黃檀屬植物化學(xué)成分和藥理活性研究進(jìn)展

廣西中醫(yī)藥大學(xué)，廣西 南寧 530001

黃檀屬DalbergiaLinn植物多為喬木、灌木或木質(zhì)藤本。該屬約100種，主要分布于亞洲、非洲和美洲的熱帶和亞熱帶地區(qū)。我國(guó)有28種，1變種，產(chǎn)西南部、南部至中部[1]。近年該屬植物化學(xué)成分和藥理研究主要集中在印度黃檀(Dalbergiasissoo)、降香(Dalbergiaodorifera)、闊葉黃檀(DalbergialatifoliaRoxb.)等。文獻(xiàn)報(bào)道從該屬植物中提取分離得到黃酮及其苷類(lèi)、香豆素類(lèi)、醌類(lèi)、三萜類(lèi)等多種活性物質(zhì)，具有抗氧化、抗炎、抗菌、成骨活性、腦保護(hù)作用、止瀉等藥理作用。筆者就該屬植物化學(xué)成分及其藥理作用的研究予以綜述，以期能為該屬植物資源的利用提供參考。

1 化學(xué)成分

目前，從黃檀屬植物中已經(jīng)發(fā)現(xiàn)的化學(xué)成分主要有黃酮類(lèi)及黃酮苷類(lèi)、香豆素類(lèi)、醌類(lèi)、三萜類(lèi)等化合物。

1.1 黃酮及黃酮苷類(lèi)化合物 黃酮類(lèi)化合物廣泛分布于植物界，從黃檀屬植物中分離得到黃酮類(lèi)化合物主要有異黃酮類(lèi)、黃酮類(lèi)、異黃烷類(lèi)、查爾酮類(lèi)及異黃酮苷類(lèi)。具體見(jiàn)表1～5，圖1～5。

表1 黃檀屬植物中異黃酮類(lèi)化合物

編號(hào)化合物類(lèi)型取代基R1R2R3R4R5R6R7文獻(xiàn)1biochanin-AⅠHOHHOHHOCH3H[2]2formononetinⅠHOHHHHOCH3H[2]3daidzeinⅠHOHHHHOHH[3]45,7-dihydroxy-2',4',5'-6-tetramethoxyisoflavoneⅠHOHOCH3OHOCH3OCH3OCH3[4]58-O-methylretusinⅠOCH3OHHHHOCH3H[5]6IsotectorigeninsⅠOCH3OHHOHHOHH[7]7(3S)-5,7,3',4'-tetramethoxyisoflavanⅠHOCH3HOCH3OCH3OCH3H[12]8DalspinosinⅠHOHOCH3OHOCH3OCH3H[18]92',7-dihydroxy-4',5'-dimethoxyisoflavoneⅠHOHHHOCH3OCH3OH[21]10(3R)-4'-methoxy-2',3,7-trihydroxyisoflavanoneⅡ[22]11millduroneⅢOCH3OCH3OCH3HHHH[8]12 2',6-dimethoxy-7-hydroxy-4',5'-methylenedioxyisoflavoneⅢOHOCH3OCH3HHHH[8]137-hydroxy-6-methoxy-3',4'methylenedioxyisoflavoneⅢOHHHHHHH[9]14baptigeninⅢOHHHHHHH[9]15 6-hydroxy-2',7-dimethoxy-4',5'-methylenedioxyisoflavoneⅢOCH3OHOCH3HHHH[13]

表2 黃檀屬植物中黃酮類(lèi)化合物

表3 黃檀屬植物中異黃烷類(lèi)化合物

編號(hào)化合物類(lèi)型取代基R1R2R3R4R5R6R7文獻(xiàn)20tectorigeninⅤHOHOCH3HOHHH[2]21vestitolⅤHOHHHOCH3HOH[3]22(3S)-2'-hydroxy-4,7-dimethoxyisoflavanⅤHOCH3HOCH3HHOH[3]237-hydroxy-4-methoxyisoflavoneⅤHOHHOCH3HHH[6]247,8-dihydroxy-4-methoxyisoflavoneⅤOHOHHOCH3HHH[6]257-hydroxy-4,8-dimethoxyisoflavoneⅤOCH3OHHOCH3HHH[6]267-methoxy-2',4'-dihydroxyisoflavanⅤHOCH3HHOHHOH[15]27mucronulatolⅤHOHHHOCH3CH3OCH3[3]

