两种桑科药用植物生物活性成分的研究
|
摘要
波罗蜜属(Artocarpus)和柘属(Cudrania)是桑科植物中非常重要的两个属。
波罗蜜属的许多植物在印度尼西亚、泰国、台湾和斯里兰卡被作为传统民间用药,治
疗肝硬化、高血压、背痛、风湿病、疟疾、发烧、痢疾和肺结核,并被用来抗炎、解
毒和控制糖尿病人的血糖水平;柘属的植物大多为药用植物,被用来治疗肝炎、风湿
病、跌打损伤、黄疸、疥疮、痛经、体内外出血和慢性胃炎等疾病。柘树[Cudrania
tricuspidata (Carr.) Bur.]的根皮提取物在临床上还被制成柘木糖浆治疗消化道肿瘤。国
外对波罗蜜属和柘属的化学成分进行了较系统的研究,结果表明波罗蜜属植物富含独
特的异戊烯基黄酮类化合物,而柘属植物富含异戊烯基口山酮类化合物。这些化合物
的生物活性显著多样,如细胞毒活性,抗血小板活性,对花生四烯酸 5-脂肪氧化酶 、
环氧酶、酪氨酸酶、组织蛋白酶 K 和 5α-还原酶的抑制活性,以及抗炎、抗疟、抗菌、
抗脂质过氧化和保肝等活性。我们对产于云南西双版纳的野树波罗(Artocarpus chama
Buch.-Ham)和柘藤[Cudrania fruticosa (Roxb) Wight ex Kurz]的粗提物进行了初步的
体外抗肿瘤活性研究。结果表明:野树波罗根皮和茎皮的乙醇提取物对 A549(肺癌)
和 MCF-7(乳腺癌)有抑制作用,对其不同极性部位的药理活性跟踪,确定了活性
部位;柘藤根皮丙酮提取物的氯仿萃取部位对 2 种人胃癌细胞株 SGC-7901 和
BGC-823 表现出细胞毒活性。然而,迄今未见国内外有关两种植物的化学成分及生
物活性研究的报道。本文对野树波罗根皮、茎皮和柘藤根皮的活性部位的化学成分进
行了系统的研究,并对单体化合物进行了细胞毒、抗 HIV 和抗真菌活性的研究,以
期阐明有效部位中的化学成分,发现有研究前景的活性化合物。
1. 从野树波罗根皮中分离鉴定了 13 个单体化合物:5 个新的异戊烯基黄酮,命
名为野树波罗甲素?戊素 artochaminsA?E (I-1?I-5);以及 8 个首次从该植物中分离
的已知异戊烯基黄酮,分别为 artocarpin(I-6),cycloartocarpinA(I-7),cudraflavone
A(I-8),artonin A(I-9),artonin U(I-10),cycloartobiloxanthone(I-11),artonin E
(I-12)和 3′, 4′, 5, 7-四羟基-8-(3-甲基-2-丁烯基)黄酮(I-13)。利用 2D- NMR 谱对化
合物 I-6 的碳信号归属进行了修正。
对分离的部分单体化合物(I-3、I-6、I-7、I-9、I-11 和 I-12)进行了多种人肿瘤
细胞株的体外细胞毒活性研究。其中,artonin E(I-12)对肿瘤细胞株 1A9 表现出很
强的抑制活性(ED50< 1.25 μg/mL),对 MCF-7 有显著细胞毒作用(ED50=2.2 μg/mL),
对 HCT-8 和 MDA-MB-231 有中等强度的抑制活性(ED50=3.3,3.0 μg/mL)。野树波
罗丙素 artochamin C(I-3)对 MCF-7、1A9、HCT-8 和 SK-MEL-2 的活性(ED50=2.0?2.3
i
两种桑科药用植物生物活性成分的研究
μg/mL)强于对 A549、KB 及其耐药株 KB-VIN 的活性(ED50=3.0?3.4 μg/mL)。
Artocarpin(I-6)对多个肿瘤细胞株显示出较弱但相对较广的细胞毒活性(ED50=
3.2?3.8 μg/mL)。对构效关系的探讨发现,化合物 6 和 12 有两套疏水基(C-3 位和 A
环的异戊烯基)和亲水基(羟基)位于化合物骨架的不同位置,提高了化合物的抑制
活性;而化合物 I-7、I-9 和 I-11 由于 C-3 位的异戊烯基与 B 环的环合可能降低了这
类化合物的细胞毒活性。
此外,还对分离的部分化合物(I-8 和 I-10 除外)进行了抗 HIV 活性研究。化合
物 3′, 4′, 5, 7-四羟基-8-(3-甲基-2-丁烯基)黄酮(I-13)显示出抗 HIV 活性,EC50和治
疗指数 TI 值分别为 2.24 μg/mL 和 7.47。
2. 从野树波罗茎皮中分离鉴定了 8 个单体化合物:4 个新的异戊烯基二苯乙烯,
命名为波罗蜜二苯乙烯甲?丁 artostilbenes A?D(II-1? II-4);4 个骨架新颖的异戊烯
基酚性化合物,命名为波罗蜜酚甲?丁 artophenols A?D(II-5? II-8)。其中,波罗蜜
二苯乙烯丁 artostilbene D(II-4)为从桑科植物中发现的第一个顺式的二苯乙烯。天
然顺式二苯乙烯化合物在整个自然界中分布局限,目前仅从蓼科大黄属、使君子科和
低等植物苔藓类植物中发现。化合物波罗蜜酚甲?丁 artophenols A?D(II-5?II-8)具
有新颖的骨架,推测生源上是从异戊烯基二苯乙烯衍生而来。
3. 从柘藤根皮中分离鉴定了 23 个单体化合物:1 个新的异戊烯基口山酮,命名
为柘藤口山酮甲 cudrafrutixanthoneA(III-1);以及 22 个首次从该植物中分离的已知
口 山酮和黄酮类化合物,分别为 gerontoxanthonesA?C(III-2? III-4)、E(III-5)、G
(III-6)和 (III-7)、cudraxanthones E(III-8)、H(III-9)和 S(III-10)、toxyloxanthones
I
C?D ( III-11?III-12 )、 alvaxanthone ( III-13 )、 isoalvaxanthone ( III-14 )、
isocudraniaxanthone A(III-15)、padiaxanthone(III-16)、8-prenyltoxyloxanthone C
(III-17)、怀特酮 wighteone(III-18)、kushenol E(III-19)、柚皮素 naringenin(III-20)、
染 料 木 素 genistein(III-21 )、 山 奈 酚 kaempferol (III-22 ) 以 及 香 橙 素 (2R,
3R)-(+)-aromadendr
Artocarpus and Cudrania are two important genera of Moraceous plants. Some
species of Artocarpus have been used as traditional folk medicines in Indonesia, Thailand,
Taiwan, and Sri Lanka to treat live cirrhosis, hypertension, backache, rheumatism, malarial,
fever, dysentery, and tuberculosis. They also were reported to possess anti-inflammatory
and detoxifying effects and control of blood sugar levels in diabetic patients. Most species
of Cudrania are Chinese folk medicines to cure hepatitis, rheumatism, bruising, jaundice,
scabies, dysmenorrhea, external and internal hemorrhage, and chronic gastritis. The extract
from the root barks of Cudrania tricuspidata are applied in clinic for the treatment of
digestive apparatus tumor, especially gastric carcinoma. Previously, a large number of
prenylated flavonoids and xanthones were isolated from Artocarpus and Cudrania species,
some of which were found to exhibit cytotoxic and antiplatelet activities, inhibitory
activities against arachidonate 5-lipoxygenase, cyclooxygenase, tyrosinase, cathepsin K,
and 5α-reductase, and effects of anti-inflammatory, antimalarial, antibacterial, antilipid
oxidation, and liver protection. In our continuing research on cytotoxic phenolic
compounds with isoprenoid groups from Moraceous plants, we investigated the
constituents of Artocarpus chama Buch.-Ham and Cudrania fruticosa (Roxb) Wight ex
Kurz, which have not been studied with respect to their chemical constituents. Our primary
bioassay showed that the chloroform-soluble fraction from an ethanol extract of the roots
of Artocarpus chama exhibited cytotoxic activity against human lung carcinoma (A549)
and breast adenocarcinoma (MCF-7) in vitro, and the chloroform-soluble fraction from an
aqueous acetone extract of the roots of Cudrania fruticosa exhibited cytotoxic activity
against human gastric carcinoma cell lines (SGC-7901 and BGC-823) in vitro. Therefore,
in order to elucidate the bioactive constituents of the two medicinal plants and search for
cytotoxic agents, the studies on the constituents and bioassay of cytotoxic, anti-HIV, and
antifungal activities were carried out.
