ESPOCH Congresses: The Ecuadorian Journal of S.T.E.A.M.

ISSN: 2789-5009

Leading Ecuadorian research in science, technology, engineering, arts, and mathematics.

Main Polar Metabolites from Leaves of the Native Andean Species Jungia rugosa Less (Asteraceae)

Published date: Nov 09 2023

Journal Title: ESPOCH Congresses: The Ecuadorian Journal of S.T.E.A.M.

Issue title: Volume 3 Issue 1

Pages: 421–433

DOI: 10.18502/espoch.v3i1.14460

Authors:

V. VerdugoDepartamento de Química, Universidad Técnica Particular de Loja, Loja, Ecuador

K. CalvopiñaDepartamento de Química, Universidad Técnica Particular de Loja, Loja, Ecuador

O. MalagónDepartamento de Química, Universidad Técnica Particular de Loja, Loja, Ecuador

G. Gilardoniggilardoni@utpl.edu.ecDepartamento de Química, Universidad Técnica Particular de Loja, Loja, Ecuador

Abstract:

The ethanolic extract of Jungia rugosa Less, a popular Andean species belonging to the family Asteraceae, was characterized chemically. The extract was deprived of chlorophyll by solid-phase extraction, using Diaion Hp-20 resin as solid phase, and eluting with a mixture of EtOH/H2O according to a decreasing polarity gradient. The chlorophyll-free extract was then repeatedly fractionated by open column chromatography in normal phase and preparative thin layer chromatography. Two main metabolites were finally purified and identified through structure elucidation. Nuclear magnetic resonance spectroscopy (NMR) and electrospray ionization-mass spectrometry (ESI-MS) were the 2 techniques used for analysis. The identified metabolites were coumarins: (1) umbelliferone and (2) coumarin-5- methyl-4α-glucoside. Compound 1 is known in the literature for having anti-inflammatory, antihyperglycemic, and antitumor activities. Compound 2 has not been described before for this botanical genus and its pharmacological effects are still uninvestigated.

Keywords: Jungia rugosa, umbelliferone, coumarin-5-methyl-4￿-glucoside, NMR, ESI-MS, Ecuador.

Resumen

Se caracterizó químicamente el extracto etanólico de Jungia rugosa Less, una popular especie andina perteneciente a la familia Asteraceae. Se eliminó las clorofilas al extracto mediante extracción en fase sólida, utilizando como fase sólida resina de Diaion Hp-20 y eluyendo con una mezcla de EtOH/H2O según un gradiente de polaridad decreciente. El extracto libre de clorofila se fraccionó repetidamente mediante cromatografía en columna abierta en fase normal y cromatografía en capa fina preparativa. Finalmente, se purificaron e identificaron dos metabolitos principales mediante la elucidación de la estructura. Se utilizaron espectroscopía de resonancia magnética nuclear (RMN) y espectrometría de masas de ionización por aspersión de electrones (ESI-MS). Los metabolitos identificados fueron las cumarinas: umbeliferona (1) y cumarina-5-metil-4α-glucósido (2). El compuesto 1 es conocido en la literatura por tener actividad antiinflamatoria, antihiperglucémica y antitumoral. El compuesto 2 no se ha descrito antes para este género botánico y sus efectos farmacológicos aún no se han investigado.

Palabras Clave: Jungia rugosa, umbeliferona, cumarina-5-metil-4-glucósido, RMN, ESI-MS, Ecuador.

References:

[1] Gallegos M. Las plantas medicinales: usos y efectos en el estado de salud de la población rural de Ecuador. 2017.

[2] Cuesta F, Peralvo M, Merino-Viteri A, Bustamante M, Baquero F, Freile JF, et al. Priority areas for biodiversity conservation in mainland Ecuador [Internet]. Neotropical Biodiversity. 2017;3(1):93–106.

[3] Aguirre Mendoza Z. Biodiversidad de la provincia de Loja, Ecuador [Internet]. Arnaldoa. 2017 Dec;24(2):523–542. [cited 2022 Feb 6] Available from: http://www.scielo.org.pe/scielo.php?script=sci_arttext&pid=S2413- 32992017000200006&lng=es&nrm=iso&tlng=es

[4] Valdes A, Cazar M. Actividad antibacteriana de extractos orgánicos y aceite esencial de Jungia rugosa Less. Universidad del Azuay. 2013;1–14.

