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天然活性成分雛菊葉龍膽酮的研究進(jìn)展△

2016-09-25 07:04:37趙維韓華銳趙雅嬋尚志強(qiáng)呂麗娟
中國(guó)現(xiàn)代中藥 2016年5期
關(guān)鍵詞:獐牙菜雛菊龍膽

趙維,韓華銳,趙雅嬋,尚志強(qiáng)*,呂麗娟*

(1.天津農(nóng)學(xué)院 基礎(chǔ)科學(xué)學(xué)院,天津 300384;2.包頭醫(yī)學(xué)院,內(nèi)蒙古 包頭 014060)

天然活性成分雛菊葉龍膽酮的研究進(jìn)展△

趙維1,韓華銳2,趙雅嬋1,尚志強(qiáng)1*,呂麗娟1*

(1.天津農(nóng)學(xué)院 基礎(chǔ)科學(xué)學(xué)院,天津 300384;2.包頭醫(yī)學(xué)院,內(nèi)蒙古 包頭 014060)

雛菊葉龍膽酮;植物分布;藥理活性;進(jìn)展

圖1 雛菊葉龍膽酮結(jié)構(gòu)式

1 雛菊葉龍膽酮在植物中的分布

表1 雛菊葉龍膽酮在植物中的分布

表1(續(xù))

2 制備方法、結(jié)構(gòu)確證及質(zhì)量評(píng)價(jià)方法

雖然雛菊葉龍膽酮在藥用植物中分布廣泛,但是其在植物中的含量比較低。截止目前,有關(guān)雛菊葉龍膽酮的制備方法多為溶劑萃取(或同時(shí)輔以超聲等手段),再借助多種分離介質(zhì),如HP-20樹(shù)脂、大孔吸附樹(shù)脂、硅膠、葡聚糖凝膠以及制備液相色譜、高速逆流色譜(HSCCC)等技術(shù)[56]來(lái)實(shí)現(xiàn)其提取分離和純化。其中HSCCC法作為一種液-液分配色譜技術(shù),無(wú)需固體支撐載體,避免了因不可逆吸附而造成的樣品損失,有著廣闊的應(yīng)用空間。

目前,該化合物的制備仍然局限于從植物中提取分離而制得,未見(jiàn)有關(guān)其生物合成或化學(xué)全合成的報(bào)道。在現(xiàn)有技術(shù)中,劉東鋒等[57]提出自己的制備方法,該方法適用于雛菊葉龍膽酮的產(chǎn)業(yè)化放大。其具體做法:將尖葉假龍膽(G.acuta)以70%~90%丙酮溶液超聲提取,提取液回收試劑經(jīng)大孔樹(shù)脂吸附,分別用40%~50%、70%甲醇溶液洗脫,得粗提物,再用高速逆流色譜儀分離。

自上述藥用植物中制備得到的雛菊葉龍膽酮,其結(jié)構(gòu)確證方法多用紫外光譜(UV)、紅外光譜(IR)、質(zhì)譜(MS)、氫譜(1HNMR)、碳譜(13CNMR)、二維核磁共振譜(2D-NMR)等技術(shù),僅有個(gè)別文獻(xiàn)[58]采用了單晶X射線衍射法(SXRD)。其檢測(cè)及質(zhì)量評(píng)價(jià)多采用HPLC法,少量報(bào)道采用高效液相色譜-電噴霧電離-多級(jí)質(zhì)譜聯(lián)用(HPLC-ESI-MSn)技術(shù)[52]、基于1H-NMR代謝物組學(xué)技術(shù)[59]完成化合物的檢測(cè)分析。

