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Chemical constituents from leaves of Momordica charantia

苦瓜叶的化学成分研究



全 文 :中草药 Chinese Traditional and Herbal Drugs 第 43 卷 第 9 期 2012 年 9 月

• 1712 •
苦瓜叶的化学成分研究
李 雯 1, 2,陈燕芬 1,吴 楠 2,池墨瑶 2,费 佳 2
1. 广东省中医院,广东 广州 510120
2. 中国药科大学,江苏 南京 210009
摘 要:目的 研究苦瓜 Momordica charantia 叶的化学成分。方法 采用硅胶、Sephadex LH-20 等多种柱色谱方法进行分
离纯化,通过理化常数和波谱分析鉴定化合物的结构。结果 从苦瓜叶 95%乙醇提取物中分离得到 11 个化合物,分别鉴定
为 (19S, 23E)-5β, 19-epoxy-19-methoxycucurbita-6, 23-diene-3β, 25-diol(1)、(19R, 23E)-5β, 19-epoxy-19-methoxycucurbita-6,
23-diene-3β, 25-diol(2)、3β, 7β, 25-trihydroxycucurbita-5, 23-dien-19-al(3)、3β, 7β, 25-trihydroxycucurbita-5, 23-dien-19-al-3-
O-β-D-glucopyranoside(4)、苦瓜素 I(5)、苦瓜素 IV(6)、大豆脑苷 I(7)、α-菠甾醇(8)、α-香树素乙酸酯(9)、β-谷甾
醇(10)和胡萝卜苷(11)。结论 化合物 1、3、8~11 为首次从该植物中分离得到。
关键词:苦瓜;苦瓜素 I;苦瓜素 IV;大豆脑苷 I;胡萝卜苷
中图分类号:R284.1 文献标志码:A 文章编号:0253 - 2670(2012)09 - 1712 - 04
Chemical constituents from leaves of Momordica charantia
LI Wen1, 2, CHEN Yan-fen1, WU Nan2, CHI Mo-yao2, FEI Jia2
1. Guangdong Provincial Hospital of Traditional Chinese Medicines, Guangzhou 510120, China
2. China Pharmaceutical University, Nanjing 210009, China
Abstract: Objective To study the chemical constituents from the leaves of Momordica charantia. Methods The compounds were
isolated and purified by column chromatography on silica gel, ODS, Sephadex LH-20, and preparative HPLC. Their structures were
identified by physicochemical properties and spectral data. Results Eleven compounds were isolated from 95% ethanol extract of M.
charantia and elucidated as (19S, 23E)-5β, 19-epoxy-19-methoxycucurbita-6, 23-diene-3β, 25-diol (1), (19R, 23E)-5β, 19-epoxy-
19-methoxycucurbita-6, 23-diene-3β, 25-diol (2), 3β, 7β, 25-trihydroxycucurbita-5, 23-dien-19-al (3), 3β, 7β, 25-trihydroxy-
cucurbita-5, 23-dien-19-al-3-O-β-D-glucopyranoside (4), momordicin I (5), momordicin IV (6), soya-cerebroside I (7), α- spinasterol
(8), α-amyrin acetate (9), β-sitosterol (10), and daucosterol (11), respectively. Conclusion Compounds 1, 3, and 8—11 are isolated
from M. charantia for the first time.
