真菌Pleosporales sp.中的萘醌和羧酸类衍生物  

Naphthoquinone and carboxylic acid derivatives from the fungus Pleosporales sp.

作　　者：戚思远 张丽花 郝轶男 胡友财 柏健 QI Si-yuan;ZHANG Li-hua;HAO Yi-nan;HU You-cai;BAI Jian(Key Laboratory of Bioactive Substance and Function of Natural Medicines,Institute of Materia Medica,Chinese Academy of Medical Sciences and Peking Union Medical College,Beijing 100050,China)

机构地区：[1]中国医学科学院、北京协和医学院药物研究所,天然药物活性物质与功能国家重点实验室,北京100050

出　　处：《药学学报》2024年第5期1327-1333,共7页Acta Pharmaceutica Sinica

基　　金：中国医学科学院医学与健康科技创新工程项目(2021-I2M-1-029)。

摘　　要：运用Sephadex LH-20凝胶柱色谱、硅胶柱色谱、反相HPLC、手性色谱等多种色谱方法,从真菌Pleosporales sp.大米发酵物的乙酸乙酯提取物中分离得到3个新化合物,包括1个萘醌类化合物、1个萘醌还原型的萘酮类化合物和1个三羧酸类化合物,以及5个已知的萘酮类衍生物。利用质谱、核磁共振、比旋光等多种波谱学方法,以及计算ECD的方法,确定了这8个化合物的结构。新化合物分别命名为pleospathone A (1)、pleospathone B(2)和pleosporalic acid A (3)。已知化合物分别鉴定为(3S,4R)-3,4,8-trihydroxy-6-methyl-3,4-dihydronaphthalen-1(2H)-one (4)、(4R)-3,4-dihydro-4,6,8-trihydroxy-1(2H)-naphthalenone (5)、(-)-scytalone (6)、(3S,4S)-3,4-dihydro-3,4,6,8-tetrahydroxy-1(2H)-naphthalenone (7)和cis-4-hydroxyscytalone (8)。其中,化合物4~8均为首次从Pleosporales属真菌中分离得到。化合物1对人宫颈癌细胞He La和小鼠白血病细胞P388有弱的细胞毒活性,IC_(50)值分别为78.93和98.80μmol·L^(-1)。Three new compounds,including a naphthoquinone,a reduced naphthoquinone derivative naphtha‐lenone,and a tricarboxylic acid,along with five known naphthalenone derivatives were isolated from ethyl acetate extract of rice fermentation products of the fungus Pleosporales sp.by multiple column chromatographic methods,including Sephadex LH-20 gel column chromatography,silica gel column chromatography,reversed-phase HPLC,and chiral chromatography.Their structures were elucidated by MS,NMR,and specific rotation spectroscopic analyses as well as ECD calculations.Three novel compounds were named as pleospathone A (1),pleospathone B(2),and pleosporalic acid A (3).Five known compounds were separately identified as (3S,4R)-3,4,8-trihydroxy-6-methyl-3,4-dihydronaphthalen-1(2H)-one (4),(4R)-3,4-dihydro-4,6,8-trihydroxy-1(2H)-naphthalenone (5),(-)-scytalone (6),(3S,4S)-3,4-dihydro-3,4,6,8-tetrahydroxy-1(2H)-naphthalenone (7),and cis-4-hydroxyscytalone (8).Compounds 4-8 were isolated from the Pleosporales fungi for the first time.Compound 1 shows inhibitory activities against human cervical carcinoma cell line He La and murine leukemia cell line P388 with the IC_(50) values of 78.93and 98.80μmol·L~(-1),respectively.

关 键 词：Pleosporales属真菌 次级代谢产物 萘醌 萘酮 三羧酸类化合物 细胞毒活性 

分 类 号：R284[医药卫生—中药学]