Pallidopenillines: Polyketides from the Alga-Derived Fungus Penicillium thomii Maire KMM 4675

Abstract

Eleven new polyketides, pallidopenillines 1-11, were isolated from the alga-derived fungus Penicillium thomii. The structures of these compounds were established based on spectroscopic methods. The absolute configuration of pallidopenilline A (1) as 4R, 5S, 8S, 9R, 10R, 13R was established using a combination of the modified Mosher's method, X-ray analysis, and NOESY data. The absolute configurations of 2-5 were determined by time-dependent density functional theory calculations of the ECD spectra and ECD and NOESY data. It was shown that 1-acetylpallidopenilline A (2) and pallidopenilline G (10) inhibit the growth of colonies of 22Rv1 cells by 40% at 2 and 1 μM, respectively.

Classification of Aspergillus, Penicillium, Talaromyces and related genera (Eurotiales): An overview of families, genera, subgenera, sections, series and species

“…Extrolites : Penicillium thomii has been reported to produce N-acetylphenylalaninol and the related 2(S)-acetamido-3-phenylpropylacetate, austalides, furan-2-carboxylic acid derivatives, guaidiol A and 4,10,11-trihydroxyguaiane, pallidopenillines, penistinraistin C and the related daldinin D, sargassopenillines, thomimarides, thomimarines, VM55599 and zesteropenillines ( Sobolevskaya et al., 2014 , Zhuravleva et al., 2014a , Zhuravleva et al., 2014b , Sobolevskaya et al., 2016a , Sobolevskaya et al., 2016b , Sobolevskaya et al., 2018 , Afiyatullov et al., 2017a , Afiyatullov et al., 2017b , Afiyatullov et al., 2018 ). Penicillium austroafricanum produces fumagillin and P .…”

Zosteropenillines: Polyketides from the Marine-Derived Fungus Penicillium thomii

“…The relative configuration of 6 was assigned on the basis of a NOESY experiment and 1 H- 1 H coupling constants (Table 2). Compound 6 was named zosteropenilline F. Zosteropenilline F is an epimer of the pallidopenilline A ( 13 ) which was earlier isolated from the P. thomii associated with the brown alga Sargassum pallidum [7]. The 1 H and 13 C NMR data observed for 6 closely resembled those obtained for pallidopenilline A (measured in CDCl 3 ) (Figures S58–S68) with the exception of the C-4, C-13 and C-14 carbon and proton signals The molecular formula of 7 was established to be C 15 H 24 O 3 from a HRESIMS peak at m / z 275.1621 [M + Na] + and by 13 C NMR analyses.…”

“…Compound 12 was named zosteropenilline L. Besides the new zosteropenillines ( 1 – 12 ), a known pallidopenilline A ( 13 ) was also isolated from this fungus. For the first time, pallidopenilline A was found in fungus P. thomii KMM 4675 [7]. …”

“…In previously published works, we described the isolation and identification of 10 new meroterpenoids–austalides and seven new 6,6-spiroketals–sargassopenillines A–G from fungi Penicillium thomii and P. lividum associated with the brown alga Sargassum miyabei [4,5] and four new eudesmane-type sesquiterpenes–thomimarines A–D from P. thomii KMM 4667 associated with the sea grass Zostera marina [6]. Recently, we have isolated 11 new polyketides, pallidopenillines that have a polyketidic decalin scaffold from P. thomii associated with the brown alga Sargassum pallidum [7]. During our ongoing search for new natural compounds from marine-derived fungi, we investigated the strain P. thomii KMM 4674 isolated from the seagrass Z. marina .…”

Pyrenosetin D, a New Pentacyclic Decalinoyltetramic Acid Derivative from the Algicolous Fungus Pyrenochaetopsis sp. FVE-087

“…Fungal metabolites with a 'decalin ring system' represent a large group of architecturally complex structural scaffolds [11]. The decalin ring system is usually substituted with, e.g., a terpene side chain [12] or γ-lactam [13], pyrone [14], diene [15], pyrrolizidine [16], and tetramic acid rings [17]. Decalin derivatives are also intriguing for their remarkable biological activities, including anticancer [18], antiviral [19], and antimicrobial [20].…”