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The Lupeol Content in Machaerium Species by HPLC- APCI-MS/MS and the Allelopathic Action

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The Lupeol Content in Machaerium Species by HPLC- APCI-MS/MS and the Allelopathic Action Vol. 13(2), pp. 44-50, April-June 2021 DOI: 10.5897/JHF2021.0668 Article Number: 81433F666917 ISSN: 2006-9782 Copyright ©2021 Author(s) retain the copyright of this article Journal of Horticulture and Forestry http://www.academicjournals.org/JHF Full Length Research Paper The lupeol content in Machaerium species by HPLC- APCI-MS/MS and the allelopathic action Luciana Sayuri Tahira1, Robson Akito Tino1, Charlyana Carvalho Bento1, Marcelo Marucci Pereira Tangerina2, Luiz Fernando Rolim de Almeida3, Danilo Miralha Franco3, Ângela Lúcia Bagnatori Sartori4 and Miriam Sannomiya1* 1Escola de Artes, Ciências e Humanidades, Universidade de São Paulo, Campus leste, CEP 03828-000, São Paulo, Brazil. 2Departamento de Botânica, Instituto de Biociências, Universidade de São Paulo, CEP 05508-090, São Paulo, Brazil. 3Departamento de Fisiologia, Instituto de Biociências, Universidade Estadual Paulista “Júlio de Mesquita Filho”, cp 610, CEP 18618-689, UNESP, Botucatu, São Paulo, Brazil. 4Universidade Federal do Mato Grosso do Sul, Campo Grande- MS, CEP 79070-900, Brazil. Received 23 April, 2021; Accepted 19 May, 2021 The use of extracts from plants and/or allelopathic compounds from natural products can minimize the use of pesticides in agriculture. This is a chemical study of Machaerium eriocarpum branch extract and the evaluation of the allelopathic potential of Machaerium hirtum (Vell.) Stellfed and M. eriocarpum Benth (Fabaceae) leaves and branches extracts. The triterpene lupeol was isolated from the hydroethanolic extract of M. eriocarpum branches. The quantification of this compound in all extracts was performed by HPLC-APCI-MS/MS and the highest amount of lupeol was observed in the leaves extract of M. eriocarpum. Allelopathy tests were carried out against seeds of Sorghum bicolor L. (sorghum), evaluating the final percentage of germination, germination speed index (GSI), root growth and number of lateral roots. The leaves extracts of both species were effective in the inhibition of the root growth as well as of the lateral roots. The branches extract of M. hirtum showed inhibitory effect in the root growth and lateral roots only in 50 and 100 mg.L-1 doses. The lupeol showed mainly a strong inhibition of seed germination, root growth and lateral root appearance at 100 μM. This study showed the potentiality of Machaerium extracts and lupeol as bioherbicides. Key words: Allelopathy, lupeol, Machaerium, Fabaceae, Sorghum bicolor, phytoxicity INTRODUCTION The continuous practice of agricultural synthetic non-biodegradable compounds accumulation in the soil herbicides can increase human health risks through the and the development of microorganisms resistance *Corresponding author. E-mail: [email protected]. Tel: 55 (11) 26480104; orcid: 0000-0003-3306-9170. Author(s) agree that this article remain permanently open access under the terms of the Creative Commons Attribution License 4.0 International License Tahira et al. 45 (Luz et al., 2010). Finding alternative strategies for weed potent allelopathic effects on the roots of Echium management is now being focused on to reduce the plantagineum (Zhu et al., 2016). According to De Oliveira dependence of farm chemicals by a sustainable et al. (2005) the leaf extract of Machaerium scleroxylon agriculture based on plant derived materials, developing showed 100% of inhibitory effect in the length of the environmentally friendly alternatives approach for the seedlings of Lactuca sativa. weed control (Kuk et al., 2001). Substances produced by Machaerium is one of the largest tropical arboreal plants can offer new and excellent opportunities to genera of Papilionoideae, with approximately 160 known diversify the control of invasive plants in agriculture, taxa and popularly known as "jacarandás" (Plant, 2020; decreasing or eradicating environmental contamination, Bastos, 1987; Polido and Sartori, 2011). According to the preserving natural resources and ensuring the availability literature, this genus is recognized by the occurrence of of quality agricultural products. Theoretically, natural different class of natural products such as triterpenes, products and plant extracts with allelopathic activity with proanthocyanidins, cinnamylphenols, alkaloids, phytotoxic effect can be used directly in the formulation of benzoquinones, steroids and the incisive presence of bioherbicides or be modified in order to increase their flavonoids (Ignoato et al., 2013; Kurosawa et al., 1978a, biological activity (Yamagushi et al., 2011). According to b; Ollis et al., 1978, 1968; Alves et al., 1966; Bento et al., Todero (2017), until now there are thirteen bioherbicides 2018; Gregson et al., 1968; elSohly et al., 1999; Seo et originating from fungi, bacteria and plant, available on the al., 2001; Adrian et al., 2007; Santos et al., 2009; Oliveira international market. However, bioherbicides show a et al., 1968; Braga et al., 1968). Based on previous shorter half-life