Indole Alkaloids Produced by a Marine Fungus Isolate of <i>Penicillium janthinellum</i> Biourge

Smetanina, O. F.; Kalinovsky, Anatoly I.; Khudyakova, Yuliya V.; Пивкин, М. В.; Dmitrenok, Pavel S.; Fedorov, Sergey N.; Ji, Hong Li; Kwak, Jong‐Young; Кузнецова, Т. А.

doi:10.1021/np060396d

Cited by 74 publications

(51 citation statements)

References 12 publications

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“…Thus, the structure of 2 was determined as 22‐hydroxy‐shearinine L. We named the new compound shearinine M. The NOESY spectrum exhibited correlations between H‐22 and H 3 ‐38 and between H‐23 and H 3 ‐37 (Figure S16), which implies that H‐22 and H‐23 are on opposite faces of ring B. The 1 H and 13 C NMR data at C‐22 and C‐23 of 2 were also in good agreement with those of shearinine D, indicating the relative H‐22β and H‐23α configurations. The relative configuration of ring fusions in shearinine M ( 2 ) is identical to shearinine L ( 1 ) based on the NOESY correlations: H 3 ‐32/H‐17α, H‐16/H 3 ‐33, H 3 ‐33/H‐14β and H‐11 and H‐14α (Figure S17B).…”

Section: Resultsmentioning

confidence: 74%

“…Compounds 3 – 5 were identified as shearinine‐type indole triterpenoids, namely shearinine D ( 3 ), shearinine E ( 4 ), and shearinine A ( 5 ) (SI), which have been characterized before from Penicillium species or its teleomorph Eupenicillium species …”

Section: Resultsmentioning

confidence: 99%

“…Shearinines have been originally identified from Eupenicillium shearii . Shearinines exhibit anticancer activities; they block large‐conductance calcium‐activated potassium channels, and are known to act against insects . Furthermore, shearinines have been found to suppress Candida albicans biofilm formation and potentiate the antifungal activity of the polyene macrolide antifungal amphotericin B .…”

Section: Discussionmentioning

confidence: 99%

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Secondary Metabolites from Escovopsis weberi and Their Role in Attacking the Garden Fungus of Leaf‐Cutting Ants

Dhodary

Schilg

Wirth

et al. 2018

Chemistry A European J

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The specialized, fungal pathogen Escovopsis weberi threatens the mutualistic symbiosis between leaf-cutting ants and their garden fungus (Leucoagaricus gongylophorus). Because E. weberi can overwhelm L. gongylophorus without direct contact, it was suspected to secrete toxins. Using NMR and mass spectrometry, we identified several secondary metabolites produced by E. weberi. E. weberi produces five shearinine-type indole triterpenoids including two novel derivatives, shearinine L and shearinine M, as well as the polyketides, emodin and cycloarthropsone. Cycloarthropsone and emodin strongly inhibited the growth of the garden fungus L. gongylophorous at 0.8 and 0.7 μmol, respectively. Emodin was also active against Streptomyces microbial symbionts (0.3 μmol) of leaf-cutting ants. Shearinine L instead did not affect the growth of L. gongylophorus in agar diffusion assays. However, in dual choice behavioral assays Acromyrmex octospinosus ants clearly avoided substrate treated with shearinine L for the garden fungus after a 2 d learning period, indicating that the ants quickly learn to avoid shearinine L.

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Section: Resultsmentioning

confidence: 74%

Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

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Secondary Metabolites from Escovopsis weberi and Their Role in Attacking the Garden Fungus of Leaf‐Cutting Ants

Dhodary

Schilg

Wirth

et al. 2018

Chemistry A European J

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“…7 Penicillium janthinellum Biourge, isolated from marine sediments collected from the Sea of Japan, afforded three new indole diterpene alkaloids, shearinines D–F, which were shown to induce apoptosis in human leukemic HL-60 cells. 8 These metabolites are analogues of paspalinine and janthitrems B–G previously discovered from terrestrial fungi. 9 …”

Section: Introductionmentioning

confidence: 96%

Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors

et al. 2013

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Marine-derived fungi have proven to be important sources of bioactive natural organohalides. The genus Penicillium is recognized as a rich source of chemically diverse bioactive secondary metabolites. This study reports the fermentation, isolation and identification of a marine-derived Penicillium species. Bioassay-guided fractionation afforded the indole diterpene alkaloids penitrems A, B, D, E and F as well as paspaline and emnidole SB (1–7). Supplementing the fermentation broth of the growing fungus with KBr afforded the new 6-bromopenitrem B (8) and the known 6-bromopenitrem E (9). These compounds showed good antiproliferative, antimigratory and anti-invasive properties against human breast cancer cells. Penitrem B also showed a good activity profile in the NCI-60 DTP human tumor cell line screen. The nematode Caenorhabditis elegans was used to assess the BK channel inhibitory activity and toxicity of select compounds. A pharmacophore model was generated to explain the structural relationships of 1–9 with respect to their antiproliferative activity against the breast cancer MCF-7 cells. The structurally less complex biosynthetic precursors, paspaline (6) and emindole SB (7), were identified as potential hits suitable for future studies.

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“…[1][2][3] In some cases, isoprenoids are attached to other moieties, such as a polyketide, 4) indole/tryptophan, 5) or (iso)flavonoid, 6) or to phenazine moieties. 7,8) Prenylated indole alkaloids such as paspalitrem A, 9) aflatrem, 10) janthitrems, 11,12) shearinines, 13,14) penitrem A, 15) lolilline, 16) and lolitrems, 17) all of which are produced by filamentous fungi, are examples of this. 18) These compounds are derived from polyprenyl diphosphates and tryptophan or its derivatives, and they show diverse chemical structures and biological activities.…”

mentioning

confidence: 99%

A fungal prenyltransferase catalyzes the regular di-prenylation at positions 20 and 21 of paxilline

Liu

Noike

Minami

et al. 2014

Bioscience, Biotechnology, and Biochemistry

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A putative indole diterpene biosynthetic gene cluster composed of eight genes was identified in a genome database of Phomopsis amygdali, and from it, biosynthetic genes of fusicoccin A were cloned and characterized. The six genes showed significant similarities to pax genes, which are essential to paxilline biosynthesis in Penicillium paxilli. Recombinants of the three putative prenyltransferase genes in the cluster were overexpressed in Escherichia coli and characterized by means of in vitro experiments. AmyG is perhaps a GGDP synthase. AmyC and AmyD were confirmed to be prenyltransferases catalyzing the transfer of GGDP to IGP and a regular di-prenylation at positions 20 and 21 of paxilline, respectively. AmyD is the first know example of an enzyme with this function. The Km values for AmyD were calculated to be 7.6 ± 0.5 μM for paxilline and 17.9 ± 1.7 μM for DMAPP at a kcat of 0.12 ± 0.003/s.

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Indole Alkaloids Produced by a Marine Fungus Isolate of Penicillium janthinellum Biourge

Cited by 74 publications

References 12 publications

Secondary Metabolites from Escovopsis weberi and Their Role in Attacking the Garden Fungus of Leaf‐Cutting Ants

Secondary Metabolites from Escovopsis weberi and Their Role in Attacking the Garden Fungus of Leaf‐Cutting Ants

Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors

A fungal prenyltransferase catalyzes the regular di-prenylation at positions 20 and 21 of paxilline

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