楊進(jìn)華,劉紅星,黃初升,陳泓霖,鄭少龍,唐劍耀
(1.廣西師范學(xué)院化學(xué)與材料科學(xué)學(xué)院,廣西 南寧 530001;2.西南民族藥協(xié)同創(chuàng)新中心(廣西師范大學(xué)),廣西 桂林 541001)
異戊烯基黃酮化合物的研究進(jìn)展
楊進(jìn)華,劉紅星?,黃初升1,2,陳泓霖,鄭少龍,唐劍耀
(1.廣西師范學(xué)院化學(xué)與材料科學(xué)學(xué)院,廣西 南寧 530001;2.西南民族藥協(xié)同創(chuàng)新中心(廣西師范大學(xué)),廣西 桂林 541001)
異戊烯基黃酮化合物由于具有抗腫瘤,抗氧化,抗炎,抗骨質(zhì)疏松等生理活性而備受青睞。本文對已分離提取的異戊烯基黃酮化合物的結(jié)構(gòu)特征、生物活性進(jìn)行了初步總結(jié),為異戊烯基黃酮資源的開發(fā)利用提供初步的參考。
異戊烯基;黃酮;生物活性
黃酮類化合物是植物中分布很廣泛的一類化合物,具有廣泛的藥理活性和較低毒性。異戊烯基黃酮化合物是在黃酮母體結(jié)構(gòu)C6-C3-C6上進(jìn)行烷基化的產(chǎn)物,他們主要分布在桑屬(Morus)植物的根、莖和根皮中。研究表明該類化合物是多種中草藥的有效成分,具有抗腫瘤[1-2]、抗艾滋病毒[3]、抗氧化[4]、抑制絡(luò)氨酸酶[5]、抗炎癥[6]、抗骨質(zhì)疏松[7]等作用。因而異戊烯基黃酮化合物具有廣泛的應(yīng)用前景,本文對近年以來分離得到的異戊烯基黃酮進(jìn)行了初步歸納總結(jié)。
1.1 已分離A環(huán)異戊烯基取代[8-15]
Beula.S.J等人從Achyranthes aspera 的種子中分離得到有生物活性的化合物1,通過對接研究實驗證明化合物1是一種有效的單胺氧化酶A的抑制劑,抑制常數(shù)為1.23μM。Ahmed.B.A等人對6位異戊烯基、香葉基、7位羥基、甲氧基、8位異戊烯基香葉基取代的chrysin衍生物進(jìn)行抑制乳腺癌抗藥蛋白ABCG-2的活性測試,通過實驗得到6位異戊烯基和8位異戊烯基取代的化合物3和化合物4對BCRP-R482的抑制IC50分別為(0.29±0.06) μM,(0.89±0.31)μM,而chrysin的抑制率IC50為(4.6±0.5) μM。
1.2 已分離C環(huán)異戊烯基黃酮[16-19]
Ho?ek. J等人對化合物13進(jìn)行了抗氧化和抗炎實驗,實驗得到化合物13對O22-、H2O2、HClO清除IC50分別為(219.0±15.0)μM、(641±31.4)μM、(1.8±0.1)μM,并且測定了ROS在J771A細(xì)胞中含量,當(dāng)加入0.25μM時是空白對照的2.13倍,當(dāng)濃度升至1.25μM時是對照的3.12倍。Hu. X等人從黑桑中分離得到兩種異戊烯基黃酮化合物17和18,實驗證明2種化合物能促進(jìn)脂肪的形成,并對3T3L1細(xì)胞中甘油三酯含量測定當(dāng)分別加入25μM 化合物細(xì)胞中甘油三酯的含量分別為145%±9.97%,317.18%±11.50%。Arung, E. T從菠蘿蜜屬植物的甲醇浸膏中分離提取得到3位異戊烯基木犀草素(化合物20),同時測定其對蘑菇絡(luò)氨酸的抑制率,得到IC50=76.3μM而測得的木犀草素并沒有活性,由此說明3位被異戊烯基取代能增加其活性。
2.1 AB環(huán)雙取代異戊烯基黃酮
Jin.Q從朝鮮淫羊藿的二氯甲烷浸膏中用甲醇提取得到16個單體化合物,其中包含2種AB環(huán)雙取代異戊烯基黃酮化合物43和化合物44,并測定2種化合物對LPS刺激產(chǎn)生的巨噬細(xì)胞RAW264中的NO和IL-1?的抑制作用,通過實驗得到化合物21對LPS刺激產(chǎn)生的NO和IL-1?的抑制率IC50分別為16.8μM、8.8μM,化合物22抑制率IC50分別為19.7μM、8.6μM。
圖1 A環(huán)異戊烯基黃酮化合物結(jié)構(gòu)Fig. 1 The chemical structures of A ring prenly flavones
圖2 C環(huán)異戊烯基黃酮化合物結(jié)構(gòu)Fig.2 The chemical structures of C ring prenly flavones
