Identification of Bioactive Coumarin(s) from Three Endophytic Fungal Species of Calophyllum tomentosum

Author(s): Channabasava, Govindappa Melappa*

Journal Name: The Natural Products Journal

Volume 10 , Issue 4 , 2020

DOI : 10.2174/2210315509666190430145906

  Journal Home
Become EABM
Become Reviewer

Graphical Abstract:


Abstract:

Background: Many biologically important bioactive compounds have been identified in Calophyllum tomentosum extract. Hence, we aimed to identify different endophytic fungal species from different parts of the plants and their bioactive compounds.

Objective: The study includes identification and characterization of bioactive compounds in the extracts of endophytic fungal species of Calophyllum tomentosum.

Methods: Different parts were used to assess the different endophytic fungi. Two different solvents were used: extracts and qualitative solvents. TLC and GC-MS were employed to identify the bioactive compounds. The bioactive compounds producing endophytes were identified by using18S rRNA.

Results: In total, 13 different fungal species were identified from different parts of the Calophyllum tomentosum. The C. tomentosum leaf part showed seven different fungal endophytes from the barks (four) and stems (two). The methanol extract of Fusarium species (stem), Cladosporium species (bark) and hexane extract of Alternaria species (bark) showed a higher amount of coumarins in qualitative methods and TLC. Based on the above results, for further GC-MS and molecular identification studies, we selected three endophytes. In the GC-MS analysis, the methanol extract of Fusarium species (stem) showed psoralen, and furocoumarin (imperatonin or ammidin); Cladosporium species (bark) showed coumarin (2H-1-benzopyran-2-one), coumaric acid (3-benzofurancarboxylic acid), hynecromone (coumarin 4), 4-hydroxy-9-(3-methyl-2-butyl)furo(3,2-g)chloronen-7- one; and hexane extract of Alternaria species (bark) showed coumaric acid (3-benzofurancarboxylic acid). The three fungal endophytes were identified as Fusarium equiseti, Cladosporium uredinicola and Alternaria alternata from 18S rRNA analysis.

Conclusion: Based on the above results, the three endophytic fungal species confirm the presence of coumarins and therefore, can be used for the production of coumarins instead of the plant.

Keywords: Calophyllum tomentosum, endophytes, coumarins, GC-MS, 18S rRNA, Alternaria alternata.