3 藥理活性、作用機(jī)制及應(yīng)用

研究表明,雛菊葉龍膽酮具有廣泛的生物學(xué)活性。

3.1 降血糖作用

Tian等[64]發(fā)現(xiàn),日本獐牙菜(S.japonica)的醇提物具有降血糖作用;紫紅獐牙菜(S.punicea)提取物對(duì)由各因素引起的高血糖均有一定的抑制作用,其中雛菊葉龍膽素通過(guò)抑制G-6-P活性,能明顯地降低空腹血糖,改善口服糖耐量,降低空腹血清胰島素。實(shí)驗(yàn)結(jié)果表明,雛菊葉龍膽素可降低血清總膽固醇(TC)、低密度脂蛋白膽固醇(LDL)和甘油三脂(TG),升高高密度脂蛋白膽固醇(HDL),通過(guò)增強(qiáng)胰島素信號(hào)轉(zhuǎn)導(dǎo),改善胰島素抵抗,增加肝糖原,降低葡萄糖激酶活性,增加葡萄糖-6-磷酸酯酶活性。雛菊葉龍膽素不僅能夠有效地治療Ⅱ型糖尿病,而且可以有效地改善機(jī)體對(duì)胰島素的耐受性[65]。

文莉[66]考察了湖北麥冬[Liriopespicata(Thunb.)Lour.var.proliferaY.T.Ma]多糖與雛菊葉龍膽酮配伍對(duì)STZ小鼠空腹血糖和糖耐量的作用。結(jié)果表明,二者均有降血糖活性,但兩者間無(wú)明顯協(xié)同作用。同時(shí),采用逆轉(zhuǎn)錄-聚合酶鏈反應(yīng)(RT-PCR)技術(shù)探究了雛菊葉龍膽酮的胰島素抵抗機(jī)理。結(jié)果表明,雛菊葉龍膽酮在過(guò)氧化物酶體增殖物激活受體γmRNA(PPARγmRNA)表達(dá)中未見(jiàn)明顯促進(jìn)PPARγmRNA表達(dá)的作用,其降低血糖活性與PPARγ無(wú)明顯關(guān)系。

3.2 抗氧化作用

3.3 抗菌作用

Saeed等[28]發(fā)現(xiàn),雛菊葉龍膽酮對(duì)5種革蘭陽(yáng)性菌(巨大芽孢桿菌、枯草芽孢桿菌、蘇云金芽孢桿菌、藤黃八疊球菌和金黃色葡萄球菌)、4種革蘭陰性菌(大腸桿菌、克雷伯肺炎菌、變形桿菌和假單胞菌)以及黑曲霉等8種真菌均有不同程度的抑制作用。

3.4 抗病毒及保肝作用

雛菊葉龍膽酮體外抗乙肝病毒實(shí)驗(yàn)表明,其對(duì)2215細(xì)胞的乙型肝炎表面抗原(HBsAg)表達(dá)有抑制作用,半數(shù)抑制濃度(IC50)為13 μg·mL-1,選擇指數(shù)(SI)為6.8,而對(duì)2215細(xì)胞DNA無(wú)明顯抑制作用[72-73]。Cao等[74]發(fā)現(xiàn),從川西獐牙菜(S.mussotii)中提取的雛菊葉龍膽酮也具有明顯的乙型肝炎表面抗原HBsAg(IC50>0.98 mM)和乙型肝炎e抗原(HBeAg)(IC50=0.35 mM)作用。

體外毒性及保肝活性實(shí)驗(yàn)表明,雛菊葉龍膽酮具有保護(hù)人肝癌細(xì)胞系HepG2細(xì)胞活性[75],通過(guò)增加谷胱甘肽的含量、減少氫氧自由基[45,47]和明顯地抑制谷丙轉(zhuǎn)氨酶(GPT)的活性[76-77],減輕對(duì)乙酰氨基酚誘導(dǎo)的藥源性HepG2肝細(xì)胞損傷。

3.5 膽堿酯酶抑制作用

3.6 單胺氧化酶抑制作用

單胺氧化酶(MAO)是一種與神經(jīng)系統(tǒng)中生物單胺的代謝有關(guān)的酶。體外實(shí)驗(yàn)發(fā)現(xiàn),雛菊葉龍膽酮是MAO的有效抑制劑,有望在治療抑郁、精神分裂等精神疾病中發(fā)揮作用[5,80-85]。