1. Five new isoprenylated flavones, artochamins A?E (I-1? I-5), were isolated from
the roots of Artocarpus chama, together with eight known comounds, artocarpin (I-6),
v
两种桑科药用植物生物活性成分的研究
cycloartocarpin A (I-7), cudraflavone A (I-8), artonin A (I-9), artonin U (I-10),
cycloartobiloxanthone (I-11), artonin E (I-12), and 3′,4′,5,7-tetrahydroxy-8-(methylbut
-2-enyl)flavone (I-13). Their structures were elucidated by spectroscopic methods.
Compounds I-3, I-6, I-7, I-9, I-11, and I-12 were screened for cytotoxicity against a
panel of human tumor cell lines. Artonin E (I-12) showed strong cytotoxicity against 1A9
(ovarian, ED50 < 1.25 μg/mL), significant activity against MCF-7 (breast adenocarcinoma,
ED50 = 2.2 μg/mL), and moderate activity against HCT-8 (ileocecal, ED50 = 3.3 μg/mL)
and MDA-MB-231 (breast adenocarcinoma, ED50 = 3.0 μg/mL) tumor cell lines.
Artochamin C (I-3) was more potent against MCF-7, 1A9, HCT-8, and SK-MEL-2
(melanoma) (ED50 = 2.0?2.3 μg/mL) than A549 (lung carcinoma), KB (epidermoid
carcinoma of the nasopharynx) and its drug-resistant (KB-VIN) variant (ED50 = 3.0?3.4
μg/mL). Artocarpin (I-6) displayed weak but relatively broad inhibitory effects (ED50 =
3.2?3.8 μg/mL) compared with I-3 and I-12.
Compounds except for I-8 and I-10 were tested for anti-HIV activity. Compound I-13
exhibited activity with EC50 and TI values of 2.24 μg/mLand 7.47, respectively.
2. Four new stilbenes with two isoprenoid groups, artostilbenes A?D (II-1? II-4), and
four mono-isoprenylated phenols with novel skeleton, artophenols A?D (II-5? II-8), were
isolated from the barks of Artocarpus chama. Their structures were elucidated on the basis
of their spectral properties and X-ray crystallographic analysis. Artostilbene D (II-4) is
波罗蜜属的许多植物在印度尼西亚、泰国、台湾和斯里兰卡被作为传统民间用药,治
疗肝硬化、高血压、背痛、风湿病、疟疾、发烧、痢疾和肺结核,并被用来抗炎、解
毒和控制糖尿病人的血糖水平;柘属的植物大多为药用植物,被用来治疗肝炎、风湿
病、跌打损伤、黄疸、疥疮、痛经、体内外出血和慢性胃炎等疾病。柘树[Cudrania
tricuspidata (Carr.) Bur.]的根皮提取物在临床上还被制成柘木糖浆治疗消化道肿瘤。国
外对波罗蜜属和柘属的化学成分进行了较系统的研究,结果表明波罗蜜属植物富含独
特的异戊烯基黄酮类化合物,而柘属植物富含异戊烯基口山酮类化合物。这些化合物
的生物活性显著多样,如细胞毒活性,抗血小板活性,对花生四烯酸 5-脂肪氧化酶 、
环氧酶、酪氨酸酶、组织蛋白酶 K 和 5α-还原酶的抑制活性,以及抗炎、抗疟、抗菌、
抗脂质过氧化和保肝等活性。我们对产于云南西双版纳的野树波罗(Artocarpus chama
Buch.-Ham)和柘藤[Cudrania fruticosa (Roxb) Wight ex Kurz]的粗提物进行了初步的
体外抗肿瘤活性研究。结果表明:野树波罗根皮和茎皮的乙醇提取物对 A549(肺癌)
和 MCF-7(乳腺癌)有抑制作用,对其不同极性部位的药理活性跟踪,确定了活性
部位;柘藤根皮丙酮提取物的氯仿萃取部位对 2 种人胃癌细胞株 SGC-7901 和
BGC-823 表现出细胞毒活性。然而,迄今未见国内外有关两种植物的化学成分及生
物活性研究的报道。本文对野树波罗根皮、茎皮和柘藤根皮的活性部位的化学成分进
行了系统的研究,并对单体化合物进行了细胞毒、抗 HIV 和抗真菌活性的研究,以
期阐明有效部位中的化学成分,发现有研究前景的活性化合物。
1. 从野树波罗根皮中分离鉴定了 13 个单体化合物:5 个新的异戊烯基黄酮,命
名为野树波罗甲素?戊素 artochaminsA?E (I-1?I-5);以及 8 个首次从该植物中分离
的已知异戊烯基黄酮,分别为 artocarpin(I-6),cycloartocarpinA(I-7),cudraflavone
A(I-8),artonin A(I-9),artonin U(I-10),cycloartobiloxanthone(I-11),artonin E
(I-12)和 3′, 4′, 5, 7-四羟基-8-(3-甲基-2-丁烯基)黄酮(I-13)。利用 2D- NMR 谱对化
合物 I-6 的碳信号归属进行了修正。
对分离的部分单体化合物(I-3、I-6、I-7、I-9、I-11 和 I-12)进行了多种人肿瘤
细胞株的体外细胞毒活性研究。其中,artonin E(I-12)对肿瘤细胞株 1A9 表现出很
强的抑制活性(ED50< 1.25 μg/mL),对 MCF-7 有显著细胞毒作用(ED50=2.2 μg/mL),
对 HCT-8 和 MDA-MB-231 有中等强度的抑制活性(ED50=3.3,3.0 μg/mL)。野树波
罗丙素 artochamin C(I-3)对 MCF-7、1A9、HCT-8 和 SK-MEL-2 的活性(ED50=2.0?2.3
i
两种桑科药用植物生物活性成分的研究
μg/mL)强于对 A549、KB 及其耐药株 KB-VIN 的活性(ED50=3.0?3.4 μg/mL)。
Artocarpin(I-6)对多个肿瘤细胞株显示出较弱但相对较广的细胞毒活性(ED50=
3.2?3.8 μg/mL)。对构效关系的探讨发现,化合物 6 和 12 有两套疏水基(C-3 位和 A
环的异戊烯基)和亲水基(羟基)位于化合物骨架的不同位置,提高了化合物的抑制
活性;而化合物 I-7、I-9 和 I-11 由于 C-3 位的异戊烯基与 B 环的环合可能降低了这
类化合物的细胞毒活性。
此外,还对分离的部分化合物(I-8 和 I-10 除外)进行了抗 HIV 活性研究。化合
物 3′, 4′, 5, 7-四羟基-8-(3-甲基-2-丁烯基)黄酮(I-13)显示出抗 HIV 活性,EC50和治
