黄檀属植物化学成分和药理活性研究进展

广西中医药大学，广西 南宁 530001

黄檀属DalbergiaLinn植物多为乔木、灌木或木质藤本。该属约100种，主要分布于亚洲、非洲和美洲的热带和亚热带地区。我国有28种，1变种，产西南部、南部至中部[1]。近年该属植物化学成分和药理研究主要集中在印度黄檀(Dalbergiasissoo)、降香(Dalbergiaodorifera)、阔叶黄檀(DalbergialatifoliaRoxb.)等。文献报道从该属植物中提取分离得到黄酮及其苷类、香豆素类、醌类、三萜类等多种活性物质，具有抗氧化、抗炎、抗菌、成骨活性、脑保护作用、止泻等药理作用。笔者就该属植物化学成分及其药理作用的研究予以综述，以期能为该属植物资源的利用提供参考。

1 化学成分

目前，从黄檀属植物中已经发现的化学成分主要有黄酮类及黄酮苷类、香豆素类、醌类、三萜类等化合物。

1.1 黄酮及黄酮苷类化合物 黄酮类化合物广泛分布于植物界，从黄檀属植物中分离得到黄酮类化合物主要有异黄酮类、黄酮类、异黄烷类、查尔酮类及异黄酮苷类。具体见表1～5，图1～5。

表1 黄檀属植物中异黄酮类化合物

编号化合物类型取代基R1R2R3R4R5R6R7文献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 黄檀属植物中黄酮类化合物

表3 黄檀属植物中异黄烷类化合物

编号化合物类型取代基R1R2R3R4R5R6R7文献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 黄檀属植物中查尔酮类化合物

编号化合物类型取代基R1R2R3R4R5R6文献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 黄檀属植物中异黄酮苷类化合物

1.2 香豆素成分 从黄檀属植物中分出4',7-dihydroxy-3'-methoxy-4-phenyl-2H-1-benzopyran-2-one等5个香豆素类化合物。详见表6。

1.3 醌类成分 黄檀属植物中醌类成分有sissoidenone、obtusaquinone等。详见表7。

表7 黄檀属植物中醌类化合物

1.4 酚类成分 黄檀属植物中还含有酚类成分，如(R)-latifolin、(R)-5-O-methyllatifolin和4’-hydroxy-2'-methoxychalcone等。详见表8。

表8 黄檀属植物中酚类化合物

1.5 三萜类成分 从黄酮属植物中分离出5个五环三萜类化合物。详见表9。

表9 黄檀属植物中三萜类化合物

1.6 其他成分 黄檀属植物中还含有其他类成分，有Salicylic acid、β-sitosterol、Mucronulatol等。详见表10。

表10 黄檀属植物中其他类化合物

2 药理作用

2.1 抗氧化作用 Promden等[47]对小花黄檀中提取出来的24个异黄酮类化合物进行抗氧化活性研究，结果发现大豆异黄酮的抗氧化性最强；Huang Xing等[48]对印度黄檀种子不同提取部位的抗氧化性进行研究，结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强，抗氧化性可能与黄酮类化合物。JiangAili等[49]考察降香黄檀叶不同提取部位的体外抗氧化活性研究，结果表明各个提取部位均有不同程度的体外抗氧化能力。Roy Nayan等[50]发现印度黄檀树皮的甲醇提取物比水提物的抗氧化活性更强。Khalid Mohammad等[51]研究发现阔叶黄檀树皮提取物具有显著的抗氧化性。

2.2 抗炎活性 Lee Dong-Sung等[52]对降香黄檀中的苯并呋喃类化合物进行抑制脂多糖诱导小鼠的小胶质细胞BV2研究。结果发现该类化合物能抑制脂多糖刺激小鼠的小胶质细胞BV2中HO-1，诱导型一氧化氮合酶、环氧化酶-2和前列腺素E2的表达，抑制TNF-α和IL-1的产生。Edayadulla等[53]以交叉菜胶诱导大鼠足肿胀模型，比较Dalbergia coromandeliana粗提物和单体化合物抗炎活性，结果发现其粗提物和单体化合物均有很高的抗炎活性。Ganga Rao B等[54]以大鼠足肿胀模型对Dalbergia paniculata 叶的甲醇提取物的体内抗炎活性进行研究，发现其具有很好的抗炎活性。Lee Dong-Sung等[55]对降香黄檀中化学成分TMC对巨噬细胞中由HO-1产生的炎症的抗炎性质进行研究。结果发现TMC能促进Nrf2通路上的抗炎的OH-1的表达从而抑制炎症介质而产生抗炎作用。Wang Juan等[56]研究印度黄檀中的黄酮类化合物对RAW264.7巨噬细胞中脂多糖引起的炎症的抗炎活性，结果发现其中sativanone的抗炎活性最强，作用机制可能是减少一氧化氮的释放和抑制炎症因子TNF-α。

2.3 抗菌活性 Koma Okwute Simon等[57]对黄檀的根材主要成分进行抗菌活性筛选，结果发现桦木酸对大肠杆菌和枯草杆菌较强的作用。Mutai Peggoty等[58]从非洲黑檀茎皮中分离出两个新的3-羟基异黄酮类化合物，活性研究发现均有抗结核分支杆菌的作用。

