Decumbenones A–C from marine fungus &amp;lt;i&amp;gt;Aspergillus sulphureus&amp;lt;/i&amp;gt; as stimulators of the initial stages of development of agricultural plants

Anisimov, M. M.; Чайкина, Е. Л.; Afiyatullov, Shamil Sh.; Zhuravleva, Olesya I.; Klykov, A. G.; Kraskovskaja, Natalya A.; Aminin, Dmitry L.

doi:10.4236/as.2012.38123

Cited by 6 publications

(8 citation statements)

References 9 publications

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“…Our results agree with published data, according to which some metabolites of marine organisms stimulate root growth of seedlings. The same effects were observed for the steroid glycosides from the starfish Asteropsis carinifera [9], diterpene glycosides from Acremonium striatisporum [10], decumbenones from Aspergillus sulphureus [11], alkaloids from Aspergillus fumigatus [12], and oxirapentyn E from the marine isolate of the fungus Isaria felina [13] on the root growth of seedlings of monocotyledon and dicotyledon plants.…”

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confidence: 57%

Oxirapentyns A, B and E from the Marine-Derived Strain of Isaria felina KMM 4639 as Stimulators of Initial Stages of Development of Agricultural Plants

Anisimov

Чайкина

Smetanina

et al. 2014

Natural Product Communications

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Oxirapentyn A (1), oxirapentyn B (2), and oxirapentyn E (3) were examined for their ability to stimulate growth of seedling roots of barley (Hordeum vulgare L.), buckwheat (Fagopyrum esculentum Moench), corn (Zea mays L.), soy {Glycine max (L.) Merr.}, and wheat (Triticum aestivum L.). It was shown that the stimulatory effects depend on the chemical structure of the oxirapentyns and on the plant species. Compounds 1, and 2 are efficient for growth of seedling roots of barley, and wheat, whereas compound 3, at different concentrations, stimulates growth of seedling roots of maize, soy, and wheat. These compounds can be recommended for field study as plant growth stimulators.

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confidence: 57%

Oxirapentyns A, B and E from the Marine-Derived Strain of Isaria felina KMM 4639 as Stimulators of Initial Stages of Development of Agricultural Plants

Anisimov

Чайкина

Smetanina

et al. 2014

Natural Product Communications

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“…Future studies could also look beyond calbistrins as molecule class and investigate the mode of action and benefits for the producers of the related decumbenones which were shown to inhibit melanisation of Magnaporthe grisea [37] and stimulating the germination of agricultural plants [38]. As our study also identified a potential calbistrin cluster in the root endophyte Colletotrichum tofieldiae which supports growth of Arabidopsis thalina under low phosphate conditions [39], it might be worth to investigate the production and role of decumbenones and calbistrins in these interactions and wether they are valuable for fending off other soil-thriving fungi or promoting growth of the host plant.…”

Section: Discussionmentioning

confidence: 99%

Identification of the decumbenone biosynthetic gene cluster in Penicillium decumbens and the importance for production of calbistrin

