桔梗中三萜皂苷類化學(xué)成分研究進(jìn)展

1、基金項目:國家自然科學(xué)基金資助項目(30772728作者簡介:郭文杰,男,碩士研究生*通訊作者:許旭東,男,副研究員,博士 Te:l (01062890291 E-m ai:l xdxui m p l ad 1ac 1cn #綜 述#桔梗中三萜皂苷類化學(xué)成分研究進(jìn)展郭文杰,許旭東*,魏建和,楊峻山(中國醫(yī)學(xué)科學(xué)院-中國協(xié)和醫(yī)科大學(xué)藥用植物研究所,北京100094摘要:目的 為深入研究和開發(fā)利用桔梗提供科學(xué)依據(jù),并對其研究開發(fā)前景進(jìn)行探討。方法 通過查閱近10年來關(guān)于桔梗研究的文獻(xiàn),對桔梗主要活性成分桔梗皂苷的化學(xué)結(jié)構(gòu)、藥理活性進(jìn)行了系統(tǒng)的總結(jié)。結(jié)果 目前已知桔梗中皂苷類成分共有40多種,桔梗皂

2、苷具有抗炎、保肝、抗癌、降血糖等藥理活性。結(jié)論 桔梗作為一種藥食兩用的植物,具有廣闊的開發(fā)應(yīng)用前景。關(guān)鍵詞:桔梗;三萜皂苷;藥理活性中圖分類號:R 28411 文獻(xiàn)標(biāo)識碼:A 文章編號:1001-2494(200811-0801-04 桔梗為桔梗科多年生植物桔梗P l atycodon grand i f l oru m (Jacp 1A 1DC 1的干燥根,又名四葉菜、土人參、苦梗菜等。廣泛分布于我國、朝鮮半島和日本;在我國東北和華北地區(qū),桔梗被廣泛種植,資源豐富。桔梗性微溫,味苦、辛、平,歸肺經(jīng),有開宣肺氣,祛痰排膿之功效,常用于外感咳嗽、咳痰不清、咽喉腫痛、胸悶腹脹、痢疾腹痛、血淤水腫、

3、癃閉等癥,系常用中藥1-3;桔梗又是一種很好的保健和功能食品?，F(xiàn)將近10年來桔梗的三萜皂苷類化學(xué)成分、藥理學(xué)等方面的研究進(jìn)展進(jìn)行總結(jié),為深入研究和開發(fā)利用桔梗提供科學(xué)依據(jù)。1 三萜皂苷類化學(xué)成分研究自20世紀(jì)50年代起,各國學(xué)者對桔梗中的化學(xué)成分進(jìn)行了系統(tǒng)的研究。發(fā)現(xiàn)其主要的生物活性成分為三萜皂苷,目前從桔梗中共分離得到了45個三萜皂苷類化學(xué)成分(表1,根據(jù)桔梗三萜皂苷的苷元類型分為遠(yuǎn)志酸(po l yga l ac ic aci d類;桔梗皂苷元(platycodi g en i n衍生物,也稱為桔梗酸(p latycod i c ac i d類和桔梗二酸(platycodi g en i

4、c acid衍生物3種結(jié)構(gòu)類型4,其糖基多連在C3或C28。桔梗皂苷元母核的化學(xué)結(jié)構(gòu)見圖1 。圖1 桔梗皂苷元母核的化學(xué)結(jié)構(gòu)F i g 11 Structure o f platycod i genin此外,桔梗中還含大量的多糖以及甾體(A -菠菜甾、v 7-豆甾烯醇、B -谷甾醇等,脂肪油、脂肪酸、氨基酸、蛋白質(zhì)、生物堿、揮發(fā)油等化學(xué)成分1,23-25。2 三萜皂苷的藥理學(xué)研究現(xiàn)代藥理學(xué)研究表明,桔梗的三萜皂苷類化學(xué)成分具有抗炎、祛痰、保肝、降血糖、抑制脂肪吸收、抗氧化、抗菌、抗腫瘤等廣泛的藥理作用26。211 抗炎止痛作用桔梗皂苷能夠抑制前列腺素E 通路和拮抗LPS 誘導(dǎo)的小鼠腹膜巨噬細(xì)胞

