VASCULAR MECHANISMS OF TRITERPENOID SAPONINS ISOLATED FROM Passiflora quadrangularis L.
Background: Passiflora quadrangularis L. has antihypertensive and anxiolytic properties observed in experimental models. Objectives: The aim of this work was to establish the vascular effects exerted by two known monodesmosidic triterpene saponins, 3-O-β-D-glucopyranosyloleanolic acid (Compound 1) (not previously described for this plant) and, 3-O-[β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl] oleanolic acid (Compound 2), isolated from the ethanolic extract of Passiflora quadrangularis L. leaves. Methods: The structural elucidation was achieved by Nuclear Magnetic Resonance (NMR) experiments and High-Resolution Mass Spectrometry (HRMS). Aortic rings from Wistar rats, previously stimulated with phenylephrine (PE, 1µM) and washed, were exposed to cumulatively concentrations of compound 1 and compound 2 (10 to 400 µM). Ethanolic extract from leaves of P. quadrangularis L. (10 to 320 µg/mL) and clonidine (1nM to 100µM) were also used for comparison. Concentration-response curves of compounds 1 and 2 were examined in presence and absence of: endothelium, the alpha-2 antagonist yohimbine (1 and 100 µM), the alpha non-selective antagonist phentolamine (1µM), the alpha-1 antagonist prazosin (1µM) and the calcium channel blocker verapamil (10 and 100 µM). In addition, a cumulative response curve of acetylcholine (ACh, 10nM to 10µM) and sodium nitroprusside (SNP, 1nM to 100µM) were assayed in rings precontracted with compounds 1 and 2 (400 µM). Results: Compounds 1 and 2 elicited a vasoconstriction response in intact aorta rings in a similar way (pEC50: 3.92±0.01 and 4.09±0.01, respectively), the effect that did not change in denuded rings (pEC50: 3.90±0.01 and 4.11±0.01). The potency order (pEC50) of compounds 1 and 2 decreased according to the following: verapamil (3.53±0.01 and 3.90±0.02; p<0.05) < yohimbine (3.65±0.01 and 3.94±0.02; p<0.05) < prazosin (3.86±0.01 and 4.30±0.02) < phentolamine (4.05±0.02 and 4.05±0.01). SNP but not ACh, was able to decrease the vasopressor effect of compounds 1 and 2 (pIC50: 8.61±0.01 and 8.24 ± 0.15, respectively). Conclusions: Compounds 1 and 2 are key metabolites responsible for the ex vivo vasoconstrictor response induced by P. quadrangularis L. Activation of voltage-dependent calcium channels and/or α2-adrenergic receptors stimulation could be mechanisms implicated.
Ocampo J, Coppens G, Jarvis A. Distribution of the Genus Passiflora L. Diversity in Colombia and Its Potential as an Indicator for Biodiversity Management in the Coffee Growing Zone. Diversity. 2010;2:1158-80. DOI: http://dx.doi.org/10.3390/ d2111158
Bareño LL, Puebla P, Guerra CM, San Feliciano A, Isaza G, Guerrero MF. Passiflora quadrangularis L. prevents experimental hypertension and vascular remodelling in rats exposed to nitric oxide deficit. Vitae. 2017;24(3):186–95. DOI: http://dx.doi. org/10.17533/udea.vitae.v24n4a04
de Castro PCF, Hoshino A, da Silva JC, Mendes FR. Possible anxiolytic effect of two extracts of Passiflora quadrangularis L. in experimental models. Phytother Res. 2007;21(5):481–4. DOI: https://doi.org/10.1002/ptr.2079
Sakalem ME, Negri G, Tabach R. Chemical composition of hydroethanolic extracts from five species of the Passiflora genus. Rev Bras Farmacogn. 2011;22(6):1219–32.DOI: http://dx.doi. org/10.1590/S0102-695X2012005000108
Costa GM, Gazola AC, Madóglio FA, Zucolotto SM, Reginatto FH, Castellanos L, et al. Vitexin derivates as chemical market in the differentation of the closely related species Passiflora alata curtis and Passiflora quadrangularis Linn. J Liq Chromatogr Relat Technol. 2013;36:1697–707.DOI: http://dx.doi.org/10.1080/108
Ingale AG, Hivrale AU. Pharmacological studies of Passiflora sp. and their bioactive compounds. African J Plant Sci. 2010;4(10):417–26. Available from: https://academicjournals.org/ article/article1380125484_Ingale%20and%20Hivrale.pdf
Orsini F, Pelizzoni F, Verotta L. Quadranguloside, a cycloartane triterpene glycoside from Passiflora quadrangularis. Phytochemistry. 1985;25(1):191–3. DOI: https://doi.org/10.1016/S0031- 9422(00)94527-8
Orsini F, Pellizzoni F, Ricca G, Verotta L. Triterpene glycosides related to quadranguloside from Passiflora quadrangularis. Phytochemistry. 1987;26(4):1101–5. DOI: http://dx.doi. org/10.1016/S0031-9422(00)82358-4
Dhawan K, Dhawan S, Sharma A. Passiflora: A review update. J Ethnopharmacol. 2004;94(1):1–23. DOI: http://dx.doi.org/10.1016/j.jep.2004.02.023