疗指数 TI 值分别为 2.24 μg/mL 和 7.47。
2. 从野树波罗茎皮中分离鉴定了 8 个单体化合物:4 个新的异戊烯基二苯乙烯,
命名为波罗蜜二苯乙烯甲?丁 artostilbenes A?D(II-1? II-4);4 个骨架新颖的异戊烯
基酚性化合物,命名为波罗蜜酚甲?丁 artophenols A?D(II-5? II-8)。其中,波罗蜜
二苯乙烯丁 artostilbene D(II-4)为从桑科植物中发现的第一个顺式的二苯乙烯。天
然顺式二苯乙烯化合物在整个自然界中分布局限,目前仅从蓼科大黄属、使君子科和
低等植物苔藓类植物中发现。化合物波罗蜜酚甲?丁 artophenols A?D(II-5?II-8)具
有新颖的骨架,推测生源上是从异戊烯基二苯乙烯衍生而来。
3. 从柘藤根皮中分离鉴定了 23 个单体化合物:1 个新的异戊烯基口山酮,命名
为柘藤口山酮甲 cudrafrutixanthoneA(III-1);以及 22 个首次从该植物中分离的已知
口 山酮和黄酮类化合物,分别为 gerontoxanthonesA?C(III-2? III-4)、E(III-5)、G
(III-6)和 (III-7)、cudraxanthones E(III-8)、H(III-9)和 S(III-10)、toxyloxanthones
I
C?D ( III-11?III-12 )、 alvaxanthone ( III-13 )、 isoalvaxanthone ( III-14 )、
isocudraniaxanthone A(III-15)、padiaxanthone(III-16)、8-prenyltoxyloxanthone C
(III-17)、怀特酮 wighteone(III-18)、kushenol E(III-19)、柚皮素 naringenin(III-20)、
染 料 木 素 genistein(III-21 )、 山 奈 酚 kaempferol (III-22 ) 以 及 香 橙 素 (2R,
3R)-(+)-aromadendr
Artocarpus and Cudrania are two important genera of Moraceous plants. Some
species of Artocarpus have been used as traditional folk medicines in Indonesia, Thailand,
Taiwan, and Sri Lanka to treat live cirrhosis, hypertension, backache, rheumatism, malarial,
fever, dysentery, and tuberculosis. They also were reported to possess anti-inflammatory
and detoxifying effects and control of blood sugar levels in diabetic patients. Most species
of Cudrania are Chinese folk medicines to cure hepatitis, rheumatism, bruising, jaundice,
scabies, dysmenorrhea, external and internal hemorrhage, and chronic gastritis. The extract
from the root barks of Cudrania tricuspidata are applied in clinic for the treatment of
digestive apparatus tumor, especially gastric carcinoma. Previously, a large number of
prenylated flavonoids and xanthones were isolated from Artocarpus and Cudrania species,
some of which were found to exhibit cytotoxic and antiplatelet activities, inhibitory
activities against arachidonate 5-lipoxygenase, cyclooxygenase, tyrosinase, cathepsin K,
and 5α-reductase, and effects of anti-inflammatory, antimalarial, antibacterial, antilipid
oxidation, and liver protection. In our continuing research on cytotoxic phenolic
compounds with isoprenoid groups from Moraceous plants, we investigated the
constituents of Artocarpus chama Buch.-Ham and Cudrania fruticosa (Roxb) Wight ex
Kurz, which have not been studied with respect to their chemical constituents. Our primary
bioassay showed that the chloroform-soluble fraction from an ethanol extract of the roots
of Artocarpus chama exhibited cytotoxic activity against human lung carcinoma (A549)
and breast adenocarcinoma (MCF-7) in vitro, and the chloroform-soluble fraction from an
aqueous acetone extract of the roots of Cudrania fruticosa exhibited cytotoxic activity
against human gastric carcinoma cell lines (SGC-7901 and BGC-823) in vitro. Therefore,
in order to elucidate the bioactive constituents of the two medicinal plants and search for
cytotoxic agents, the studies on the constituents and bioassay of cytotoxic, anti-HIV, and
antifungal activities were carried out.
1. Five new isoprenylated flavones, artochamins A?E (I-1? I-5), were isolated from
the roots of Artocarpus chama, together with eight known comounds, artocarpin (I-6),
v
两种桑科药用植物生物活性成分的研究
cycloartocarpin A (I-7), cudraflavone A (I-8), artonin A (I-9), artonin U (I-10),
cycloartobiloxanthone (I-11), artonin E (I-12), and 3′,4′,5,7-tetrahydroxy-8-(methylbut
-2-enyl)flavone (I-13). Their structures were elucidated by spectroscopic methods.