Key words: Momordica charantia L.; momordicin I; momordicin IV; soya-cerebroside I; daucosterol

苦瓜 Momordica charantia L.,又名锦荔枝、癞
葡萄、癞瓜、凉瓜等,为葫芦科苦瓜属攀援性草本
植物,广泛分布于热带、亚热带和温带地区。苦瓜
性苦、味寒,具有清热解毒、明目、滋养强壮、降
血糖、抗突变、抗肿瘤以及提高免疫力等功效,是
民间常用中药,用于热病烦渴、中暑、痢疾、赤眼
疼痛、痈肿丹毒、恶疮等症的治疗[1]。近年来,对
苦瓜的研究主要集中在果实和种子,已从苦瓜果实
和种子中分离纯化出多种化学成分,并对其中一些
有活性的化合物进行了药理作用研究[2]。为了进一
步研究苦瓜的活性成分,本实验对苦瓜叶 95%乙醇
提取物进行研究,从中分离得到 11 个化合物,分别
鉴 定 为 (19S, 23E)-5β, 19-epoxy-19-methoxy-
cucurbita-6, 23-diene-3β, 25-diol(1)、(19R, 23E)-5β,
19-epoxy-19-methoxycucurbita-6, 23-diene-3β, 25-diol
(2)、3β, 7β, 25-trihydroxycucurbita-5, 23-dien-19-al
(3)、3β, 7β, 25-trihydroxycucurbita-5, 23-dien-19-al-
3-O-β-D-glucopyranoside(4)、苦瓜素 I(momordicin
I,5)、苦瓜素 IV(momordicin IV,6)、大豆脑苷
I(soya-cerebroside I,7)、α-菠甾醇(α-spinasterol,
8)、α-香树素乙酸酯(α-amyrin acetate,9)、β-谷甾
醇(β-sitosterol,10)和胡萝卜苷(daucosterol,11)。
其中,化合物 1、3、8~11 为首次从该植物中分离
得到。

收稿日期:2011-12-08
作者简介:李 雯(1984—),女,硕士研究生,主要从事中药及天然产物活性成分研究。Tel: (020)81506429 E-mail: tracyliwen@hotmail. com
中草药 Chinese Traditional and Herbal Drugs 第 43 卷 第 9 期 2012 年 9 月

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1 仪器和材料
X—4 型显微熔点测定仪(北京泰克仪器有限公
司);Jasco V—550 紫外/可见光谱仪;Jasco FI/IR—
480 Plus Fourier Transform 红外光谱仪;Bruker AV—
400 FT 型核磁共振仪;Finnigan LCQ Advantage
MAX 质谱仪。柱色谱用硅胶为青岛海洋化工厂产
品;硅胶 GF254 薄层预制板为烟台化学工业研究所
产品;Sephadex LH-20 柱色谱材料为 Pharmacia 公
司产品;色谱纯甲醇为江苏汉邦公司产品;其余试
剂均为化学纯或分析纯。
药材样品于2009年9月采购自广东省广州市清
平药材市场,经广东省中医院董玉珍主任中药师鉴
定为葫芦科植物苦瓜 Momordica charantia L. 的
叶,药材样本(编号 20090927)保存于广东省中医
院制剂室。
2 提取与分离
干燥的苦瓜叶 5 kg,粉碎,用 95%乙醇室温下
渗漉提取,合并提取液,减压浓缩,得到总浸膏 927
g。总浸膏用适量水混悬,依次用等量石油醚、醋酸
乙酯、正丁醇萃取,合并萃取液,减压浓缩,分别
得到石油醚部分 140 g、醋酸乙酯部分 298 g、正丁
醇部分 165 g 和水部分 324 g。对醋酸乙酯部分进行
反复硅胶柱色谱(氯仿-甲醇系统),用 Sephadex
LH-20 柱(氯仿-甲醇、甲醇-水系统)及制备 HPLC
进行纯化,分别得到化合物 1(20 mg)、2(17 mg)、
3(15 mg)、4(12 mg)、5(9 mg)、6(10 mg)、7
(8 mg)、8(13 mg)、9(21 mg)、10(30 mg)和
11(14 mg)。
3 结构鉴定
化合物 1:白色片晶(甲醇),mp 116~118 ℃。
ESI-MS m/z: 509 [M+Na]+。IR υKBr max (cm−l): 3 475,
2 943, 1 468, 1 373, 1 159, 1 080, 973, 862。1H-NMR
(400 MHz, CD3OD) δ: 6.13 (1H, dd, J = 10.0, 2.0 Hz,
H-6), 5.58 (2H, m, H-23, 24), 5.55 (1H, dd, J = 10.0,
3.6 Hz, H-7), 4.45 (1H, s, H-19), 3.40 (1H, brs, H-3α),
