Isolation of stigmaterol from hexanic extract of the leaves of Sphagneticola trilobata Pruski (Asteraceae)
DOI:
https://doi.org/10.5433/1679-0367.2020v41n1p43Keywords:
Sphagneticola trilobata Pruski, Stigmasterol, Chromatography, Phytosterol.Abstract
The interest of researchers and the general population is quite evident, and has grown considerably today, in the use of medicinal plants. The species of interest in this work, Sphagneticola trilobata Pruski is a herbaceous plant, belonging to Asteraceae family. Some reports have shown the presence of several chemical constituents in this plant, mainly diterpenes. The present work carried out the phytochemical study of a fraction of the hexane extract, due to the low yield of the dichloromethane fraction, by several chromatographic methods, in which the phytosterol estigmasterol was isolated. This compound has been confirmed by means of spectroscopic and literature data, and the isolation of compounds of this class of substances indicates a new strand for the medicinal use of this plant as a hypocholesterolemic future. For this, studies will be directed to the isolation of phytosterols, with subsequent biological tests.Downloads
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References
Adil Q. Isolation and structure elucidation studies in the Chemical constituents of Thevetia Nerifolia Juss [master's thesis]. Karachi (Pakistan): Research Institute of Chemistry University of Karachi Pakistan; 1994.
Agra MF, SILVA KN, Basílio IJLD, Freitas PF, Barbosa JM Filho. Survey of medicinal plants used in the region Northeast of Brazil. Rev. Bras. Farmacogn. 2008;18(3):472-508.
Assis LR Jr, Gracez FR, Garcez WF, Guterres ZR. Pregnanos e Outros constituintes das raízes de Macrosiphinia petrea (A. St. Hill) Kuntze (Apocynaceae). Quím Nova. 2013;36(4):S1-S19.
Awad AB, Fink CS. Phytosterols as anticancer dietary components: evidence and mechanism of action. J Nutr. 2000;130:2127-30.
Baccarin T, Czepula AI, Ferreira RA, Lucinda-Silva RM. Análise morfoanatômica das partes aéreas de Wedelia paludosa DC. (Acmela brasiliensis, Sphagneticola trilobata), Asteraceae. Rev. Bras. Farmacogn. 2009 Nov;19(2b):612-6.
Breitmaier E, Voelter W. Carbon-13 NMR Spectroscopy: high-resolution methods and applications in organic chemistry and biochemistry. 3a ed. Weinheim: Gordon & Breach Science Pub; 1987. p. 363-4.
Chaturvedula VSP, Prakash I. Isolation of stigmasterol and β-sitosterol from the dichloromethane extract of rubus suavissimus. Int J Curr Pharm Res. 2012;1(9):239-42.
Chiari E, Duarte DS, Raslan DS, Saúde DA, Perry KSP, Boaventura MAD, et al. In vitro screening of asteraceae plant species against Trypanosoma cruzi. Phytother Res. 1996;10.
De-Eknamkul W, Potduang B. Biosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry. 2003;62(3):389-98.
Fidelis I, Casali VWD, Andrade N, Lima JC, Lopes FA, Soares NFF, et al. Influência das embalagens e do armazenamento no crescimento microbiológico e na concentração de tanino em Sphagneticola trilobata (L.) Pruski. Rev Ceres. 2015;52(303):647-657.
Flora Avancine. Vedelia [Internet]. 2019. [Citado 2019 jan. 10]. Disponível em: http://avancine.com.br/produto/vedelia/.
Forgo P, Kövér KE. Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain ressonances of stigmasterol, a phytosterol derivative. Steroids. 2004;69:43-50.
Fucina G, Rocha LW, Silva GF, Hoepers SM, Ferreira FP, Guaratini T, et al. Topical anti-inflammatory phytomedicine based on Sphagneticola trilobata dried extracts. Pharm Biol. 2016 Nov; 54(11):2465-74.
