Main Article Content
Abstract
Background: Genus Trichoderma of fungal kingdom are largely used as biological control agents due to broad-spectrum activity against plant pathogens.
Objective: This study aimed to investigate Trichoderma harzianum, an endophytic fungus obtained from ginger (Zingiber officinale) leaves.
Methods: The chemical structures of the isolated compounds were deduced on the basis of UV, 1H NMR and MS data analyses, as well as comparison with literature.
Results: Two known tetramic acid derivatives were isolated from this fungus, including harzianic acid (A) and isoharzianic acid (B). Compound B inhibited the growth of a corn pathogenic fungus, Ustilago maydis, with inhibition zone diameter (39 ± 0.33 mm) larger than nystatin (29 mm). Additionally, iso-HA (B) revealed antibacterial effect towards Staphylococcus aureus with MIC value of 25 µM. However, both compounds showed no cytotoxicity against human cervical and ovarian cancer cell lines.
Conclusion: T. harzianum produced antimicrobial compound like iso-HA which has potential application either in agricultural or health.
Keywords
Article Details
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References
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- Chen SL, Yu H, Luo HM, Wu Q, Li CF, Steinmetz A. Conservation and sustainable use of medicinal plants: Problems, progress, and prospects. Chinese Medicine. 2016;11(37):1–10.
- Venieraki A, Dimou M, Katinakis P. Endophytic fungi residing in medicinal plants have the ability to produce the same or similar pharmacologically active secondary metabolites as their hosts. Hell Plant Protection Journal. 2017;10(2):51–66.
- Cragg GM, Newman DJ. Natural products: A continuing source of novel drug leads. Biochimica et Biophysica Acta (BBA)–General Subjects. 2013;1830:3670–95.
- Ancheeva E, Daletos G, Proksch P. Bioactive secondary metabolites from endophytic fungi. Current Medicinal Chemistry. 2020;27(11):1836–54.
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- Elfahmi E, Woerdenbag HJ, Kayser O. Jamu: Indonesian traditional herbal medicine towards rational phytopharmacological use. Journal of Herbal Medicine. 2014;4(2):51–73.
- Beristain-Bauza SDC, Hernández-Carranza P, Cid-Pérez TS, Ávila-Sosa R, Ruiz-López II, Ochoa-Velasco CE. Antimicrobial activity of ginger (Zingiber officinale) and its application in food products. Food Reviews International. 2019;35(5):407–26.
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- Vinale F, Flematti G, Sivasithamparam K, Lorito M, Marra R, Skelton BW, et al. Harzianic acid, an antifungal and plant growth promoting metabolite from Trichoderma harzianum. Journal of Natural Products. 2009;72(11):2032–5.
- Vinale F, Manganiello G, Nigro M, Mazzei P, Piccolo A, Pascale A, et al. A novel fungal metabolite with beneficial properties for agricultural applications. Molecules. 2014;19(7):9760–72.
- Healy AR, Vinale F, Lorito M, Westwood NJ. Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers. Organic Letters. 2015;17(3):692–5.
- Mo X, Lib Q, Ju J. Naturally occurring tetramic acid products: Isolation, structure elucidation and biological activity. RSC Advances. 2014;4(92):50566–93.
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- Prabowo A, Prihatiningsih N, Soesanto L. Potency of Trichoderma harzianum in controlling nine isolates of Fusarium oxysporum Schlecht. f.sp. zingiberi trujillo on galanga. Jurnal Ilmu-Ilmu Pertanian Indonesia. 2006;8(2):76–84.
- Mueller DS, Wise KA, Sisson AJ, Allen TW, Bergstrom GC, Bissonnette KM, et al. Corn yield loss estimates due to diseases in the United States and Ontario, Canada from 2012 to 2015. Plant Health Progress. 2016;17(3):211-222.
- Abdul JA, Posangi J, Wowor PM, Bara RA. Uji efek daya hambat jamur endofit rimpang jahe (Zingiber officinale Rosc) terhadap bakteri Staphylococcus aureus dan Escherichia coli. Jurnal Biomedik?: Jbm. 2020;12(2):88–93.
- Handayani D, Pratiwi EMI, Fajrina A. Antimicrobial compounds from the endophytic fungus Trichoderma koningiopsis SaKB1 isolated from the mangrove plant Sonneratia alba Sm. Jurnal Sains Farmasi & Klinis. 2019;6(2):78–84.
- Marra R, Lombardi N, d’Errico G, Troisi J, Scala G, Vinale F, et al. Application of Trichoderma strains and metabolites enhances soybean productivity and nutrient content. Journal of Agricultural and Food Chemistry. 2019;67(7):1814–22.
- Triastuti A. Fungal endophytes as the source of medicinal natural product. Scientific Journal of Pharmacy. 2020;16(1):52–73.
- Xiao G, Zhang X, Gao Q. Bioinformatic approaches for fungal omics. BioMed Research International. 2017;(7270485):1.
References
Singh R, Dubey AK. Endophytic actinomycetes as emerging source for therapeutic compounds. Indo Global Journal of Pharmaceutical Sciences. 2015;5(2):106–16.
Chen SL, Yu H, Luo HM, Wu Q, Li CF, Steinmetz A. Conservation and sustainable use of medicinal plants: Problems, progress, and prospects. Chinese Medicine. 2016;11(37):1–10.
