全 文 ：泽兰属植物中的倍半萜化学成分*
丁智慧 1 刘吉开 1 丁靖垲 1 古 昆 2
( 1.中国科学院昆明植物研究所植物化学研究室 昆明 650204;
2.云南大学化学系 昆明 650091)
摘 要 倍半萜化合物是菊科泽兰属植物中的一类主要化学成分 ,迄今从该属 46种植物中共分离鉴定
了近 200余个倍半萜化学成分。 本文介绍了这些化合物的名称、存在的植物 ,以及这些化合物的生物活
性。
关键词 泽兰属 ;倍半萜
天然产物研究与开发
NA TURAL PRODUCT RESEARCH AND DEVELO PM EN T Vo1. 13 No. 3
0 概 述
菊科 ( Composi tae )泽兰属 (Eupatorium )植物 ,
为一年生或多年生草本植物 ,约 1200种 ,主产于美
洲 ,少数产欧洲、非洲和亚洲。我国有 14种 ,除新疆、
西藏外 ,全国均产 [1a]。据报道 ,该属在我国有八种植
物有药用价值 ,有治疗感冒咳喘、痈疮肿瘤、跌打损
伤及活血止血等功效 [1b ]。
迄今从该属植物中分离鉴定出的化学成分有单
萜、倍半萜、二萜、三萜、植物甾醇、黄酮、香豆素、色
烯、生物碱、麝香草酚衍生物、苯乙酮衍生物、苯并呋
喃衍生物及其它酚酸类化合物 [1b, 2a, 2b, 2c, 2d ]。 其中倍
半萜化合物是该属植物中的一类主要化学成分 ,其
主要骨架类型包括杜松烷型、愈创木烷型、吉马烷
型、桉烷型等。由于泽兰属植物中一些倍半萜化合物
的抗癌活性和昆虫拒食及杀虫活性 ,一直受到人们
的普遍关注。迄今从该属 46种植物中共分离鉴定了
近 200个倍半萜化学成分。本文介绍了这些化合物
的名称、存在的植物 ,以及这些化合物的生物活性。
1 泽兰属植物中的倍半萜化学成分
1. 1 杜松烷型 (Cadinane type)倍半萜
收稿日期: 2000-09-18 修回日期: 2000-11-21
* 云南省应用基础研究基金资助项目 ( 2000B0067M ) Financial Support from Natural Sciences Foundation of Yunnan ( NSFY) ( No.
2000B0067M )
表 1 杜松烷型倍半萜
Table 1 Cadinane type sesquiterpene compounds
序号
No.
化合物名称
Name
分子式
M. F.
mp (℃ ) [α]D 文献
Ref.
存在植物
Existen t plants
1 2-acetoxy-3, 4, 6, 11-tetradeh ydrocadinan-7-one C17H24O3 78～ 79. 5 + 137 2d, 2f E .adenophorum
5a E . pet iolari s
12a E . trapezoideum
2 eupatoranolide C17H22O4 182～ 184 + 173. 7 2d E .adenophorum
3 6H-β-7-oxo-agerapho ron e C15H22O2 73～ 75 + 178. 2 2d, 2e E .adenophorum
oil + 50 2f E .adenophorum
gum + 52 12a E . trapezoideum
4 6H-α-7-ox o-ageraph orone C15H22O2 gum + 156 12a E . trapezoideum
5 7β-h yd rox y-ageraph orone C15H24O2 oil + 44 2e, 2f E .adenophorum
oil + 48 12a E . trapezoideum
6 7-oxo-6, 11-deh yd roageraph orone C15H20O2 oil + 297 2f E .adenophorum
7 7-oxo-12-hydroxy-6, 11-dehydroageraphorone C15H20O3 oil + 40 2f E .adenophorum
8 6β-h yd rox y-7-ox o-ageraph orone C15H22O3 2f E .adenophorum
9 2-oxo-3-hydroxy-4, 7-epoxycadinane C15H24O3 + 30 12a E . trapezoideum
10 11, 12, 13-t rinor-3-am orph ene-2, 7-dione C12H16O2 + 49. 6 12a E . trapezoideum
11 11-hydroxy-3, 9-cadinadiene C15H24O 11b E . serotinum
12 γ-muu rolene C15H24 2a E .adenophorum
13 δ-cadinol C15H26O 2a E .adenophorum
14 laevigatin C15H16O 16e E . laevigatum
76
1. 2 愈创木烷型 (Guaiane type)倍半萜
表 2 愈创木烷型倍半萜
Table 2 Guaiane type sesquiterpene compounds
序号
No.