3.38 (3H, s, -OCH3), 2.37 (1H, m, H-10), 2.24 (1H,
brs, H-8), 1.39 (6H, s, H-26, 27), 1.26 (3H, d, J = 4.8
Hz, H-21), 0.95, 0.94, 0.91, 0.90 (各 3H, s, 4×-CH3);
13C-NMR (100 MHz, CD3OD) δ: 140.9 (C-24), 133.9
(C-6), 131.5 (C-7), 125.8 (C-23), 116.2 (C-19), 86.4
(C-5), 77.8 (C-3), 71.1 (C-25), 57.8 (-OCH3), 51.4
(C-17), 51.1 (C-8), 50.3 (C-9), 49.2 (C-14), 46.3
(C-13), 40.3 (C-22), 39.1 (C-10), 38.1 (C-20), 37.6
(C-4), 34.5 (C-15), 31.7 (C-12), 30.2 (C-26), 30.1
(C-27), 28.9 (C-16), 28.0 (C-2), 24.7 (C-29), 22.5
(C-11), 19.2 (C-21), 16.5 (C-1), 21.0 (C-28), 20.5
(C-30), 15.5 (C-18)。以上数据与文献报道一致[3],故
鉴定化合物 1 为 (19S, 23E)-5β, 19-epoxy-19-
methoxycucurbita-6, 23-diene-3β, 25-diol。
化合物 2:白色片晶(甲醇),mp 143~145 ℃。
ESI-MS m/z: 509 [M+Na]+。IR υKBr max (cm−l): 3 450,
2 943, 1 649, 1 466, 1 377, 1 080, 973, 913。1H-NMR
(400 MHz, CD3OD) δ: 5.97 (1H, dd, J = 9.8, 2.3 Hz,
H-6), 5.59 (2H, m, H-23, 24), 5.54 (1H, dd, J = 9.7,
3.5 Hz, H-7), 4.70 (1H, s, H-19), 3.38 (1H, brs, H-3α),
3.41 (3H, s, -OCH3), 2.46 (1H, m, H-10), 2.16 (1H,
brs, H-8), 1.26 (6H, s, H-26, 27), 1.18 (3H, d, J = 4.6
Hz, H-21), 0.92, 0.91, 0.90, 0.88 (各 3H, s, 4×-CH3);
13C-NMR (100 MHz, CD3OD) δ: 140.8 (C-24), 133.7
(C-6), 132.0 (C-7), 125.9 (C-23), 113.2 (C-19), 88.0
(C-5), 77.6 (C-3), 71.1 (C-25), 58.1 (-OCH3), 51.3
(C-17), 49.5 (C-14), 49.1 (C-9), 46.2 (C-13), 43.1
(C-8), 41.9 (C-10), 40.3 (C-22), 38.4 (C-4), 37.6
(C-20), 34.6 (C-15), 31.8 (C-12), 30.1 (C-26), 30.0
(C-27), 29.0 (C-16), 28.1 (C-2), 24.4 (C-29), 24.2
(C-11), 19.1 (C-21), 18.4 (C-1), 20.7 (C-28), 20.3
(C-30), 15.2 (C-18)。以上数据与文献报道一致[4],故
鉴定化合物 2 为 (19R, 23E)-5β, 19-epoxy-19-
methoxycucurbita-6, 23-diene-3β, 25-diol。
化合物 3:白色片晶(甲醇),ESI-MS m/z: 495
[M+Na]+。IR υKBr max (cm−l): 3 437, 2 927, 1 637, 1 546,
1 453, 962 cm−1。1H-NMR (400 MHz, CD3OD) δ: 9.87
(1H, s, H-19), 5.57 (2H, brs, H-23, 24), 3.99 (1H, brd,
J = 5.6 Hz, H-7), 3.54 (1H, brs, H-3), 1.25 (6H, s,
H-26, 27), 0.94 (3H, d, J = 5.6 Hz, H-21), 1.24, 1.07,
0.86, 0.81 (各 3H, s, 4×-CH3);13C-NMR (100 MHz,
CD3OD) δ: 209.4 (C-19), 147.2 (C-23), 140.7 (C-5),
125.7 (C-24), 123.8 (C-6), 77.0 (C-3), 71.1 (C-25),
