降香檀心材化学成分及抗炎活性研究

Chemical Constituents and Anti-inflammatory Activity from Heartwood of Dalbergia odorifera

采用硅胶柱、反相C18及半制备HPLC等柱色谱方法对降香檀心材95%乙醇提取物进行分离纯化,利用紫外、质谱及核磁共振谱等方法和文献数据对比鉴定化合物的结构。从降香檀心材中分离得到了19个化合物,包括4个倍半萜类化合物和15个黄酮类化合物,分别鉴定为3'-hydoxymelanettin(1),sativanone(2),pinocembrin(3),6aR,11aR-medicarpin(4),3'-hydroxy-2,4,5,-trimethoxy dalbergiquinol(5),rel-(3S,6R,7S)-3,7,11-trimethyl-3,6-epoxy-1,10-dodecadien-7-ol(6),rel-(3R,6R,7S)-3,7,11-trimethyl-3,7-epoxy-1,10-dodecadien-6-ol(7),7,3',5'-trihydroxyflavanone(8),5,7-dihydroxy-2',4'-dimethoxyisoflavanone(9),R(+)-4-methoxydalbergione(10),nerolidol(11),6-methyl-2-(5-methyl-5-vinyltetrahydrofuran-2-yl)hept-5-en-2-ol(12),bolusanthin IV(13),4-methoxymedicarpin(14),5,7-dihydroxy-2',3',4'-trimethoxyisoflavanone(15),5,7-dihydroxy-4'-methoxyisoflavanone(16),acacetin(17),7-methoxy-3',4'-dimethoxyisoflavanone(18),(6aR,11aR)-variabiin(19)。化合物8~13,15~18为首次从降香檀心材中分离鉴定得到。同时,对化合物1~19抑制NO产生活性筛选,发现化合物1~3、10、15和18对LPS诱导RAW 264.7细胞NO生成具有较强的抑制活性,IC50<50μM,且以化合物2和3活性最强,IC50值分别为(34.9±5.4)和(22.5±2.7)μM。

The constituents were isolated and purified from 95% ethanolic extract of Dalbergia odorifera by silica gel chromatography and HPLC repeatedly,and the structures were identified by spectra analysis and comparison of literature data. Nineteen compounds were isolated from the heartwood of Dalbergia odorifera including four sesquiterpenoids and fifteen flavonoids. The structures were identified as 3＇-hydoxymelanettin（ 1）,sativanone（ 2）,pinocembrin（ 3）,6 aR,11 aR-medicarpin（4）,3＇-hydroxy-2,4,5,-trimethoxydalbergiquinol（5）,rel-（3 S,6 R,7 S）-3,7,11-trimethyl-3,6-epoxy-1,10-dodecadien-7-ol（ 6）,rel-（ 3 R,6 R,7 S）-3,7,11-trimethyl-3,7-epoxy-1,10-dodecadien-6-ol（ 7）,7,3＇,5＇-trihydroxyflavanone（8）,5,7-dihydroxy-2＇,4＇-dimethoxyisoflavanone（ 9）,R（ ＋）-4-methoxydalbergione（ 10）,nerolidol（11）,6-methyl-2-（5-methyl-5-vinyltetrahydrofuran-2-yl） hept-5-en-2-ol（12）,bolusanthin IV（13）,4-methoxymedicarpin（14）,5,7-dihydroxy-2＇,3＇,4＇-trimethoxyisoflavanone（15）,5,7-dihydroxy-4＇-methoxyisoflavanone（16）,acacetin（17）,7-methoxy-3＇,4＇-dimethoxyisoflavanone（18） and（6 aR,11 aR）-variabiin（19）,respectively. Compounds 8-13 and 15-18 are obtained from Dalbergia odorifera for the first time. Inhibitory effects of the isolated compounds 1-19 onthe LPS-induced NO production in RAW 264. 7 cells were also evaluated and compounds 1-3,10,15 and 18 showed good inhibitory activities. The IC50 value of compounds 2 and 3 were（34. 9 ± 5. 4）,（22. 5 ± 2. 7） μM,respectively.