Phomapyrrolidones A-C, Antitubercular Alkaloids from the Endophytic Fungus Phoma Sp. NRRL 46751

Overview

Journal J Nat Prod

Date 2013 Oct 2

PMID 24079882

Citations 12

Authors

E M Kithsiri Wijeratne

Hongping He

Scott G Franzblau

Angela M Hoffman

A A Leslie Gunatilaka

Affiliations

Soon will be listed here.

Abstract

Three new alkaloids, phomapyrrolidones A-C (1-3), bearing a cyclopenta[b]fluorene ring system were isolated from the mycelium extract of the endophytic fungal strain Phoma sp. NRRL 46751, inhabiting Saurauia scaberrinae. Methylation of 1 afforded its N-methyl derivative 4. The planar structures and relative configurations of 1-4 were elucidated by extensive spectroscopic analysis. Phomapyrrolidones B (2) and C (3) exhibited weak antitubercular activity at subcytotoxic concentrations.

Citing Articles

Bioactive compounds and biomedical applications of endophytic fungi: a recent review.

Hashem A, Attia M, Kandil E, Fawzi M, Abdelrahman A, Khader M Microb Cell Fact. 2023; 22(1):107.

PMID: 37280587 PMC: 10243280. DOI: 10.1186/s12934-023-02118-x.

Embellicines C-E: Macrocyclic Alkaloids with a Cyclopenta[b]fluorene Ring System from the Fungus sp.

Al Subeh Z, Flores-Bocanegra L, Raja H, Burdette J, Pearce C, Oberlies N J Nat Prod. 2023; 86(3):596-603.

PMID: 36884371 PMC: 10043936. DOI: 10.1021/acs.jnatprod.2c01048.

Promising antimicrobials from Phoma spp.: progress and prospects.

Rai M, Zimowska B, Gade A, Ingle P AMB Express. 2022; 12(1):60.

PMID: 35604500 PMC: 9125353. DOI: 10.1186/s13568-022-01404-y.

Didymellanosine, a new decahydrofluorene analogue, and ascolactone C from sp. IEA-3B.1, an endophyte of .

Ariantari N, Ancheeva E, Frank M, Stuhldreier F, Meier D, Groner Y RSC Adv. 2022; 10(12):7232-7240.

PMID: 35493894 PMC: 9049863. DOI: 10.1039/c9ra10685e.

Antibiotics from Extremophilic Micromycetes.

Baranova A, Alferova V, Korshun V, Tyurin A Russ J Bioorg Chem. 2021; 46(6):903-971.

PMID: 33390684 PMC: 7768999. DOI: 10.1134/S1068162020060023.

References

Strobel G, Daisy B, Castillo U, Harper J . Natural products from endophytic microorganisms. J Nat Prod. 2004; 67(2):257-68. DOI: 10.1021/np030397v. View

Isaka M, Prathumpai W, Wongsa P, Tanticharoen M . Hirsutellone F, a dimer of antitubercular alkaloids from the seed fungus Trichoderma species BCC 7579. Org Lett. 2006; 8(13):2815-7. DOI: 10.1021/ol060926x. View

Strobel G, Singh S, Riyaz-Ul-Hassan S, Mitchell A, Geary B, Sears J . An endophytic/pathogenic Phoma sp. from creosote bush producing biologically active volatile compounds having fuel potential. FEMS Microbiol Lett. 2011; 320(2):87-94. DOI: 10.1111/j.1574-6968.2011.02297.x. View

Dai J, Hussain H, Drager S, Schulz B, Kurtan T, Pescitelli G . Metabolites from the fungus Phoma sp. 7210, associated with Aizoon canariense. Nat Prod Commun. 2010; 5(8):1175-80. View

Arnold A, Mejia L, Kyllo D, Rojas E, Maynard Z, Robbins N . Fungal endophytes limit pathogen damage in a tropical tree. Proc Natl Acad Sci U S A. 2003; 100(26):15649-54. PMC: 307622. DOI: 10.1073/pnas.2533483100. View

Oikawa H . Biosynthesis of structurally unique fungal metabolite GKK1032A(2): indication of novel carbocyclic formation mechanism in polyketide biosynthesis. J Org Chem. 2003; 68(9):3552-7. DOI: 10.1021/jo0267596. View

