阔叶黄檀心材新黄酮类化学成分研究
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摘要
降香为我国Ⅱ级珍稀濒危保护植物降香黄檀的心材,资源稀缺,价格昂贵。为寻找降香药材替代品,该课题组综合运用硅胶、Sephadex LH-20和半制备高效液相色谱等色谱技术方法,对其同属植物阔叶黄檀心材的70%乙醇提取物进行系统化学成分研究,结果从该植物中分离鉴定出新黄酮类成分16个,包括8个黄檀酚类(1～8)、3个黄檀醌类(9～11)、2个黄檀内酯类(12,13)、2个苯酰苯类(14,15)、1个其他类型新黄酮(16),其中化合物3,7,11为首次从黄檀属植物中分离得到,化合物2,4,5,6,8,14,15为首次从阔叶黄檀中分离得到,且16个新黄酮类成分中有10个与文献报道的降香药材中新黄酮类成分相同。
Dalbergiae Odoriferae Lignum is derived from heartwood of Dalbergia odorifera,which is national Ⅱ level of rare and endangered protective plants in China. Its resources are scarce and its price is high. In order to find substitutes of D. odorifera,the chemical constituents of 70% ethanol extract of heartwood of D. catifolia were systematically studied by using silica gel,Sephadex LH-20 column chromatography,and semi-preparative HPLC. Sixteen neoflavanoids were isolated and identified as eight dalbergiphenols( 1-8),three dalbergiones( 9-11),two dalbergins( 12,13),two benzophenones( 14,15) and one other type neoflavanoids( 16) based on spectroscopic data analyses and/or comparing the spectroscopic data with those in literature. Among them,compounds 3,7 and 11 were isolated from the genus Dalbergia for the first time,and compounds 2,4-6,8,14 and 15 were isolated from the D. latifolia for the first time. Ten neoflavonoids were both discovered from D. latifolia and D. odorifera.
Dalbergiae Odoriferae Lignum is derived from heartwood of Dalbergia odorifera,which is national Ⅱ level of rare and endangered protective plants in China. Its resources are scarce and its price is high. In order to find substitutes of D. odorifera,the chemical constituents of 70% ethanol extract of heartwood of D. catifolia were systematically studied by using silica gel,Sephadex LH-20 column chromatography,and semi-preparative HPLC. Sixteen neoflavanoids were isolated and identified as eight dalbergiphenols( 1-8),three dalbergiones( 9-11),two dalbergins( 12,13),two benzophenones( 14,15) and one other type neoflavanoids( 16) based on spectroscopic data analyses and/or comparing the spectroscopic data with those in literature. Among them,compounds 3,7 and 11 were isolated from the genus Dalbergia for the first time,and compounds 2,4-6,8,14 and 15 were isolated from the D. latifolia for the first time. Ten neoflavonoids were both discovered from D. latifolia and D. odorifera.
引文
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[2]范竹鸣,王佑华,谢瑞芳,等.降香化学成分和药理作用研究进展[J].时珍国医国药,2016,27(10):2478.
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[12]Wu S F,Chang F R S,Wang S Y,et al.Anti-inflammatory and cytotoxic neoflavonoids and benzofurans from Pterocarpus santalinus[J].J Nat Prod,2011,74(5):989.
[13]Umehara K,Nemoto K,Kimijima K,et al.Estrogentic constituents of the heartwood of Dalbergia parviflora[J].Phytochemistry,2008,69(2):546.
[14]Philippe Bissel,Abdesslame Nazih,Rafael Sablong,et al.Stereoselective synthesis of(R)and(S)-4-methoxydalbergione via asymmetric catalytic hydrogenation[J].Org Lett,1999,1(8):1283.
[15]Donnelly B J,Donnelly D M X,O'Sullivan A M,et al.Dalbergia species-Ⅶ:the isolation and structure of melanoxin a new dihydrobenzofuran from Dalbergia melanoxylon guill.and per.(leguminoseae)[J].Tetrahedron,1969,25(18):4409.
[16]Shrestha S P,Narukawa Y,Takeda T.Chemical constituents of nepalese propolis:isolation of new dalbergiones and related compounds[J].J Nat Med,2007,61(1):73.
[17]Kite G C,Green P W C,Veitch N C,et al.Dalnigrin,a neoflavonoid marker for the identification of Brazilian rose wood(dalbergianigra)in CITES enforcement[J].Phytochemistry,2010,71(10):1122.
[18]Wang Wen,Zhu Qixiu,Huang Minghuan,et al.A new compound from Dalbergia odorifera T.Chen[J].Chin Chem Lett,2000,11(11):993.
[19]Pathak V,Shirota O,Sekita S,et al.Antiandrogenic phenolic constituents from Dalbergia cochinchinensis[J].Phytochemistry,1997,46(7):1219.