化合物名称
Name
分子式
M. F.
mp(℃ ) [α]D 文献Ref. 存在植物Existen t plants
15 petiolarid C20H26O6 - 52. 5 5a E. petiolar is
16 euparot in C20H24O7 199～ 200 - 124 8b E. rotundi folium
8e E. scabridum
17 euparot in acetate C22H26O8 156～ 157 - 191 8b E. rotundi folium
18 eupach lorin C20 H25O 7Cl 219～ 221 - 110 8b E. rotundi folium
19 eupach lorin acetate C22 H27O 8Cl 161～ 164 - 192 8b E. rotundi folium
20 eupatundin C20H24O7 188～ 189 - 80 6b E. rotundi folium
L. Spp ovatum
8b E. rotundi folium
8e E. scabridum
21 eupach loroxin C20 H25O 8Cl 8b E. rotundi folium
8e E. scabridum
22 10-epieupatoroxin C20H24O8 230～ 232 - 109 6b E. rotundi folium
L. Spp ovatum
8b E. rotundi folium
23 8β-angeloyloxy-5α-hydroxy-3, 4, 10, 14-diepoxypreeu-patundin-2-O-acetate C22H26O9 oi l
8c E. rotundi folium
24 8β-angeloyloxy-5α-hydroxy-10, 14-diepoxypreeupatundin-2-O-acetate
C22H26O8 oi l 8c E. rotundi folium
25 eupatoroxin C20H22O8 197～ 200 - 98 8b E. rotundi folium
8e E. scabridum
26 5α-h ydroxyeu pases sifolid B C20H22O7 oi l 8d E. rotundi folium
27 5α-h ydroxy-8β-angeloyloxyp reeu patundin C20H24O6 8d E. rotundi folium
28 eupasessi folid A C20H22O6 oi l 14b E. sessil ifol ium
29 eupasessi folid B C20H22O6 184 14b E. sessil ifol ium
30 8β-5′-[5″-hydroxyt igloylox y ] ti gloyloxy-3-dehydro-4β , 15-dihyd ro zaluzanin C C25H30O8 9c E. sal ti llensis
31 8β-5′-[ 5″-h yd rox ytig loyloxy ] ti gloylox y-4β , 15-dih yd roza-luzanin C C25H32O8 9c E. sal ti llensis
32 spathulenol C15H24O 9d E. salvia
33 8β-[5′-[4″, 5″-dihyd rox ytigloyloxy ] ti gloylox y ]k au niolide C25H30O8 oi l 12b E. tri st is
34 ligus t rin C15H18O3 135～ 137 + 56 12d E. ligustrunum
15c E. del toideum
35 anomalide C20H26O8 152～ 3 12e E. anomalum
E.mohr ii
36 8β-[3′-meth ylbutanoyloxy ]-2β , 14: 3α, 4α-diepoxy-2α, 10α-dihyd rox y-1α, 5α-g uai-11( 13)-en-12, 6α-olide C20H26O8 12e E. anomalum
37
8-epi-8-[5′-( 4″-hyd rox ytigloxyloxy ) -tigloyloxy ] rupicolin
A
C25H30O9 13a E. tomen tel la
38 euponin C20H24O6 148～ 150 - 69 13b E. japon icum
39 3, 4-epoxy-8β-angeloyloxy-14-oxo-1 ( 10) , 11 ( 13) -guaiadi-en-12, 6α-olide C20H22O6 170～ 171 - 88 13c E. japon icum
40 4α-h ydroxy-8β-angeloyloxy-14-oxo-1 ( 10) , 2, 11( 13 )-g ua-iatrien-12, 6α-olide C20H22O6
151～ 153 - 179 13c E. japon icum
41 perox yeupahakonin A C20H24O8 143～ 146 - 165 14a E. chinense
42 perox yeupahakonin B C20H24O8 147～ 8 + 35. 4 14a E. chinense
43 eupahakonin A C20H24O7 oi l - 146 14a E. chinense
44 eupahakonin B C20H24O7 oi l + 65. 3 14a E. chinense
45 eupahakonenin A C20H24O6 oi l - 95 14a E. chinense
46 eupahakonenin B C20H24O6 oi l + 22 14a E. chinense
47 eupahakonesin C22H26O8 oi l - 49. 5 14a E. chinense
48 euperfolid C20H22O7 - 48 6b E. perfoliatum
49 11, 13α-dih ydroeu perfolid C20H24O7 - 110 6b E. perfoliatum
50 8β-angeloyoxypreeupatundin C20H24O5 - 14. 6 6b E. rotundi folium
L. Spp ovatum
51 8β -angeloyox y-5α-h yd roxypreeupatundin C22H26O7 - 18. 3 6b E. rotundi folium
-2-acetate L. Spp ovatum
Vo 771. 13 No. 3 丁智慧等:泽兰属植物中的倍半萜化学成分
续表 2
序号
No.
化合物名称
Name
分子式
M. F.
mp(℃ ) [α]D 文献
Ref.
存在植物
Existen t plants
52 5α-h ydroxy-8β-tigloyloxypreeupatundin C20H24O6 - 20 6b E. rotundi folium
L. Spp ovatum
53 eupatundin acetate C22H26O8 6b E. rotundi folium
L. Spp ovatum
54 8β-tiglinoyloxypreeupatundin-10, 15-epoxide C20H24O6 - 37 6b E. rotundi folium
L. Spp ovatum
55 1α, 2β , 5α-acetox y-8β-tigloylox y-10β , 14- C22H26O7 6b E. rotundi folium
epox y-3, 11( 13)-guaiadien-12, 6α-olide L. Spp ovatum
56 10-epieuparotin acetate C22H26O8 6b E. rotundi folium
L. Spp ovatum
57 4′-h ydroxyeupases sifolide B C20H22O7 gum 15a E. alt issim um
58 8β-[4′, 5′-dih ydroxytigloylox y ]cumambrin B C20H26O7 gum 15a E. alt issim um
59 8β-[4′, 5′-dih ydroxytigloylox y ]-4β-hyd rox y-2, 10 ( 14) , 11( 13) - guaiat rien-12, 6α-olid e C20H24O7 gum 15a E. alt issim um
60 eu foliat in C20H26O8 227～ 9 - 27. 5 15d E. perfoliatum
61 eu foliatorin C20H24O7 224 15d E. perfoliatum
1. 3 吉马烷型 (Germacrane type)倍半萜
表 3 吉马烷型倍半萜
Table 3 Germacrane type sesquiterpene compounds
序号
No.