Compounds I-3, I-6, I-7, I-9, I-11, and I-12 were screened for cytotoxicity against a
panel of human tumor cell lines. Artonin E (I-12) showed strong cytotoxicity against 1A9
(ovarian, ED50 < 1.25 μg/mL), significant activity against MCF-7 (breast adenocarcinoma,
ED50 = 2.2 μg/mL), and moderate activity against HCT-8 (ileocecal, ED50 = 3.3 μg/mL)
and MDA-MB-231 (breast adenocarcinoma, ED50 = 3.0 μg/mL) tumor cell lines.
Artochamin C (I-3) was more potent against MCF-7, 1A9, HCT-8, and SK-MEL-2
(melanoma) (ED50 = 2.0?2.3 μg/mL) than A549 (lung carcinoma), KB (epidermoid
carcinoma of the nasopharynx) and its drug-resistant (KB-VIN) variant (ED50 = 3.0?3.4
μg/mL). Artocarpin (I-6) displayed weak but relatively broad inhibitory effects (ED50 =
3.2?3.8 μg/mL) compared with I-3 and I-12.
Compounds except for I-8 and I-10 were tested for anti-HIV activity. Compound I-13
exhibited activity with EC50 and TI values of 2.24 μg/mLand 7.47, respectively.
2. Four new stilbenes with two isoprenoid groups, artostilbenes A?D (II-1? II-4), and
four mono-isoprenylated phenols with novel skeleton, artophenols A?D (II-5? II-8), were
isolated from the barks of Artocarpus chama. Their structures were elucidated on the basis
of their spectral properties and X-ray crystallographic analysis. Artostilbene D (II-4) is
引文
参考文献
[1] Suhartati, T.; Achmad, S. A.; Aimi, N.; Hakim, E. H.; Kitajima, M.; Takayama, H.;
Takeya, K. Artoindonesianin L, a new prenylated flavone with cytotoxic activity from
Artocarpus rotunda. Fitoterapia 2001, 72, 912-918.
[2] 中国科学院中国植物志编辑委员会编. 中国植物志. 科学出版社:北京,1998,
23(1),42-55, 58-63.
[3] Chen, C.-C.; Huang, Y.-L.; Ou, J.-C. Three new prenylflavones from Artocarpus altilis.
J. Nat. Prod. 1993, 56, 1594-1597.
[4] Patil, A. D.; Freyer, A. J.; Killmer, L.; Offen, P.; Taylor, P. B.; Votta, B. J.; Johnson, R.
K. A new dimeric dihydrochalcone and a new prenylated flavone from the bud covers
of Artocarpus altilis: potent inhibitors of cathepsin K. J. Nat. Prod. 2002, 65, 624-627.
[5] Lien, T. P.; Hipperger, H.; Porzel, A.; Sung, T. V.; Adam, G. Constituents of Artocarpus
tonkinensis. Pharmazie 1998, 53, 5.
[6] Hakim, E. H.; Asnizar; Yurnawilis,; Aimi, N.; Kitajima, M.; Takayama, H.
Artoindesianin P, a new prenylated flavone with cytotoxic activity from Artocarpus
lanceifolius. Fitoterapia 2002, 73, 668-673.
[7] Fernado, M. R.; Nalinie Wickramasinghe, S. M. D.; Thabrew, M. I..; Ariyananda, P. L.;
Karunanayake, E. H. Effects of Artocarpus heterophyllus and Asteracanthus longifolia
on glucose tolerance in normal human subjects and in maturity-onset diabetic patients.
Journal of Ethnopharmcology 1991, 31, 277-282
[8] Boonlaksiri, C.; Oonanant, W.; Kongsaeree, P.; Kittakoop, P.; Tanticharoen, M.;
Thebtaranonth Y. An Antimalarial Stilbene from Artocarpus integer. Phytochemistry
2000, 54, 415-417.
[9] 江苏新医学院编.中药大辞典,上海科学技术出版社:上海,1977,1713.
[10]曹根生. 抗肿瘤新药—柘木注射液.中成药研究 1980, 1, 34.
[11]云南中草药公司. 云南中药资源名录. 科学出版社:北京,1993,77.
[12]柘树根皮抗肿瘤活性成分研究. 复旦大学邹迎曙学位论文:上海,2004.
[13]Chang, C.-H.; Lin, C.-C.; Hattori, M.; Namba, T. Four prenylated xanthones from
Cudrania cochinchinensis. Phytochemistry 1989, 28, 595-598.
[14]Chang, C.-H.; Lin, C.-C.; Kawata, Y.; Hattori, M.; Namba, T. Prenylated xanthones
from Cudrania cochinchinensis. Phytochemistry 1989, 28, 2823-2826.
[15]Hano, Y.; Matsumoto, Y.; Sun, J.-Y.; Nomura, T. Structures of three new isoprenylated
xanthones, cudraxanthones E, F, and G. Planta Medica 1990, 56, 399-402.
59
两种桑科药用植物生物活性成分的研究
[16]Hano, Y.; Matsumoto, Y.; Sun, J.-Y.; Nomura, T. Structures of four new isoprenylated
xanthones, cudraxanthones H, I, J, and K. Planta Medica 1990, 56, 478-481.
[17]Hakim, E. H.; Fahriyati, A.; Kau, M. S.; Achmad, S. A.; Makmur, L.; Ghisaberti, E. L.;
Nomura, T. Artoindonesianins A and B, two new prenylated flavonoes from the Root
of Artocarpus champeden. J. Nat. Prod. 1999, 62, 613-615.
[18]Syah, Y. M.; Achmad, S. A.; Ghisalberti, E. L.; Hakim, E. H.; Makmur, L.; Mujahidin,
D. Artoindonesianins G-I, three new isoprenylated flavones from Artocarpus
lanceifolius. Fitoterapia 2001, 72, 765-773.
[19]Nomura, T.; Hano, Y.; Aida, M. Isoprenoid-substituted flavonoids from Artocarpus
plants (Moraceae). Heterocycles 1998, 47, 1179-1205.
[20]Su, B.-N.; Cuendet, M.; Hawthorne, N. E.; Kardono, L. B. S.; Riswan, S.; Fong, H. H.
S.; Mehta, R. G.; Pezzuto, J. M.; Douglas Kinghorn, A. Constituents of the bark and
twigs of Artocarpus dadah with cyclooxygenase inhibitory activity. J. Nat. Prod. 2002,
65, 163-169.
[21]Likhitwitayawuid, K.; Sritularak, B. A new dimeric stilbene with tyrosinase inhibitory
activity from Artocarpus gomezianus. J. Nat. Prod. 2001, 64, 1457-1459.
[22]Shimizu, K.; Kondo, R.; Sakai, K. Inhibitory of tyrosinase by flavonoids, stilbenes and
related 4-substituted resorcinols: structure-activity investigations. Planta Medica 2000,
66, 11-15
[23]Likhitwitayawuid, K.; Sritularak, B.; De-Eknamkul, W. Tyrosinase inhibitory from
Artocarpus goezianus. Planta Medica 2000, 66, 275-277.