Ebrahim W, Aly A, Wray V, Mandi A, Teiten M, Gaascht F . Embellicines A and B: absolute configuration and NF-κB transcriptional inhibitory activity. J Med Chem. 2013; 56(7):2991-9. DOI: 10.1021/jm400034b. View

Zhang H, Song Y, Tan R . Biology and chemistry of endophytes. Nat Prod Rep. 2006; 23(5):753-71. DOI: 10.1039/b609472b. View

Weber R, Stenger E, Meffert A, Hahn M . Brefeldin A production by Phoma medicaginis in dead pre-colonized plant tissue: a strategy for habitat conquest?. Mycol Res. 2004; 108(Pt 6):662-71. DOI: 10.1017/s0953756204000243. View

10.

Wang L, Xu B, Wang J, Su Z, Lin F, Zhang C . Bioactive metabolites from Phoma species, an endophytic fungus from the Chinese medicinal plant Arisaema erubescens. Appl Microbiol Biotechnol. 2011; 93(3):1231-9. DOI: 10.1007/s00253-011-3472-3. View

11.

Gunatilaka A . Natural products from plant-associated microorganisms: distribution, structural diversity, bioactivity, and implications of their occurrence. J Nat Prod. 2006; 69(3):509-26. PMC: 3362121. DOI: 10.1021/np058128n. View

12.

Chan E, Iseman M . Current medical treatment for tuberculosis. BMJ. 2002; 325(7375):1282-6. PMC: 1124748. DOI: 10.1136/bmj.325.7375.1282. View

13.

Collins L, Franzblau S . Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium. Antimicrob Agents Chemother. 1997; 41(5):1004-9. PMC: 163841. DOI: 10.1128/AAC.41.5.1004. View

14.

Shiono Y, Shimanuki K, Hiramatsu F, Koseki T, Tetsuya M, Fujisawa N . Pyrrospirones A and B, apoptosis inducers in HL-60 cells, from an endophytic fungus, Neonectria ramulariae Wollenw KS-246. Bioorg Med Chem Lett. 2008; 18(23):6050-3. DOI: 10.1016/j.bmcl.2008.10.032. View

15.

Falzari K, Zhu Z, Pan D, Liu H, Hongmanee P, Franzblau S . In vitro and in vivo activities of macrolide derivatives against Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2005; 49(4):1447-54. PMC: 1068601. DOI: 10.1128/AAC.49.4.1447-1454.2005. View

16.

Wijeratne E, Bashyal B, Liu M, Rocha D, Gunaherath G, URen J . Geopyxins A-E, ent-kaurane diterpenoids from endolichenic fungal strains Geopyxis aff. majalis and Geopyxis sp. AZ0066: structure-activity relationships of geopyxins and their analogues. J Nat Prod. 2012; 75(3):361-9. PMC: 3359839. DOI: 10.1021/np200769q. View

17.

Hoffman A, Mayer S, Strobel G, Hess W, Sovocool G, Grange A . Purification, identification and activity of phomodione, a furandione from an endophytic Phoma species. Phytochemistry. 2007; 69(4):1049-56. DOI: 10.1016/j.phytochem.2007.10.031. View

18.

Wang X, Bashyal B, Wijeratne E, URen J, Liu M, Gunatilaka M . Smardaesidins A-G, isopimarane and 20-nor-isopimarane diterpenoids from Smardaea sp., a fungal endophyte of the moss Ceratodon purpureus. J Nat Prod. 2011; 74(10):2052-61. PMC: 3371368. DOI: 10.1021/np2000864. View

19.

Verma V, Kharwar R, Strobel G . Chemical and functional diversity of natural products from plant associated endophytic fungi. Nat Prod Commun. 2009; 4(11):1511-32. View

20.

Cho S, Warit S, Wan B, Hwang C, Pauli G, Franzblau S . Low-oxygen-recovery assay for high-throughput screening of compounds against nonreplicating Mycobacterium tuberculosis. Antimicrob Agents Chemother. 2007; 51(4):1380-5. PMC: 1855511. DOI: 10.1128/AAC.00055-06. View