Kamibayashi T, Maze M. Clinical Uses of α 2-Adrenergic Agonists. Anesthesiology. 2000;93:1345–9. Available from: https://anesthesiology.pubs.asahq.org/article.aspx?articleid=1945301
Grześk E, Stolarek W, Wicińsk M, Szadujkis-Szadurska K, Malinowski B, Tejza B, et al. Effect of acetylcholine on
vascular smooth muscle contraction induced by phenylephrine, angiotensin II and mastoparan-7. Folia Medica Copernicana. 2014;2(3):98–101. Available from: https://journals.viamedica.pl/medical_research_ journal/article/view/40506/27925
Thornin E, Huang PL, Fishman MC, Bevan JA. Nitric oxide inhibits α2-adrenoceptor-mediated endothelium-dependent vasodilation. Circ Res. 1998;82(12):1323–9. DOI: 1. DOI: https://doi.org/10.1161/01.RES.82.12.1323
Rameshrad M, Babaei H, Azarmi Y, Fadaei D. Rat aorta as a pharmacological tool for in vitro and in vivo studies. Life Sci. 2016;145:190-204. DOI: http://dx.doi.org/10.1016/j.lfs.2015.12.043
Copyright Notice and Open Access Statement
The Journal Vitae works under the Open Access license, and the published manuscripts remain available for the public, both on the Journal's website and in databases, under the Creative Commons license, "Non-commercial Attribution" and "No-derivative Works" systems, adopted in Colombia. Hence, when the authors agree to publish in the Journal Vitae, they also give the exclusive license and the copyrights to the Journal Vitae and the University of Antioquia, without the right to economic retributions on publications and reproductions through different diffusion media. The documents are freely available to the internet public, permitting any users to read, download, copy, distribute, print, search, or link to the full texts, pass them as data to software. The only constraint on reproduction and distribution, and the only role for copyright in this domain, should be to give authors control over the integrity of their work and the right to be appropriately acknowledged and cited.
Authors declare that:
They are the intellectual property owners and responsible for all the information stated in the article.
This manuscript has not been submitted or published in other printed or digital media. They accept the responsibility for the judgments, opinions, and points of view expressed in the published article and, therefore, they exonerate Universidad de Antioquia and Journal Vitae from any process.
They exempt Universidad de Antioquia and Journal Vitae from the settlement of conflicts or disputes related to the authorship of the referred article.
They accept the revision of the original manuscript by suitable personnel, and they bind themselves to perform the corrections appointed or suggested by the assessors.
They know the editorial process and, therefore, will not bind the Editorial Board of the Journal to assume any obligations regarding the volume and issue in which the article is published.
They transfer the rights of publication, reprinting, and distribution of the article from the moment of its approval, in print and digital format, without the right to economic rewards, and under the licensing conditions considered relevant by Journal Vitae.
They fully authorize Universidad de Antioquia and Journal Vitae to submit the published material to the diverse databases and indexing systems where the Journal can be found to comply with the requirements of the regulatory authorities to maintain the national classification of journals.
They will assume the article publication costs established for the current issue, and they will make the payment as soon as they are informed about the volume and the issue in which the final version of the article is published.
After the article is published, you can share digital or printed copies in a non-commercial manner. You will be able to use the paper in your institution or company for educational or research purposes, including the use in course programs.
Conflict of interest: Authors are responsible for recognizing and disclosing any financial or other benefits that could be perceived to bias their work, acknowledging all financial support and any personal connections with potential sponsors. Examples of such conflicts include receiving research funds or honoraria, serving on advisory boards, stock ownership, or employment and consulting arrangements. Authors without such connections should clearly state that they have no financial support or personal relationships that could be perceived to bias their work. All conflicts of interest should be disclosed on the author's identification page of the manuscript.