[24]Shimizu, K.; Kondo, R.; Sakai, K.; Buabarn, S.; Dilokkunanant, U. A geranlated
chalcone with 5α-reductase inhibitory properties from Artocarpus incisus.
Phytochemistry 2000, 54, 737-739.
[25]Syah, Y. M.; Achmad, S. A.; Ghisalberti, E. L.; Hakim, E. H.; Mujahidin, D. Two new
cytotoxic isoprenylated flavones, artoindonesianins U and V, from the heartwood of
Artocarpus champeden. Fitoterapia 2004, 75, 134-140.
[26]Lu, Y.-H.; Lin, C.-N. Two novel and anti-inflammatory constituents of Artocarpus
rigida. Helvetica Chimica Acta 2002, 85, 1626-1632.
[27]Ko, H.-H.; Lin C.-N. New constituents of Artocarpus rigida. Helvetica Chimica Acta
2000, 83, 3000-3005.
[28]Hou, A.-J.; Fukai, T.; Shimazaki, M.; Sakagami, H.; Sun, H.-D.; Nomura, T.
Benzophenones and xanthones with isoprenoid groups from Cudrania cochinchinensis.
J Nat Prod 2001, 64, 65-70.
60
参考文献
[29]Fukai, T.; Yonekawa, M.; Hou, A.-J; Nomura, T.; Sun, H.-D.; Uno, J. Antifungal
agents from the roots of Cudrania cochinchinensis against Candida, Cryptococcus,
and Aspergillus species. J Nat Prod 2003, 66, 1118-1120.
[30]Zou, Y.-S.; Hou, A.-J.; Zhu, G.-F.; Chen, Y.-F.; Sun, H.-D.; Zhao, Q.-S. Cytotoxic
isoprenylated xanthones from Cudrania tricuspidata. Bioorganic & Medicinal
Chemistry 2004, 12,1947-1953.
[31]Rama Rao, A. V.; Rathi, S. S.; Venkataraman, K. Chaplashin, a flavone containing an
oxepine ring from the heartwood of Artocarpus chaplasha Roxb. Indian Journal of
Chemistry 1972, 10, 905-907.
[32]Lin, C.-N.; Lu, C.-M.; Huang, P.-L. Flavonoids from Artocarpus heterophyllus.
Phytochemistry 1995, 39, 1447-1451.
[33]Lu, C.-M.; Lin, C.-N. Flavones and 9-hydroxyreidecyl docosanoate from, Artocarpus
heterophyllus. Phytochemistry 1994, 35, 781-783.
[34]Fujimoto, T.; Hano, Y.; Nomura, T.; Uzawa, J. Components of root bark of Cudrania
tricuspidata 2. structures of two new isoprenylated flavones, cudraflavones A and B.
Planta Medica 1984, 50, 161-163..
[35]Hano, Y; Aida, M.; Shiina, M.; Nomura, T.; Kawai, T.; Ohe, H.; Kagei, K. Artonins A
and B, two new prenylflavones from the root bark of Artocarpus heterophyllus Lamk.
Heterocycles 1989, 29, 1447-453.
[36]Aida, M.; Shinomiya, K.; Matsuzawa, K.; Hano, Y.; Nomura, T. Artonins Q, R, S, T,
and U, five new isoprenylated phenols from the bark of Artocarpus heterophyllus
Lamk. Heterocycles 1994, 39, 847-858.
[37]Sultanbawa, M. U. S.; Surendrakumar, S. Two pyranodihydrobenzoxanthones from
Artocarpus nobilis. Phytochemitry 1989, 28, 599-605.
[38]Hano, Y.; Yamagami, Y.; Kobayashi, M.; Isohata, R.; Nomura, T. Artonins E and F,
two new prenylflavones from the bark of Artocarpus communis Forst. Heterocycles
1990, 31, 877-882.
[39]Lin, Y.-L.; Shiao, M.-S.; Kuo, Y.-H.; Tsai, W.-J. Chin. Pharm. J. (Taipei) 1999, 51,
397-401
[40]Lin, C.-N.; Shieh, W.-L. Prenylflavonoids and a pyranodihydrobenzoxanthone from
Artocarpus communis. Phytochemistry 1991, 30, 1669-1671.
[41]Hano, Y.; Inami, R.; Nomura, T. A novel flavone, artonin V, from the root bark of
Artocarpus altilis. J. Chem. Research (s) 1994, 348-349.
61
两种桑科药用植物生物活性成分的研究
[42](a) Sakagami, H.; Jiang, Y.; Kusama, K.; Atsumi, T.; Ueha, T.; Toguchi, M.; Iwakura,
I.; Satoh, K.; Fukai, T.; Nomura, T. Induction of apoptosis by flavones, flavonols
(3-hydroxyflavones) and isoprenoid-substituted flavonoids in human oral tumor cell
lines. Anticancer Research 2000, 20, 271-278. (b) Fukai, T.; Sakagami, H.; Toguchi,
M.; Takayama, F.; Iwakura, I.; Atsumi, T.; Ueha, T.; Nakashima, H.; Nomura, T.
Cytotoxic activities of low molecular weight polyphenols against human oral cell lines.
Anticancer Research 2000, 20, 2525-2536..
[43]Cheng, H.-H.; Wang, H.-K.; Ito, J.; Bastow, K. F., Tachibana, Y.; Nakanishi, Y.; Xu, Z.;
Luo, T.-Y.; Lee, K.-H. Cytotoxic pheophorbide-related compounds from
Clerodendrum calamitosum and C. cyrtophyllum. J. Nat. Prod. 2001, 64, 915-919.
[44](a) Xia, P.; Yang, Z.-Y.; Xia, Y.; Zheng, Y.-Q.; Mark Cosentino, L.; Lee, K.-H.
Anti-AIDS agents. Park 36:1 17-carboxylated steroids as potential anti-HIV agents.
Bioorganic & Medicinal Chemisrtry 1999, 7, 1907-1911. (b) Ishida, J.; Wang, H.-K.;
Oyama, M.; Cosentino, M. L.; Hu, C.-Q.; Lee, K.-H. Anti-AIDS agents. 46. Anti-HIV
activity of Harman, an anti-Hiv principles from Symplocos setchuensis, and its
derivatives. J. Nat. Prod. 2001, 64, 958?960.
[45]Shimizu, K.; Kondo, R.; Sakai, K. A stilbene derivative from Artocarpus incisus.
Phytochemistry 1997, 45, 1297-1298.
[46]Hakim, E. H.; Ulinnuha, U. Z.; Syah, Y. N.; Ghisalberti, E. L. Artoindonesianins N and
O, new prenylated stibene and prenylated arylbenzofuran derivatives from Artocarpus
gomezianus. Fitoterapia 2002, 73, 597-603.