表4 黃檀屬植物中查爾酮類(lèi)化合物

編號(hào)化合物類(lèi)型取代基R1R2R3R4R5R6文獻(xiàn)28(E)-2-(2,4-dihydroxy-5-(3-(3-hydroxy-4-(3-methylbut-2-en-1-yl)phenyl)acryloyl)phenyl)acetaldehydeⅥOHOHCH2CHO(CH3)2HCH2CHC(CH3)2OH[20]294'-hydroxy-2'-methoxychalconeⅥOCH3OHHHHH[40]30isoliquiritigeninⅥHHHOHOHH[3]

表5 黃檀屬植物中異黃酮苷類(lèi)化合物

1.2 香豆素成分 從黃檀屬植物中分出4',7-dihydroxy-3'-methoxy-4-phenyl-2H-1-benzopyran-2-one等5個(gè)香豆素類(lèi)化合物。詳見(jiàn)表6。

1.3 醌類(lèi)成分 黃檀屬植物中醌類(lèi)成分有sissoidenone、obtusaquinone等。詳見(jiàn)表7。

表7 黃檀屬植物中醌類(lèi)化合物

1.4 酚類(lèi)成分 黃檀屬植物中還含有酚類(lèi)成分，如(R)-latifolin、(R)-5-O-methyllatifolin和4’-hydroxy-2'-methoxychalcone等。詳見(jiàn)表8。

表8 黃檀屬植物中酚類(lèi)化合物

1.5 三萜類(lèi)成分 從黃酮屬植物中分離出5個(gè)五環(huán)三萜類(lèi)化合物。詳見(jiàn)表9。

表9 黃檀屬植物中三萜類(lèi)化合物

1.6 其他成分 黃檀屬植物中還含有其他類(lèi)成分，有Salicylic acid、β-sitosterol、Mucronulatol等。詳見(jiàn)表10。

表10 黃檀屬植物中其他類(lèi)化合物

2 藥理作用

2.1 抗氧化作用 Promden等[47]對(duì)小花黃檀中提取出來(lái)的24個(gè)異黃酮類(lèi)化合物進(jìn)行抗氧化活性研究，結(jié)果發(fā)現(xiàn)大豆異黃酮的抗氧化性最強(qiáng)；Huang Xing等[48]對(duì)印度黃檀種子不同提取部位的抗氧化性進(jìn)行研究，結(jié)果表明所有提取物均有抗氧化性，其中乙酸乙酯提取物作用最強(qiáng)，抗氧化性可能與黃酮類(lèi)化合物。JiangAili等[49]考察降香黃檀葉不同提取部位的體外抗氧化活性研究，結(jié)果表明各個(gè)提取部位均有不同程度的體外抗氧化能力。Roy Nayan等[50]發(fā)現(xiàn)印度黃檀樹(shù)皮的甲醇提取物比水提物的抗氧化活性更強(qiáng)。Khalid Mohammad等[51]研究發(fā)現(xiàn)闊葉黃檀樹(shù)皮提取物具有顯著的抗氧化性。

2.2 抗炎活性 Lee Dong-Sung等[52]對(duì)降香黃檀中的苯并呋喃類(lèi)化合物進(jìn)行抑制脂多糖誘導(dǎo)小鼠的小膠質(zhì)細(xì)胞BV2研究。結(jié)果發(fā)現(xiàn)該類(lèi)化合物能抑制脂多糖刺激小鼠的小膠質(zhì)細(xì)胞BV2中HO-1，誘導(dǎo)型一氧化氮合酶、環(huán)氧化酶-2和前列腺素E2的表達(dá)，抑制TNF-α和IL-1的產(chǎn)生。Edayadulla等[53]以交叉菜膠誘導(dǎo)大鼠足腫脹模型，比較Dalbergia coromandeliana粗提物和單體化合物抗炎活性，結(jié)果發(fā)現(xiàn)其粗提物和單體化合物均有很高的抗炎活性。Ganga Rao B等[54]以大鼠足腫脹模型對(duì)Dalbergia paniculata 葉的甲醇提取物的體內(nèi)抗炎活性進(jìn)行研究，發(fā)現(xiàn)其具有很好的抗炎活性。Lee Dong-Sung等[55]對(duì)降香黃檀中化學(xué)成分TMC對(duì)巨噬細(xì)胞中由HO-1產(chǎn)生的炎癥的抗炎性質(zhì)進(jìn)行研究。結(jié)果發(fā)現(xiàn)TMC能促進(jìn)Nrf2通路上的抗炎的OH-1的表達(dá)從而抑制炎癥介質(zhì)而產(chǎn)生抗炎作用。Wang Juan等[56]研究印度黃檀中的黃酮類(lèi)化合物對(duì)RAW264.7巨噬細(xì)胞中脂多糖引起的炎癥的抗炎活性，結(jié)果發(fā)現(xiàn)其中sativanone的抗炎活性最強(qiáng)，作用機(jī)制可能是減少一氧化氮的釋放和抑制炎癥因子TNF-α。