[1]
Kostova, I.; Momekov, G. New zirconium (IV) complexes of coumarins with cytotoxic activity. Eur. J. Med. Chem., 2006, 41(6), 717-726.
[http://dx.doi.org/10.1016/j.ejmech.2006.03.020] [PMID: 16697491]
[2]
Murray, R.D.H.; Mendez, J.; Beown, S.A. The natural coumarins – Occurrence, chemistry and biochemistry; John Wiley & Sons Ltd.: Chichester, UK, 1982.
[3]
Uvais, M. Xanthones and triterpenes of Calophyllum tomentosum. Phytochemistry, 1982, 20(6), pp. 1303-1304.
[4]
Banerji, A.; Deshpande, A.D.; Prabhu, B.R.; Padmanava, P. Tomentonone, a new xanthonoid from the stem bark of Calophyllum tomentosum. J. Nat. Pro., 1994, 57(3), 396-399.
[http://dx.doi.org/10.1021/np50105a012]
[5]
Theatana, T.; Hyde, K.D.; Lumyong, S. Asparginase production by endophytic fungi from Thai medicinal plants: Cytotoxic properties. Int. J. Integr. Biol., 2009, 7(1), 1-8.
[6]
Barnett, H.L.; Hunter, B.B. Illustrated genera of imperfect fungi, 2nded; Burgess Publishing Company: Minneapolis, Minnesota, USA, 1972, p. 241.
[7]
Pegler, D.N. Fungi without Gills (Hymenomycetes and Gasteromycetes). An Identification Handbook. Ellis, M.B; Ellis, J.P., Ed.; Chapman and Hall: London, New York, Tokyo, Melbourne, Madras, 1990, p. 266.
[8]
Farhan, H.; Rammal, H.; Hijazi, A.; Hamad, H. Phytochemical screening and extraction of polyphenol from stems and leaves of a Lebanese Euphorbia macrolada schyzoceras Boiss. Ann. Biol. Res., 2012, 3(1), 149-156.
[9]
Umashankar, T.; Govindappa, M.; Ramachandra, Y.L.; Channabasava, R. Isolation and purification of p-coumaric acid from endophytic fungi, Alternaria species of Crotalaria pallida and in vitro cytotoxicity. Int. J. Biol. Pharm. Res., 2015, 6(2), 96-104.
[10]
Xiao, Z.; Chen, S.; Cai, R.; Lin, S.; Hong, K.; She, Z. New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242. Beilstein J. Org. Chem., 2016, 12, 2077-2085.
[http://dx.doi.org/10.3762/bjoc.12.196] [PMID: 27829913]
[11]
Huang, Z.; Yang, J.; She, Z.; Lin, Y. A new isoflavone from the mangrove endophytic fungus Fusarium sp. (ZZF60). Nat. Prod. Res., 2012, 26(1), 11-15.
[http://dx.doi.org/10.1080/14786419.2010.529444] [PMID: 21714733]
[12]
Danagoudar, A.; Joshi, C.G.; Kumar, R.S.; Poyya, J.; Nivya, T.; Hulikere, M.M.; Appaiah, K.A.A. Molecular profiling and antioxidant as well as antibacterial potential of polyphenol producing endophytic fungus- Aspergillus austroafricanus CGJ-B3. Mycol, 2017, 8(1), 28-36.
[http://dx.doi.org/10.1080/21501203.2017.1281358]
[13]
Umashankar, T.; Govindappa, M.; Ramachandra, Y.L.; Chandrappa, C.P.; Rai, P.S.; Channabasava, R. Isolation, purification and in vitro cytotoxicity activities of coumarin isolated from endophytic fungi, Alternaria species of Crotalaria pallida. Indo Amer. J. Pham. Res., 2015, 5(2), 926-936.
[14]
Nagy, N.; Kuipers, H.F.; Frymoyer, A.R.; Ishak, H.D.; Bollyky, J.B.; Wight, T.N.; Bollyky, P.L. 4-methylumbelliferone treatment and hyaluronan inhibition as a therapeutic strategy in inflammation, autoimmunity, and cancer. Front. Immunol., 2015, 6, 123.
[http://dx.doi.org/10.3389/fimmu.2015.00123] [PMID: 25852691]
[15]
Piao, X.L.; Park, I.H.; Baek, S.H.; Kim, H.Y.; Park, M.K.; Park, J.H. Antioxidative activity of furanocoumarins isolated from Angelicae dahuricae. J. Ethnopharmacol., 2004, 93(2-3), 243-246.
[http://dx.doi.org/10.1016/j.jep.2004.03.054] [PMID: 15234759]
[16]
White, T.J.; Bruns, T.; Lee, S.J.W.T.; Taylor, J.L. Amplification and direct sequencing of fungal ribosomal RNA genes for phylogenetics. PCR protocols, 1990, 18(1), 315-322.
[17]
Pillai, T.G.; Nair, B.; Swamy, G.E.M. Isolation of host specific endophytic fungus, Fusarium equiseti, from Nothopegia bedomei var. wayanadica occurring in the Southern parts of India. J. Plant Pathol. Microbiol., 2015, 6, 308.
[18]
Hawas, U.W.; El-Desouky, S.; El-Kassem, L.A.; Elkhateeb, W. Alternariol derivatives from Alternaria alternata, an endophytic fungus residing in red sea soft coral, inhibit HCV NS3/4A protease. Appl. Biochem. Microbiol., 2015, 51(5), 579-584.
[http://dx.doi.org/10.1134/S0003683815050099]
[19]
Singh, V.; Bhagat, J.; Chadha, B.S.; Manhas, R.K.; Kaur, S. Acetylcholinesterase inhibitory potential of endophytic fungi inhabiting three Indian medicinal plants. Int. J. Pharm., 2016, 6(1), 129-136.


Rights & PermissionsPrintExport Cite as

Article Details

VOLUME: 10
ISSUE: 4
Year: 2020
Published on: 21 August, 2020
Page: [502 - 512]
Pages: 11
DOI: 10.2174/2210315509666190430145906
Price: $25

Article Metrics

PDF: 17
HTML: 1



Most Downloaded Article(s)