[47]Soekamto, N. H.; Achmad, S. A.; Ghisalberti, E. L.; Hakim, E. H.; Syah, Y. M.
Artoindonesianins X and Y, two isoprenylated 2-arylbenzofurans, from Artocarpus
fretessi (Moraceae). Phytochemistry 2003, 64, 831-834.
[48]Soekamto, N. H.; Achmad, S. A; Ghisalberti, E. L.; Hakim, E. H.; Syah, Y. M.
Artoindonesianins X and Y, two isoprenylated 2-arylbenzofurans, from Artocarpus
fretessi (Moraceae). Phyotochemistry 2003, 64, 831-834.
[49]Wang, Y.-H.; Hou, A.-J.; Chen, L.; Chen, D.-F.; Sun, H.-D.; Zhao, Q.-S.; Bastow, K. F.;
Nakanish, Y.; Wang, X.-H.; Lee K.-H. New isoprenylated flavones, artochamins A?E,
and cytotoxic principles from Artocarpus chama. J. Nat. Prod. 2004, 67..
[50]彭司勋主编. 药物化学进展. 化学工业出版社:北京,2003,134-160.
[51]Deshpande, V.H.; Rama Rao, A. V.; Mala, V.; Venkataraman, K. Wood & bark
phenolics of Maclura pomifera: four new xanthones. Indian Journal of Chemistry
1973, 11, 518-524.
62
参考文献
[52]Wolfrom, M.-L.; Komitsky, F (Jr).; Mundell, P. M. Osage orange pigments. XVI. The
structure of alvaxanthone. J Org Chem 1965, 30, 1088-1091.
[53]Kobayashi, M.; Mahmud, J.; Yoshioka, N.; Shibuya, H.; Kitagawa, I. Indonesian
medicinal plants. XXI. Inhibitors of Na+/H+ exchanger from the bark of Erythrina
variegata and the roots of Maclura cochinchinensis. Chem Pharm Bull 1997, 45,
1615-1619.
[54]Ishiguro, K.; Fukumoto, H.; Suitani, A.; Nakajima, M.; Isoi, K. Prenylated xanthones
from cell suspension cultures of Hypericum patulum. Phytochemistry 1996, 42,
435-437.
[55]Monache, F. D.; Ferrari, F.; Pomponi, M. Flavanones and xanthones from Maclura
pomifera. Phytochemistry 1984, 23, 1489-1491.
[56]Ingham, J. L.; Keen, N. T.; Hymowitz, T. A new isoflavone phytoalexin from
fungus-inoculated stems of Glycine wightii. Phytochemistry 1977, 16, 1943-1946.
[57]Wu, L. J.; Miyase, T.; Ueno, A.; Kuroyanagi, M.; Noro, T.; Fukushima, S. Studies on
the constituents of Sophora flavescens Ait. III. Yakugaku Zasshi 1985, 105, 736-741.
[58]Agrawal, P. K.; Thakur, R. S.; Bansal, M. C. Studies in Organic Chemistry. In:
Agrawal, P. K. editor. Amsterdam: Elsevier 1989, p. 102.
[59] 谭鸣鸿;张照荣;秦红岩;刘建华. 紫荆花化学成分的研究(2).中草药,1990,
21,246-248.
[60]Takahashi, H.; Li, S.; Harigaya, Y.; Onda, M. Heterocycles. XXII.1) Stereoselective
synthesis of (+)-aromadendrin trimethyl ether and its enantiomer, and their reduction.
Chem Pharm Bull 1988, 36, 1877-1881.
[61]Hou, A.-J.; Li, M.-L.; Jiang, B.; Lin, Z.-W.; Ji, S.-Y.; Zhou, Y.-P.; Sun, H.-D. New 7,20:
14,20-diepoxy ent-kauranoids from Isodon xerophilus. J Nat Prod 2000, 63, 599-601.
[62]Yang, S.-P.; Dong, L.; Wang, Y.; Wu, Y.; Yue, J.-M. Antifungal diterpenoids of
Pseudolarix kaempferi, and their structure?activity relationship study. Bioorganic &
Medicinal Chemistry 2003, 63, 4577-4584.
63
[1] Suhartati, T.; Achmad, S. A.; Aimi, N.; Hakim, E. H.; Kitajima, M.; Takayama, H.;
Takeya, K. Artoindonesianin L, a new prenylated flavone with cytotoxic activity from
Artocarpus rotunda. Fitoterapia 2001, 72, 912-918.
[2] 中国科学院中国植物志编辑委员会编. 中国植物志. 科学出版社:北京,1998,
23(1),42-55, 58-63.
[3] Chen, C.-C.; Huang, Y.-L.; Ou, J.-C. Three new prenylflavones from Artocarpus altilis.
J. Nat. Prod. 1993, 56, 1594-1597.
[4] Patil, A. D.; Freyer, A. J.; Killmer, L.; Offen, P.; Taylor, P. B.; Votta, B. J.; Johnson, R.
K. A new dimeric dihydrochalcone and a new prenylated flavone from the bud covers
of Artocarpus altilis: potent inhibitors of cathepsin K. J. Nat. Prod. 2002, 65, 624-627.
[5] Lien, T. P.; Hipperger, H.; Porzel, A.; Sung, T. V.; Adam, G. Constituents of Artocarpus
tonkinensis. Pharmazie 1998, 53, 5.
[6] Hakim, E. H.; Asnizar; Yurnawilis,; Aimi, N.; Kitajima, M.; Takayama, H.
Artoindesianin P, a new prenylated flavone with cytotoxic activity from Artocarpus
lanceifolius. Fitoterapia 2002, 73, 668-673.
[7] Fernado, M. R.; Nalinie Wickramasinghe, S. M. D.; Thabrew, M. I..; Ariyananda, P. L.;
Karunanayake, E. H. Effects of Artocarpus heterophyllus and Asteracanthus longifolia
on glucose tolerance in normal human subjects and in maturity-onset diabetic patients.
Journal of Ethnopharmcology 1991, 31, 277-282
[8] Boonlaksiri, C.; Oonanant, W.; Kongsaeree, P.; Kittakoop, P.; Tanticharoen, M.;
Thebtaranonth Y. An Antimalarial Stilbene from Artocarpus integer. Phytochemistry
2000, 54, 415-417.
[9] 江苏新医学院编.中药大辞典,上海科学技术出版社:上海,1977,1713.
[10]曹根生. 抗肿瘤新药—柘木注射液.中成药研究 1980, 1, 34.
[11]云南中草药公司. 云南中药资源名录. 科学出版社:北京,1993,77.
[12]柘树根皮抗肿瘤活性成分研究. 复旦大学邹迎曙学位论文:上海,2004.
[13]Chang, C.-H.; Lin, C.-C.; Hattori, M.; Namba, T. Four prenylated xanthones from
Cudrania cochinchinensis. Phytochemistry 1989, 28, 595-598.
