A novel compound from Penicillium sp. (M207142)

Abstract

Marine fungi have proved to be rich sources of bioactive secondary metabolites [1][2][3][4]. During our systematic screening for bioactive compounds from marine-derived fungi, the strain of Penicillium sp. (M207142) was regarded as having one of the highest potentials among 174 strains isolated from sea sediment. The main active components of the strain are in the ethyl acetate extracts [5]. The extracts were subjected to a succession of chromatographic procedures to afford six pure components, the structures of which were established by spectral methods (IR, ESI-MS, and 1D and 2D NMR).Compound 1 ((2E,4E)-1-(2,6-dihydroxy-3,5-dimethyl-phenyl)hexa-2,4-dien-1-one)), yellow needle-like crystal, easily soluble in methanol. main correlation between the protons and carbons shown in Fig. 1. Compound 2, colorless solid, easily soluble in chloroform. IR (KBr, Q max , cm -1 ): 3440.72, 2925.81, 2855.30, 1722.32, 1598.51, 1383.93, 1025.13. The ESI-MS spectrum showed a molecular ion peak at m/z 251.2 [M+1] corresponding to the molecular formula C 14 H 18 O 4 , with molecular weight 250.2. Furthermore, the structure of compound 2 was confirmed by PMR, 13 C NMR, DEPT, COSY, HSQC, and HMBC experiments (Table 2), which is consistent with the structure of penicillone A [6]. Compound 3, colorless solid, IR (KBr, Q max , cm -1 ): 3355.81, 2926.10, 1625.97, 1383.45, 1158.12, 1026.36. ESI-MS spectrum of compound 3 showed a molecular ion peak at m/z 235.3 [M+1] + , with molecular weight 234.3 corresponding to the molecular formula C 14 H 18 O 3 . 1D and 2D NMR spectrum showed that the structure of compound 3 was consistent with the known compound dihydrosorbicillin [7].Compounds 4 to 6 were identified as 4-methoxybenzoic acid (4), 4-hydroxyphenylacetic acid (5), and methyl-4hydroxybenzoate (6). All of them are important chemical products used widely in industry.Compounds 1 and 3 exhibited potent cytotoxicity (IC 50 11.2 PM and 104.2 PM) against Hela cell line. Compounds 1 and 2 also showed potent cytotoxity against SW620 cell line, with inhibition 74 and 44% and tested concentration 10 Pg/mL.The cytotoxic values demonstrate the strong potential of compound 1 as a promising lead compound and the strain of Penicillium sp. (M207142) as a promising fungi source of new agents for cancer chemotherapy.

Anti-inflammatory Mono- and Dimeric Sorbicillinoids from the Marine-Derived Fungus Trichoderma reesei 4670

“…Additionally, the known compounds were identified as bisvertinol ( 4 ), sohirnone A ( 21 ), 2′,3′-dihydrosorbicillin ( 22 ), ( E )-6-(2,4-dihydroxyl-5-methylphenyl)-6-oxo2-hexenoic acid ( 23 ), and (2 E ,4 E )-1-(2,6-dihydroxy-3,5-dimethylphenyl)­hexa-2,4-dien-1-one ( 24 ) by comparing their spectroscopic data with published literature values.…”

“…Its 1 H NMR spectrum (Table 1) displayed signals corresponding to four olefinic protons (H-10 to H-13), three methines (H-4, H-7, H-8), one methylene (H 2 -16), and four methyls (H 3 -14, H 3 -17, H 3 -18, H 3 -19). The 13 C NMR and DEPT data (Table 1) of 1 showed the presence of 19 carbons. Six sp 2 The relative configuration (1R*,4S*,5S*,7S*,8S*)-1 was determined by the NOESY correlations of H-4 with H-10 and H 3 -18 and of H-7 with H-8, H 3 -17, and H 3 -19 (Figure 2), as well as X-ray crystallographic analysis (Figure 3).…”

Major bioactive metabolites from marine fungi: A Review

“…(South China Sea). It suppressed the proliferation of six cancer cell lines derived from human breast cancer, prostate cancer, glioma and hepatoma [ 24 ].…”

New Marine Natural Products of Microbial Origin from 2010 to 2013

“…来自 Penicillium sp. M207142(来源未知)的化合物 374 对 Hela (IC 50 为 11.2 μmol/L)和 SW620 细胞(10 μg/mL 时的抑制 率为 44%)有抑制作用 [154] . 桔霉素类似物 375～381 来自 桔青霉(P. citrinum, 福建) [155,156] , 其中 375 和 377 对 HL-60 有弱的细胞毒活性 [155] .…”