Rhizovagine A, an unusual dibenzo-α-pyrone alkaloid from the endophytic fungus Rhizopycnis vagum Nitaf22

Rhizovagine A (1), a novel dibenzo-α-pyrone alkaloid with an unprecedented 5/5/6/6/6 fused pentacyclic skeleton, was isolated from the endophytic fungus Rhizopycnis vagum Nitaf22. The structure was elucidated by comprehensive spectroscopic analysis, in combination with quantum chemical 13C NMR and electronic circular dichroism (ECD) calculations for configurational assignment. A plausible biosynthetic pathway for 1 was proposed. Compound 1 displayed acetylcholinesterase inhibitory activity.

[1]  Wei-Lun Chen,et al.  C-H Functionalization of Amino Alcohols by Osmium Tetroxide/NMO or TPAP/NMO: Protecting Group-Free Synthesis of Indolizidines (-)-223AB and 3-epi -(-)-223AB , 2020 .

[2]  Jie Guo,et al.  Alkaloids from the roots of Stemona tuberosa and their anti-tobacco mosaic virus activities , 2019, Tetrahedron.

[3]  Han-Dong Sun,et al.  (+)- and (-)-Alternarilactone A: Enantiomers with a Diepoxy-Cage-like Scaffold from an Endophytic Alternaria sp. , 2019, Journal of natural products.

[4]  Peng Li,et al.  Two New Anisic Acid Derivatives from Endophytic Fungus Rhizopycnis vagum Nitaf22 and Their Antibacterial Activity , 2018, Molecules.

[5]  G. Genta‐Jouve,et al.  Antiplasmodial Securinega alkaloids from Phyllanthus fraternus: Discovery of natural (+)-allonorsecurinine , 2017 .

[6]  J. Meng,et al.  Dibenzo-α-pyrones: a new class of larvicidal metabolites against Aedes aegypti from the endophytic fungus Hyalodendriella sp. Ponipodef12. , 2017, Pest management science.

[7]  Jin-Ying Tian,et al.  Dibenzo-α-pyrones from the endophytic fungus Alternaria sp. Samif01: isolation, structure elucidation, and their antibacterial and antioxidant activities , 2017, Natural product research.

[8]  Yuheng Cao,et al.  Bioactive Dibenzo-α-pyrone Derivatives from the Endophytic Fungus Rhizopycnis vagum Nitaf22. , 2016, Journal of natural products.

[9]  C. Darsih,et al.  Cytotoxic metabolites from the endophytic fungus Penicillium chermesinum: discovery of a cysteine-targeted Michael acceptor as a pharmacophore for fragment-based drug discovery, bioconjugation and click reactions , 2015 .

[10]  P. Solomon,et al.  SnPKS19 Encodes the Polyketide Synthase for Alternariol Mycotoxin Biosynthesis in the Wheat Pathogen Parastagonospora nodorum , 2015, Applied and Environmental Microbiology.

[11]  D. Lai,et al.  Natural Dibenzo-α-Pyrones and Their Bioactivities , 2014, Molecules.

[12]  Guo-dong Chen,et al.  Xinshengin, the first altenusin with tetracyclic skeleton core from Phialophora spp.☆ , 2013 .

[13]  G. Bringmann,et al.  SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. , 2013, Chirality.

[14]  Liang Xu,et al.  Benzopyranones from the Endophytic Fungus Hyalodendriella sp. Ponipodef12 and Their Bioactivities , 2012, Molecules.

[15]  Dean J. Tantillo,et al.  Computational prediction of 1H and 13C chemical shifts: a useful tool for natural product, mechanistic, and synthetic organic chemistry. , 2012, Chemical reviews.

[16]  H. Zhai,et al.  Total synthesis of (±)-cephalosol. , 2012, Organic letters.

[17]  M. Jaspars,et al.  Synoxazolidinone C; a bicyclic member of the synoxazolidinone family with antibacterial and anticancer activities , 2011 .

[18]  J. Vederas,et al.  Biosynthesis: "Aromatic Polyketides, Isoprenoids, Alkaloids" , 2010 .

[19]  A. Arlt,et al.  Total Synthesis of (±)-Cephalosolvia Silyl Enol Ether Acylation , 2010 .

[20]  D. Xie,et al.  Cephalosol: an antimicrobial metabolite with an unprecedented skeleton from endophytic Cephalosporium acremonium IFB-E007. , 2008, Chemistry.

[21]  P. Houghton,et al.  Acetylcholinesterase inhibitors from plants and fungi. , 2006, Natural product reports.

[22]  H. Abe,et al.  Synthesis of graphislactones A-D through a palladium-mediated biaryl coupling reaction of phenyl benzoate derivatives , 2005 .

[23]  T. Okuda,et al.  TMC-264, a novel antiallergic heptaketide produced by the fungus Phoma sp. TC 1674. , 2003, Organic letters.

[24]  T. Hemscheidt.  Tropane and Related Alkaloids , 2000 .

[25]  T. Hartmann,et al.  Biosynthesis and Metabolism of Pyrrolizidine Alkaloids in Plants and Specialized Insect Herbivores , 2000 .

[26]  T. Eisner,et al.  Pyrrolidinoöxazolidine alkaloids from two species of ladybird beetles. , 1997, Journal of Natural Products.

[27]  T. Tanahashi,et al.  For Phenolics from the Cultured Lichen Mycobiont of Graphis scripta var. pulverulenta , 1997 .

[28]  G. Martin,et al.  Kimbasines A and B, novel hexacyclic norsesterterpene alkaloids from the sponge Igernella notabilis☆ , 1991 .