[14]Chang, C.-H.; Lin, C.-C.; Kawata, Y.; Hattori, M.; Namba, T. Prenylated xanthones
from Cudrania cochinchinensis. Phytochemistry 1989, 28, 2823-2826.
[15]Hano, Y.; Matsumoto, Y.; Sun, J.-Y.; Nomura, T. Structures of three new isoprenylated
xanthones, cudraxanthones E, F, and G. Planta Medica 1990, 56, 399-402.
59
两种桑科药用植物生物活性成分的研究
[16]Hano, Y.; Matsumoto, Y.; Sun, J.-Y.; Nomura, T. Structures of four new isoprenylated
xanthones, cudraxanthones H, I, J, and K. Planta Medica 1990, 56, 478-481.
[17]Hakim, E. H.; Fahriyati, A.; Kau, M. S.; Achmad, S. A.; Makmur, L.; Ghisaberti, E. L.;
Nomura, T. Artoindonesianins A and B, two new prenylated flavonoes from the Root
of Artocarpus champeden. J. Nat. Prod. 1999, 62, 613-615.
[18]Syah, Y. M.; Achmad, S. A.; Ghisalberti, E. L.; Hakim, E. H.; Makmur, L.; Mujahidin,
D. Artoindonesianins G-I, three new isoprenylated flavones from Artocarpus
lanceifolius. Fitoterapia 2001, 72, 765-773.
[19]Nomura, T.; Hano, Y.; Aida, M. Isoprenoid-substituted flavonoids from Artocarpus
plants (Moraceae). Heterocycles 1998, 47, 1179-1205.
[20]Su, B.-N.; Cuendet, M.; Hawthorne, N. E.; Kardono, L. B. S.; Riswan, S.; Fong, H. H.
S.; Mehta, R. G.; Pezzuto, J. M.; Douglas Kinghorn, A. Constituents of the bark and
twigs of Artocarpus dadah with cyclooxygenase inhibitory activity. J. Nat. Prod. 2002,
65, 163-169.
[21]Likhitwitayawuid, K.; Sritularak, B. A new dimeric stilbene with tyrosinase inhibitory
activity from Artocarpus gomezianus. J. Nat. Prod. 2001, 64, 1457-1459.
[22]Shimizu, K.; Kondo, R.; Sakai, K. Inhibitory of tyrosinase by flavonoids, stilbenes and
related 4-substituted resorcinols: structure-activity investigations. Planta Medica 2000,
66, 11-15
[23]Likhitwitayawuid, K.; Sritularak, B.; De-Eknamkul, W. Tyrosinase inhibitory from
Artocarpus goezianus. Planta Medica 2000, 66, 275-277.
[24]Shimizu, K.; Kondo, R.; Sakai, K.; Buabarn, S.; Dilokkunanant, U. A geranlated
chalcone with 5α-reductase inhibitory properties from Artocarpus incisus.
Phytochemistry 2000, 54, 737-739.
[25]Syah, Y. M.; Achmad, S. A.; Ghisalberti, E. L.; Hakim, E. H.; Mujahidin, D. Two new
cytotoxic isoprenylated flavones, artoindonesianins U and V, from the heartwood of
Artocarpus champeden. Fitoterapia 2004, 75, 134-140.
[26]Lu, Y.-H.; Lin, C.-N. Two novel and anti-inflammatory constituents of Artocarpus
rigida. Helvetica Chimica Acta 2002, 85, 1626-1632.
[27]Ko, H.-H.; Lin C.-N. New constituents of Artocarpus rigida. Helvetica Chimica Acta
2000, 83, 3000-3005.
[28]Hou, A.-J.; Fukai, T.; Shimazaki, M.; Sakagami, H.; Sun, H.-D.; Nomura, T.
Benzophenones and xanthones with isoprenoid groups from Cudrania cochinchinensis.
J Nat Prod 2001, 64, 65-70.
60
参考文献
[29]Fukai, T.; Yonekawa, M.; Hou, A.-J; Nomura, T.; Sun, H.-D.; Uno, J. Antifungal
agents from the roots of Cudrania cochinchinensis against Candida, Cryptococcus,
and Aspergillus species. J Nat Prod 2003, 66, 1118-1120.
[30]Zou, Y.-S.; Hou, A.-J.; Zhu, G.-F.; Chen, Y.-F.; Sun, H.-D.; Zhao, Q.-S. Cytotoxic
isoprenylated xanthones from Cudrania tricuspidata. Bioorganic & Medicinal
Chemistry 2004, 12,1947-1953.
[31]Rama Rao, A. V.; Rathi, S. S.; Venkataraman, K. Chaplashin, a flavone containing an
oxepine ring from the heartwood of Artocarpus chaplasha Roxb. Indian Journal of
Chemistry 1972, 10, 905-907.
[32]Lin, C.-N.; Lu, C.-M.; Huang, P.-L. Flavonoids from Artocarpus heterophyllus.
Phytochemistry 1995, 39, 1447-1451.
[33]Lu, C.-M.; Lin, C.-N. Flavones and 9-hydroxyreidecyl docosanoate from, Artocarpus
heterophyllus. Phytochemistry 1994, 35, 781-783.
[34]Fujimoto, T.; Hano, Y.; Nomura, T.; Uzawa, J. Components of root bark of Cudrania
tricuspidata 2. structures of two new isoprenylated flavones, cudraflavones A and B.
Planta Medica 1984, 50, 161-163..
[35]Hano, Y; Aida, M.; Shiina, M.; Nomura, T.; Kawai, T.; Ohe, H.; Kagei, K. Artonins A
and B, two new prenylflavones from the root bark of Artocarpus heterophyllus Lamk.
Heterocycles 1989, 29, 1447-453.
[36]Aida, M.; Shinomiya, K.; Matsuzawa, K.; Hano, Y.; Nomura, T. Artonins Q, R, S, T,
and U, five new isoprenylated phenols from the bark of Artocarpus heterophyllus
Lamk. Heterocycles 1994, 39, 847-858.
[37]Sultanbawa, M. U. S.; Surendrakumar, S. Two pyranodihydrobenzoxanthones from
Artocarpus nobilis. Phytochemitry 1989, 28, 599-605.
[38]Hano, Y.; Yamagami, Y.; Kobayashi, M.; Isohata, R.; Nomura, T. Artonins E and F,
two new prenylflavones from the bark of Artocarpus communis Forst. Heterocycles
1990, 31, 877-882.
[39]Lin, Y.-L.; Shiao, M.-S.; Kuo, Y.-H.; Tsai, W.-J. Chin. Pharm. J. (Taipei) 1999, 51,
397-401
[40]Lin, C.-N.; Shieh, W.-L. Prenylflavonoids and a pyranodihydrobenzoxanthone from
Artocarpus communis. Phytochemistry 1991, 30, 1669-1671.