圖3 AB環(huán)異戊烯基黃酮化合物結(jié)構(gòu)Fig.3 The chemical structures of AB ring prenly flavones
2.2 AC環(huán)雙異戊烯基黃酮[21-23]
Cho.J. K對Morus lhou的莖中分離提取得到黃酮化合物進(jìn)行了?-secretase抑制活性測試,實驗測得化合物45對?-secretase抑制率IC50=3.4μM是其對照化合物的20倍,并通過對比得到3位有異戊烯基取代的黃酮能增加其對?-secretase抑制活性。Arung.E.T從波羅蜜屬木材的甲醇浸膏中分離提取得到9種單體化合物,其中包含3種AC環(huán)雙異戊烯基黃酮化合物化合物45、47、49并分別測定其對B16細(xì)胞黑色素瘤的抑制作用測得抑制率分別為10.7μM、9.2μM、14.2μM,并同無異戊烯基取代黃酮化合物活性進(jìn)行對比得到有異戊烯基取代能增加黃酮化合物的生物活性。
2.3 三及三個以上異戊烯基黃酮[24-26]
Cerqueira.F從Artocarpus elasticus中分離得到8種異戊烯基黃酮化合物,其中包含2種3個異戊烯基取代黃酮化合物60、61,并對上述化合物進(jìn)行抗淋巴癌細(xì)胞增殖的活性測試,測得其對淋巴癌細(xì)胞抑制率IC50分別為(9.21±0.52)μM、(13.70±0.34) μM。
圖4 AC環(huán)異戊烯基黃酮化合物結(jié)構(gòu)Fig.4 The chemical structures of AC ring prenly flavones
圖5 三及三個以上環(huán)異戊烯基黃酮化合物結(jié)構(gòu)Fig.5 The chemical structures of more than 3 prenly flavones
目前國內(nèi)外對天然異戊烯基黃酮化合物從不同的生物活性方面進(jìn)行構(gòu)效關(guān)系的研究,研究表明該類化合物的生物活性與其結(jié)構(gòu)密切相關(guān)。黃酮經(jīng)異戊烯基修飾之后,其脂溶性和對生物膜的親和力增加,很多生理活性被影響。同時,異戊烯基取代位置不同,對不同細(xì)胞表現(xiàn)出不同的活性。本文對已經(jīng)分離異戊烯基黃酮進(jìn)行了初步總結(jié),以期為多甲氧基黃酮的分離、開發(fā)提供參考。
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Advances of Prenly Flavones
YANG Jin-hua, LIU Hong-xing, HUANG Chu-sheng, CHEN Hong-lin, ZHENG Shao-long, TANG jian-yao
(1.Chemistry and Materials Science, Guangxi Teachers’ Education University, Nanning 530001,China; 2.Collaborative Innovation Center of Southwest Ethnic Medicine, Guilin 541001,China)
Prenly f avones were found to have anti-inf ammatory, anti-oxidant, anti-cancer, anti -atherosclerotic and other biological activity. The research progress of structural features, biological activity of the prenly f avones to provide useful references for the research of prenly f avones, were described.
isopentene group; f avone; biological activity
TQ 253.1
A
1671-9905(2015)03-00 -
廣西自然科學(xué)基金(2013GXNSFAAO19041),廣西研究生教育創(chuàng)新計劃項目(20121106030703M02),西南民族藥協(xié)同創(chuàng)新中心資助課題(CICSEM 2013-B6)
楊進(jìn)華 (1989-), 男,安徽安慶人,在讀碩士研究生,研究方向:天然產(chǎn)物研究與開發(fā),E-mail:yjh2319@163.com