2.3 抗菌活性 Koma Okwute Simon等[57]對(duì)黃檀的根材主要成分進(jìn)行抗菌活性篩選，結(jié)果發(fā)現(xiàn)樺木酸對(duì)大腸桿菌和枯草桿菌較強(qiáng)的作用。Mutai Peggoty等[58]從非洲黑檀莖皮中分離出兩個(gè)新的3-羥基異黃酮類(lèi)化合物，活性研究發(fā)現(xiàn)均有抗結(jié)核分支桿菌的作用。

2.4 成骨活性 Im Nam Kyung等[59]對(duì)降香黃檀心材化學(xué)成分DMF抑制破骨細(xì)胞分化和作用進(jìn)行研究。結(jié)果表明DMF能抑制受體活化劑核因子κ，通過(guò)破壞激動(dòng)蛋白環(huán)的形成降低破骨細(xì)胞功能，抑制有絲分裂原蛋白激酶信號(hào)通路的核轉(zhuǎn)錄因子(激動(dòng)的T細(xì)胞、活化T細(xì)胞核因子1蛋白(NFATc1)和c-Fos)。KumarPadam等[60]對(duì)降香黃酮心材的新黃酮類(lèi)化合物的抗骨質(zhì)疏松活性進(jìn)行研究，共分出8個(gè)化合物，顱骨成骨細(xì)胞的堿性磷酸酶活性和礦化來(lái)評(píng)估其活性，發(fā)現(xiàn)化合物 1, 3, 5-8有顯著的促進(jìn)新骨形成的作用。 Khedgikar Vikram等[61]用絕經(jīng)后骨質(zhì)疏松小鼠模型研究印度黃檀葉和豆莢的正丁醇提取物(BSSF)對(duì)骨骼的影響。成年的S-D大鼠切除卵巢后，連續(xù)12周口服給BSSF(50和100 mg/kg-1·d-1)或者雌激素。對(duì)骨微結(jié)構(gòu)、骨轉(zhuǎn)化標(biāo)記物、生物力學(xué)強(qiáng)度、新骨形成、破骨細(xì)胞骨骼表達(dá)和再吸收基因標(biāo)志物進(jìn)行研究。結(jié)果發(fā)現(xiàn)，BSSF治療能提高長(zhǎng)骨的骨小梁微構(gòu)筑和脊椎和股骨的生物力學(xué)強(qiáng)度，降低骨轉(zhuǎn)化標(biāo)記物和骨骼破骨細(xì)胞基因的表達(dá)以及提高新骨形成和股骨中破骨基因的表達(dá)。

2.5 腦保護(hù)作用 KulkarniSudhir C等[62]以腦缺血再灌注引發(fā)的腦梗死大鼠模型研究闊葉黃檀中黃檀的腦保護(hù)活性可能的機(jī)制，研究表明闊葉黃檀樹(shù)皮的甲醇提取物對(duì)環(huán)氧合酶抑制劑表現(xiàn)出協(xié)同作用，其作用機(jī)制可能是抑制環(huán)氧合酶途徑。Li Bohui等[63]研究包括印度黃檀在內(nèi)的三種代表性的中藥治療心血管疾病(CVD)的作用機(jī)制。通過(guò)藥物的吸收、分布、代謝及排泄(ADME)的結(jié)合使用篩選和網(wǎng)絡(luò)藥理學(xué)方法，發(fā)現(xiàn)其治療CVD的活性成分和蛋白質(zhì)靶點(diǎn)。揭示了活性成分和和潛在靶點(diǎn)、疾病和信號(hào)系統(tǒng)的關(guān)系。

2.6 止瀉活性 Chandra Phool等[64]研究印度黃檀葉的乙醇提取物(EDSL)對(duì)小鼠腹瀉和腸蠕動(dòng)的保護(hù)作用，利用蓖麻油引起的腹瀉和硫酸鎂引起的腹瀉測(cè)試對(duì)印度黃檀的抗腹瀉活性進(jìn)行評(píng)價(jià)，結(jié)果表明EDSL能顯著減少排便量和腹瀉情況，能延緩腹瀉的發(fā)作時(shí)間。 Kalaskar M. G[65]用蓖麻油引起腹瀉的小鼠模型研究印度黃檀樹(shù)皮的抗腹瀉活性，結(jié)果顯示其有顯著的、劑量依賴(lài)性的抗腹瀉活性，提取物還能減少小腸炭末推進(jìn)實(shí)驗(yàn)的小腸轉(zhuǎn)運(yùn)時(shí)間，與硫酸阿托品有相同的作用。