5、(M NO 生成量增加,從而對各種炎癥顯示有較強(qiáng)的抗炎作用27。結(jié)果顯示,桔梗皂苷濃度為10mm o l #L -1和30mm o l #L -1時,能抑制大鼠促癌物12-O -十四烷酰佛波醇-13-乙酯(TPA 誘導(dǎo)的腹腔巨噬細(xì)胞中PG E 2產(chǎn)生28。212 祛痰作用桔梗有促進(jìn)支氣管黏膜分泌從而有祛痰的作用29。體外藥理學(xué)研究表明,桔梗皂苷D 和桔梗皂苷D 3均能增加SD 大鼠氣管上皮金黃倉鼠細(xì)胞(RTSE 細(xì)胞黏蛋白的分泌。體外實驗中,桔梗皂苷D 和桔梗皂苷D 3的質(zhì)量濃度為200m g #L -1時S D 大鼠氣管上皮細(xì)胞(rat tracheat surpace ep ithe -l

6、i a l cells ,RT SE 細(xì)胞黏蛋白的分泌分別增加25217%和37012%;在體內(nèi)實驗中,20mg #L -1的桔梗皂苷D 3對大鼠黏蛋白釋放的增加作用比質(zhì)量濃度均為200m g #L -1的ATP 和氨溴索的作用更強(qiáng)27。213 保肝作用桔梗皂苷類成分具有抗肝纖維化,抗肝脂質(zhì)過氧化,保護(hù)肝細(xì)胞,促進(jìn)肝臟的物質(zhì)和能量代謝加速肝損傷恢復(fù),改善肝臟微循環(huán),抑制肝腫瘤細(xì)胞等作用30。桔梗中皂苷類成分能抑制四氯化碳誘導(dǎo)的肝毒性和其所導(dǎo)致的肝炎和肝部腫大,試驗發(fā)現(xiàn),喂食桔梗皂苷100m g #kg -1的小鼠其血清中丙氨酸轉(zhuǎn)氨酶(ALT 和天門冬酸氨基轉(zhuǎn)移酶(AST 是表1桔梗中三萜皂苷成

7、分Tab11Saponi ns i n P lat y codon grandifloru m(Jacp1A1DC1No1N a m e CatSub1R2R6R7Re f11P l a t ycodi n D A G l u H A ra2-1Rha4-1Xy l3-1Ap i5 2P l a t ycodi n A A G l u Ara2-1Rha(2-OA c4-1Xy l3-1A pi H6 3P l a t ycodi n B A G l u Ara2-1Rha(3-OA c4-1Xy l3-1A pi H6 4Deapi o-pl a t ycodi n D A G l u Ar

8、a2-1Rha4-1Xyl H7 5P l a t ycodi n D2A Am i Ara2-1Rha4-1Xyl3-1Api H8 62d-O-acet y l pl atycodi n D2A Am i Ara2-1Rha(2-OA c4-1Xy l3-1A pi H8 73d-O-acet y l pl atycodi n D2A Am i Ara2-1Rha(3-OA c4-1Xy l3-1A pi H8 8P l a t ycodi n D3A Gen Ara2-1Rha4-1Xyl3-1Api H9 9Deapi o-pl a t ycodi n D3A Gen Ara2-1Rh

9、a4-1Xyl H7 10P l a t ycodi n E A Gen6-1G lc Ara2-1Rha4-1Xyl3-1Api H10 11P l a t ycodi n G1A Gen6-1G lc Ara2-1Rha4-1Xyl H10 12P l a t ycodi n G2A Gen6-1G lc Ara2-1Rha4-1Xyl H10 133-O-B-D-g l ucopyranosyl pl a t ycodi g e ni n m e t hy l ester A G l u C H3H11 143-O-B-D-l a m i n ari bi osy l pl a t yc