Gabay O, Sanchez C, Salvat C, Chevy F, Breton M, Nourissat G, et al. Stigmasterol: a phytosterol with potential anti-osteoarthritic properties. Osteoarthr. Cartil. 18(1):106-16.
Habib MR, Nikkon F, Rahman M, Haque ME, Karim MR. Isolation of Stigmasterol and b-Sitosterol from Methanolic Extract of Root Bark of Calotropis gigantean (Linn). J. Biol. Sci. 2007;10(22):4174-6.
Jamal AK, Yaacob WA, Din LB. A Chemical Study on Phyllanthus columnaris. Eur J Sci Res, 2009;28:76-81.
Kamboj A, Saluja AK. Isolation of stigmasterol and β¬sitosterol from petroleum ether extract of aerial parts of ageratum conyzoides (Asteraceae). Int. J. Pharm. Pharm. Sci. 2011;3(1):94-6.
Katan MB. Efficacy and safety of plant stanols and sterols in the management of blood cholesterol levels. Mayo Clin. Proc. 2003;78:965-78.
Kreis W, Munkert J, Pádua RM. Biossíntese de metabólitos primáros e secundários. In: Simões CMO, Schenkel EP, Mello JCP, Mentz LA, Petrovick PR. Farmacognosia: do produto natural ao medicamento. 7a ed. Porto Alegre: Artmed; 2017. p. 147-165.
Maldini M, Sosa S, Montoro P, Giangaspero A, Balick MJ, Pizza C, et al. Screening of the topical anti-inflammatory activity of the bark of Acacia cornigera Willdenow, Byrsonima crassifolia Kunth, Sweetia panamensis Yakovlev and the leaves of Sphagneticola trilobata Hitchcock. J Ethnopharmacol. 2009;122(3):430-3.
Moghaddam FM, Farimani MM, Salahvarzi S, Amim G. Chemical constituents of dichloromethan extract of cultivated satureja khuzistanica. Evid Based Complement Alternat Med. 2006;4:95-8.
Montanari CA, Bolzani VS. Planejamento racional de fármacos baseado em produtos naturais. Quím Nova. 2001 fev;24(1):105-11.
Noldin VF, Isaias DB, Cechinel V Filho. Gênero Calophyllum: importância química e farmacológica. Quím Nova. 2006;29(3):549-54.
Oliveira AB. Microencapsulamento de estigmasterol proveniente de Musa paradisiaca L., Musaceae. [Dissertação]. Curitiba-PR: Universidade Federal do Paraná; 2007.
Panda S, Jafri M, Kar A, Meheta BK. Thyroid inhibitory, antiperoxidative and hypoglycemic effects of stigmasterol isolated from Butea monosperma. Fitoterapia. 2009;80(2):123-6.
Parisenti J. Determinação dos esteróis e dos ácidos graxos em ostras da região de Florianópolis-SC e efeito do seu consumo no colesterol sérico de ratos. Florianópolis-SC: UFSC, 2006. p. 24-28. [Dissertação]. Florianópolis-SC: Universidade Federal de Santa Catarina; 2006.
Patočka J. Biologically active pentacyclic triterpenes and their current medicine signification. J Appl Biomed. 2003;1:7-12.
Penteado JCP, Magalhaes D, Masini JC. Experimento didático sobre cromatografia gasosa: uma abordagem analítica e ambiental. Quím Nova. 2008;31(8):2190-93.
Quilez J, Garci£a-Lorda P, Salas-Salvadol J. Potential uses and benefits of phytosteros in diet: present situation and future directions. Clin Nutr. 2003;22(4):343-351.
Santos RAF. Avaliação das propriedades biológicas dos derivados sintéticos do β-sitosterol e triterpenos. [Dissertação]. Salvador–BA: Universidade Federal da Bahia; 2010.
Sartori MRK, Pretto JB, Cruz AB, Bresciani LFV, Yunes RA, Sortino M, et al. Antifungal activity of fractions and two pure compounds of flowers from Wedelia paludosa (Acmela brasiliensis) (Asteraceae). Pharmazie. 2003 Aug;58(8):567-9.
