Chemical Characterization of Secondary Metabolite from the Endophytic Fungus Trichordema reecei isolated from The Twig of Syzygium aqueum

Ummi H Habisukan, Elfita Elfita, Hary Widjajanti, Arum Setiawan

Abstract

Endophytic fungi are microorganisms that live in plants, without negative effects and are mutually related to hosting plants. Exploration of bioactive compounds from Endophytic fungi is easier and cheaper because they do not require a large area, a short growing time, and uncomplicated mixed compounds. Endophytic fungi are new and patent base secondary metabolites but they are not extensively characterized and investigated for the exploration of raw materials for drugs. The purpose of this study was to obtain antioxidant secondary metabolites from Endophytic fungi that live in the Syzygium aqueum medicinal plant. In this study, Endophytic
fungi were isolated from S. aqueum twigs and molecular identification. The secondary metabolites were isolated by chromatographic method and chemical structure identified by spectroscopy. Antioxidant activity was evaluated by method 1,1diphenyl-2-picryl hydrazyl (DPPH). Phylogenetic analysis showed the Endophytic fungi of S. aqueum twig have a high similarity with the Trichordema reecei twig 19MSr.B2.3. The secondary metabolites from the ethyl acetate extract of the liquid culture of the fungus were identified as (4-hydroxy-3-(4-hydroxyphenyl)-5 oxotetrahydrofuran-2-yl) methyl acetate with IC50= 75.13 ????g/mL. The secondary metabolites can be developed into starting molecules for potential antioxidant agents.

