全 文 ：武汉植物学研究 2000, 18 (2) : 143～ 145
J ourna l of W uhan B otan ica l Resea rch
刺异叶花椒中的生物碱和香豆素类成分Ξ
向　瑛　郑庆安　张灿奎　李　贞　屠治本ΞΞ
(中国科学院武汉植物研究所　武汉　430074)
提　要　从刺异叶花椒根的木质部中分得 6 种生物碱, 分别为铁屎米262酮、乙氧基白屈菜红
碱、N 2去甲基白屈菜红碱、白藓碱、勒木党碱、氧化勒木党碱, 以及 3 种香豆素类化合物, 滨蒿内
酯、东莨菪内酯和异东莨菪内酯。利用化学方法和光谱数据证实了它们的结构。这些生物碱
和香豆素类成分在广义花椒属的化学分类和应用研究中均具有重要意义。
关键词　刺异叶花椒, 生物碱, 香豆素, 化学分类
AL KALO ID S AND COUM AR INS FROM ZAN THOX YLUM
D IM OR PHO PH YLLUM HEM SL 1VAR1SP IN IFOL IUM
REHD 1ET W IL S13
X iang Y ing　Zheng Q ing’an　Zhang Canku i　L i Zhen　T u Zh iben3 3
(W uhan Institu te of B otany , T he Ch inese A cad emy of S ciences　W uhan　430074)
Abstract 　 Six alkalo ids, can th in262one, ethoxycheleryth rine, N 2des2m ethylcheleryth rine,
dictam nine, avicine and oxyavicine as w ell as th ree coum arins, scoparone, scopo let in and
iso scopo let in w ere iso la ted from the roo t xylem of Z anthoxy lum d im orp hop hy llum
var1sp in if olium 1T heir structu res w ere iden tified on the basis of spectra l and chem ical data1
T hese alkalo ids are sign ifican t to the chemo taxonom y of Z anthoxy lum L 1and have p ractical
app licat ion1
Key words 　 Z anthoxy lum d im orp hop hy llum var1sp in if olium , A lkalo ids, Coum arins,
Chemo taxonom y
T he alkalo ids of Z an thoxy lum species po ssess severa l in terest ing b io logica l
act ivit ies, e1g1, tumo r and A ID S inh ib ito rs〔1〕 1 It is a sign if ican t m arker of
chemo taxonom y on ru taceou s p lan ts w h ich have strong argum en ts in mo rpho logica l
taxonom y1W e have repo rted compounds iso la ted from Z an thoxy lum species〔2～ 8〕1E specia lly, w e have repo rted fou r a lkalo ids iso la ted from the roo t bark of
Z 1d im orp hop hy llum var1sp in if olium 1 In con t inuat ion of ou r studies on the chem ical
con st ituen ts, w e repo rt the iso la t ion and structu ra l iden t if ica t ion of six alkalo ids and
th ree coum arin s from th is p lan t1B ioassay show s that can th in262one has st rong
an t ibacteria l act ivity and an t i2arrhythm ia effect1 It has a ligh t concen tra t ion bo th in theΞΞΞ 通讯联系人。收稿日: 1999201228, 修回日: 1999204222。第一作者: 女, 1974 年 2 月出生, 硕士研究生, 从事植物化学研究。国家自然科学基金资助项目 (批准号 39470064)。
roo t xylem and roo t bark1Benzophenan th rid ines and qu ino lin s have been u sed as
m arkers fo r chemo taxonom y1 In mo lecu lar ev o lu t ion view s, tyro sin derived alkalo ids
e1g1benzophenan th rid ines are regarded as p rim ary structu re and an th ran ilic acid derived
alkalo ids e1g1qu ino lin s are modern structu re〔9〕1 It is in te2rest ing that bo th of them are
found in th is p lan t1W e w ill d iscu ss it in o ther paper1Q u ino lin alkalo id dictam n ine is
iso la ted from th is p lan t fo r the first t im e1
Exper im en ta l
Genera l　M p s are unco rrected1NM R spectra w ere m easu red on a B ruker AM 2400