Tomaz ACA, Nogueira RBSS, Pinto DS, Agra MF, Souza MFV, Cunha EVL. Chemical constiuents from Richardia grandifl ora (Cham. & Schltdl.) Steud. (Rubiaceae). Rev Bras Farmacogn. 2008;18:47-52.
Agra MF, SILVA KN, Basílio IJLD, Freitas PF, Barbosa JM Filho. Survey of medicinal plants used in the region Northeast of Brazil. Rev. Bras. Farmacogn. 2008;18(3):472-508.
Assis LR Jr, Gracez FR, Garcez WF, Guterres ZR. Pregnanos e Outros constituintes das raízes de Macrosiphinia petrea (A. St. Hill) Kuntze (Apocynaceae). Quím Nova. 2013;36(4):S1-S19.
Awad AB, Fink CS. Phytosterols as anticancer dietary components: evidence and mechanism of action. J Nutr. 2000;130:2127-30.
Baccarin T, Czepula AI, Ferreira RA, Lucinda-Silva RM. Análise morfoanatômica das partes aéreas de Wedelia paludosa DC. (Acmela brasiliensis, Sphagneticola trilobata), Asteraceae. Rev. Bras. Farmacogn. 2009 Nov;19(2b):612-6.
Breitmaier E, Voelter W. Carbon-13 NMR Spectroscopy: high-resolution methods and applications in organic chemistry and biochemistry. 3a ed. Weinheim: Gordon & Breach Science Pub; 1987. p. 363-4.
Chaturvedula VSP, Prakash I. Isolation of stigmasterol and β-sitosterol from the dichloromethane extract of rubus suavissimus. Int J Curr Pharm Res. 2012;1(9):239-42.
Chiari E, Duarte DS, Raslan DS, Saúde DA, Perry KSP, Boaventura MAD, et al. In vitro screening of asteraceae plant species against Trypanosoma cruzi. Phytother Res. 1996;10.
De-Eknamkul W, Potduang B. Biosynthesis of β-sitosterol and stigmasterol in Croton sublyratus proceeds via a mixed origin of isoprene units. Phytochemistry. 2003;62(3):389-98.
Fidelis I, Casali VWD, Andrade N, Lima JC, Lopes FA, Soares NFF, et al. Influência das embalagens e do armazenamento no crescimento microbiológico e na concentração de tanino em Sphagneticola trilobata (L.) Pruski. Rev Ceres. 2015;52(303):647-657.
Flora Avancine. Vedelia [Internet]. 2019. [Citado 2019 jan. 10]. Disponível em: http://avancine.com.br/produto/vedelia/.
Forgo P, Kövér KE. Gradient enhanced selective experiments in the 1H NMR chemical shift assignment of the skeleton and side-chain ressonances of stigmasterol, a phytosterol derivative. Steroids. 2004;69:43-50.
Fucina G, Rocha LW, Silva GF, Hoepers SM, Ferreira FP, Guaratini T, et al. Topical anti-inflammatory phytomedicine based on Sphagneticola trilobata dried extracts. Pharm Biol. 2016 Nov; 54(11):2465-74.
Gabay O, Sanchez C, Salvat C, Chevy F, Breton M, Nourissat G, et al. Stigmasterol: a phytosterol with potential anti-osteoarthritic properties. Osteoarthr. Cartil. 18(1):106-16.
Habib MR, Nikkon F, Rahman M, Haque ME, Karim MR. Isolation of Stigmasterol and b-Sitosterol from Methanolic Extract of Root Bark of Calotropis gigantean (Linn). J. Biol. Sci. 2007;10(22):4174-6.
Jamal AK, Yaacob WA, Din LB. A Chemical Study on Phyllanthus columnaris. Eur J Sci Res, 2009;28:76-81.
Kamboj A, Saluja AK. Isolation of stigmasterol and β¬sitosterol from petroleum ether extract of aerial parts of ageratum conyzoides (Asteraceae). Int. J. Pharm. Pharm. Sci. 2011;3(1):94-6.
