太子参内生真菌草酸青霉中1个新的香豆酮类化合物

A new benzofuran from Penicillium oxalicum,an endophytic fungus isolated from Pseudostellaria heterophylla

目的研究太子参Pseudostellaria heterophylla内生真菌草酸青霉Penicillium oxalicum的次级代谢产物。方法采用正、反相硅胶柱色谱,葡聚糖凝胶Sephadex LH-20柱色谱以及制备薄层色谱(pTLC)等色谱技术进行系统分离纯化,采用质谱(MS)、核磁共振(NMR)等波谱学手段对单体化合物进行结构鉴定。结果从草酸青霉发酵产物的醋酸乙酯萃取液中分离鉴定了12个化合物,包括1个香豆酮类化合物5,7-二羟基-2-甲基苯并呋喃-3-羧酸(1)、5个异香豆素类化合物(3R,4R)-(-)-4-hydroxymellein(2)、O-methylmellein(3)、acremonone G(4)、decarboxycitrinone(5)和decarboxyhydroxycitrinone(6),4个没药烷型倍半萜类化合物(7S,11S)-(+)-12-acetoxysydonic acid(7)、(S)-(+)-11-dehydrosydonic acid(8)、sydonic acid(9)和1-hydroxy-boivinianinA(10),2个混源萜类化合物decaturin D(11)和decaturin C(12)。结论化合物1为新化合物,命名为草酸苯并呋喃酸A,化合物2~6、10为首次从草酸青霉中分离得到。

Objective To study the secondary metabolites of Penicillium oxalicum,an endophytic fungus isolated from the medicinal plant Pseudostellaria heterophylla.Methods The secondary metabolites were isolated by silica gel,Sephadex LH-20 column chromatographies,and prep-TLC methods.Their structures were elucidated by using various spectroscopic techniques including HRESIMS and NMR spectra.Results A benzofuran compound 5,7-dihydroxy-2-methylbenzofuran-3-carboxylic acid(1),five isocoumarins including(3 R,4 R)-(-)-4-hydroxymellein(2),O-methylmellein(3),acremonone G(4),decarboxycitrinone(5)and decarboxyhydroxycitrinone(6),four bisabolane-type sesquiterpenoids including(7S,11S)-(+)-12-acetoxysydonic acid(7),(S)-(+)-11-dehydrosydonic acid(8),sydonic acid(9)and 1-hydroxy-boivinianin A(10),as well as two meroterpenoid-type alkaloids decaturin D(11)and decaturin C(12)were isolated.Conclusion Compound 1 is a new benzofuran compound and named as oxafuranone A,while compounds 2—6 and 10 are characterized from P.oxalicum for the first time.