Anti-allergic activity of compounds from Kaempferia parviflora
Anti-allergic activity of compounds from Kaempferia parviflora
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DOI：
10.1016/j.jep.2007.10.042
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发表时间：
2008-02-28
影响因子：
5.4
通讯作者：
Kummee, Sopa
中科院分区：
文献类型：
--
作者：
Tewtrakul, Supinya;Subhadhirasakul, Sanan;Kummee, Sopa
小花山奈是姜科植物之一，在泰语中被称为 kra-chai-dam。在泰国传统医学中，据报道，小花山柰粉与酒精的汤剂可以治疗过敏、哮喘、阳痿、痛风、腹泻、痢疾、消化性溃疡和糖尿病。因此，本研究旨在研究该植物的抗过敏物质。通过生物测定引导的分级分离，从小花山柰提取物中分离出七种甲氧基黄酮衍生物 (1-7)，并根据光谱方法对其进行了鉴定。在测试的化合物中，5-羟基-3,7,3,4'-四甲氧基黄酮 (5) 对作为 RBL-2H3 细胞脱粒标记的抗原诱导的 β-己糖胺酶释放具有最高的抗过敏活性，IC50 值为 8.0 μM，其次是 5-羟基-7-甲氧基黄酮 (2，IC50 = 20.6 μM) 和5-羟基-7,4'-二甲氧基黄酮（4，IC50 = 26.0 μM），而其他则表现出中等活性（IC50 = 37.5-66.5 μM）。 7-甲氧基黄酮衍生物的抗过敏活性的结构-活性趋势可总结如下：（1）3'和4'位上的邻位甲氧基取代比仅一个甲氧基化具有更高的活性，（2）3位上的甲氧基化降低了活性，（3）5位上的甲氧基化比羟基化显示出更高的活性。还确定了化合物 2、4 和 5 对离子霉素诱导的 β-氨基己糖苷酶释放的机制。结果表明，化合物2和5抑制细胞脱颗粒的机制主要涉及抑制Ca2+向细胞内流，而化合物4的抑制作用可能部分是由于这种抑制作用。关于小花山奈的抗过敏活性成分，5-羟基-3,7,3',4'-四甲氧基黄酮 (5)、5-羟基7-甲氧基黄酮 (2) 和 5-羟基-7,4'-二甲氧基黄酮 (4) 负责该植物的抗过敏作用。该研究结果支持小花山柰根茎用于治疗过敏和过敏相关疾病的传统用途。 (c) 2007 Elsevier Ireland Ltd. 保留所有权利。
Kaempferia parviflora is one of the plants in the Zingiberaceae family, locally known in Thai as kra-chai-dam. In Thai traditional medicine, the decoction of Kaempferia parviflora powder with alcohol has been reported to cure allergy, asthma, impotence, gout, diarrhea, dysentery, peptic ulcer and diabetes. Therefore, the present study aimed to investigate anti-allergic substances from this plant. Bioassay-guided fractionation led to the isolation of seven methoxyflavone derivatives (1-7) from Kaempferia parviflora extract and they were identified on the basis of spectroscopic methods. Among the compounds tested, 5-hydroxy-3,7,3,4'-tetramethoxyflavone (5) possessed the highest anti-allergic activity against antigen-induced beta-hexosaminidase release as a marker of degranulation in RBL-2H3 cells with an IC50 value of 8.0 mu M, followed by 5-hydroxy-7-methoxyflavone (2, IC50 = 20.6 mu M) and 5-hydroxy-7,4'-dimethoxyflavone (4, IC50 = 26.0 mu M), whereas others showed moderate activities (IC50 = 37.5-66.5 mu M). Structure-activity trends of 7-methoxyflavone derivatives on anti-allergic activity can be summarized as follows: (1) substitution with vicinal methoxyl groups at positions 3' and 4' conferred higher activity than only one methoxylation, (2) methoxylation at position 3 reduced activity and (3) methoxylation at position 5 showed higher activity than hydroxylation. Compounds 2, 4 and 5 were also determined for their mechanisms on ionomycin-induced beta-hexosaminidase release. The results indicated that the mechanism on inhibition of cell degranulation of compounds 2 and 5 mainly involve the inhibition of Ca2+ influx to the cells, whereas that of 4 may be partly due to this inhibition. In regards to the active constituents for anti-allergic activity of Kaempferia parviflora, 5-hydroxy-3,7,3',4'-tetramethoxyflavone (5), 5-hydroxy7-methoxyflavone (2) and 5-hydi-oxy-7,4'-dimethoxyflavone (4) are responsible for anti-allergic effect of this plant. The findings support the traditional use of Kaempferia parviflora rhizomes for treatment of allergy and allergy-related diseases. (c) 2007 Elsevier Ireland Ltd. All rights reserved.