3.7 心血管系統(tǒng)的作用

武海軍等[86]研究了雛菊葉龍膽酮對(duì)正常大鼠心率及心電圖的影響。結(jié)果表明,大鼠心率隨雛菊葉龍膽酮?jiǎng)┝吭黾佣鴾p慢;P波時(shí)間和P波電壓略有抬高,心房到心室傳導(dǎo)所需時(shí)間(P-R)間期明顯縮短,心室除極和復(fù)極的全過(guò)程所需時(shí)間(Q-T)間期在大劑量組(0.024 mg·kg-1)、中劑量組(0.012 mg·kg-1)延長(zhǎng),而小劑量組(0.006 mg·kg-1)無(wú)明顯變化,心室除極(QRS)時(shí)限隨劑量增加而延長(zhǎng)。

李旻輝等[87]采用維拉帕米作為陽(yáng)性對(duì)照組,研究雛菊葉龍膽酮對(duì)氯化鋇致大鼠心律失常的防治作用。結(jié)果表明,與對(duì)照組相比,3個(gè)劑量組(0.05、0.025、0.0125 mg·kg-1)均使大鼠心律失常發(fā)生時(shí)間推遲,嚴(yán)重程度減輕,并且0.05、0.025 mg·kg-1劑量組心律失常持續(xù)時(shí)間明顯縮短。

3.8 對(duì)缺血性腦損傷的保護(hù)作用

宋慧君等[88]研究雛菊葉龍膽酮對(duì)小鼠永久性、完全性全腦缺血損傷和大鼠彌散性不完全性全腦缺血損傷的保護(hù)作用。結(jié)果表明,雛菊葉龍膽酮可減輕大鼠腦缺血后的腦損傷程度;延長(zhǎng)小鼠斷頭后的張口喘息時(shí)間;降低大鼠腦缺血后的腦指數(shù),說(shuō)明雛菊葉龍膽酮對(duì)缺血性腦損傷具有顯著的腦保護(hù)作用。同時(shí)發(fā)現(xiàn),大鼠腦缺血后,腦內(nèi)MDA含量增加,超氧化物歧化酶(SOD)活力下降,腦內(nèi)谷氨酸(GLu)及γ-氨基丁酸(GABA)含量明顯增加。給予一定劑量雛菊葉龍膽酮后,可顯著升高大鼠腦內(nèi)SOD活力,降低MDA及Glu含量,說(shuō)明雛菊葉龍膽酮的腦保護(hù)作用有抗氧化及減輕興奮毒性損傷機(jī)制的介入。而給藥后使GABA含量顯著降低的確切機(jī)制還有待進(jìn)一步探討。

另外,張劍輝等[89]利用電凝法制作大鼠右側(cè)大腦中動(dòng)脈阻塞(MCAO)模型,證明了口服給藥雛菊葉龍膽酮能改善MCAO缺血后神經(jīng)功能障礙,并縮小腦梗塞面積,減輕相關(guān)腦區(qū)神經(jīng)元損傷程度,顯著抑制大鼠局灶性腦缺血損傷細(xì)胞間黏附分子-1(ICAM-1)表達(dá),上調(diào)缺血周邊區(qū)神經(jīng)元B淋巴細(xì)胞瘤-2(Bcl-2)抗凋亡蛋白的表達(dá)。說(shuō)明雛菊葉龍膽酮對(duì)大鼠局灶性腦缺血損傷有保護(hù)作用,其作用機(jī)制可能與抑制ICAM-1表達(dá)和促進(jìn)Bcl-2表達(dá)有關(guān)。

4 毒性研究

4.1 急性毒性

丁莉等[90]以小鼠為研究對(duì)象,經(jīng)口灌胃方式給藥,通過(guò)急性毒性實(shí)驗(yàn)證明,在實(shí)驗(yàn)期間小鼠未出現(xiàn)明顯中毒癥狀和死亡;小鼠對(duì)雛菊葉龍膽酮最大耐受量(MTD)為15 g·kg-1。表明該化合物安全可靠,可為其制劑開(kāi)發(fā)提供一定的理論依據(jù)。