化合物名称
Name
分子式
M. F.
mp(℃ ) [α]D 文献
Ref.
存在植物
Existen t plants
62 4′-d esox y-4″-hyd rox yprovincialin C27H34O10 oi l 3a E. anisochroma
12b E. tri st is
63 desacetyl-24-d esox yp rovincialin-25-O-acetate C27H34O10 gum 3a E. anisochroma
64 8β-[4′-hydroxy-5′-sarracinoylox ytigloylocy ]-1( 10 ) E, 4Z,11( 13) -germacratrien-12, 6α-olide C25H32O8 3a E. anisochroma
65 3β-h yd rox y-8β-[ 5′-O-acetyl sarracinoyloxy-4′-hydrox-ytig loyloxy ]cos tunolide C27H34O10 gum 3a E. anisochroma
66 eupatoriopicrin C20H26O6 157～ 161 + 95 3b, 3c, 18 E. cannabinum
9b E. sachal inense
16a E. fortunei
67 eupatolide C15H20O3 186～ 188 + 41. 3 3c E. cannabinum
188～ 190 4a E. formosanum
68 eucannabinolide C22H28O8 oi l - 212 3c E. cannabinum
69 eupacunin C22H28O7 166～ 167 + 55 3d E. cunei fol ium
10b E. lanci folium
70 eupatocu nin C22H28O7 163～ 164 - 129 3d E. cunei fol ium
71 eupacunoxin C22H28O8 171～ 172 + 27 3d E. cunei fol ium
72 eupatocu noxin C22H28O8 200～ 201 - 209 3d E. cunei fol ium
73 eupacunolin C22H28O8 164～ 165 + 46 3d E. cunei fol ium
10b E. lanci folium
74 eupaformonin C17H22O5 216～ 218 4b E. formosanum
75 eupah ys sopin C20H26O7 125 - 138. 9 6a E.h yssop ifol ium
76 8β-acetox ycos tunolide C17H22O4 3a E. ligustr ina
77 8β-[4′-hydroxy tigloyloxytigloyloxy ]cos tunolide C20H26O5 3a E. ligustr ina
78 8β-sarracinoyloxycos tu nolide C20H26O5 3a E. ligustr ina
79 8β-[4′-hydroxy-5′-tigloyloxy tigloyloxy ]cos tu nolide C25H32O7 3a E. ligustr ina
80 3β-acetox y-8β-hyd rox ycostunolid e C17H22O5 oi l 3a E. ligustr ina
12b E. tri st is
81 hiyodorilactone C C17H22O5 3a E. ligustr ina
9a E. sachal inense
12b E. tri st is
82 hiyodorilactone C acetate C19H24O6 13a E. tomen tel la
83 5″- d esox y-3-epi-4″-h ydroxyprovincialin C27H34O10 13a E. tomen tel la
84 3β-h yd rox y-8β-t iglin oyloxycos tu nolide C20H26O5 oi l + 95. 2 14b E. sessil ifol ium
78 天然产物研究与开发 Vo1. 13 No. 3
续表 3
序号
No.
化合物名称
Name
分子式
M. F.
mp(℃ ) [α]D 文献
Ref.
