( C-7) ,
130. 6 s ( C-8) , 141. 4 s ( C-9) , 106. 4 s ( C-10) ,
121. 2 s ( C-1′) , 128. 8 d ( 2C, C-2′and C-6′) ,
161. 4 s ( C-4′) , 116. 0 d ( 2C, C-3′and C-5′) ,
60. 5 q ( 6-OCH3) , 61. 2 q ( 7-OCH3 ) .
Compound ⅩⅣ ( ursolic acid ) : C30 H48 O3 ,
w hite pow der. EI-MS ( 70 eV ) m/ z ( %) : 456
[ M
+
] ( 10) , 438 ( 3) , 410 ( 5) , 395 ( 2) , 300 ( 5) ,
248 ( 100) , 233 ( 10) , 219 ( 15) , 203 ( 75) , 189
( 31) , 175 ( 23) , 147 ( 24) , 133 ( 62) , 119 ( 46) ,
105 ( 40) , 95 ( 41) , 81 ( 44) , 69 ( 55) , 55 ( 61) .
Compound ⅩⅤ ( 2A-hydroxyurso lic acid ) :
C30H48O 3, w hite pow der. EI-MS ( 70 eV ) m/ z
( %) : 472 [ M
+
] ( 4) , 454 ( 2) , 426 ( 11) , 408 ( 3) ,
248 ( 100) , 223 ( 7) , 203 ( 43) , 189 ( 17) , 145
( 11) , 133 ( 26) , 119 ( 22) , 105 ( 21) , 81 ( 18) , 69
( 27) , 55 ( 35) .
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·303·中草药　Chinese T raditional and Herbal D rug s　第 34 卷第 4 期 2003年 4月