The Lecanindoles, Nonsteroidal Progestins from the Terrestrial Fungus <i>Verticillium lecanii</i> 6144

Roll, Deborah M.; Barbieri, Laurel R.; Bigelis, Ramunas; McDonald, Leonard A.; Arias, Daniel A.; Chang, Liping; Singh, Manpreet; Luckman, Scott W.; Berrodin, Thomas J.; Yudt, Matthew R.

doi:10.1021/np9004882

Cited by 43 publications

(37 citation statements)

References 23 publications

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“…It has potent inhibitory activity on lipid droplet synthesis in mouse macrophages . Structurally related lecanindoles were isolated from a terrestrial fungus Verticillium lecanii 6144 . Different from ISTs isolated from plants and Actinomyces species, compound 1 is unique, in that it has modified prenyl side chains on the indole ring.…”

Section: Figurementioning

confidence: 99%

Heterologous Biosynthesis of Fungal Indole Sesquiterpene Sespendole

et al. 2018

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Indole sesquiterpene sespendole, which has been isolated from the filamentous fungus Pseudobotrytis terrestris FKA-25, is a specific inhibitor of lipid droplet synthesis in mouse macrophages. The biosynthetic pathway that involves genes encoding six enzymes (spdEMBQHJ) was elucidated through heterologous expression of spd genes in Aspergillus oryzae, biotransformation experiments, and in vitro enzymatic reactions with a recombinant protein, thereby revealing the mechanism underlying the characteristic modification on the indole ring, catalyzed by a set of prenyltransferase (SpdE)/cytochrome P450 (SpdJ) enzymes. Functional analysis of the homologous genes encoding these enzymes involved in the biosynthesis of lolitrem allowed a biosynthetic pathway for the bicyclic ring skeleton fused to the indole ring to be proposed.

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Section: Figurementioning

confidence: 99%

Heterologous Biosynthesis of Fungal Indole Sesquiterpene Sespendole

et al. 2018

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“…The absolute configuration of suaveolindole (541) was determined by total synthesis [352]. Lecanindoles A-D (545-548) were isolated from a terrestrial fungus Verticillium lecanii 6144 [357], while oridamycins A-B (549-550) were characterized from the fermentation broth of Streptomyces sp. Sespendole is the first reported fungal metabolite having an indolosesquiterpene core structure.…”

Section: Occurrence Classification and Biosynthesis Of Amino Acid-mmentioning

confidence: 99%

Drimane-Related Merosesquiterpenoids, a Promising Library of Metabolites for Drug Development

Shan

Ying

et al. 2015

Studies in Natural Products Chemistry

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“…CPA-type alkaloids (1)(2)(3)(4), namely speradines B (1), C (2), D (3), and E (4). The isolation, structure elucidation, and bioactivity of compounds 1-4 are presented in the current study.…”

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confidence: 94%

Speradines B-E, Four Novel Tetracyclic Oxindole Alkaloids from the Marine-Derived Fungus Aspergillus oryzae

Chen¹,

Zhang²,

Hu³

et al. 2014

HETEROCYCLES

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Four novel tetracyclic oxindole alkaloids, namely, speradines B (1), C(2), D (3), and E (4) were isolated from the marine-derived fungus Aspergillus oryzae. The structures of these compounds without the absolute configurations were elucidated through 1D and 2D nuclear magnetic resonance and high-resolution mass spectrometric analyses. Among these compounds, 1 and 4 showed weak cytotoxic effects on the HeLa cell line.Indole-terpenes are fungal and bacterial secondary metabolites with unique biological activities such as inhibitory activity of calcium-activated potassium channels, 1 antitumor activity, 2 tremorgenic activity, 3 potent and selective progesterone receptor agonistic activity, 4 and anti-MRSA activity. 5 Cyclopiazonic acid (CPA)-type alkaloids are one important group of indole-terpenes, and they usually contain three structural units: an indole, a dimethylallyl (DMA), and two acetic acids. Only six analogous natural products have been reported to date, including α-cyclopiazonic acid, 6 iso-α-cyclopiazonic acid, 7 β-cyclopiazonic acid, 6 α-acetyl-γ-(β-indolyl)methyl-tetramic acid, 8 speradine A, 9 and 3-hydroxyl speradine A. 10 In our search for novel anticancer compounds, 11 a strain of Aspergillus oryzae showed significant cytotoxic activity. Further chemical study led to isolation and structure elucidation of four new

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The Lecanindoles, Nonsteroidal Progestins from the Terrestrial Fungus Verticillium lecanii 6144

Cited by 43 publications

References 23 publications

Heterologous Biosynthesis of Fungal Indole Sesquiterpene Sespendole

Heterologous Biosynthesis of Fungal Indole Sesquiterpene Sespendole

Drimane-Related Merosesquiterpenoids, a Promising Library of Metabolites for Drug Development

Speradines B-E, Four Novel Tetracyclic Oxindole Alkaloids from the Marine-Derived Fungus Aspergillus oryzae

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