Naphthoquinone and carboxylic acid derivatives from the fungus Pleosporales sp.
10.16438/j.0513-4870.2023-1269
- VernacularTitle:真菌Pleosporales sp.中的萘醌和羧酸类衍生物
- Author:
Si-yuan QI
;
Li-hua ZHANG
;
Yi-nan HAO
;
You-cai HU
;
Jian BAI
- Publication Type:Research Article
- Keywords:
italic>Pleosporales fungus;
secondary metabolite;
naphthoquinone;
naphthalenone;
tricarboxylic acid;
cytotoxic activity
- From:
Acta Pharmaceutica Sinica
2024;59(5):1327-1333
- CountryChina
- Language:Chinese
-
Abstract:
Three new compounds, including a naphthoquinone, a reduced naphthoquinone derivative naphthalenone, 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 HeLa and murine leukemia cell line P388 with the IC50 values of 78.93 and 98.80 μmol·L-1, respectively.