10、ogeni n m e t hy l ester A Am i C H3H11 153-O-B-D-genti obi osy l plat ycodi g e n i n m e t hy l ester A Gen C H3H11 16P l a t ycogenic ac i d A B H H H12 17P l a t ycogenic ac i d B C H H OH12 18M e t hy-l p l at y coge nate A D G l u Ara2-1Rha4-1Xyl3-1Api H13 19M e t hy-l2-O-m ethy l plat y c og

11、e nate A E G l u Ara2-1Rha4-1Xyl3-1Api H13 20D i m ethy-l3-O-B-D-g l u copy ra nosy l pl atycogena t e A D G l u C H3H1421D i m e t hy-l2-O-m e t hy-l3-O-B-D-g l ucopy ra nosy l plat y c og e nate A E G l u C H3H1422P l a t yconic ac i d A lact one J G l u Ara2-1Rha4-1Xyl3-1Api-15 23D-gl ucopy ra no

12、sy l pl atycogeni n A lacto ne m e t hy l ester J G l u C H3-15 24P ol yga l ac i n D G G l u Ara2-1Rha4-1Xyl3-1Api H16 252d-O-acet y l po l yga l ac i n D G G l u Ara2-1Rha(2-OA c4-1Xy l3-1A pi H16 263d-O-acet y l ace t y l pygalaci n D G G l u Ara2-1Rha(3-OA c4-1Xy l3-1A pi H16 27P ol yga l ac i n

13、 D2G Am i Ara2-1Rha4-1Xyl3-1Api H16 282d-O-aeet y l po l yga l ae i n D2G Am i Ara2-1Rha(2-OA c4-1Xy l3-1A pi H16 293d-O-aeet y l po l yga l ae i n D2G Am i Ara2-1Rha4-1Xyl H16 30P l a t ycos i de A G G l u C H3H17 31P l a t ycos i de B G Am i Ara2-1Rha(3-OA c4-1Xy l H17 32P l a t ycos i de C G Gen

14、Ara2-1Rha4-1Xyl3-1Api H18 33P l a t ycos i de D G G l u Ara2-1Rha(2-OA c4-1Xy l H18 34P l a t ycos i de G3G G l u Ara2-1Rha4-1Xyl3-1Api H18 35M e t hy-l3-O-B-D-g l ueopy ra nosy l po l yga l aeate G G l u C H3H18 36M e t hy-l3-O-B-l a m i nari bi osyl po l yga l aea t e G Gen C H3H10 37P l a t ycoge

15、nic-ac i d C H H H OH13 38P l a t ycodi n H G Gen Ara2-1Rha4-1Xyl H19 39P l a t ycodi n I G G l c6-1G l c6-1G lc Ara2-1Rha4-1Xyl H19 40P l a t ycodi n J G G l u Ara2-1Rha4-1Xyl H19 41P l a t ycodi n K A Am i H H19 42P l a t ycodi n L A Gen H H19 43Deapi o-pl a t ycodi n E A Gen6-1G l u Ara2-1Rha(2-O

16、A c4-1Xy l H20 44P l a t ycodi n F I G l u Ara2-1Rha H21 4516-Oxo-p l at y co d i n D F G l u-P ra n Api1-3Xyl1-4Rha1-2Ara H22未喂食桔梗皂苷小鼠血清中的011倍;同時桔?？傇碥者€能抑制a l pha-肌動蛋白(al pha-S M A的上升31;桔梗總皂苷能阻斷肝藥酶對乙酰氨基酚的生物激活從而起到保護(hù)對乙酰氨基酚引起的肝損傷的作用32。214降血糖作用桔梗能夠明顯降低肥胖型和瘦型的Zucker大鼠的血漿中的甘油三酸酯的濃度,桔梗還能夠降低膽固醇和增加血漿中胰島素的含量;

