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In Vitro Antimycotic Activity of Chemical Constituents from Dipterocarpus

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In Vitro Antimycotic Activity of Chemical Constituents from Dipterocarpus Asian J Agric & Biol. 2019;7(3):344-354. Original Article AJAB In vitro antimycotic activity of chemical constituents from Dipterocarpus verrucosus, Dipterocarpus cornutus and Dipterocarpus crinitus against opportunistic filamentous fungi Wan Zuraida Wan Mohd Zain1,2,3*, Norizan Ahmat3,4, Yaya Rukayadi5, Che Puteh Osman3,4, Nor Asma Husna Yusoff5, Neneng Winda6 1Faculty of Plantation and Agrotechnology, Universiti Teknologi MARA, Jasin Campus, 77300 Merlimau, Melaka, Malaysia 2 Faculty of Plantation and Agrotechnology, Universiti Teknologi MARA, Shah Alam Campus, 40450, Shah Alam, Selangor, Malaysia 3Faculty of Applied Sciences, Universiti Teknologi MARA, 40450 Shah Alam, Selangor, Malaysia 4Atta-ur-Rahman Institute for Natural Product Discovery, Universiti Teknologi MARA Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor, Malaysia 5Faculty of Food Science and Technology and Laboratory of Natural Products, Institute of Bioscience, Universiti Putra Malaysia, 43400 UPM Serdang, Selangor Darul Ehsan, Malaysia 6Department of Science Education, Faculty of Tarbiyah and Education, Sunan Gunung Djati State Islamic University, Bandung, Indonesia Received: Abstract May 31, 2018 This paper will discuss, in vitro investigation of chemical constituents extracted from the stem Accepted: bark of Dipterocarpus verrucosus, Dipterocarpus crinitus and Dipterocarpus cornutus against October 31, 2018 opportunistic filamentous fungi. In this research, 17 compounds comprised of twelve Published: oligostilbenoids, (-)--viniferin ,(-)-laevifonol, (-)-hopeaphenol , (-)-isohopeaphenol, vaticanol September 30, 2019 B, diptoindonesin E, hemsleyanol D, davidiol A, resveratrol, ampelopsin A, ampelopsin F, together with three other phenolic; gallic acid derivative, (-)-bergenin, scopoletin and 4- methoxygallocathecin and also two terpene; β-sitosterol and β-sitosterol glucoside have been isolated. In this study, the crude extracts and isolated compounds were evaluated regarding to their antifungal activity; in terms of MIC, MFC and germination assay against pathogenic fungi strains, namely Aspergillus flavus (AF), Aspergillus oligosporus (AO), Rhizophus oryzae (RO) and Fusarium oxysporum (FO) using Clinical and Laboratory Standard Institute (CLSI) methods. The MIC of crude extracts and isolated compounds against all fungi ranged from 3.8 - 500 µg/mL. F. oxysporum shows the most sensitive microorganisms on crude extract: D. verrucosus, D. cornutus and isolated compound: ε-viniferin with MIC of 3.8 µg/mL. The MIC was lower compared to amphotericin B (4 µg/ml). The strain was killed at the MFC of 31.3, 31.3 and 15.6 µg/mL respectively, as compared to amphotericin B (8 µg/mL). Compounds: resveratrol, laevifonol, ε-viniferin, ampelopsin F, vaticanol B, vaticanol A, isomer of hopeaphenol and isohopeaphenol, β-sitosterol and β-sitosterolglucoside possessed an inhibitory activity on the conidial germination of F. oxysporum at the concentration of 4× MIC. On top of that, D. cornutus, ampelopsin A and hemsleyanol D possessed a complete sterility at the concentration of 2×MIC while D.verrucosus achieved its inhibitory activity at 1× MIC. To the best of our study, there is no data discussing the inhibition of conidial germination of filamentous fungi using the tested compounds and crudes tested. Keywords: Antifungal, In vitro, Opportunistic fungi, Phenolic compounds, Stilbenoid How to cite this: Zain WWM, Ahmat N, Rukayadi Y, Osman CP, Yusoff NAH and Winda N. 2019. In vitro antimycotic activity of chemical constituents from Dipterocarpus verrucosus, Dipterocarpus *Corresponding author email: cornutus and Dipterocarpus crinitus against opportunistic filamentous fungi. Asian J. Agric. [email protected] Biol. 7(3):344-354. This is an Open Access article distributed under the terms of the Creative Commons Attribution 3.0 License. (https://creativecommons.org/licenses/by/3.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Asian J Agric & Biol. 2019;7(3):344-354. 