[5] Enciso E, Arroyo J. Efecto antiinflamatorio y antioxidante de los flavonoides de las hojas de Jungia rugosa Less (matico de puna) en un modelo experimental en ratas. An la Fac Med [Internet]. 2013 [cited 2022 Feb 18];72(4):231. Available from: http://www.scielo.org.pe/scielo.php?script=sci_arttext&pid=S1025- 55832011000400002&lng=es&nrm=iso&tlng=es

[6] Criollo Sumba K, Molina Fernadez N, Leon F. Evaluacion de la Estabilidad de Extractatos obtenidos a partir de distintos procesos de secado de Jungia Rugosa. [Internet]. 2016. Available from: http://dspace.ucuenca.edu.ec/bitstream/123456789/26236/1/PROYECTO DE INVESTIGACIÓN.pdf

[7] Campoverde Lupercio J de L. Verdugo Pillaga VM. Determinación del efecto cicatrizante de las hojas de carne humana ( Jungla cf. rugosa) [Internet]. 2008. Available from: http://dspace.ucuenca.edu.ec/handle/123456789/20266

[8] Calvopina K, Malagon O, Capetti F, Sgorbini B, Verdugo V, Gilardoni G. A new sesquiterpene essential oil from the native andean species Jungia rugosa Less (Asteraceae): chemical analysis, enantiomeric evaluation, and cholinergic activity [Internet]. Plants. 2021 Oct;10(10):2102. [cited 2022 Feb 6] Available from: https://www.mdpi.com/2223-7747/10/10/2102/htm

[9] Torre Pascual I. Produccion biotecnologica de acido D-Lactico a partir de residuos de naranja. Univ Complut Madrid [Internet]. 2019;219. Available from: https://eprints.ucm.es/id/eprint/58053/1/T41519.pdf

[10] Azeved L, Faqueti L, Kritsanida M, Efstathiou A, Smirlis D, Franchi GC, et al. Three new trixane glycosides obtained from the leaves of Jungia sellowii Less. using centrifugal partition chromatography. Beilstein Journal of Organic Chemistry [Internet]. 2016 Apr 12 [cited 2022 Feb 6];12:674. Available from: /pmc/articles/PMC4902082/

[11] Duschatzky CB, Possetto ML, Talarico LB, Garcia CC, Michis F, Almeida NV, et al. Evaluation of chemical and antiviral properties of essential oils from South American plants [Internet]. Antiviral Chemistry and Chemotherapy. 2005;16(4):247–251. [cited 2022 Feb 6] Available from: https://journals.sagepub.com/doi/abs/10.1177/095632020501600404

[12] Carrion A, Garcia C. “Preparacion De Extractos Vegetales: Determinacion De Eficiencia De Metodica. University of Cuenca [Internet]. 2010;(Tesis previa a la obtencion del titulo de Bioquimica y Farmeceutica):27–31. Available from: http://dspace.ucuenca.edu.ec/bitstream/123456789/2483/1/tq1005.pdf

[13] Younas KA, Khan A, Shehzad O, Seo EK, Onder A, Khan S. Anti-allergic activities of Umbelliferone against histamine- and Picryl chloride-induced ear edema by targeting Nrf2/iNOS signaling in mice [Internet]. BMC Complementary Medicine and Therapies. 2021 Aug;21(1):215. [cited 2022 Feb 18] Available from: https://bmccomplementmedtherapies.biomedcentral.com/articles/10.1186/s12906- 021-03384-1

[14] Cruz LF, Figueiredo GF, Pedro LP, Amorin YM, Andrade JT, Passos TF, et al. Umbelliferone (7-hydroxycoumarin): A non-toxic antidiarrheal and antiulcerogenic coumarin. Biomedicine & Pharmacotherapy. 2020 Sep;129:110432.

[15] Chu LL, Pandey RP, Lim HN, Jung HJ, Thuan NH, Kim TS, et al. Synthesis of umbelliferone derivatives in Escherichia coli and their biological activities. Journal of Biological Engineering [Internet]. 2017 Apr 5 [cited 2022 Feb 18];11(1). Available from: /pmc/articles/PMC5382406/

[16] Mazimba O. Umbelliferone: Sources, chemistry and bioactivities review [Internet]. Bulletin of Faculty of Pharmacy, Cairo University. 2017;55(2):223–232.