spectrom eter u sing TM S as in ternal standard1E I2M S spectra w ere m easu red w ith V G2
7070 E2H F ( 70ev) m ass spectrom eter1 IR spectra w ere reco rded in Perk in2E lm er 983
spectrom eter (KB r) 1
Plan t ma ter ia l　Roo ts of Z 1d im orp hop hy llum var1sp in if olium w ere co llected in
A ugu st 1993 in W ufeng coun ty of H ubei P rovince1A voucher specim en w as iden t if ied by
P rof1L i Hongjun and depo sited in the H erbarium of W uhan In st itu te of Bo tany1
Extraction and isola tion 　 D ried and pow dered roo ts xylem ( 510 kg ) w ere
exhau st ively ex tracted w ith 95% E tOH at 50℃1T he ethano l so lu t ion w as conden sed
under vacuum p ressu re to give a 115 kg ex tract1T he ex tract w as disso lved in 2 mo löL
HC l and filtered1T he acid ic so lu t ion w as ex tracted w ith ch lo rofo rm to give fr11 (20 g)1T he aquou s phase w as then basif ied w ith amon ia liquo r to pH 12 and part it ioned w ith
ch lo rofo rm to give fr12 (30 g) 1T hese tw o parts w ere ch rom atographed on silica gel
co lum n elu t ing w ith CHC l3 and CHC l32M eOH 1Co lum n ch rom atography of fr11 yielded
compounds 1 ( 100 m g ) and 2 ( 50 m g ) 1Co lum n ch rom atography of fr12 yielded
compounds 3 (2 g) , 4 (200 m g) , 5 (200 m g) , 6 (50 m g) , 7 (40 m g) , 8 (70 m g) and 9 (30
m g) 1
Can th in - 6-one (1) 　pale yellow needles (CHC l3) , mp 160～ 161℃1 IR ΤKB rm ax (cm - 1 ) :
16601E I2M S (m öe, % ) : 220 (M + , 100) , 192 (85) , 166 (10) , 139 (18) , 114 (13) 11H 2NM R
(CDC l3) , ∆(ppm ) : 6195 (d, 1H , J = 10H z) , 7195 (d, 1H , J = 10H z) , 8175 (d, 1H , J = 5H z) ,
7180 (d, 1H , J = 5H z) , 8160 (d, 1H ) , 7130～ 8100 (m , 3H ) 1
Scoparone (2)　w h ite needles (CHC l32M eOH ) , mp 143～ 144℃1UV ΚEtOHm ax (nm ) : 229,
294, 3421E I2M S (m öe, % ) : 206 (M + , 100) , 191 (51) , 163 (38) , 135 (30) , 107 (20) , 92 (16) ,
69 (21) 11H 2NM R (CDC l3) , ∆(ppm ) : 3187 ( s, 3H ) , 3189 ( s, 3H ) , 6122 (d, 1H , J = 917H z) ,
6178 (s, 1H ) , 6179 ( s, 1H ) , 7157 (d, 1H , J = 917H z) 1
D ictamn ine (3) 　w h ite needles (CHC l3 ) , mp 137℃1UV ΚE tOHm ax (nm ) : 236, 293, 310,
3301E I2M S (m öe, % ) : 199 (M + , 100) , 184 (85) , 156 (74) , 128 (30) , 130 (17) , 101 (39) , 76
( 3) 11H 2NM R (CDC l3) , ∆(ppm ) : 4135 ( s, 3H ) , 8101 (d, 1H , J = 815H z) , 8123 (d, 1H , J =
815H z) , 7102 (d, 1H , J = 218H z) , 7159 (d, 1H , J = 218H z) , 7143 ( t, 1H ) , 7167 ( t, 1H ) 1
N-des-m ethylchelerythr ine ( 4 ) 　pale yellow o r co lo rless needles (CHC l3 ) , mp
212～ 215℃. UV ΚE tOHm ax (nm ) : 240, 254, 273, 3221 IR ΤKB rm ax (cm - 1 ) : 1600, 1581, 1526, 1465,
1285, 1195, 1046, 946, 8531E I2M S (m öe, % ) : 333 (M + , 100) , 318 (16) , 304 (5) , 290 (40) ,
275 (17) , 232 (7) , 217 (8) , 201 (2) , 188 (9) 11H 2NM R (CDC l3) , ∆(ppm ) : 9175 ( s, 1H ) , 8172