66.9 (C-7), 51.3 (C-9), 51.1 (C-17), 50.8 (C-14), 46.6
(C-13), 42.3 (C-4), 40.3 (C-22), 37.6 (C-10), 35.7
(C-11), 30.2 (C-8), 30.1 (C-20), 29.9 (C-16), 29.8
(C-2), 28.6 (C-15), 27.8 (C-28), 27.6 (C-12), 26.0
(C-26), 23.3 (C-27), 22.3 (C-29), 21.9 (C-1), 19.3
(C-30), 18.8 (C-18), 15.4 (C-21)。以上数据与文献报
道一致[3],故鉴定化合物 3 为 3β, 7β, 25-trihydroxy-
cucurbita-5, 23-dien-19-al。
中草药 Chinese Traditional and Herbal Drugs 第 43 卷 第 9 期 2012 年 9 月

• 1714 •
化合物 4:白色晶体(甲醇),mp 200~202 ℃,
ESI-MS m/z: 629 [M+Na]+。IR υKBr max (cm−l): 3 388,
2 918, 1 640, 1 537, 1 468, 1 080, 964。1H-NMR (400
MHz, pyridine-d5) δ: 0.78 (3H, s, H-30), 0.89 (3H, s,
H-18), 0.96 (3H, d, J = 5.6 Hz, H-21), 1.14 (3H, s,
H-29), 1.24 (1H, m, H-16), 1.53 (3H, s, H-28), 1.55
(3H, brs, H-26), 1.59 (3H, brs, H-27), 1.76 (1H, m,
H-l), 1.85 (1H, m, H-22), 1.98 (2H, m, H-1, 2), 2.24
(1H, m, H-22), 5.60 (1H, m, H-24), 5.61 (1H, m,
H-23), 6.19 (1H, brd, J = 4.8 Hz, H-6), 10.51 (1H, s,
H-19);13C-NMR (100 MHz, pyridine-d5) δ: 207.4
(C-19), 147.6 (C-5), 137.7 (C-24), 128.4 (C-23), 122.4
(C-6), 101.8 (C-1′), 78.7 (C-3′), 78.7 (C-5′), 75.6
(C-3), 75.0 (C-2′), 74.8 (C-25), 71.9 (C-4′), 71.8 (C-7),
63.1 (C-1′), 50.3 (C-9), 50.2 (C-17), 48.1 (C-14), 45.8
(C-13), 45.2 (C-8), 41.9 (C-4), 39.7 (C-22), 36.7 (C-10),
36.4 (C-20), 34.9 (C-15), 29.8 (C-2), 29.4 (C-12), 27.6
(C-16), 27.4 (C-29), 26.5 (C-26), 26.3 (C-28), 26.1
(C-27), 22.7 (C-11), 21.9 (C-1), 19.0 (C-21), 18.2
(C-30), 15.1 (C-18)。以上数据与文献报道一致[5],故
鉴定化合物 4 为 3β, 7β, 25-trihydroxycucurbita-5, 23-
dien-19-al-3-O-β-D-glucopyranoside。
化合物 5:白色粉末,ESI-MS m/z: 495 [M+
Na]+。IR υKBr max (cm−l): 3 450, 2 951, 1 641, 1 556, 1 450,
973。1H-NMR (400 MHz, CD3OD) δ: 0.82, 0.93, 1.08,
1.25 (各 3H, s, H-18, 28, 29, 30), 1.00 (3H, d, J = 6.4
Hz, H-21), 1.67 (3H, s, H-26), 1.70 (3H, s, H-27), 1.98
(1H, m, H-20), 2.40 (1H, m, H-8), 2.58 (1H, m, H-10),
3.55 (1H, brs, H-3), 4.00 (1H, d, J = 5.2 Hz, H-7),
4.41 (1H, m, H-23), 5.16 (1H, d, J = 8.8 Hz, H-24),
5.91 (1H, d, J = 4.0 Hz, H-6), 9.88 (1H, s, H-19);
13C-NMR (100 MHz, CD3OD) δ: 209.7 (C-19), 147.3
(C-5), 133.4 (C-24), 130.5 (C-25), 124.0 (C-6), 77.1