[17] Singh R, Singh B, Singh S, Kumar N, Kumar S, Arora S. Umbelliferone - An antioxidant isolated from Acacia nilotica (L.) Willd Ex Del Food Chemistry [Internet]. 2010 [cited 2022 Feb 6];120(3):825–830. Available from: https://revistas.unitru.edu.pe/index.php/ECCBB/article/view/476

[18] Singh R, Singh B, Singh S, Kumar N, Kumar S, Arora S. Umbelliferone - An antioxidant isolated from Acacia nilotica (L.) Willd Ex Del Food Chemistry [Internet]. 2010 [cited 2022 Feb 6];120(3):825–30. Available from: http://ri.uaemex.mx/handle/20.500.11799/99723

[19] Ojala T, Remes S, Haansuu P, Vuorela H, Hiltunen R, Haahtela K, et al. Antimicrobial activity of some coumarin containing herbal plants growing in Finland. Journal of Ethnopharmacology. 2000 Nov;73(1-2):299–305.

[20] Yu SM, Hu DH, Zhang JJ. Umbelliferone exhibits anticancer activity via the induction of apoptosis and cell cycle arrest in HepG2 hepatocellular carcinoma cells. Molecular Medicine Reports 2015 Sep;12(3):3869–3873.

[21] Kanimozhi G, Prasad NR, Ramachandran S, Pugalendi KV. Umbelliferone modulates gamma-radiation induced reactive oxygen species generation and subsequent oxidative damage in human blood lymphocytes [Internet]. European Journal of Pharmacology. 2011 Dec;672(1-3):20–29. [cited 2022 Feb 6] Available from: https://pubmed.ncbi.nlm.nih.gov/21946110/

[22] Ramesh B, Pugalendi KV. Antihyperglycemic effect of umbelliferone in streptozotocin-diabetic rats. Journal of Medicinal Food. 2006;9(4):562–566.

[23] Muthu R, Thangavel P, Selvaraj N, Ramalingam R, Vaiyapuri M. Synergistic and individual effects of umbelliferone with 5-flurouracil on the status of lipid peroxidation and antioxidant defense against 1, 2-dimethylhydrazine induced rat colon carcinogenesis. Biomedicine & Preventive Nutrition [Internet]. 2013 Jan [cited 2022 Feb 6];3(1):74–82. Available from: https://www.infona.pl//resource/bwmeta1.element.elsevier-668f539d-c83e-3a21- 9791-b85085c2ee81

[24] Walasek M, Grzegorczyk A, Malm A, Skalicka-Wozniak K. Bioactivity-guided isolation of antimicrobial coumarins from Heracleum mantegazzianum Sommier & Levier (Apiaceae) fruits by high-performance counter-current chromatography. Food Chemistry. 2015 Nov;186:133–138.

[25] Dupuy OA, Murillo R, Bonilla JA. Lactonas sesquiterpenicas de las plantas Viguiera sylvatica y Decachaeta thieleana (Asteraceae) modulan la produccion de oxido nitrico y la fagocitosis de macrófagos RAW [Internet]. Revista de Biologia Tropical. 2008 Sep;56(3):1063–1073. [cited 2022 Feb 6] Available from: http://www.scielo.sa.cr/scielo.php?script=sci_arttext&pid=S0034- 77442008000300008&lng=en&nrm=iso&tlng=es

[26] Seaman FC. Sesquiterpene lactones as taxonomic. 1982;48(2):121– 592. The Botanical Review. Available from: https://scihub. se/https://link.springer.com/article/10.1007/BF02919190#article-info

[27] Flores Y, Rodrigo G, Mollinedo P, Akesson B, Sterner O, Almanza GR. 5- Methylcoumarin Glucoside and a Coumestan Derivative from Mutisia orbignyana. Revista Boliviana de Quimica [Internet]. 2009 [cited 2022 Feb 6];26(1):21–26. Available from: http://www.scielo.org.bo/scielo.php?script=sci_arttext&pid=S0250- 54602009000100003&lng=es&nrm=iso&tlng=en

[28] Inoue T, Toyonaga T, Nagumo S, Nagai M. Biosynthesis of 4-hydroxy-5- methylcoumarin in a Gerbera jamesonii hybrid. Phytochemistry. 1989;28(9):2329– 2330.

[29] Mazimba O. Umbelliferone: Sources, chemistry and bioactivities review. Bulletin of Faculty of Pharmacy, Cairo University. 2017 Dec;55(2):223–232.

[30] Fattori J, Rodrigues FH, Pontes JG, Paula Espíndola A, Tasic L. Monitoring Intermolecular and Intramolecular Interactions by NMR Spectroscopy. Applications of NMR Spectroscopy. Bentham Science Publishers; 2015;180–266.

Download
HTML
Cite
Share
statistics

249 Abstract Views

130 PDF Downloads