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Molecules 2019, 24(2), 218; https://doi.org/10.3390/molecules24020218

Ent-homocyclopiamine B, a Prenylated Indole Alkaloid of Biogenetic Interest from the Endophytic Fungus Penicillium concentricum

1
Division of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, The Ohio State University, Columbus, OH 43210, USA
2
Department of Microbiology, College of Arts and Sciences, The Ohio State University, Columbus, OH 43210, USA
3
Infectious Diseases Institute, The Ohio State University, Columbus, OH 43210, USA
4
Center for Applied Plant Sciences, The Ohio State University, Columbus, OH 43210, USA
*
Author to whom correspondence should be addressed.
Academic Editor: Josphat Matasyoh
Received: 14 December 2018 / Revised: 4 January 2019 / Accepted: 8 January 2019 / Published: 9 January 2019
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Abstract

Ent-homocyclopiamine B (1), a new prenylated indole alkaloid bearing an alicyclic nitro group along with 2-methylbutane-1,2,4-triol (2) were isolated from an endophytic fungus Penicillium concentricum of the liverwort Trichocolea tomentella (Trichocoleaceae). The structure of 1 was elucidated through extensive spectroscopic analyses and comparison with data reported for a structurally related nitro-bearing Penicillium metabolite, clopiamine C (3), which contain an indolizidine ring instead of the quinolizine ring in 1. The new compound, ent-homocyclopiamine B, exhibited slight growth inhibition against Gram-positive bacteria. Based on the reported biosynthesis of related compounds and the isolation of the mevalonic acid derived compound 2-methyl-1,2,4-butanetriol (2), we proposed that ent-homocylopiamine B (1) was biosynthesized from lysine and prenyl group-producing mevalonic pathway. View Full-Text
Keywords: liverwort; endophyte; fungus; Penicillium; metabolite; indole alkaloid; antimicrobial liverwort; endophyte; fungus; Penicillium; metabolite; indole alkaloid; antimicrobial
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Ali, T.; Pham, T.M.; Ju, K.-S.; Rakotondraibe, H.L. Ent-homocyclopiamine B, a Prenylated Indole Alkaloid of Biogenetic Interest from the Endophytic Fungus Penicillium concentricum. Molecules 2019, 24, 218.

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