[41]Hano, Y.; Inami, R.; Nomura, T. A novel flavone, artonin V, from the root bark of
Artocarpus altilis. J. Chem. Research (s) 1994, 348-349.
61
两种桑科药用植物生物活性成分的研究
[42](a) Sakagami, H.; Jiang, Y.; Kusama, K.; Atsumi, T.; Ueha, T.; Toguchi, M.; Iwakura,
I.; Satoh, K.; Fukai, T.; Nomura, T. Induction of apoptosis by flavones, flavonols
(3-hydroxyflavones) and isoprenoid-substituted flavonoids in human oral tumor cell
lines. Anticancer Research 2000, 20, 271-278. (b) Fukai, T.; Sakagami, H.; Toguchi,
M.; Takayama, F.; Iwakura, I.; Atsumi, T.; Ueha, T.; Nakashima, H.; Nomura, T.
Cytotoxic activities of low molecular weight polyphenols against human oral cell lines.
Anticancer Research 2000, 20, 2525-2536..
[43]Cheng, H.-H.; Wang, H.-K.; Ito, J.; Bastow, K. F., Tachibana, Y.; Nakanishi, Y.; Xu, Z.;
Luo, T.-Y.; Lee, K.-H. Cytotoxic pheophorbide-related compounds from
Clerodendrum calamitosum and C. cyrtophyllum. J. Nat. Prod. 2001, 64, 915-919.
[44](a) Xia, P.; Yang, Z.-Y.; Xia, Y.; Zheng, Y.-Q.; Mark Cosentino, L.; Lee, K.-H.
Anti-AIDS agents. Park 36:1 17-carboxylated steroids as potential anti-HIV agents.
Bioorganic & Medicinal Chemisrtry 1999, 7, 1907-1911. (b) Ishida, J.; Wang, H.-K.;
Oyama, M.; Cosentino, M. L.; Hu, C.-Q.; Lee, K.-H. Anti-AIDS agents. 46. Anti-HIV
activity of Harman, an anti-Hiv principles from Symplocos setchuensis, and its
derivatives. J. Nat. Prod. 2001, 64, 958?960.
[45]Shimizu, K.; Kondo, R.; Sakai, K. A stilbene derivative from Artocarpus incisus.
Phytochemistry 1997, 45, 1297-1298.
[46]Hakim, E. H.; Ulinnuha, U. Z.; Syah, Y. N.; Ghisalberti, E. L. Artoindonesianins N and
O, new prenylated stibene and prenylated arylbenzofuran derivatives from Artocarpus
gomezianus. Fitoterapia 2002, 73, 597-603.
[47]Soekamto, N. H.; Achmad, S. A.; Ghisalberti, E. L.; Hakim, E. H.; Syah, Y. M.
Artoindonesianins X and Y, two isoprenylated 2-arylbenzofurans, from Artocarpus
fretessi (Moraceae). Phytochemistry 2003, 64, 831-834.
[48]Soekamto, N. H.; Achmad, S. A; Ghisalberti, E. L.; Hakim, E. H.; Syah, Y. M.
Artoindonesianins X and Y, two isoprenylated 2-arylbenzofurans, from Artocarpus
fretessi (Moraceae). Phyotochemistry 2003, 64, 831-834.
[49]Wang, Y.-H.; Hou, A.-J.; Chen, L.; Chen, D.-F.; Sun, H.-D.; Zhao, Q.-S.; Bastow, K. F.;
Nakanish, Y.; Wang, X.-H.; Lee K.-H. New isoprenylated flavones, artochamins A?E,
and cytotoxic principles from Artocarpus chama. J. Nat. Prod. 2004, 67..
[50]彭司勋主编. 药物化学进展. 化学工业出版社:北京,2003,134-160.
[51]Deshpande, V.H.; Rama Rao, A. V.; Mala, V.; Venkataraman, K. Wood & bark
phenolics of Maclura pomifera: four new xanthones. Indian Journal of Chemistry
1973, 11, 518-524.
62
参考文献
[52]Wolfrom, M.-L.; Komitsky, F (Jr).; Mundell, P. M. Osage orange pigments. XVI. The
structure of alvaxanthone. J Org Chem 1965, 30, 1088-1091.
[53]Kobayashi, M.; Mahmud, J.; Yoshioka, N.; Shibuya, H.; Kitagawa, I. Indonesian
medicinal plants. XXI. Inhibitors of Na+/H+ exchanger from the bark of Erythrina
variegata and the roots of Maclura cochinchinensis. Chem Pharm Bull 1997, 45,
1615-1619.
[54]Ishiguro, K.; Fukumoto, H.; Suitani, A.; Nakajima, M.; Isoi, K. Prenylated xanthones
from cell suspension cultures of Hypericum patulum. Phytochemistry 1996, 42,
435-437.
[55]Monache, F. D.; Ferrari, F.; Pomponi, M. Flavanones and xanthones from Maclura
pomifera. Phytochemistry 1984, 23, 1489-1491.
[56]Ingham, J. L.; Keen, N. T.; Hymowitz, T. A new isoflavone phytoalexin from
fungus-inoculated stems of Glycine wightii. Phytochemistry 1977, 16, 1943-1946.
[57]Wu, L. J.; Miyase, T.; Ueno, A.; Kuroyanagi, M.; Noro, T.; Fukushima, S. Studies on
the constituents of Sophora flavescens Ait. III. Yakugaku Zasshi 1985, 105, 736-741.
[58]Agrawal, P. K.; Thakur, R. S.; Bansal, M. C. Studies in Organic Chemistry. In:
Agrawal, P. K. editor. Amsterdam: Elsevier 1989, p. 102.
[59] 谭鸣鸿;张照荣;秦红岩;刘建华. 紫荆花化学成分的研究(2).中草药,1990,
21,246-248.
[60]Takahashi, H.; Li, S.; Harigaya, Y.; Onda, M. Heterocycles. XXII.1) Stereoselective
synthesis of (+)-aromadendrin trimethyl ether and its enantiomer, and their reduction.
Chem Pharm Bull 1988, 36, 1877-1881.
[61]Hou, A.-J.; Li, M.-L.; Jiang, B.; Lin, Z.-W.; Ji, S.-Y.; Zhou, Y.-P.; Sun, H.-D. New 7,20:
14,20-diepoxy ent-kauranoids from Isodon xerophilus. J Nat Prod 2000, 63, 599-601.
[62]Yang, S.-P.; Dong, L.; Wang, Y.; Wu, Y.; Yue, J.-M. Antifungal diterpenoids of
Pseudolarix kaempferi, and their structure?activity relationship study. Bioorganic &
Medicinal Chemistry 2003, 63, 4577-4584.
63