17、并能夠降低餐后葡萄糖的含量。桔?？梢允刮故?周后肥胖Zucker大鼠血漿中的葡萄糖的轉(zhuǎn)運蛋白4 (G LUT4的蛋白水平有明顯的上升33。215對脂肪代謝的研究桔梗水提取物能抑制三油酸甘油酯與卵磷脂混合形成的乳膠微粒分解34。桔?？傇碥站哂幸种埔戎久富钚?減少對食物中脂肪的吸收,從而減輕肥胖35。桔梗能顯著降低高脂血癥大鼠血清和肝臟脂肪濃度,顯著降低血清和肝臟中總膽固醇和甘油三酯的濃度,降低低密度脂蛋白(LDL和升高高密度脂蛋白(HDL的濃度,同時桔梗組的動脈硬化指標(biāo)也較模型組低36。桔?？傇碥湛墒挂戎久傅幕钚砸种圃?117%水平以下;桔梗皂苷D、桔梗皂苷A、桔梗皂苷C可使其活性分別抑制在

18、3148%,313%,512%水平37。大劑量(200 mg#kg-1#d-1的桔梗總皂苷對胰脂肪酶的降低作用極其顯著(P<0101,遠(yuǎn)超過陽性藥物絞股藍(lán)的作用(P<0105,并且對其余的HDL-C,LDL-C等次要因素的影響也在陽性藥物之上,這主要是由于桔?？傇碥蘸懈鞣N降脂作用的苷元從而對外源性膽固醇具有很強(qiáng)的清除作用38。216對中樞神經(jīng)系統(tǒng)的作用桔梗皂苷D在011L g#g-1的劑量下腹腔內(nèi)、腦室內(nèi)和鞘內(nèi)注射對小鼠甩尾、扭體和福爾馬林實驗有劑量依賴性的抗傷害性感受作用。同時研究還得出桔梗皂苷D作用于神經(jīng)中樞,與去甲腎上腺素和5-羥色胺下行通路有關(guān)39。217抗氧化作用桔?？?/p>

19、皂苷可以抑制酪氨酸酶的活性,在質(zhì)量濃度為1g#L-1時,總皂苷抑制率達(dá)388%,其中桔梗皂苷D抑制酪氨酸酶的活性最強(qiáng),在質(zhì)量濃度為1g#L-1時,其抑制率達(dá)56217%40。218抗菌的協(xié)同作用桔梗單味藥無抗菌作用,甘草單味藥抗菌活性較差,桔梗與甘草配伍,其具有顯著的抑菌作用,復(fù)方水提取液達(dá)到一定的濃度時,還具有殺菌的作用。其抗菌作用的機(jī)制還有待進(jìn)一步的深入研究41。219抗腫瘤作用桔梗皂苷中去芹菜糖桔梗皂苷E具有抑制S K-OV-3, A549、S K-M EL-2等腫瘤細(xì)胞增殖的作用20。此外,桔梗三萜皂苷類化學(xué)成分還具有鎮(zhèn)咳、抗?jié)儭⒔笛獕?、擴(kuò)張血管、解熱鎮(zhèn)痛、鎮(zhèn)靜、抗膽堿、促進(jìn)膽酸分泌

20、等藥理作用26。3展望桔梗作為一種藥食兩用的植物,資源豐富,三萜皂苷類為其主要化學(xué)成分,生物活性多樣,幾無毒副作用,在臨床上具有廣泛用途和良好療效,是一種很具開發(fā)潛力的常用中藥。近年來,隨著對桔梗研究的深入,新的三萜皂苷類化合物不斷被發(fā)現(xiàn),并發(fā)現(xiàn)其有顯著的抗癌活性。因此,桔梗在新藥和開發(fā)保健食品兩個方面均具有很好的開發(fā)前景。但目前對桔梗的藥理活性研究尚不夠深入,更缺乏在生物活性研究的指導(dǎo)下對其活性成分的研究,所以有必要對桔梗在藥理學(xué)、天然藥物化學(xué)和保健食品等方面進(jìn)行深入系統(tǒng)的研究,確定桔梗的生物活性的物質(zhì)基礎(chǔ),為桔梗的可持續(xù)開發(fā)和利用提供科學(xué)依據(jù)。REFERENCES1GAO W Y,L I

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