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
引文
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