References

Aung E E, Kristanti A N, Aminah N S, Takaya Y, and Ramadhan R. (2020). Plant description, phytochemical constituents and bioactivities of Syzygium genus: A review. De Gruyter Open Chemistry. 18: 1256–1281.
Doi:10.1515/chem-2020-0175.
Budiono, Elfita, Muharni, Yohandini Y, and Widjajanti H. (2019). Antioxidant Activity of Syzygium samarangense L. and Their Endophytic Fungi. Molekul. 14(1): 48 – 55.
Doi:10.20884/1.jm.2019.14.1.503.
Cruz J S, Silva C A and Hamerski L. (2020). Natural Products from Endophytic Fungi Associated with Rubiaceae Species. Journal of Fungi. 2020(6): 1-28.
Doi:10.3390/jof6030128.
Ding Z, Tao T, Wang L, Zhao Y, Huang H, Zhang D, Liu M, Wang Z, and Han J. (2019). Bioprospecting of Novel and Bioactive Metabolites from Endophytic Fungi Isolated from Rubber Tree Ficus elastica Leaves. J. Microbiol. Biotechnol. 29(5): 731–738.
doi:10.4014/jmb.1901.01015.
Elfita, Mardiyanto, Fitrya, Larasati J E, Julinar, Widjajanti H, and Muharni. (2019). Antibacterial Activity of Cordyline Fruticosa Leaf Extracts and Its Endophytic Fungi Extracts. Biodiversitas. 20(12): 3804-3812.
Doi:10.13057/biodiv/d201245.
Elfita, Munawar, Muharni, and Sudrajat M A .(2014). Identification of New Lactone Derivatives Isolated from Trichoderma sp., An Endophytic Fungus of Brotowali (Tinaspora crispa). HAYATI Journal of Biosciences. 21(1): 15-20.
DOI: 10.4308/hjb.21.1.15.
El-hawary S S, Moawad A S, Bahr S H, Abdelmohsen U R, and Mohammed R .(2020). Natural Product Diversity From The Endophytic Fungi Of The Genus Aspergillus. RSC Adv. 2020 (10): 22058–22079.
Doi:10.1039/d0ra04290k.
Fadhillah, Elfita, Muharni, Yohandini H, and Widjajanti H. (2019). Chemical Compound Isolated From Antioxidant Active Extract Of Endophytic Fungus Cladosporium tenuissimum in Swietenia mahagoni Leaf Stalks. Biodiversitas. 20(9): 2645-2650.
DOI:10.13057/biodiv/d200929.
Fessenden, R.J. and Fessenden, J.S. (1992) Kimia Organik Jilid 2. Erlangga: Jakarta.
Gustianingtyas M, Herlinda S, Suwandi, Suparman, Hamidson H, Hasbi, Setiawan A, Verawaty M, Elfita, and Arsi. (2020). Toxicity of entomopathogenic fungal culture filtrate of lowland and highland soil of South Sumatra (Indonesia) against Spodoptera litura larvae. Biodiversitas. 21(5): 1839-1849.
Doi:10.13057/biodiv/d210510.
Harwoko H, Daletos G, Stuhldreier F, Lee J, Wesselborg S, Feldbrügge M, Müller W E G, Kalscheuer R, Ancheeva E, and Proksch P. (2021). Dithiodiketopiperazine derivatives from endophytic fungi Trichoderma harzianum and Epicoccum nigrum. Natural Product Research. 35(2): 257-265.
Doi:10.1080/14786419.2019.1627348.
Khan R, Naqvi S T Q, Fatima N and Muhammad S A. (2019). Study of Antidiabetic Activities Of Endophytic Fungi Isolated from Plants. Pure Appl. Biol. 8(2): 1287-129.
Doi:10.19045/bspab.2019.80071.
Leylaie S and Zafari D. (2018). Antiproliferative and Antimicrobial Activities of Secondary Metabolites and Phylogenetic Study of Endophytic Trichoderma Species From Vinca Plants. Bioactivity of Secondary Metabolites. 9(1484): 1-16.
Doi:10.3389/fmicb.2018.01484
Liu K, Ding X, Deng B, and Chen, W. (2009). Isolation and characterization of endophytic taxol-producing fungi from Taxus chinensis. J Ind Microbiol Biotechno.l 36: 1171–1177.
Doi: http://dx.doi.org/10.1007/s10295-009-0598-8.
Manganyi M C and Ateba C N. (2020). Untapped Potentials of Endophytic Fungi: A Reviewof Novel Bioactive Compounds with Biological Applications. Microorganisms. 2020(8): 1-25.
Doi:10.3390/microorganisms8121934.
Mbilu M, Wanyoike W, Kangogo M, Bii C, Agnes M, and Kihia C (2018) Isolation and Characterization of Endophytic Fungi from Medicinal Plant Warburgia ugandensis. Journal of Biology, Agriculture and Healthcare. 8(12): 57-66.
Muharni, Fitrya, Ruliza M O, Susanti D A, and Elfita. (2014). Di-(2-Ethylhexyl)Phthalate And Pyranon Derivated From Endophytic Fungi Penicillium sp The Leave Of Kunyit Putih (Curcuma zedoaria). Indo. J. Chem. 14(3): 290 – 296.
Doi:10.22146/ijc.21241.
Osman H, Rahim A A, Isa N M, and Bakhir N M. (2009). Antioxidant Activity and Phenolic Content of Paederia foetida and Syzygium aqueum. Molecules. 14: 970-978.
Doi:10.3390/molecules14030970.
Palanisamy U D, Ling L T, Manaharan T, Sivapalan V, Subramaniam T, Helme M H, and Masilamani T. (2011). Standardized Extract of Syzygium aqueum: a Safe Cosmetic Ingredient. International Journal of Cosmetic Science. 33: 269–275.
doi:10.1111/j.14682494.2010.00637.x.
Shentu X, Zhan X, Ma Z, Yu X, and Zhang C. (2014). Antifungal activity of metabolites of the endophytic fungus Trichoderma brevicompactum from garlic. Brazilian Journal of Microbiology. 45(1): 248-254.
Doi: http://dx.doi.org/10.1590/S1517-83822014005000036.
Sobeh M, Mahmoud M F, Petruk G, Rezq S, Ashour M L, Youssef F S, El-Shazly A M, Monti D M, Abdel-Naim A B, and Wink M. (2018). Syzygium aqueum: A Polyphenol- Rich Leaf Extract Exhibits Antioxidant, Hepatoprotective, Pain-Killing and Anti-inflammatory Activities in Animal Models. Frontiers of Pharmacology. 9 (566): 1-14. doi:10.3389/fphar.2018.00566.
Specian V, Sarragiotto M H, Pamphile J A, and Clemente E. (2012). Chemical Characterization Of Bioactive Compounds From The Endophytic Fungus Diaporthe Helianthi Isolated From Luehea Divaricata. Brazilian Journal of Microbiology. 2012: 1174-1182
Doi:10.1590/s1517838220120003000045.
Wu S, Zhao L, Chena Y, Huang R, Miao C, and Wanga J. (2011). Sesquiterpenoids from the Endophytic Fungus Trichoderma sp. PR-35 of Paeonia delavayi. Chemistry & Biodiversity. 8(2011): 1717-1723.
Doi 10.1007/s10295-009-0598-8.
Yohandini H, Julinar and Muharni. (2015) Isolation and Phylogenetic Analysis of Thermophile Community Within Tanjung Sakti Hot Spring, South Sumatera, Indonesia. HAYATI Journal of Biosciences. 22: 143-148.
Doi:10.1016/j.hjb.2015.10.006.

Authors

Ummi H Habisukan
Elfita Elfita
elfita69@gmail.com (Primary Contact)
Hary Widjajanti
Arum Setiawan
Hiras Habisukan, U., Elfita, E., Widjajanti, H. ., & Setiawan, A. . (2021). Chemical Characterization of Secondary Metabolite from the Endophytic Fungus Trichordema reecei isolated from The Twig of Syzygium aqueum. Science and Technology Indonesia, 6(3), 137–143. https://doi.org/10.26554/sti.2021.6.3.137-143

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