2.6 抗糖尿病活性 Pund Kiran V等[66]研究印度黃檀乙醇提取物對(duì)地塞米松引起的胰島素抵抗小鼠的影響，觀察小鼠血漿、血液葡萄糖、血漿甘油三酯、肝臟抗氧化酶(LPO, GSH, SOD和過(guò)氧化氫酶)等水平，結(jié)果顯示高劑量組顯著地降低血漿葡萄糖、甘油三酯水平和LPO的水平，增強(qiáng)GSH, SOD和過(guò)氧化氫酶水平。 Niranjan Pankaj Singh[67]等研究印度黃檀葉乙醇提取物對(duì)四氧嘧啶導(dǎo)致糖尿病的小鼠模型的降血糖活性，口服給藥，連續(xù)21 d給藥后，低劑量組血糖水平降低至125 mg/dL，高劑量組降低至104 mg/dL，格列本脲組，比格列本脲的降血糖效果(降低至120 mg/dL)更顯著。

2.7 抗生育作用 Verma Hari Prakash等[68]研究印度黃檀葉水提物對(duì)雄鼠的形成和生育能力的影響，連續(xù)35 d口服給藥后，結(jié)果發(fā)現(xiàn)附睪的精子活力、生存能力和數(shù)量顯著降低，提取物組血清睪酮水平也顯著降低。Vasudeva Neeru等[69]對(duì)印度黃檀莖皮乙醇提取物對(duì)抗精子形成的影響進(jìn)行研究，結(jié)果發(fā)現(xiàn)印度黃檀乙醇提取物對(duì)精子的活力和生存能力產(chǎn)生劑量依賴(lài)性和時(shí)間依賴(lài)性的影響，200 mg/kg的乙醇提取物能顯著降低睪丸和附睪的重量，附睪中的精子活力和數(shù)量也顯著降低。

2.8 其他作用 Jaiganesh K P等[70]對(duì) dalbergia spinosa roxb根提取物的利尿活性進(jìn)行研究，結(jié)果發(fā)現(xiàn)乙醇提取物能增加尿量和電解質(zhì)(鈉、鉀、氯)，效果與強(qiáng)效利尿藥呋塞米的效果相當(dāng)。Choi Chun Whan等[71]對(duì)降香黃檀心材甲醇提取物的抗癌成分的研究，結(jié)果顯示提取物能顯著抑制增生期的癌細(xì)胞，抗癌活性主要成分是研究黃酮類(lèi)和酚類(lèi)化合物。 Hood M. M.[72]對(duì)印度黃檀不同提取物(石油醚、四氯化碳、苯和乙醇)的抗蚯蚓蠕蟲(chóng)活性進(jìn)行研究，結(jié)果發(fā)現(xiàn)四種提取物有均有抗蠕蟲(chóng)活型，其中四氯化碳提取物的活性最高。

3 小結(jié)與展望

通過(guò)分析黃檀屬植物國(guó)內(nèi)外有關(guān)化學(xué)成分和藥理活性的研究文獻(xiàn)，發(fā)現(xiàn)黃檀屬植物主要的化學(xué)成分是黃酮及其苷類(lèi)化合物，且有著廣泛而顯著的藥理作用，如抗氧化、抗炎、抗菌、成骨活性、腦保護(hù)作用、止瀉等。從目前的研究來(lái)看，對(duì)黃檀屬研究取得了一定的成果，尤其國(guó)外對(duì)其研究得比較多，但在國(guó)內(nèi)其化學(xué)成分以及藥理作用的研究尚不夠深入。對(duì)生物活性的作用機(jī)制及藥效物質(zhì)基礎(chǔ)仍未得到較好的闡明。亟待今后對(duì)其特色藥理作用機(jī)制和活性成分進(jìn)行深入研究，闡明其藥效物質(zhì)基礎(chǔ)，一方面可以為黃檀屬植物的開(kāi)發(fā)利用提供科學(xué)依據(jù)，另一方面可為從天然產(chǎn)物中開(kāi)發(fā)新藥或藥物先導(dǎo)化合物積累經(jīng)驗(yàn)。

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