[20]Shirota O,Pathak V,Sekita S,et al.Phenolic constituents from Dalbergia cochinchinensis[J].J Nat Prod,2003,66(8):1128.
[21]刘荣华,林帅,张普照,等.黄檀属植物新黄酮类化学成分与药理活性研究进展[J].中国中药杂志,2017,42(24):4707.
[22]刘荣华,王定清,林帅,等.阔叶黄檀三萜类化学成分分析[J].中国实验方剂学杂志,2017(20):42.
[23]Liu Rong-hua,Wang Ding-qing,Zhang Pu-zhao,et al.A new diaryl 1,2-diketone from the heartwood of Dalbergia latifolia[J].Nat Prod Res,2018,32(1):91.
[2]范竹鸣,王佑华,谢瑞芳,等.降香化学成分和药理作用研究进展[J].时珍国医国药,2016,27(10):2478.
[3]李雪亮,陈兰英,官紫祎,等.降香新黄酮latifolin对大鼠急性心肌缺血影响及介导Nrf2信号通路机制研究[J].中国中药杂志,2017,42(20):3974.
[4]Sekine N,Ashitani T,Murayama T,et al.Bioactivity of latifolin and its derivatives against termites and fungi[J].J Agric Food Chem,2009,57(13):5707.
[5]中国科学院《中国植物志》编辑委员会.中国植物志[M].北京:科学出版社,1981.
[6]霄迪.东印度珍贵木材阔叶黄檀[J].中国木材,2017(6):19.
[7]Rao M M,Seshadri T R.Components of the heart wood of Dalbergia latifolia[J].Tetrahedron Lett,1963,4(4):211.
[8]Donnelly D M X,Criodain T O,O'Sullivan M.Dalbergia Species:XV.Dalcriodain,a binary neoflavanoid[J].Proc R Ir Acad B,1983,83B:39.
[9]Lee J W,Lee C,Jin Q,et al.Chemical constituents from Belamcanda chinensis and their inhibitory effects on nitric oxide production in RAW 264.7 macrophage cells[J].Arch Pharm Res,2015,38(6):991.
[10]Fullas F,Kornberg L J,Wani M C,et al.Two new aromatic constitutents from the root wood of Aeschynomene mimosifolia[J].JNat Prod,1996,59(2):190.
[11]Chan S,Chang Y,Kuo S.Neoflavonoids from Dalbergia odorifera[J].Phytochemistry,1997,46(5):947.
[12]Wu S F,Chang F R S,Wang S Y,et al.Anti-inflammatory and cytotoxic neoflavonoids and benzofurans from Pterocarpus santalinus[J].J Nat Prod,2011,74(5):989.
[13]Umehara K,Nemoto K,Kimijima K,et al.Estrogentic constituents of the heartwood of Dalbergia parviflora[J].Phytochemistry,2008,69(2):546.
[14]Philippe Bissel,Abdesslame Nazih,Rafael Sablong,et al.Stereoselective synthesis of(R)and(S)-4-methoxydalbergione via asymmetric catalytic hydrogenation[J].Org Lett,1999,1(8):1283.
[15]Donnelly B J,Donnelly D M X,O'Sullivan A M,et al.Dalbergia species-Ⅶ:the isolation and structure of melanoxin a new dihydrobenzofuran from Dalbergia melanoxylon guill.and per.(leguminoseae)[J].Tetrahedron,1969,25(18):4409.
[16]Shrestha S P,Narukawa Y,Takeda T.Chemical constituents of nepalese propolis:isolation of new dalbergiones and related compounds[J].J Nat Med,2007,61(1):73.
[17]Kite G C,Green P W C,Veitch N C,et al.Dalnigrin,a neoflavonoid marker for the identification of Brazilian rose wood(dalbergianigra)in CITES enforcement[J].Phytochemistry,2010,71(10):1122.
[18]Wang Wen,Zhu Qixiu,Huang Minghuan,et al.A new compound from Dalbergia odorifera T.Chen[J].Chin Chem Lett,2000,11(11):993.
[19]Pathak V,Shirota O,Sekita S,et al.Antiandrogenic phenolic constituents from Dalbergia cochinchinensis[J].Phytochemistry,1997,46(7):1219.
[20]Shirota O,Pathak V,Sekita S,et al.Phenolic constituents from Dalbergia cochinchinensis[J].J Nat Prod,2003,66(8):1128.
[21]刘荣华,林帅,张普照,等.黄檀属植物新黄酮类化学成分与药理活性研究进展[J].中国中药杂志,2017,42(24):4707.
[22]刘荣华,王定清,林帅,等.阔叶黄檀三萜类化学成分分析[J].中国实验方剂学杂志,2017(20):42.
[23]Liu Rong-hua,Wang Ding-qing,Zhang Pu-zhao,et al.A new diaryl 1,2-diketone from the heartwood of Dalbergia latifolia[J].Nat Prod Res,2018,32(1):91.
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