Isolation and Biosynthesis of Preussin B, a Pyrrolidine Alkaloid from <i>Simplicillium lanosoniveum</i>

Fukuda, Takao; Sudoh, Yuri; Tsuchiya, Y.; Okuda, Tôru; Igarashi, Yasuhiro

doi:10.1021/np400910r

Cited by 40 publications

(22 citation statements)

References 41 publications

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“…[17,20], respectively. They are not related to secondary metabolites isolated from the genus Simplicillium so far [21][22][23][24][25][26]. Simplicilone compounds have a core-shell structure related to congeners produced by other fungi [19,20].…”

Section: Discussionmentioning

confidence: 97%

Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

et al. 2020

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Two new tetracyclic polyketides with a spirocenter, simplicilones A (1) and B (2) were isolated from the broth-culture of the endophytic fungus Simplicilliumsubtropicum (SPC3) in the course of our screening for new bioactive secondary metabolites. This endophytoic fungus is naturally harboured in the fresh bark of the Cameroonian medicinal plant Duguetia staudtii (Engl. and Diels) Chatrou. The planar structures of the simplicilones were elucidated by MS and 1D as well as 2D NMR spectroscopic techniques. The relative configuration was assigned by NOESY experiments in conjunction with coupling constants; subsequently, the absolute configurations were assigned by the modified Mosher’s method. The compounds showed weak cytotoxic effects against the cell line KB3.1 (in vitro cytotoxicity (IC50) = 25 µg/mL for 1, 29 µg/mL for 2), but were inactive against the tested Gram-positive and Gram-negative bacteria as well as fungi.

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Section: Discussionmentioning

confidence: 97%

Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

et al. 2020

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“…Other substrata were found later, such as limstone and wood (Liu and Cai 2012; Zhang et al 2017). Many bioactive compounds were discovered in Simplicillium , such as alkaloids (Fukuda et al 2014), peptides (Liang et al 2016; 2017; Dai et al 2018), diketopiperazine (Yan et al 2015), xylanases (Roy et al 2013), anthraquinones (Huang et al 2015), antibiotics (Takata et al 2013; Dong et al 2018), and especially Simpotentin, which is a new potentiator of amphotericin B activity against Candida albicans (C. P. Robin) Berkhout and has showed great potential applications in medicine (Uchida et al 2019). Furthermore, the antimicrobial activities and entomopathogenicity has meant that Simplicillium has potential applications in biocontrol (Ward et al 2012; Zhao et al 2013; Le Dang et al 2014; Lim et al 2014; Chen et al 2017; Skaptsov et al 2017).…”

Section: Introductionmentioning

confidence: 99%

Three novel insect-associated species of Simplicillium (Cordycipitaceae, Hypocreales) from Southwest China

Chen¹,

Liu²,

Han³

et al. 2019

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In this paper, we introduce three new species of Simplicillium, viz. S. cicadellidae, S. formicidae and S. lepidopterorum, which were isolated from an infected leafhopper, ant and carpenterworm, respectively. Morphological comparisons and phylogenetic analyses based on multigene datasets (LSU+RPB1+RPB2+TEF and ITS+LSU) support the establishment of the three new species. Simplicillium cicadellidae was distinguished from other species in morphological characteristics by having smaller phialides and ellipsoidal conidia, and lacking octahedral crystals. The reverse of colonies were yellowish (#FFBF00), especially in the middle, and radially sulcate. Simplicillium formicidae was morphologically distinguished from other by having longer phialides and filiform to fusoid conidia, and by lacking octahedral crystals. Simplicillium lepidopterorum was morphologically distinguished from other species by having smaller, ellipsoidal to fusiform conidia, and by lacking octahedral crystals. The reverse of the colony was pale white. The three new species are likely to be nourished by plant to animal (especially insect) nutrients based on the evolutionary pattern of the Hypocreales, and they are described herein as being clearly distinct from other species in Simplicillium.