Venieraki A, Dimou M, Katinakis P. Endophytic fungi residing in medicinal plants have the ability to produce the same or similar pharmacologically active secondary metabolites as their hosts. Hell Plant Protection Journal. 2017;10(2):51–66.
Cragg GM, Newman DJ. Natural products: A continuing source of novel drug leads. Biochimica et Biophysica Acta (BBA)–General Subjects. 2013;1830:3670–95.
Ancheeva E, Daletos G, Proksch P. Bioactive secondary metabolites from endophytic fungi. Current Medicinal Chemistry. 2020;27(11):1836–54.
Jia M, Chen L, Xin H-L, Zheng C-J, Rahman K, Han T, et al. A friendly relationship between endophytic fungi and medicinal plants: A systematic review. Frontiers in Microbiology. 2016;7(906).
Elfahmi E, Woerdenbag HJ, Kayser O. Jamu: Indonesian traditional herbal medicine towards rational phytopharmacological use. Journal of Herbal Medicine. 2014;4(2):51–73.
Beristain-Bauza SDC, Hernández-Carranza P, Cid-Pérez TS, Ávila-Sosa R, Ruiz-López II, Ochoa-Velasco CE. Antimicrobial activity of ginger (Zingiber officinale) and its application in food products. Food Reviews International. 2019;35(5):407–26.
Rajan P, Gupta S, Sarma Y, Jackson G. Diseases of ginger and their control with Trichoderma harzianum. Indian Phytopathology. 2002;55(2):173–7.
Harwoko H, Daletos G, Stuhldreier F, Lee J, Wesselborg S, Feldbrügge M, et al. Dithiodiketopiperazine derivatives from endophytic fungi Trichoderma harzianum and Epicoccum nigrum. Natural Product Research. 2021;35(2):257–65.
Ariantari NP, Ancheeva E, Wang C, Mándi A, Knedel TO, Kurtán T, et al. Indole diterpenoids from an endophytic Penicillium sp. Journal of Natural Products. 2019;82(6):1412–23.
Sawa R, Mori Y, Iinuma H, Naganawa H, Hamada M, Yoshida S, et al. Harzianic acid, a new antimicrobial antibiotic from a fungus. Journal of Antibiotics. 1994;47(6):731–2.
Vinale F, Flematti G, Sivasithamparam K, Lorito M, Marra R, Skelton BW, et al. Harzianic acid, an antifungal and plant growth promoting metabolite from Trichoderma harzianum. Journal of Natural Products. 2009;72(11):2032–5.
Vinale F, Manganiello G, Nigro M, Mazzei P, Piccolo A, Pascale A, et al. A novel fungal metabolite with beneficial properties for agricultural applications. Molecules. 2014;19(7):9760–72.
Healy AR, Vinale F, Lorito M, Westwood NJ. Total synthesis and biological evaluation of the tetramic acid based natural product harzianic acid and its stereoisomers. Organic Letters. 2015;17(3):692–5.
Mo X, Lib Q, Ju J. Naturally occurring tetramic acid products: Isolation, structure elucidation and biological activity. RSC Advances. 2014;4(92):50566–93.
Sood M, Kapoor D, Kumar V, Sheteiwy MS, Ramakrishnan M, Landi M, et al. Trichoderma: The “secrets” of a multitalented biocontrol agent. Plants. 2020;9(6):762.
Soesanto L, Soedharmono S, Prihatiningsih N, Manan A, Iriani E, Pramono J. Potency of biological and botanical agents in controlling ginger rhizome rot. Jurnal Hama dan Penyakit Tumbuhan Tropika. 2005;5(1):50–7.
Prabowo A, Prihatiningsih N, Soesanto L. Potency of Trichoderma harzianum in controlling nine isolates of Fusarium oxysporum Schlecht. f.sp. zingiberi trujillo on galanga. Jurnal Ilmu-Ilmu Pertanian Indonesia. 2006;8(2):76–84.
Mueller DS, Wise KA, Sisson AJ, Allen TW, Bergstrom GC, Bissonnette KM, et al. Corn yield loss estimates due to diseases in the United States and Ontario, Canada from 2012 to 2015. Plant Health Progress. 2016;17(3):211-222.
Abdul JA, Posangi J, Wowor PM, Bara RA. Uji efek daya hambat jamur endofit rimpang jahe (Zingiber officinale Rosc) terhadap bakteri Staphylococcus aureus dan Escherichia coli. Jurnal Biomedik?: Jbm. 2020;12(2):88–93.
Handayani D, Pratiwi EMI, Fajrina A. Antimicrobial compounds from the endophytic fungus Trichoderma koningiopsis SaKB1 isolated from the mangrove plant Sonneratia alba Sm. Jurnal Sains Farmasi & Klinis. 2019;6(2):78–84.
Marra R, Lombardi N, d’Errico G, Troisi J, Scala G, Vinale F, et al. Application of Trichoderma strains and metabolites enhances soybean productivity and nutrient content. Journal of Agricultural and Food Chemistry. 2019;67(7):1814–22.
Triastuti A. Fungal endophytes as the source of medicinal natural product. Scientific Journal of Pharmacy. 2020;16(1):52–73.
Xiao G, Zhang X, Gao Q. Bioinformatic approaches for fungal omics. BioMed Research International. 2017;(7270485):1.