(C-3), 66.9 (C-7), 66.6 (C-23), 52.1 (C-9), 51.3
(C-17), 50.8 (C-8), 49.0 (C-14), 46.8 (C-13), 45.6
(C-22), 42.3 (C-4), 37.7 (C-10), 35.6 (C-15), 33.7
(C-20), 30.3 (C-2), 29.8 (C-12), 28.6 (C-16), 27.8
(C-29), 26.0 (C-27), 25.9 (C-28), 23.3 (C-11), 22.2
(C-1), 19.3 (C-21), 18.8 (C-26), 18.1 (C-30), 15.3
(C-18)。以上数据与文献报道一致[6],故鉴定化合物
5 为苦瓜素 I。
化合物 6:白色粉末,ESI-MS m/z: 657 [M+
Na]+。IR υKBr max (cm−l): 3 446, 2 947, 1 649, 1 551, 1 456,
965。1H-NMR (400 MHz, pyridine-d5) δ: 0.87, 0.90,
1.12, 1.48 (各 3H, s, H-18, 28, 29, 30), 1.19 (3H, d,
J = 6.4 Hz, H-21), 1.71 (3H, s, H-26), 1.75 (3H, s,
H-27), 2.07 (1H, m, H-20), 2.37 (1H, m, H-8), 2.71
(1H, m, H-10), 3.81 (1H, brs, H-3), 4.35 (1H, d, J =
5.2 Hz, H-7), 4.96 (1H, d, J = 7.8 Hz, H-1′), 5.61 (1H,
d, J = 7.8 Hz, H-24), 6.27 (1H, d, J = 4.4 Hz, H-6),
10.65 (1H, s, H-19);13C-NMR (100 MHz, pyridine-d5)
δ: 207.7 (C-19), 145.7 (C-5), 132.2 (C-25), 129.1
(C-24), 124.3 (C-6), 104.1 (C-1′), 78.9 (C-3′), 78.2
(C-5′), 75.6 (C-2′), 75.6 (C-3), 75.3 (C-23), 71.9
(C-4′), 65.7 (C-7), 63.0 (C-6′), 51.2 (C-17), 50.6
(C-9), 50.5 (C-8), 48.2 (C-14), 45.9 (C-13), 43.7
(C-22), 41.7 (C-4), 36.8 (C-10), 34.9 (C-15), 32.6
(C-20), 29.8 (C-2), 29.6 (C-12), 27.8 (C-16), 27.3
(C-29), 26.2 (C-27), 25.8 (C-28), 22.7 (C-11), 21.7
(C-1), 19.4 (C-21), 18.2 (C-26), 18.2 (C-30), 14.9
(C-18)。以上数据与文献报道一致[7],故鉴定化合物
6 为苦瓜素 IV。
化合物 7:白色粉末,mp 250~252 ℃,ESI-MS
m/z: 712 [M-H]−。1H-NMR (400 MHz, pyridine-d5)
δ: 7.69 (1H, brs, -NH), 6.00 (1H, brd, J = 15.6 Hz,
H-5), 5.94 (1H, dd, J = 6.4, 15.6 Hz, H-4), 5.50 (2H,
m, H-8, 9), 4.39 (1H, d, J = 7.5 Hz, H-1′), 4.23 (1H,
dd, J = 4.0, 10.2 Hz, H-2′), 3.83 (1H, m, H-6″), 3.77
(1H, m, H-6″), 2.00 (2H, brs, H-6, 7), 1.84 (1H, m,
H-10), 1.26~1.39 (19H, m, H-11~17, 4′~15′), 0.85
(6H, d, J = 7.0 Hz, H-16′, 18);13C-NMR (100 MHz,
pyridine-d5) δ: 175.7 (C-1′), 132.1 (C-5), 132.1 (C-4),
131.2 (C-9), 130.0 (C-8), 105.7 (Glc-C-1″), 78.6
(Glc-C-5″), 78.5 (Glc-C-3″), 75.2 (Glc-C-2″), 72.4
(C-2′), 72.4 (C-3), 71.6 (Glc-C-4″), 70.2 (C-1), 62.7
(Glc-C-6″), 55.7 (C-2), 35.7 (C-3′), 33.0 (C-6), 32.9
(C-7), 32.8 (C-10), 29.6~29.9 (C-11~16, 5′~14′),