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“…The structures of palmitic acid, clionasterol [ 22 ], ergosterol 5,8-endoperoxides [ 14 ], chrysophanic acid ( 1a ) [ 13 ], emodin ( 1b ) [ 14 ], asterriquinol D dimethyl ether ( 2a ) [ 15 ], petromurin C ( 2b ) [ 16 ], kumbicin B ( 2c ) [ 15 ], kumbicin A ( 2d ) [ 15 ], 2″-oxoasterriquinol D methyl ether ( 3 ) [ 17 ], kumbicin D ( 4 ) [ 15 ], preussin ( 5a ) [ 18 , 19 , 20 ], (3 S , 6 S )-3,6-dibenzylpiperazine-2,5-dione ( 6 ) [ 21 ] and 4-(acetylamino) benzoic acid ( 7 ) [ 22 ] were elucidated by analysis of their 1D and 2D NMR spectra as well as HRMS data, and also by comparison of their spectral data to those reported in the literature ( Supplementary Materials, Figures S2–S17, S20–S25, S32–S35 and Tables S1–S4 ).…”

Section: Resultsmentioning

confidence: 99%

“…Chromatographic fractionation and further purification of the crude ethyl acetate extract of the cultures of A. candidus KUFA 0062, furnished two previously undescribed compounds named candidusin D ( 2e ) and preussin C ( 5b ), as well as the previously reported chrysophanic acid ( 1a ) [ 13 ], emodin ( 1b ) [ 14 ], six bis -indolyl benzenoids including asterriquinol D dimethyl ether ( 2a ) [ 15 ], petromurin C ( 2b ) [ 16 ], kumbicin B ( 2c ) [ 15 ], kumbicin A ( 2d ) [ 15 ], 2″-oxoasterriquinol D methyl ether ( 3 ) [ 17 ], kumbicin D ( 4 ) [ 15 ], the hydroxypyrrolidine alkaloid preussin ( 5a ) [ 18 , 19 , 20 ], (3 S , 6 S )-3,6-dibenzylpiperazine-2,5-dione ( 6 ) [ 21 ], and 4-(acetylamino) benzoic acid ( 7 ) [ 22 ] ( Figure 1 ). Additionally, the common fungal metabolites, i.e., palmitic acid, clionasterol [ 23 ], and ergosterol 5,8-endoperoxides [ 14 ] were also isolated ( Supplementary Material, Figure S1 ).…”

Section: Introductionmentioning

confidence: 99%

Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062

et al. 2018

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A previously unreported bis-indolyl benzenoid, candidusin D (2e) and a new hydroxypyrrolidine alkaloid, preussin C (5b) were isolated together with fourteen previously described compounds: palmitic acid, clionasterol, ergosterol 5,8-endoperoxides, chrysophanic acid (1a), emodin (1b), six bis-indolyl benzenoids including asterriquinol D dimethyl ether (2a), petromurin C (2b), kumbicin B (2c), kumbicin A (2d), 2″-oxoasterriquinol D methyl ether (3), kumbicin D (4), the hydroxypyrrolidine alkaloid preussin (5a), (3S, 6S)-3,6-dibenzylpiperazine-2,5-dione (6) and 4-(acetylamino) benzoic acid (7), from the cultures of the marine sponge-associated fungus Aspergillus candidus KUFA 0062. Compounds 1a, 2a–e, 3, 4, 5a–b, and 6 were tested for their antibacterial activity against Gram-positive and Gram-negative reference and multidrug-resistant strains isolated from the environment. Only 5a exhibited an inhibitory effect against S. aureus ATCC 29213 and E. faecalis ATCC29212 as well as both methicillin-resistant S. aureus (MRSA) and vancomycin-resistant enterococci (VRE) strains. Both 1a and 5a also reduced significant biofilm formation in E. coli ATCC 25922. Moreover, 2b and 5a revealed a synergistic effect with oxacillin against MRSA S. aureus 66/1 while 5a exhibited a strong synergistic effect with the antibiotic colistin against E. coli 1410/1. Compound 1a, 2a–e, 3, 4, 5a–b, and 6 were also tested, together with the crude extract, for cytotoxic effect against eight cancer cell lines: HepG2, HT29, HCT116, A549, A 375, MCF-7, U-251, and T98G. Except for 1a, 2a, 2d, 4, and 6, all the compounds showed cytotoxicity against all the cancer cell lines tested.

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Isolation and Biosynthesis of Preussin B, a Pyrrolidine Alkaloid from Simplicillium lanosoniveum

Cited by 40 publications

References 41 publications

Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Simplicilones A and B Isolated from the Endophytic Fungus Simplicillium subtropicum SPC3

Three novel insect-associated species of Simplicillium (Cordycipitaceae, Hypocreales) from Southwest China

Bis-Indolyl Benzenoids, Hydroxypyrrolidine Derivatives and Other Constituents from Cultures of the Marine Sponge-Associated Fungus Aspergillus candidus KUFA0062

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