New brefeldins and penialidins from marine fungus Penicillium janthinellum DT-F29

Abstract

A fermentation of marine fungus Penicillium janthinellum DT-F29 on solid rice medium led to the isolation of three new compounds, brefeldin D (1) and penialidins D-E (5-6), along with other five known brefeldins and penialidins. The structures of above compounds were determined on the basis of MS and NMR analysis.

Chromone Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Penicillium erubescens KUFA0220 and Their Antibacterial Activity

“…The analysis of the 1 H, 13 C NMR (Table 2, Figures S28 and S29) and the (+)-HRESIMS spectra of 3a revealed that its planar structure was the same as that of penialidin F, previously isolated from the culture of Penicillium janthinellum DT-F29, collected from marine sediments [9]. Curiously, even though the authors reported the optical rotation of penialidin F as levorotatory ([α]${}_{\mathrm{normalD}}^{25}$ −4.13, c = 1.0, MeOH), they did not determine the absolute configuration of its stereogenic carbon (C-2).…”

“…The structure of β-sitostenone [3], ergosterol 5,8-endoperoxide [4] (Figure S1), citromycin ( 1a ) [5], 12-methoxycitromycin ( 1b ) [5], myxotrichin D ( 1d ) [6], 12-methoxycitromycetin ( 1e ) [5], anhydrofulvic acid ( 2a ) [7,8], myxotrichin C ( 2b ) [6], penialidin D ( 2c ) [9], penialidin F ( 3a ) [9,10], SPF-3059-30 ( 7 ) [11], GKK1032B ( 8 ) [12,13,14], and secalonic acid A ( 9 ) [3,15] (Figure 1) were elucidated by analysis of their 1D and 2D NMR spectra as well as HRMS data, and also by comparison of their spectral data (Figures S2–S11, S15–S29, S45–S50, S52 and S53) to those reported in the literature. In the case of GKK1032B ( 8 ), the X-ray analysis was also performed to confirm the absolute configurations of all the stereogenic centers (Figure S51).…”

“…Sfrs 147–151 were combined (221.0 mg) and applied on a Sephadex LH-20 column (10 g) and eluted with MeOH to give 10.0 mg of a mixture of 2b (major component) [6] and 3b . Sfrs 189–201 were combined (72.3 mg) and purified by TLC (Silica gel G 254 , CHCl 3 :MeOH:HCO 2 H, 95: 5: 0.1) to give 7.1 mg of 3a [9]. Frs 387–444 were combined (2.73 g) and applied on a column of Sephadex LH-20 (20 g) and eluted with MeOH, wherein 20 mL of 30 fractions were collected.…”

“…Frs 517–529 were combined (1.40 g) and crystallized in MeOH to give 26.6 mg of 1e [5], and the mother liquor was combined with frs 445–516 (6.90 g) and applied on a column of Sephadex LH-20 column (30 g) and eluted with MeOH, wherein 20 mL fractions were collected. Sfrs 21–30 were combined (106.2 mg) and purified by TLC (Silica gel G 254 , CHCl 3 :MeOH:HCO 2 H, 9:1:0.01) to give 10 mg of 3a [9,10] and 12 mg of 6 . Sfrs 31–60 were combined (5.90 g) and applied on a column chromatography of silica gal (110 g) and eluted with petrol-CHCl 3 , CHCl 3 , CHCl 3 -Me 2 CO and Me 2 CO, wherein 100 mL fractions were collected as follows, Sfrs 1–26 (petrol-CHCl 3 , 1:1), 27–56 (petrol-CHCl 3 , 3:7), 57–98 (petrol-CHCl 3 , 1:9), 99–200 (CHCl 3 ), 201–297 (CHCl 3 -Me 2 CO, 9:1), 298–320 (CHCl 3 -Me 2 CO, 7:3), 321–332 (CHCl 3 -Me 2 CO, 1:9), 333–358 (Me 2 CO).…”

“…Chromatographic fractionation and the further purification of the crude ethyl acetate extract of the cultures of P. erubescens KUFA 0220, furnished an unreported chromene derivative, 1-hydroxy-12-methoxycitromycin ( 1c ), and four previously undescribed chromone derivatives, including a pyanochromone ( 3b ), a spirofuranochromone ( 4 ), 7-hydroxy-6-methoxy-4-oxo-3-[(1 E )-3-oxobut-1-en-1-yl]-4 H -chromene-5-carboxylic acid ( 5 ), and a pyranochromone dimer ( 6 ) (Figure 1), in addition to thirteen known compounds: β-sitostenone [3,4], citromycin ( 1a ) [5], 12-methoxycitromycin ( 1b ) [5], myxotrichin D ( 1d ) [6], 12-methoxycitromycetin ( 1e ) [5], anhydrofulvic acid ( 2a ) [7,8], myxotrichin C ( 2b ) [6], penialidin D ( 2c ) [9], penialidin F ( 3a ) [9,10], SPF-3059-30 ( 7 ) [11], GKK1032B ( 8 ) [12,13,14] and secalonic acid A ( 9 ) [3] (Figure 1). The structures of the previously undescribed compounds were established based on extensive analyses of their 1D and 2D NMR as well as HRMS data while the identity of the known compounds was elucidated by comparison of their 1 H and 13 C NMR data with those reported in the literature.…”