Scalusamides A−C, New Pyrrolidine Alkaloids from the Marine-Derived Fungus <i>Penicillium c</i><i>itrinum</i>

Tsuda, Masashi; Sasaki, Munetaka; Mugishima, Takao; Komatsu, Keiichi; Sone, Toshio; Tanaka, Michiko; Mikami, Yuzuru; Kobayashi, Jun’ichi

doi:10.1021/np049661q

Cited by 54 publications

(47 citation statements)

References 13 publications

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“…After toxicity evaluation with unlabeled sodium acetate, added to the growth medium of P. citrinum (up to 5 g L -1 ), for which no morphology alterations of the fungus in the growth medium or even alterations in the production yield of 1 and 2 were observed, experiments with sodium[1-13 C]acetate, sodium[1,2-13 C 2 ]acetate, sodium [2,[3][4][5][6][7][8][9][10][11][12][13] C 2 ]propionate, [methyl-13 C]methionine, [U-13 C 5 ]ornithine and [U-13 C 5 ]proline were performed. 13 C-Labeled precursors were added at the fourth day of growth, at a final concentration of 1 mg mL -1 for each precursor, using previously optimized growth conditions.…”

Section: Resultsmentioning

confidence: 99%

“…[ 13 C-6, 13 C-8, 13 C-10, 13 C-12, 13 [ 13 C-6, 13 C-8, 13 C-10, 13 C-12, 13 C-14]-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione (2) Incolor gum. [ 13 C-6, 13 C-7, 13 C-8, 13 C-9, 13 C-10, 13 C-11, 13 C-12, 13 C-13, 13 C-14, 13 [ 13 C-6, 13 C-7, 13 C-8, 13 C-9, 13 C-10, 13 C-11, 13 C-12, 13 C-13, 13 C-14,…”

Section: Small Scale Experiments With Soluble Starch and Acetatementioning

confidence: 99%

“…[ 13 C-6, 13 C-7, 13 C-8, 13 C-9, 13 C-10, 13 C-11, 13 C-12, 13 C-13, 13 C-14, 13 [ 13 C-6, 13 C-7, 13 C-8, 13 C-9, 13 C-10, 13 C-11, 13 C-12, 13 C-13, 13 C-14,…”

Section: Small Scale Experiments With Soluble Starch and Acetatementioning

confidence: 99%

“…Cultures were harvested after 14 days for each growth experiment using distinct 13 C-labeled precursors. After growth media filtration and solid phase extraction, fractions were evaporated and subjected to HPLC-UV-ESI-MS analysis.Preliminary small-scale experiments in 50 mL of growth media for each 13 C-labeled precursor gave, after the growth media clean-up, fractions containing both 1 and 2 which clearly showed the incorporation of sodium[1- 13 . After growth in the presence of the labeled precursors, solid-phase extraction of the growth media and extensive purification of both 1 and 2 by HPLC, 13 C NMR analyses clearly showed the incorporation of the labeled precursors.…”

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confidence: 99%

“…Fractions F2 and F3 were collected, dried in vacuo and weighed. Aliquots of 1 mg of each F2 and F3 were analyzed by HPLC-UV-MS using a reversed-phase C 18 column (X-Terra® MS, 50 × 2.1 mm, 3.5 µm), eluted with a MeOH/H 2 O gradient.[ 13 C-6, 13 C-8, 13 C-10, 13 C-12, 13 [ 13 C-6, 13 C-8, 13 C-10, 13 C-12, 13 C-14]-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione (2) Incolor gum. [ 13 C-6, 13 C-7, 13 C-8, 13 C-9, 13 C-10, 13 C-11, 13 C-12, 13 C-13, 13 C-14, 13 [ 13 C-6, 13 C-7, 13 C-8, 13 C-9, 13 C-10, 13 C-11, 13 C-12, 13 C-13, 13 C-14,…”

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Biosynthesis of two dihydropyrrole-polyketides from a marine-derived Penicillium citrinum