25.9 (C-4′), 23.0 (C-17, 15′), 14.3 (C-18, 16′)。以上数据
与文献报道一致[8],故鉴定化合物 7 为大豆脑苷 I。
化合物 8:白色粉末,mp 167~158 ℃(甲醇)。
IR υKBr max (cm−l): 3 420, 1 640, 1 451, 1 370, 1 360, 980。
1H-NMR (400 Hz, CDCl3) δ: 5.17 (2H, dd, J = 8.8, 8.7
Hz, H-7, 23), 5.03 (1H, dd, J = 8.8, 8.7 Hz, H-22),
3.60 (1H, m, H-3), 1.04 (3H, d, J = 6.6 Hz, 21-CH3),
0.87 (3H, d, J = 6.6 Hz, 29-CH3), 0.82 (3H, s, 26-CH3),
0.83 (3H, s, 27-CH3), 0.81 (3H, s, 19-CH3), 0.57 (3H,
中草药 Chinese Traditional and Herbal Drugs 第 43 卷 第 9 期 2012 年 9 月

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s, 18-CH3);13C-NMR (100 Hz, CDCl3) δ: 139.6 (C-8),
138.1 (C-22), 129.5 (C-23), 117.5 (C-7), 71.1 (C-3),
55.9 (C-17), 55.1 (C-14), 51.3 (C-24), 49.5 (C-9), 43.3
(C-13), 40.8 (C-20), 40.3 (C-5), 39.5 (C-12), 38.0
(C-4), 34.2 (C-10), 31.9 (C-25), 31.5 (C-2), 31.2
(C-1), 29.7 (C-6), 28.5 (C-16), 25.4 (C-28), 23.0
(C-15), 21.6 (C-26), 21.1 (C-11), 21.0 (C-21), 19.1
(C-27), 13.0 (C-19), 12.2 (C-29), 12.0 (C-18)。以上数
据与文献报道一致[9],故鉴定化合物 8 为 α-菠甾醇。
化合物 9:白色晶体(甲醇),mp 224~226 ℃,
ESI-MS m/z: 491 [M+Na]+。1H-NMR (400 MHz,
CDCl3) δ: 5.11 (1H, t, J = 6.6 Hz, H-12), 4.51 (1H, dd,
J = 5.6, 3.6 Hz, H-3), 2.01 (3H, s, -COCH3), 1.11 (3H,
s, H-26), 0.96 (3H, s, H-27), 0.89 (3H, d, J = 6.2 Hz,
H-30), 0.86 (3H, d, J = 6.2 Hz, H-29), 0.86 (3H, s,
H-28), 0.81 (3H, s, H-25), 0.77 (3H, s, H-24), 0.74
(3H, s, H-23);13C-NMR (100 MHz, CDCl3) δ: 38.1
(C-1), 23.5 (C-2), 81.0 (C-3), 37.8 (C-4), 55.2 (C-5),
18.2 (C-6), 33.0 (C-7), 39.8 (C-8), 47.7 (C-9), 36.8
(C-10), 23.4 (C-11), 124.5 (C-12), 139.6 (C-13), 42.0
(C-14), 28.7 (C-15), 26.7 (C-16), 33.6 (C-17), 59.1
(C-18), 39.7 (C-19), 39.7 (C-20), 31.2 (C-21), 41.5
(C-22), 28.0 (C-23), 16.8 (C-24), 15.6 (C-25), 16.8
(C-26), 23.1 (C-27), 28.0 (C-28), 17.5 (C-29), 21.4
(C-30), 170.9 (-COCH3), 21.7 (-COCH3)。化合物的波
谱数据与文献报道一致[10],故鉴定化合物 9 为 α-
香树素乙酸酯。
化合物 10:白色粉末,易溶于氯仿。IR、TLC
的 Rf 值及显色行为与 β-谷甾醇对照品一致,与 β-
谷甾醇对照品混合后熔点不下降,故鉴定化合物 10
为 β-谷甾醇。
化合物 11:白色粉末,Libermann-Burchard 反
应呈阳性。ESI-MS m/z: 599 [M+Na]+。IR、TLC 的
Rf值及显色行为与胡萝卜苷对照品一致,与胡萝卜
苷对照品混合后熔点不下降,故鉴定化合物 11 为胡
萝卜苷。
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