存在植物
Existen t plants
85 3β-h yd rox y-8β-[4′-h ydroxyt igloylox y ]cos tunolid C20H26O6 gum 15a E. alt issim um
86 3β-h yd rox y-8β-[4′, 5′-dih ydroxytigloyloxy ]costunolid C20H26O7 gum 15a E. alt issim um
87 germacren D C15 H24 2f E. adenophorum
5a E. petiolar is
11b E. serot inum
6b E. alt issim a
6b, 16d E. aschenbornia
6b E.m aisetiana
14b E. sessil ifol ium
88 quad rang olide C15H20O3 118～ 120 + 227 7a E. quadrangularae
89 hiyodorilactone A C22H28O8 9a E. sachal inense
90 hiyodorilactone B C22H28O7 9a E. sachal inense
91 hiyodorilactone D C22H28O8 oi l + 81 9a E. sachal inense
92 hiyodorilactone E C22H28O8 149 + 119 9a E. sachal inense
18 E. cannabinum
93 hiyodorilactone F C24H30O9 oi l + 141 9a E. sachal inense
94 perox ysachalinin C20H26O8 9b E. sachal inense
95 sachalinin C20H26O7 9b E. sachal inense
96 sachalin C15H20O4 9b E. sachal inense
97 4′-d esox y-3-d esacetoxyl-3β-h ydroxyprovincialin C25H32O8 9c E. sal ti llensis
98 4′-d esox y-3-d esacetoxyl-3α-h ydroxyprovincialin C25H32O8 9c E. sal ti llensis
99 5′-[5″-hyd rox ytigloyloxy ]-5′-h ydroxyhehiangine C25H32O9 9c E. sal ti llensis
100 3β-acetox yliacylind rolid C27H34O9 9c E. sal ti llensis
101 liacylindrolide C25H32O7 9c E. sal ti llensis
102 eupaserrin C22H28O7 153～ 154 + 71. 2 8e E. scabridum
10a E. sem iserratum
103 2α-h ydroxyeu patolide C15H20O4 184～ 186 8e E. scabridum
16c E.m ikanioides
104 2α-h yd rox y-8β-[ 2R, 3R-epoxy-2-meth ylbu tanoyloxy ] eu-patolid e C20H26O6 gum
+ 67. 7 16c E.m ikanioides
105 2α-h ydroxy-8β-[ 2R, 3R-epoxy-2-hydroxyb utanoylox y ] eu-patolid e
C20H26O7 170～ 172 + 97. 5 16c E.m ikanioides
106 2α-h ydroxy-8β-[ 2S-hyd rox y-2-h ydroxymeth yl-3 S-m ercap-tob utanoylox y ]eupatolide C20H28O7 S 180～ 181 + 102 16c E.m ikanioides
107 2α-h ydroxy-8β-[ 3S-hyd rox y-2-methylenebutanoyloxy ] eu-patolid e C20H26O6 gum + 80. 5 16c E.m ikanioides
108 deacetyleupas errin C20H26O6 132～ 135 + 75 8e E. scabridum
10a E. sem iserratum
16c E.m ikanioides
109 3β-h yd rox yeupaserrin C22H28O8 + 92. 8 10b E. lanci folium
110 desacetyleupacunolin C22H26O6 gum + 95. 8 10b E. lanci folium
111 3β , 9β-dihydroxy-8β-angeloylox ycostunolid e C20H26O6 gum 8e E. scabridum
112 3β , 9α-dihyd roxy-8β-ang eloylox ycos tunolide C20H26O6 oi l 6b E. rotundi folium
L. Spp ovatum
113 8β-tigloylox ycos tun olide C20H26O4 oi l + 59 11a E. serot inum
114 14-h yd rox y-8β-acetox y-1( 10) , 4E, 11 ( 13) -germacrat rien-12, 6α-olide C17H22O5 + 30 11c E. serot inum
115 14-h ydroxy-8β-tigloyloxy-1 ( 10) , 4E, 11 ( 13 ) -germacra-t rien-12, 6α-olide C20H26O5 11c E. serot inum
116 8β-[5′-hydroxy tigloyloxy ]eu patolide C20H26O5 110 + 47. 5 11c E. serot inum
117 8β -[5′-acetoxyt igloylox y ]eupatolide C22H28O6 162～ 163 + 90 11c E. serot inum
118 8β-angeloyloxy-14-hyd rox yparth enolide C20H26O6 125～ 129 - 163 11a E. serot inum
119 8β-tigloylox y-14-h ydroxyparthenolide C20H26O6 125～ 129 - 163 11a E. serot inum
120 8β-[3-m ethylpent-2E-enoyloxy ]-14-hydroxyparthenolide C21H28O6 55～ 60 11a E. serot inum
121 8β-[3-m ethylpent-2E-enoyloxy ]parth enolide C21H28O5 11a, 11c E. serot inum
122 8β-tigloylox yparth enolid e C20H26O5 11c, 11d E. serot inum
123 del toidin A C20H26O5 159～ 161 - 145. 1 11c E. serot inum
Vo 791. 13 No. 3 丁智慧等:泽兰属植物中的倍半萜化学成分
续表 3
序号
No.
化合物名称
Name
分子式
M. F.
mp(℃ ) [α]D 文献
Ref.