2.4 成骨活性 Im Nam Kyung等[59]对降香黄檀心材化学成分DMF抑制破骨细胞分化和作用进行研究。结果表明DMF能抑制受体活化剂核因子κ，通过破坏激动蛋白环的形成降低破骨细胞功能，抑制有丝分裂原蛋白激酶信号通路的核转录因子(激动的T细胞、活化T细胞核因子1蛋白(NFATc1)和c-Fos)。KumarPadam等[60]对降香黄酮心材的新黄酮类化合物的抗骨质疏松活性进行研究，共分出8个化合物，颅骨成骨细胞的碱性磷酸酶活性和矿化来评估其活性，发现化合物 1, 3, 5-8有显著的促进新骨形成的作用。 Khedgikar Vikram等[61]用绝经后骨质疏松小鼠模型研究印度黄檀叶和豆荚的正丁醇提取物(BSSF)对骨骼的影响。成年的S-D大鼠切除卵巢后，连续12周口服给BSSF(50和100 mg/kg-1·d-1)或者雌激素。对骨微结构、骨转化标记物、生物力学强度、新骨形成、破骨细胞骨骼表达和再吸收基因标志物进行研究。结果发现，BSSF治疗能提高长骨的骨小梁微构筑和脊椎和股骨的生物力学强度，降低骨转化标记物和骨骼破骨细胞基因的表达以及提高新骨形成和股骨中破骨基因的表达。

2.5 脑保护作用 KulkarniSudhir C等[62]以脑缺血再灌注引发的脑梗死大鼠模型研究阔叶黄檀中黄檀的脑保护活性可能的机制，研究表明阔叶黄檀树皮的甲醇提取物对环氧合酶抑制剂表现出协同作用，其作用机制可能是抑制环氧合酶途径。Li Bohui等[63]研究包括印度黄檀在内的三种代表性的中药治疗心血管疾病(CVD)的作用机制。通过药物的吸收、分布、代谢及排泄(ADME)的结合使用筛选和网络药理学方法，发现其治疗CVD的活性成分和蛋白质靶点。揭示了活性成分和和潜在靶点、疾病和信号系统的关系。

2.6 止泻活性 Chandra Phool等[64]研究印度黄檀叶的乙醇提取物(EDSL)对小鼠腹泻和肠蠕动的保护作用，利用蓖麻油引起的腹泻和硫酸镁引起的腹泻测试对印度黄檀的抗腹泻活性进行评价，结果表明EDSL能显著减少排便量和腹泻情况，能延缓腹泻的发作时间。 Kalaskar M. G[65]用蓖麻油引起腹泻的小鼠模型研究印度黄檀树皮的抗腹泻活性，结果显示其有显著的、剂量依赖性的抗腹泻活性，提取物还能减少小肠炭末推进实验的小肠转运时间，与硫酸阿托品有相同的作用。

2.6 抗糖尿病活性 Pund Kiran V等[66]研究印度黄檀乙醇提取物对地塞米松引起的胰岛素抵抗小鼠的影响，观察小鼠血浆、血液葡萄糖、血浆甘油三酯、肝脏抗氧化酶(LPO, GSH, SOD和过氧化氢酶)等水平，结果显示高剂量组显著地降低血浆葡萄糖、甘油三酯水平和LPO的水平，增强GSH, SOD和过氧化氢酶水平。 Niranjan Pankaj Singh[67]等研究印度黄檀叶乙醇提取物对四氧嘧啶导致糖尿病的小鼠模型的降血糖活性，口服给药，连续21 d给药后，低剂量组血糖水平降低至125 mg/dL，高剂量组降低至104 mg/dL，格列本脲组，比格列本脲的降血糖效果(降低至120 mg/dL)更显著。

2.7 抗生育作用 Verma Hari Prakash等[68]研究印度黄檀叶水提物对雄鼠的形成和生育能力的影响，连续35 d口服给药后，结果发现附睾的精子活力、生存能力和数量显著降低，提取物组血清睾酮水平也显著降低。Vasudeva Neeru等[69]对印度黄檀茎皮乙醇提取物对抗精子形成的影响进行研究，结果发现印度黄檀乙醇提取物对精子的活力和生存能力产生剂量依赖性和时间依赖性的影响，200 mg/kg的乙醇提取物能显著降低睾丸和附睾的重量，附睾中的精子活力和数量也显著降低。

2.8 其他作用 Jaiganesh K P等[70]对 dalbergia spinosa roxb根提取物的利尿活性进行研究，结果发现乙醇提取物能增加尿量和电解质(钠、钾、氯)，效果与强效利尿药呋塞米的效果相当。Choi Chun Whan等[71]对降香黄檀心材甲醇提取物的抗癌成分的研究，结果显示提取物能显著抑制增生期的癌细胞，抗癌活性主要成分是研究黄酮类和酚类化合物。 Hood M. M.[72]对印度黄檀不同提取物(石油醚、四氯化碳、苯和乙醇)的抗蚯蚓蠕虫活性进行研究，结果发现四种提取物有均有抗蠕虫活型，其中四氯化碳提取物的活性最高。

3 小结与展望

通过分析黄檀属植物国内外有关化学成分和药理活性的研究文献，发现黄檀属植物主要的化学成分是黄酮及其苷类化合物，且有着广泛而显著的药理作用，如抗氧化、抗炎、抗菌、成骨活性、脑保护作用、止泻等。从目前的研究来看，对黄檀属研究取得了一定的成果，尤其国外对其研究得比较多，但在国内其化学成分以及药理作用的研究尚不够深入。对生物活性的作用机制及药效物质基础仍未得到较好的阐明。亟待今后对其特色药理作用机制和活性成分进行深入研究，阐明其药效物质基础，一方面可以为黄檀属植物的开发利用提供科学依据，另一方面可为从天然产物中开发新药或药物先导化合物积累经验。

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