(s, 1H ) , 8136 (d, 1H , J = 912H z) , 8134 (d, 1H , J = 817H z) , 7185 (d, 1H , J = 912H z) , 7160
441 武 汉 植 物 学 研 究　　　　　　　　　　　　　　　第 18 卷　　
(d, 1H , J = 817H z) , 7126 ( s, 1H ) , 6114 ( s, 2H ) , 4113 ( s, 3H ) , 4106 (s, 3H ) 1
Ethoxychelerythr ine (5) 　w h ite crysta ls (CHC l3) , mp 203～ 204℃1UV ΚE tOHm ax (nm ) :
228, 283, 3201 IR ΤKB rm ax (cm - 1 ) : 935, 28301E I2M S (m öe, % ) : 393 (M + , 18) , 348 (100) , 333
( 11) , 332 (8) , 316 (6) , 305 (1) , 304 (4) , 290 (8) 11H 2NM R (CDC l3) , ∆(ppm ) : 1110 ( t, 3H , J
= 7H z) , 3190 (m , 2H ) , 2180 ( s, 3H ) , 3195 ( s, 3H ) , 3197 ( s, 3H ) , 5155 ( s, 1H ) , 6109 ( s,
2H ) , 7110 ( s, 1H ) , 7170 (s, 1H ) , 7106 (d, 1H ) , 7162 ( s, 1H ) , 7146 (d, 1H ) , 7177 (d, 1H ) 1
Scopoletine (6) 　 ligh t yellow crysta ls (CHC l3 ) , mp 203～ 205℃1UV ΚEtOHm ax (nm ) :
253, 300, 3491 IR ΤKB rm ax (cm - 1) : 3321, 1690, 1600, 1558, 1510, 1435, 1280, 11301E I2M S (m ö
e, % ) : 192 (M + , 100) , 177 (68) , 164 (43) , 149 (75) , 121 (32) 11H 2NM R (CDC l3) , ∆(ppm ) :
6126 (d, 1H ) , 7160 (d, 1H ) , 6190 ( s, 1H ) , 6138 ( s, 1H ) , 6111 (s, 1H ) , 3169 ( s, 3H ) 1
Isoscopoletine (7)　ligh t yellow needles (CHC l32M e2CO ) ,mp 205～ 206℃1UV ΚE tOHm ax
(nm ) : 253, 300, 3491 IR ΤKB rm ax (cm - 1) : 3321, 1690, 1600, 1558, 1510, 1435, 1280, 11301 E I2M S
(m öe, % ) : 192 (M + , 100) , 177 (68) , 164 (43) , 149 (75) , 121 (32) 11H 2NM R (CDC l3 ) , ∆
(ppm ) : 6126 (d, 1H ) , 7160 (d, 1H ) , 6190 ( s, 1H ) , 6138 ( s, 1H ) , 6111 ( s, 1H ) , 3169 (s, 3H ) 1
Av ic ine (8)　yellow crysta ls (CHC l32M eOH ) , mp mo re than 310℃1 IR ΤKB rm ax (cm - 1) :
9301E I2M S (m öe, % ) : 332 (M + , 616) , 317 (100) , 316 (1417) , 288 (515) , 287 (315) , 260
(918) , 259 (14) , 201 (24) 11H 2NM R (CF 3COOH ) , ∆(ppm ) : 5105 ( s, 3H ) , 6135 ( s, 2H ) ,
6150 (s, 2H ) , 7160 ( s, 1H ) , 7170 (s, 1H ) , 8120 ( s, 1H ) , 8125 ( s, 1H ) , 8125 (d, 1H , J = 9H z) ,
8155 (d, 1H , J = 9H z) , 9140 ( s, 1H ) 1
Oxyav ic ine (9)　co lo rless crysta ls (CHC l32M eOH ) , mp 272～ 274℃. UV ΚE tOHm ax (nm ) :
250, 280, 285, 322, 3351 IR ΤKB rm ax (cm - 1) : 930, 1640. E I2M S (m öe, % ) : 347 (M + ) 11H 2NM R
(CDC l3) , ∆(ppm ) : 4110 ( s, 3H ) , 6128 ( s, 2H ) , 6130 ( s, 2H ) , 7140 ( s, 1H ) , 7182 ( s, 1H ) ,
7185 (s, 1H ) , 8117 ( s, 1H ) , 7185 (d, 1H , J = 9H z) , 8115 (d, 1H , J = 9H z) 1
Acknowledgemen t　F inancial suppo rt fo r th is p ro ject w as p rovided by N SFC1E I2M S spectra w ere
m easured at the Inst itu te of H ydrob io logy, T he Ch inese A cadem y of Sciences1NM R spectra w ere
m easured at the Kunm ing Institu te of Bo tany, T he Ch inese A cadem y of Sciences1
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541　第 2 期　　　　　　　　　向瑛等: 刺异叶花椒中的生物碱和香豆素类成分