Grijseels

Pohl

Wasil

et al. 2018

Fungal Biol Biotechnol

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BackgroundFilamentous fungi are important producers of secondary metabolites, low molecular weight molecules that often have bioactive properties. Calbistrin A is a secondary metabolite with an interesting structure that was recently found to have bioactivity against leukemia cells. It consists of two polyketides linked by an ester bond: a bicyclic decalin containing polyketide with structural similarities to lovastatin, and a linear 12 carbon dioic acid structure. Calbistrin A is known to be produced by several uniseriate black Aspergilli, Aspergillus versicolor-related species, and Penicillia. Penicillium decumbens produces calbistrin A and B as well as several putative intermediates of the calbistrin pathway, such as decumbenone A-B and versiol. ResultsA comparative genomics study focused on the polyketide synthase (PKS) sets found in three full genome sequence calbistrin producing fungal species, P. decumbens, A. aculeatus and A. versicolor, resulted in the identification of a novel, putative 13-membered calbistrin producing gene cluster (calA to calM). Implementation of the CRISPR/Cas9 technology in P. decumbens allowed the targeted deletion of genes encoding a polyketide synthase (calA), a major facilitator pump (calB) and a binuclear zinc cluster transcription factor (calC). Detailed metabolic profiling, using UHPLC-MS, of the ∆calA (PKS) and ∆calC (TF) strains confirmed the suspected involvement in calbistrin productions as neither strains produced calbistrin nor any of the putative intermediates in the pathway. Similarly analysis of the excreted metabolites in the ∆calB (MFC-pump) strain showed that the encoded pump was required for efficient export of calbistrin A and B. ConclusionHere we report the discovery of a gene cluster (calA-M) involved in the biosynthesis of the polyketide calbistrin in P. decumbens. Targeted gene deletions proved the involvement of CalA (polyketide synthase) in the biosynthesis of calbistrin, CalB (major facilitator pump) for the export of calbistrin A and B and CalC for the transcriptional regulation of the cal-cluster. This study lays the foundation for further characterization of the calbistrin biosynthetic pathway in multiple species and the development of an efficient calbistrin producing cell factory.Electronic supplementary materialThe online version of this article (10.1186/s40694-018-0063-4) contains supplementary material, which is available to authorized users.

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“…Polyketides containing “decalin” moiety exhibit diverse biological properties such as anticancer, antimicrobial, neurotrophic, and growth-stimulating activity [23,24,25,26,27]. Twelve new polyketides, named zosteropenillines A–L ( 1 – 12 ), have been isolated from the extract of the marine-derived fungus Penicillium thomii .…”

Section: Discussionmentioning

confidence: 99%

“…Zosteropenillines A–L ( 1 – 12 ) belong to the series of lovastatin-related polyketides that are formed by an enzymatic intramolecular Diels–Alder cycloaddition of a linear hexaketide precursor [ 20 , 21 , 22 ]. Polyketides containing “decalin” moiety exhibit diverse biological properties such as anticancer, antimicrobial, neurotrophic, and growth-stimulating activity [ 23 , 24 , 25 , 26 , 27 ]. Twelve new polyketides, named zosteropenillines A–L ( 1 – 12 ), have been isolated from the extract of the marine-derived fungus Penicillium thomii .…”

Section: Discussionmentioning

confidence: 99%

Zosteropenillines: Polyketides from the Marine-Derived Fungus Penicillium thomii

et al. 2017

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Twelve new polyketides, zosteropenillines A–L (1–12), together with known polyketide pallidopenilline A (13), were isolated from the ethylacetate extract of the fungus Penicillium thomii associated with the seagrass Zostera marina. Their structures were established based on spectroscopic methods. The absolute configuration of zosteropenilline A (1) as 4R, 5S, 8S, 9R, 10R, and 13S was determined by a combination of the modified Mosher’s method, X-ray analysis, and NOESY data. Absolute configurations of zosteropenillines B–D (2–4) were determined by time-dependent density functional theory (TD-DFT) calculations of ECD spectra. The effect of compounds 1–3, 7, 8, 10, and 11 on the viability of human drug-resistant prostate cancer cells PC3 as well as on autophagy in these cancer cells and inhibitory effects of compounds 1, 2, and 8–10 on NO production in LPS-induced RAW 264.7 murine macrophages were examined.

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Decumbenones A–C from marine fungus <i>Aspergillus sulphureus</i> as stimulators of the initial stages of development of agricultural plants

Cited by 6 publications

References 9 publications

Oxirapentyns A, B and E from the Marine-Derived Strain of Isaria felina KMM 4639 as Stimulators of Initial Stages of Development of Agricultural Plants

Oxirapentyns A, B and E from the Marine-Derived Strain of Isaria felina KMM 4639 as Stimulators of Initial Stages of Development of Agricultural Plants

Identification of the decumbenone biosynthetic gene cluster in Penicillium decumbens and the importance for production of calbistrin

Zosteropenillines: Polyketides from the Marine-Derived Fungus Penicillium thomii

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