Anti-allergic triterpenes isolated from olive milled waste
Anti-allergic triterpenes isolated from olive milled waste
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DOI：
10.1007/s10616-016-0058-z
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发表时间：
2017-01
期刊：
影响因子：
2.2
通讯作者：
Asuka Kishikawa;Yhiya Amen;Kuniyoshi Shimizu
中科院分区：
文献类型：
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作者：
Asuka Kishikawa;Yhiya Amen;Kuniyoshi Shimizu
抗原刺激的嗜碱性粒细胞脱颗粒是速发型超敏反应的过敏机制之一。在之前的一项研究中，由 IgE 交联刺激的大鼠嗜碱性白血病 (RBL-2H3) 细胞的 β-己糖胺酶释放被橄榄磨碎废物 (OMW) 的乙醇提取物特异性抑制。 OMW 是三萜的潜在来源，具有多种生物活性。然而，关于 OMW 中三萜对 β-己糖胺酶释放的影响知之甚少。在这里，我们研究了 OMW 乙醇提取物中的抗过敏三萜，并讨论了其构效关系。我们对 OMW 的乙醇提取物进行活性引导分级分离；由此分离出五种已知的三萜，即山楂酸 (1)、齐墩果酸 (2)、石榴酸 (3)、2-O-乙酰基山楂酸 (4) 和表山楂酸 (5)，以及一种新的三萜，11-氧代山楂酸 (6)。抗过敏测定表明，2-O-乙酰山楂酸 (4) 和 11-氧代-山楂酸 (6) 具有抗过敏活性。考虑到这些三萜的构效关系，C-11 处酮基或 C-2 处乙酰基的存在似乎会影响其抗过敏活性。
The degranulation of basophils stimulated by antigen is one of the allergic mechanisms of immediate hypersensitivity reactions. In a previous study, the β-hexosaminidase release of rat basophilic leukemia (RBL-2H3) cells stimulated by IgE cross-linking was specifically inhibited by ethanol extract of olive milled waste (OMW). OMW is a potential source of triterpenes, which show several biological activities. However, little is known about the effect of triterpenes in OMW on β-hexosaminidase release. Here we investigated anti-allergic triterpenes from the ethanol extract of OMW, and we discuss the structure–activity relationship. We subjected ethanol extract of OMW to activity-guided fractionation; this led to the isolation of five known triterpenes, i.e., maslinic acid (1), oleanolic acid (2), punicanolic acid (3), 2-O-acetylmaslinic acid (4), and epimaslinic acid (5) as well as one new triterpene, 11-oxo-maslinic acid (6). An anti-allergic assay revealed that 2-O-acetylmaslinic acid (4) and 11-oxo-maslinic acid (6) showed anti-allergic activity. Considering the structure–activity relationship of these triterpenes, it appears that the existence of a ketone group at C-11 or an acetyl group at C-2 would influence the anti-allergic activity.