when compared with synthetic herbicides studies involving the allelopathic activity of isovitexin and (Duke et al., 2000; Bailey, 2014; Todero, 2017). Despite Machaerium eriocarpum leaf extract, associated with the its natural origin, it is important to take into account the absence of phytochemical studies of branch extract of toxic potential for living beings when produced on a large this species, in this work the triterpene lupeol was scale, as well as the environmental impact of this isolated and its quantification was performed by HPLC- production due to the demand for food for a growing APCI-MS/MS and their allelopathic action. population. According to Abd-ElGawad et al. (2020) the essential oil of Bassia muricata reduces the germination and MATERIALS AND METHODS seedling development of the weed Chenopodium murale. The aqueous extract of Sphenoclea zeylanica Gaertn. Plant material had an inhibitory effect on rice germination and seedling -1 The plant material M. eriocarpum Benth was collected in Porto growth at concentrations higher than 50 g.L , while Murtinho-MS, by A. L. B. Sartori, E. S. S. Lima and F. J. completely inhibited rice seed germination at the Kochanovski. An exsiccate of the species is deposited in the concentration of 100 g.L-1 (Krumsri et al., 2020). The Herbarium of the Federal University of Mato Grosso do Sul, Campo flavonol quercetin and its derivatives from Fagopyrum Grande campus (CGMS411323). The branches and leaves of Machaerium hirtum (Vell.) Stellfeld were collected by Almeida, L. F. esculentum root showed on haustorium induction in R. in Botucatu, São Paulo. The exsiccate is deposited in the Phelipanche ramose at concentration range 0.1 to 0.05 Herbarium of the Department of Botany (BOTU 027643), Institute of mM (Fernández-Aparicio et al., 2021). The methyl oleate, Bioscience, Sao Paulo State University, Botucatu campus. The methyl stearate, methyl palmitate and methyl linoleate data collected was recorded in the SisGen platform (National inhibited the seed germination of Avena fatua, System of Management of Genetic Heritage and Associated Chenopodium album, Euphorbia helioscopia, Rumex Traditional Knowledge) as genetic patrimony under the registration number A32A22B and A1BB684. dentatus and Phalaris minor in a dose-dependent manner All material was dried at 40°C and ground using a knife mill with (Anwar et al., 2021). The main compound of Glycyrrhiza an average particle size of 1 to 3 mm. uralensis Fisch, liquiritin displays inhibitory effects on the growth of lettuce (Yan et al., 2020). Chou and Waller (1980), caffeine, theobromine, Extract fractionation and lupeol isolation theophylline, paraxanthine, scopoletin, chlorogenic, Separately, the plant materials of M. eriocarpum and M. hirtum vanillic, ferulic and p-hydroxybenzoic acids, which are were submitted to the percolation process in 70% ethanol. The present in the Coffea arabica extract showed allelopathic material was weighed and swollen in 2 L of 70% (v/v) ethanol. The action on lettuce growth at the concentration of 100 ppm. solvent was evaporated under reduced pressure at a temperature Jose et al. (2016) described the allelopathic effect of of 40°C and then stored in a sealed amber bottle (Table 1). Merostachys riedeliana extract, fractions and phenolic The branches extract of M. eriocarpum (1.54 g) was solubilized in acids on Mimosa bimucronata seeds. The constituents 12 mL of methanol/H2O (8:2, v/v) and centrifuged at 10,000 rpm during 10 min. The supernatant was fractionated using a Sephadex present in the extract of Cinnamomum septentrionale LH-20 column (57 cm × 3.0 cm d.i) and eluted with methanol with a leaves presented potent phytotoxic action on corn growth flow rate of 4 mL min-1. The 230 subfractions were analyzed by TLC (Yang et al., 2017); while the naphtoquinones presented using CHCl3/methanol/H2O 80:18:2 (v/v), which in turn, produced 46 J. Hortic. For. Table 1. Yield of extract and the concentration of lupeol observed in the Machaerium extracts. Sample Dried material (g) Weight Yield (%) Peak area average Amount (ppm) MHL 1000 170 17 19568.5 0.23 MHB 500 79.1 15.8 69794.0 0.79 MEL 500 58.2 11.6 207040.3 1.51 MEB 499.7 69.7 13.5 134966.7 2.31 MHL: Machaerium hirtum leaves extract; MHB: M. hirtum branches extract; MEL: M. eriocarpum leaves extract; MEB: M. eriocarpum branches extract. 11 groups of fractions (G1-G11). The G4 fraction group (50 mg) energy of 20%, as well as activation time of 30 min/s, in the same was applied on preparative TLC which was divided in two sides. On source conditions as described earlier. Chromatographic method the left side, G4 was applied as a line (15 cm) and on the right side consisted of A (0.1% formic acid in H2O) and B (0.1% of formic acid as a point using a capillary glass tube. After elution of the in MeOH), in a gradient elution system (92-100%) of B in 6 min chromatographic plate using CHCl3/methanol 98:2 (v/v) as mobile followed by a hold of 100% B for 3 min, where the first 0.8 min were phase, the left side was covered with a glass plate and the right discarded, flow of 0.4 mL min-1, injection volume 10 µL, column side sprayed with sulfuric anisaldehyde.
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