存在植物
Existen t plants
15c E. del toidenum
124 eu serotin C21H26O6 172～ 173 + 75. 2 11d E. serot inum
125 3α-acetox y-8β-hyd rox y-1 ( 10 ) E, 4Z, 11 ( 13 ) -germacra-t rien-12, 6α-olide C17H22O5
12b E. tri st is
126
14-acetoxy-8β -[ 4′-h yd rox ytig linoyloxy ]-4, 5-cis-cos tuno-
lide
C22H28O7 oi l - 101. 5 6b E.h yssop ifol ium
127 8β-[ 4′-( 3″-h ydroxyoctad ecanolox y) - 2E- butenoylox y ]parth enolide C38H60O8 6b E.h yssop ifol ium
128 eupas sopilin C20H26O6 gum - 161 6b, 6c E.h yssop ifol ium
6b E.mohr ii
129 14-hydroxy-8β-[4′-h yd rox ytig linoylox y]-costunolid e C20H26O6 oi l + 20 6b E.h yssop ifol ium
6b E.mohr ii
130 eupas sopin C20H26O7 gum - 137. 5 6b, 6c E.h yssop ifol ium
6b E.mohr ii
131
14-hyd rox y-8β-[4′-hydroxy tiglinoyloxy ]-4, 5-cis-cos tuno-
lide
C20H26O6 oi l - 80 6b E.h yssop ifol ium
6b E.mohr ii
132 germacradienolid e glucos ide C21H32O8 gum + 23. 54 15b E. alt issim um
133 del toidin B C20H26O6 170～ 171 - 87. 8 15c E. del toidenum
134 euperfolit in C20H28O7 190～ 192 - 5. 81 15d E. perfoliatum
135 euperfolin C20H28O6 173 - 13. 9 15d E. perfoliatum
136 eupas sofi lin C38H60O9 - 143 6c E.h yssop ifol ium
137 eupafortunin C22H28O8 oi l + 10. 7 16a E. fortunei
138 eu recurvin C22H30O8 185～ 186 + 42. 3 16b E. recurvans
139 3β-acetox y-1α-h yd rox y-8β-[ 2′-meth ylbu tanoyloxy ]-4Z,9Z, 11( 13) -germacrat rien-12, 6α-olide C22H30O7 113～ 114 + 52. 9 16b E. recurvans
140 3β-acetox y-8β-hyd rox y-9β-[2′-m ethylbutanoylox y ]-1 ( 10)E, 4Z, 11( 13)-g ermacrat rien-12, 6α-olid e C22H30O7 129～ 131 + 82. 0 16b E. recurvans
141 eupalinin A C22H26O8 17a E. lin dleyanum
142 eupalinin B C22H26O8 17a E. lin dleyanum
143 eupalinin C C22H26O8 17a E. lin dleyanum
144 eupalinin D C22H26O8 17a E. lin dleyanum
145 eupachi folin A C20H26O6 17b E. chinense var
simpl ici fol ium
1. 4 桉烷型 ( Eudesmane type)倍半萜
表 4 桉烷型倍半萜
Table 4 Eudesmane type sesquiterpene compounds
序号
No.
化合物名称
Name
分子式
M. F.
mp(℃ ) [α]D 文献Ref. 存在植物Existen t plants
146 3-oxo-isocos tussau re C15H20O3 153 5a E. glabrata
147 isocos tuss au re C15H22O2 5a E. glabrata
148 1β , 6α-dihyd roxy-4( 14) -eudesmene C15H26O2 oi l 5b E. glechonophylla
149 4-desoxy-8-epi-ivangus tin C15H20O2 + 43. 8 7a E. quadrangularae
150 isoalantolactone C15H20O2 7a E. quadrangularae
151 diploph ylloide C15H20O2 + 18. 6 7a E. quadrangularae
152 (+ ) -3-oxodiploph yl lin C15H18O3 145～ 147 + 161 7b E. quadrangularae
153 quad rang ulin A C16H24O3 oi l 7c E. quadrangulare
154 arbusculin B C15H20O2 7c E. quadrangulare
155 β-cyclocostunolide C15H20O2 7c E. quadrangulare
156 α-cyclocostunolid e C15H20O2 7c E. quadrangulare
157 6-eud esmene-4α-ol C15H26O 9c E. sal ti llensis
158 6, 15α-epoxy-1β , 4β-dihydroxyeudesmane C15H26O3 9c E. sal ti llensis
159 cos tic acid C15H22O2 86～ 87 12c E. capil li folium
80 天然产物研究与开发 Vo1. 13 No. 3
1. 5 其它类型倍半萜 ( Miscellaneous sesqui terpenoids)
表 5 其它类型倍半萜
Table 5 Miscellaneous sesquiterpenoids
序号
No.
化合物名称
Name
类型
Type
分子式
M. F.
mp(℃ ) [α]D 文献Ref. 存在植物Exis ten t plants
160 eu patorenone C15H22O2 66～ 67 + 72. 2 2g E. adenophorum
161 15-cin namoylox yoplopanone Oplopanane C24H32O4 oi l 3a E. ligustr ina
162 β-farnes en e Farnesane C15 H24 2a, 2f E. adenophorum
163 1, 3, 11( 13) -elemat rien-12, 8-olid e Elemane C15H20O2 65～ 67 + 40. 6 7b E. quadrangu-larae