Katan MB. Efficacy and safety of plant stanols and sterols in the management of blood cholesterol levels. Mayo Clin. Proc. 2003;78:965-78.
Kreis W, Munkert J, Pádua RM. Biossíntese de metabólitos primáros e secundários. In: Simões CMO, Schenkel EP, Mello JCP, Mentz LA, Petrovick PR. Farmacognosia: do produto natural ao medicamento. 7a ed. Porto Alegre: Artmed; 2017. p. 147-165.
Maldini M, Sosa S, Montoro P, Giangaspero A, Balick MJ, Pizza C, et al. Screening of the topical anti-inflammatory activity of the bark of Acacia cornigera Willdenow, Byrsonima crassifolia Kunth, Sweetia panamensis Yakovlev and the leaves of Sphagneticola trilobata Hitchcock. J Ethnopharmacol. 2009;122(3):430-3.
Moghaddam FM, Farimani MM, Salahvarzi S, Amim G. Chemical constituents of dichloromethan extract of cultivated satureja khuzistanica. Evid Based Complement Alternat Med. 2006;4:95-8.
Montanari CA, Bolzani VS. Planejamento racional de fármacos baseado em produtos naturais. Quím Nova. 2001 fev;24(1):105-11.
Noldin VF, Isaias DB, Cechinel V Filho. Gênero Calophyllum: importância química e farmacológica. Quím Nova. 2006;29(3):549-54.
Oliveira AB. Microencapsulamento de estigmasterol proveniente de Musa paradisiaca L., Musaceae. [Dissertação]. Curitiba-PR: Universidade Federal do Paraná; 2007.
Panda S, Jafri M, Kar A, Meheta BK. Thyroid inhibitory, antiperoxidative and hypoglycemic effects of stigmasterol isolated from Butea monosperma. Fitoterapia. 2009;80(2):123-6.
Parisenti J. Determinação dos esteróis e dos ácidos graxos em ostras da região de Florianópolis-SC e efeito do seu consumo no colesterol sérico de ratos. Florianópolis-SC: UFSC, 2006. p. 24-28. [Dissertação]. Florianópolis-SC: Universidade Federal de Santa Catarina; 2006.
Patočka J. Biologically active pentacyclic triterpenes and their current medicine signification. J Appl Biomed. 2003;1:7-12.
Penteado JCP, Magalhaes D, Masini JC. Experimento didático sobre cromatografia gasosa: uma abordagem analítica e ambiental. Quím Nova. 2008;31(8):2190-93.
Quilez J, Garci£a-Lorda P, Salas-Salvadol J. Potential uses and benefits of phytosteros in diet: present situation and future directions. Clin Nutr. 2003;22(4):343-351.
Santos RAF. Avaliação das propriedades biológicas dos derivados sintéticos do β-sitosterol e triterpenos. [Dissertação]. Salvador–BA: Universidade Federal da Bahia; 2010.
Sartori MRK, Pretto JB, Cruz AB, Bresciani LFV, Yunes RA, Sortino M, et al. Antifungal activity of fractions and two pure compounds of flowers from Wedelia paludosa (Acmela brasiliensis) (Asteraceae). Pharmazie. 2003 Aug;58(8):567-9.
Tomaz ACA, Nogueira RBSS, Pinto DS, Agra MF, Souza MFV, Cunha EVL. Chemical constiuents from Richardia grandifl ora (Cham. & Schltdl.) Steud. (Rubiaceae). Rev Bras Farmacogn. 2008;18:47-52.
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Published
2020-05-06
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Egashira GO, Matos RLN de, Arakawa NS. Isolation of stigmaterol from hexanic extract of the leaves of Sphagneticola trilobata Pruski (Asteraceae). Semin. Cienc. Biol. Saude [Internet]. 2020 May 6 [cited 2025 Feb. 17];41(1):43-54. Available from: https://ojs.uel.br/revistas/uel/index.php/seminabio/article/view/35398
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