Romminger¹,

Pimenta²,

Nascimento³

et al. 2012

J. Braz. Chem. Soc.

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Experimentos de incorporação com precursores marcados com 13 C foram realizados objetivando-se estabelecer a biossíntese de dois dihidropirróis N-acilados, (8E)-1-(2,3-dihidro-1H-pirrol-1-il)-2-metildec-8-eno-1,3-diona (1) e 1-(2,3-dihidro-1H-pirrol-1-il)-2-metildecano-1,3-diona (2), isolados de culturas de Penicillium citrinum de origem marinha. A biossíntese de ambos, 1 e 2, procede através da incorporação de acetato, metionina e ornitina.Feeding experiments with 13 C-labeled precursors were performed in order to establish the biosynthesis of two N-acylated dihydropyrroles, (8E)-1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldec-8-ene-1,3-dione (1) and 1-(2,3-dihydro-1H-pyrrol-1-yl)-2-methyldecane-1,3-dione (2), isolated from the cultures of a marine-derived Penicillium citrinum. The biosynthesis of both, 1 and 2, involves the incorporation of acetate, methionine and ornithine. Keywords: Penicillium citrinum, marine-derived fungus, mixed biosynthesis, dihydropyrrole IntroductionPyrrole, dihydropyrrole (pyrroline) and tetrahydropyrrole (pyrrolidine) alkaloids constitute a unique class of secondary metabolites, which include several bioactive members such as the tropane alkaloids, 1 tambjamines 2-4 and prodigiosin, 5 anatoxin-a, 6 as well as 2-alkyl or 2,5-dialkyl-branched pyrrolidine and pyrroline ant chemical defenses. 7 However, such alkaloids are extremely rare in fungi, the only examples found in literature 8 include the dihydropyrrole-bearing peptide brevigellin isolated from Penicillium brevicompactum, 9 the dihydropyrrole b-keto amides 1 and 2 also isolated from P. brevicompactum, [10][11][12] the mildly antibiotic scalusamides A−C (3-5), which have been isolated from a marine-derived P. citrinum, 13 as well as the tetrahydropyrrole-citrinin conjugate perinadine A, isolated from P. citrinum of marine origin. 14 Compounds 1 and 2 display insecticidal, fungicidal activities and induce precocious metamorphosis in the milkweed bug Oncopeltus fasciatus (Insecta). 12 We have recently isolated the same compounds 1 and 2 from a marine-derived P. citrinum, 15 and became interested to Braz. Chem. Soc. 1784 establish the actual biosynthetic pathway leading to 1 and 2. This is because while pyrrole, dihydropyrrole or pyrrolidine alkaloids isolated from non-fungal sources are typically derived from proline, 16,17 ornithine, 1 or even from acetate, 16 the biosynthesis of the above mentioned dihydropyrroles isolated from fungi have not yet been investigated. Particularly, we aimed to verify if the dihydropyrrole moiety in 1 and 2 is derived from proline or ornithine, and if the branched moiety is derived from propionate or from acetate plus methionine. To the best of our knowledge, this is the first report on the biosynthesis of fungal dihydropyrrole-bearing secondary metabolites. Results and DiscussionAfter toxicity evaluation with unlabeled sodium acetate, added to the growth medium of P. citrinum (up to 5 g L -1 ), for which no morphology alterations of the fungus in the growth medium or even alterations in the product...

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Section: Resultsmentioning

confidence: 99%

Section: Small Scale Experiments With Soluble Starch and Acetatementioning

confidence: 99%

“…[ 13 C-6, 13 C-7, 13 C-8, 13 C-9, 13 C-10, 13 C-11, 13 C-12, 13 C-13, 13 C-14, 13 [ 13 C-6, 13 C-7, 13 C-8, 13 C-9, 13 C-10, 13 C-11, 13 C-12, 13 C-13, 13 C-14,…”

Section: Small Scale Experiments With Soluble Starch and Acetatementioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Biosynthesis of two dihydropyrrole-polyketides from a marine-derived Penicillium citrinum

Romminger¹,

Pimenta²,

Nascimento³

et al. 2012

J. Braz. Chem. Soc.

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Fungi

Kornprobst

2014

Encyclopedia of Marine Natural Products

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The article contains sections titled: The Fungal Kingdom: The Concept of Marine Fungi Mastigomycetes and Eumycetes (True Fungi) Elements of Classification of Eumycetes Background Information on the Structure of Chitin Fatty Acids Sterols Membrane Peptides of Fungi: Peptaibols General Comments on Secondary Metabolites of Marine Fungi Substances Isolated from Fungi Collected from the Surface of the Sea Substances Isolated from Fungi from Sediments and other Inert Substrates Substances Isolated from Fungi Associated with Cyanobacteria Algicolous Fungi: General Remarks Substances Isolated from Fungi Associated with Green Algae and Marine Spermatophyta Substances Isolated from Fungi Associated with Red Algae Substances Isolated from Fungi Associated with Brown Algae Substances Isolated from Lignicolous Fungi Substances Isolated from Fungi Associated with Sponges Substances Isolated from Fungi Associated with Cnidarians Substances Isolated from Fungi Associated with Mollusks Substances Isolated from Fungi Associated with Bryozoans Substances Isolated from Fungi Associated with Echinoderms Substances Isolated from Fungi Associated with Crustaceans Substances Isolated from Fungi Associated with Tunicates (Ascidians) Substances Isolated from Fungi Associated with Fish Summary of Marine‐Derived Fungi

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Structure determination of two unusual C25 steroids with bicyclo[4.4.1]A/B rings fromPenicillium decumbensby NMR spectroscopy

Lin

Chen

et al. 2014

Magn. Reson. Chem.

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Scalusamides A−C, New Pyrrolidine Alkaloids from the Marine-Derived Fungus Penicillium citrinum

Cited by 54 publications

References 13 publications

Biosynthesis of two dihydropyrrole-polyketides from a marine-derived Penicillium citrinum

Biosynthesis of two dihydropyrrole-polyketides from a marine-derived Penicillium citrinum

Fungi

Structure determination of two unusual C25 steroids with bicyclo[4.4.1]A/B rings fromPenicillium decumbensby NMR spectroscopy

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