164 8β-[ 3-meth ylpen t-2E-enoyloxy ]-elemacron-quistanth us acid Elemane C21H26O6 164 + 22 11a E. serot inum
165 10, 11-epoxy-9-angeloyloxy-3-hydroxy-3, 7, 11-t rimeth yly-1, 4, 6-dodecatriene Farnesane C20H30O4 5a E. scorodon ioides
6b E.mohri i
166 9-angeloyloxy-3-hydroxy-3, 7, 11-trim ethyl-1, 4,6, 10-dodecatr traen e Farnesane C20H30O4
6b E.h yssop ifolium
6b E.mohri i
167 β-bis abolen e Bisabolane C15 H24 2a, 2f E. adenophorum
168 β-caryoph yllene Caryoph yllene C15 H24 2a, 2f E. A denophorum
169 ari stolone C15 H24 2a E. adenophorum
170 β-cubebene C15 H24 11b E. serot inum
171 11-hydroxy-β-cub ebene C15 H24O 11b E. serot inum
172 11-hydroxy-α-cubebene C15 H24O 11b E. serot inum
173 α-humulene Humulane C15 H24 11b E. serot inum
174 α-bergamoten e C15 H24 2a E. adenophorum
175 γ-elemene Elemane C15 H24 2a E. adenophorum
176 hum ulenol Humulane C15 H26O 2a E. adenophorum
177 elemol Elemane C15 H26O 2a E. adenophorum
178 nerolidol Farnesane C15 H26O 2a E. adenophorum
6b E. perfoliatum
179 11, 13-deh ydro-8β-tigloylox yeleman-12-oic acid Elemane C20H28O4 6b E. tomen tel la
180 7α-angeloyloxy-1-oxo-α-longipinen longipinane C20H28O3 oi l 6b E.h yssop ifolium
181 isoh umulene Humulane C15 H24 6b E.h yssop ifolium
6b E. rotundi folium
L. Spp.ovatum
6b E. perfoliatum
182 3( Z)-6, 7-dih ydro-5, 6-deh yd ro- Farnesane C15 H24O oi l 6b E. perfoliatum
7-hydroxy-α-farn es ene Farnesane 16d E. aschenbornia
183 3( E) -6, 7-dihyd ro-5, 6-dehydro- Farnesane C15 H24O oi l 16d E. aschenbornia
7-hydroxy-α-farn es ene
184 ag eraborniol Farnesane C15H24O2 oi l 16d E. aschenbornia
2 泽兰属植物倍半萜成分的生物活性
及应用价值
倍半萜化合物在泽兰属植物的地上部分如茎、
叶和花中都有分布。纯化后的倍半萜化合物有些呈
一定的晶型 ,有些则为无色油状物。一些低极性的倍
半萜是泽兰属植物精油中的香气成分之一。作者等
曾从泽兰属植物紫茎泽兰地上部分的精油中经色谱
-质谱分析 ,鉴定了 45个成分 ,其中所含的倍半萜化
合物有 β -丁香烯、α-香柠檬烯、金合欢烯、γ-木罗烯、
γ-榄香烯、β -甜没药烯、蛇麻醇、榄香醇、橙花叔醇、δ-
杜松醇及土青木香酮等 [2a]。
泽兰属植物中的一些愈创木烷型和吉马烷型倍
半萜具有显著的抑制肿瘤细胞的活性 ,已引起人们
的普遍关注 ,如化合物 16～ 22, 25, 66, 67, 69, 74,
75, 81, 89～ 93, 102, 108等 ,泽兰属植物中还有一些
倍半萜则具有昆虫拒食及杀虫活性 ,如化合物 88,
149～ 151, 163等 ,以及幼虫生长抑制成分如化合物
38～ 40等。作者等曾从泽兰属植物紫茎泽兰中分离
得到二十多个成分 [2b, 2c, 2d ]。 紫茎泽兰 ( Eupatorium
adenopherum Spreng )属多年生草本植物 ,原产墨西
哥 , 50年代自缅甸传入我国云南省。因其生长及繁
殖能力极强 ,也可能其体内含有某种异株克生物质 ,
Vo 811. 13 No. 3 丁智慧等:泽兰属植物中的倍半萜化学成分
已在云南省许多地方广泛分布 ,且不断向北延伸。由
于它对生态环境的破坏 ,给农林牧副业带来了严重
危害。 通过紫茎泽兰中杀虫及昆虫拒食活性化学成
分以及可能的植物生长抑制成分的系统深入研究 ,
可对紫茎泽兰这一恶性杂草的合理利用 ,新的高效、
低毒植物农药的研制开发提供科学依据。 作者等从
紫茎泽兰花中分离得到三个 cadinene类型的倍半
萜: 高含量的 2-acetox y-3, 4, 6, 11-tetradehydro-
cadinen-7-one( 1) (为干重的 0. 3% ) ,一个新的倍半
萜内酯—紫茎泽兰内酯 eupa to ranolide ( 2) , 7-
oxoageraphorone( 6)
[6 ]。 在前期的研究工作中发现
2-aceto xy-3, 4, 6, 11-tet radehydro cadinen-7-one
( 1)、紫茎泽兰花的石油醚提取物等对菜粉蝶幼虫有
明显的拒食活性 ,其他化合物和提取物对南美斑潜
蝇、小菜蛾等也有一定的杀虫活性。
参 考 文 献
1 a)侯宽昭编 .中国种子植物名录 (第二版 ) .北京: 科学出版社 ,
1982, 189
b )江苏植物研究所等编 .新华本草纲要 (第三册 ) .上海:上海科
学技术出版社 , 1990, 418
2 a)丁靖垲等 .紫茎泽兰精油的香气成分及应用研究 .《云南植物研
究》 , 1991, 13: 441
b )李蓉涛等 .紫茎泽兰的化学成分 .《云南植物研究》 , 1997, 19:
196
c) Ding , Zh. H et al . Eupatoranolide, a new sesquiterp ene lactone
f rom Eupatorium adenophorum. Chin.Chem. Let t. 1999, 10: 491
d)丁智慧等 .紫茎泽兰花的化学成分 .《云南植物研究》 , 1999, 21:
505
e)朱正方等 .紫茎泽兰化学成分的研究 (Ⅰ ) .《天然产物研究与开
发》 , 1997, 9: 35
f ) Bohlmann , F et a l. Six cadinene deriv atives f rom Ageratina
a denophora . Phytochemist ry, 1981, 20: 1432
g) Ananv oranich S et al . Determination of a new sesqui terpene
skeleton th rough selectiv e INEPT spect ros copy. J. Org .