344 Wan Zuraida Wan Mohd Zain et al. Introduction which is the main source of antifungal compounds. Antifungal compounds can act as phytoalexin, a Filamentous fungi; anatomically viewed from its natural antibiotic in plants which acts like a toxin that shape, can possibly facilitate problematic infections, attack harmful organism (Sotheeswaran & Pasupathy, consequently causing invasive mycoses in both non- 1993). Therefore, secondary metabolism is immunocompromised and immunocompromised considered as a promising source of novel antifungal individuals. These infections require prompt systemic properties due to the fact that it has been successfully antifungal therapy, where the effectiveness of which used by plant as their defense mechanism (Basri et al., depends, among other things, on the in vitro 2012). In an attempt to explore new antifungal leads, susceptibility of the fungus to antifungal drugs the stem bark of Dipterocarpus from (Meletiadis et al., 2000). Although Candida albicans Dipterocarpaceae family which is often neglected in is the species that is most often associated with serious timber industry was utilised. Dipterocarpaceae is the fungal infections, other species of Candida as well as large family of tropical plants, extensively distributed filamentous fungi such as Aspergillus and Fusarium across Kalimantan and Malay Peninsula (Seo, 2000). are now considered as imperative pathogens in Interestingly, this stem carries an ability to produce immunocompromised hosts (Morison et al., 1993). various secondary metabolites such as The incidence of invasive opportunistic filamentous oligostilbennoid, triterpenoid, flavonoid, volatile oil fungal infections, particularly in immunosuppressed and arylpropanoid (Sotheeswaran & Pasupathy, patients, have increased in past 25 years and is now 1993). Resveratrol or known as 3, 5, 4- becoming a significant cause of morbidity and trihydroystilbene and their oligomer is a polyphenolic mortality (Rukayadi & Hwang, 2007). This is commonly exists in edible foods and beverages such particularly true in infected patients with as mulberries, peanuts, grapes and wines (Xue et al., hematological malignancies undergoing induction or 2014). Since the discovery of those natural consolidation chemotherapy (Annaise, 1992), in compounds, scientists have found the chemical immunosuppressed organ transplant recipients, in structure of the derivatives of resveratrol and its patients with acquired immunodeficiency, and is positive effects on cellular and biological activities. secondary to the infection of human For that reason, there is a growing demand and interest immunodeficiency viruses (Hadley & Karchmer, in exploring resveratrol produced by plants. Vitaceae, 1995). Amphotericin B and azole derivatives are Leguminosae, Gnetaceae, Dipterocarpaceae, and among the primary drugs used for treatment of serious Cyperaceae were five plant families isolated on fungal infections. Nevertheless, limitations in efficacy resveratrol oligomers (Seo, 2000, Xue et al., 2014, or tolerability of these chemicals create an alarming Zain et al., 2011, Zain et al., 2018a, Zain et al., 2018b) call for further research to discover new drugs with a . However, there is a paucity of reports on antifungal wide spectrum of effectiveness in treating said properties (Lee & Lee, 2015) especially on the diseases caused by filamentous fungi pathogens chemical constituents of Dipterocarpaceae against (Rukayadi & Hwang, 2007) human fungal pathogens. The first study on antifungal The past 25 years is a mark of the advent of plants was evaluated on 1977 (Pryce, 1977) and the full resource advancement as an effective alternative review of antimicrobial from stilbenoids was source, replacing antibiotics for clinical applications published in 1993 (Sootheeswaran & Pasupathy, (Fenner et al., 2005). Malaysia is known as one of the 1993). However, until now, there is only one reported 12th mega biodiversity countries that offer a plethora literature published about the use of stilbenoids from of natural resources to facilitate numerous researches the family of Dipterocarpaceae against filamentous in the quest of a novel compound discovery. fungi; by discussing on the effect of stilbenoid from Malaysia’s rich rainforest and a wide array of Hopea exalata against Fusarium oxysporum (FO). In biodiversity should be supported by the collective and fact, the study (Ge et al., 2006) evaluated the same continuous efforts in compiling and screening those compounds with this research which are α-viniferin floras, to prevent the loss of valuable sources that is and vaticanol A, mostly as an approach in agricultural possible to be developed into environmentally safe sectors to prevent microbial pathogens and pests’ antifungal agents. Hence, to achieve such attainment, attack using natural defenses. Both compounds these valuable compounds or known as secondary exhibit the capabilities of inhibiting FO with the MIC metabolites, should be harvested from the plants, values of 25.2 µg/mL and 6.22 µg/mL, respectively, Asian J Agric & Biol. 2019;7(3):344-354. 345 Wan Zuraida Wan Mohd Zain et al. and the compounds performed closely to the standard ground and extracted with methanol. Further ketoconazole at 2.21 µg/mL. Another finding fractionation using various chromatography evaluated on antifungal against C. albicans towards techniques were carried out consecutively (Wibowo et two stilbenoids; 3, 4’, 5-trihydroxystilbene and 3, 5- al., 2014, Wibowo
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