4.2 遺傳毒性

文莉等[91]以0.9%氯化鈉溶液作為陰性對(duì)照,環(huán)磷酰胺作為陽(yáng)性對(duì)照,通過(guò)小鼠骨髓嗜多染紅細(xì)胞(PCE)微核實(shí)驗(yàn)證明,雛菊葉龍膽酮各組小鼠骨髓嗜多染紅細(xì)胞細(xì)胞微核發(fā)生率明顯低于陽(yáng)性對(duì)照組,且差異有統(tǒng)計(jì)學(xué)意義,而與陰性對(duì)照組比較差異無(wú)統(tǒng)計(jì)學(xué)意義,說(shuō)明雛菊葉龍膽酮對(duì)體細(xì)胞無(wú)明顯的致突變作用。另外,選用已知致突變物二氨基芴、1,8-二羥基蒽醌、敵克松、疊氮化鈉作為陽(yáng)性對(duì)照,二甲基亞砜為陰性對(duì)照,通過(guò)Ames實(shí)驗(yàn)證明,無(wú)論是否加入誘導(dǎo)劑,0.5~5000 μg·mL-1的雛菊葉龍膽酮對(duì)實(shí)驗(yàn)用4種菌株(鼠傷寒沙門(mén)菌組氨酸營(yíng)養(yǎng)缺陷型TA97、TA98、TA100、TA102)所誘發(fā)的回變菌落數(shù)均與自發(fā)回變和陰性對(duì)照相近,與超過(guò)陰性對(duì)照組的2倍才判斷為能導(dǎo)致突變的評(píng)價(jià)標(biāo)準(zhǔn)還有較大距離。

5 展望

綜上所述,雛菊葉龍膽酮主要分布于龍膽科獐牙菜屬(33種)、假龍膽屬(20種)、龍膽屬(7種)植物中。此外,其在龍膽科扁蕾屬(1種)、腺鱗草屬(1種)、蘿藦科娃兒藤屬(1種)和鳶尾科鳶尾屬(1種)植物中也有少量分布。雛菊葉龍膽酮在降血糖、抗氧化、抗菌、抗病毒、抑制膽堿酯酶及單胺氧化酶、保護(hù)心血管系統(tǒng)及缺血性腦損傷等方面具有一定的療效。同時(shí)毒性研究證實(shí),該化合物安全,且沒(méi)有表現(xiàn)出明顯的致突變作用。

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ResearchProgressonBellidifolin

ZHAO Wei1,HANHuarui2,ZHAOYachan1,SHANGZhiqiang1,LYULijuan1

(1.DepartmentofBasicScience,TianjinAgriculturalUniversity,Tianjin300384,China;2.BaotouMedicalCollege,Baotou,InnerMongolia014060,China)

Bellidifolin,a kinds of natural tetraoxygenated xanthone,was mainly distributed among genusSwertia,Gentianella,andGentianain family Gentianaceae and possesses multifarious pharmacological activities,including hypoglycemic,anti-oxidant,anti-bacterial,anti-viral,protecting cardiovascular and cerebral is chemia injuries,etc.In order to provide scientific references for the in-depth study,development and utilization of the compound,this review comprehensively summarizes the distribution,preparation,quality evaluation,pharmacological activities and toxicity studies of bellidifolin.

Bellidifolin;distribution;pharmacological activities;progress

2015-04-25)

國(guó)家自然科學(xué)基金項(xiàng)目(81303306,81160504);天津市應(yīng)用基礎(chǔ)與前沿技術(shù)研究計(jì)劃(15JCQNJC13400);天津市大學(xué)生創(chuàng)新創(chuàng)業(yè)訓(xùn)練計(jì)劃項(xiàng)目(201410061052,201410061159)

*

尚志強(qiáng),博士,講師,研究方向:藥物合成化學(xué),E-mail:shangzq1978@sina.com;呂麗娟,博士,講師,研究方向:藥物分析與晶型藥物研究,E-mail:lv_lijuan@aliyun.com

10.13313/j.issn.1673-4890.2016.5.029

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