Chem . 1989, 54: 2253
3 a ) Tamayo-cas till o G et al . Germ acranolides and oth er con-
st ituents f rom Ageratina species. Phytochem istry , 1988, 27:
2893
b) Dolejs L et al . On terp enes. CX LV. Con sti tution of eupatori-
opicrin , a g ermacranolid e f rom Eupatorium cannabinum L. .
Coll . Czechoslov. Chem. Comm un. 1962, 27: 2654
c ) Dolejs B et a l. On terpenes. CX LV I. Sesqui terpenic lacton es
f rom Eupatorium cannabinum L. Revision of th e s t ructure of
eupato riopicrin. Col l . Czechoslov. Chem . Comm un. 1972, 37:
1546
d ) Kupchan S M et al . St ructu ral elucid at ion of novel tumor-in-
hibitory s esqui terpene lacton es f rom Eupatorium cunei foli-
um. J .Org. Chem. 1973, 38: 2189
4 a) Lee K H et al . An titumo r agents Ⅱ : Eu patolide, a new cyto-
toxic principle f rom Eupa tor ium formosanum HAY. . J . of
Pharma . Sci . 1972, 61: 629
b ) McPhail A T et al . St ructu re and s terecohemis t ry of eu pafor-
m onin, a novel cytotoxic sesquiterpene lactone f rom Eupatori-
um formosanum HAY. . Tetrahedron Lett . 1974, 3203
5 a) Bohlmann F et al . Natǜ rlich v orkommende terpen-d erivate,
761) Uber inhal tss toffe der Eupatoriumgru ppe. Chem . Ber.
1977, 110: 301
b ) Gonzalez A G et al . Chromenes and benzofurans f rom A gerat i-
na g lechonophyl la. Phytochem istr y 1989, 28: 2520
6 a) Lee K H et al . Th e st ructure and stereoch emis t ry of eu pah ys-
sopin , a new an titumo r germacranolide f rom Eupatorium h ys-
sop ifol ium. Tetrahedron Lett . 1976, 1051
b) Bohlmann F et al . Neue sesqui terpenlactone und and ere in-
halt ss tof fe aus v ert retern der Eupatorium -g ruppe. Phytochem -
ist ry , 1976, 16: 1973
c ) Hera W et al . Sesqui terpene lactones of Eupator ium hyssopi-
fol ium. A germacranolide w ith an unusual lipid es ter side
chain. J . Org. Chem . 1976, 41: 1015
7 a) Hubert T et al . Quad rangolide, a h eliangolid e f rom Eupatorium
quad rangularae. Phytochemistr y, 1987, 26: 1751
b) Okunade A L et al . Ant-rep ellen t sesqui terpen e lactones f rom
Eupator ium quad rangularae. Phytochemist ry, 1985, 24: 1199
c) Gonzalez A G et al . Eud esman e sesquiterpenes f rom Eupatori-
um quadrangularae. Phytochemist ry , 1985, 24: 1847
8 a ) Kupchan S M et al . Eupach lorin acetate, a nov el ch loro-
sesquiterpenoid lactone tumor inhibi to r f rom Eupator ium ro-
tun di fol ium . Tetrah ed ron Lett . 1968, 3517
b) Kupchan S M et al . Tumor inhibitors. XLI. st ructu ral elucida-
tion of tumor-inhibi tory sesqui terpen e lactones f rom Eupato-
rium rotun di fol ium . J. Org. Cem . 1969, 34: 3876
c ) Boh lmann F et al . Cis-k olavenins a u re und w ei tere in-
h al t ss tof fe au s v ert retern der t rib us Eupatorieae. Phyto-
chemist ry , 1978, 17: 2101
d ) Boh lmann F et al . Neu e guaianolide aus Eupatorium rotundi-
fol ium . Phytoch emistr y, 1982, 19: 1233
e ) Herz W et al . Sesqui terpene lactones of Eupatorium
scabr id um . Phytochemist ry , 1982, 21: 2475
9 a) Takahashi T et al . Hiyodorilactones D, E, and F, new cytotoxic
sesquiterpene lactones f rom Eupatorium sachal inense Makino.
Chem . Pharm .B ull . 1979, 27: 2539
b ) Kazuo I et al . New sesquiterpene lacton es f rom Eupatorium
scabridum ( Fr. Schmid t ) Makino. Chem .Lett . 1979, 12: 1503
c) Fang N B et al . Terpenoids f rom A gerat ina sal t ill ensis. Phyto-
chemistry , 1988, 27: 3187
d ) Gonzalez, A G et al . Di terpenes and other cons ti tuents of Eu-
patorium salvia . Phytoch emistr y, 1990, 29: 321
10 a) Kupchan S M et a l. Th e is olation and s tructural elucidat ion of
eu paserrin and deacetyleupas er rin new an tileuk emic
sesquiterpene lactones f rom Eupatorium sem iserratum. J.
Org .Chem . 1973, 38: 1260
b ) Her zW et al . Sesqui terpene lactones and oth er cons ti tuents of
Eupatorium lanci fol ium and E. semiserra tum. Phytochem istry ,
1981, 20: 1343
82 天然产物研究与开发 Vo1. 13 No. 3
11 a) Boh lmann F et al . Further g ermacranolid es f rom Eupatorium
serotinum . Plan ta Med ica. 1985, 76
b) Bohlmann F et a l. 11-Hydroxy-α-and β -cubebene f rom Eupa-
tor ium serot inum. Phytochemist ry 1982, 21: 1153
c) Bohlmann F et al . Addi tional germacranolides f rom Eupatori-
um serotinum . Phytochemist ry 1984, 23: 1189
d) Herz W et al . Sesqui terpene lactones of Eupatorium serot-
inum. J .Org. Chem. 1979, 44: 2784
12 a) Shukla V S et al . Absolute s tereochemis try of the cadinen es
f rom Eupatorium trapezoideum . Tetrahed ron , 1986, 42: 1157
b) Bohlmann F et al . Sesqui terpene lactones, geranylnerol and
t remeton e d erivativ es f rom A gera tina species. Phytochem -
istry , 1985, 24: 1319
c) Koppaka V Ret al . An tibio tic principle of Eupatorium capi ll i-
folium . J. N at . Prod . 1981, 44: 252
d ) Romo Jet al . Ligus t rin, a guaianolide i solated f rom Eupatori-
um l ig ustrin um DC. Tetrahedron , 1968, 24: 6087
e) Cox P Jet a l. S tructure elucidation of a mix tu re of tw o nov el
isom eric s esqui terpenoid s. Tetrahydron Lett . 1979, 3569
13 a) Fang N et al . Sesqui terpen es f rom Agera tina tomentel la . Phy-
tochem istry , 1988, 27: 283
b) Nak ajima S et al . Coumarin and euponin , tw o inhibi tors for in-
sect dev elopmen t f rom leav es of Eupator ium japonicum. A-
g ric.B iol . Chem . 1980, 44: 2893
c)河津一仪等 .ヒヨドリズナの叶の幼虫成长阻害成分— 2种
の新ゲアイアノリドの单离と构造 .《日本化学会志 》 , 1981,
678
14 a) Ito K et al . Sev en guaianolides f rom Eupatorium ch inense.
Phytoch emistr y, 1982, 21: 725
b) Bohlmann F et al . Neu e sesquiterpenlacton e aus Eupatorium
sessil i fol ium . Phytochemistr y, 1979, 18: 1401
15 a) Jak upovic Jet a l. Further sesquiterp ene lactones f rom Eupa-
tor ium alt issim um. Planta med ica , 1987, 97
b) Herz W et al . A g lycosidic germacradienolid e f rom Eupatori-
um alt issim um. Phytochemist ry , 1978, 17: 1853
c ) Qui jan o L et a l. Deltoidin A and B, tw o new germacrolides
f rom Eupatorium d eltoideum . Phytochemistr y, 1980, 19: 1975
d ) Herz W et al . Sesquiterpene lactones of Eupatorium per fol ia-
tum. J . Ohem . 1977, 42: 2264
16 a) Haruna M et al . St ructu re and con formation of eu pafortunin, a
new g ermacrane-typ e sesquiterpene lactone f rom Eupatorium
fortunei Tu rcz.Chem . Pharm . Bul l . 1986, 34: 5157
b) Her z W et al . Sesqui terpene lactones of Eupatorium recur-
vans. J. Org .Chem . 1978, 43: 3559
c ) Her z W et al . A th iol-containing es ter sid e ch ain in a
sesquiterpene lactone f rom Eupatorium mikanioid es. Ab so-
lute configuration of deacetyleupaserrin and it s congeners.
J .Org. Chem. 1980, 45: 489
d ) Bohlmann F et al . Neue nerolidol-deriv ate aus Ageratina as-
chenbornia. Phytochem istry , 1978, 17: 566
e)Oliveira A B et al . Laevigatin, a sesquiterpenoid fu ran f rom E -
upatorium laevigatum Lam. . Tetrah ydron La tt . 1978, 2653
17 a) Ito K et al . Four new germacranolides f rom Eupatorium lin d-
leyanum DC. .Chem. Let t. 1979, 1469
b ) Ito K et al . New sesqui terpene lactones f rom Eupatorium chi-
nense var. simpl ici fol ium ( Makino) Ki tam. . Chem. Lett . 1979,
1473
18 Woerdenbag H Jet al . Evaluation of th e in vi tro cyto toxici ty of
s ome sesqui terpen e lactones on a h uman lung carcinoma cell line
using th e fast g reen dye ex clusion assay. Plan ta Med ica , 1986,
112
SESQUITERPENE COMPONENTS FROMEUPATORIUM GENUS
DIN G Zhi-hui1 , L IU Ji-kai1 , DIN G Jing-kai1 , GU Kun2
( 1. The laboratory of Phytochemist ry ,Kunm ing Inst itu te of Botany , The Chinese Acad emy of Sciences , Kunming 650204, China;
2. Depa rtment of Chem istr y, Yunnan Universi ty , Kunming 650091, China)
Abstract Sesqui terpene compounds are main components in the Eupatorium genus. This paper review s
about 200 sesqui terpene compounds isolated f rom 46 species of Eupatorium genus. Their name, phy sical da-
ta, plant resources and references according to thei r type are in Tables introduced.
Key words Eupatorium; Sesqui terpene
Vo 831. 13 No. 3 丁智慧等:泽兰属植物中的倍半萜化学成分