Abstract
Studies were carried out to select conditions for the spectrophotometric determination of total alkaloid content using bromocresol green (BCG): buffer pH, formation time of the BCG-alkaloid ion pair, and stability time of the BCG-alkaloid ion pair. It is shown that the method is applicable for tropane, isoquinoline, indole, and pyridine alkaloids. The method was used for rapid assessment of alkaloid content in the biomass of Ruta graveolens L. regenerated plants and in the pharmaceutical preparation Ruta graveolens herb. Using a minimum volume of dry plant material (20 mg), it was determined that the content of alkaloids in regenerated plants was 10.55 mg/g dry weight, which is 1.62 times less than in pharmaceutical drug samples. Using reverse-phase HPLC, 16 compounds of varying intensity were identified in purified alkaloid fractions, six of which were common to regenerating plants and to the pharmaceutical preparation.
REFERENCES
Thomis, G. N. and Kotionis, A. Z., Les indicateurs acides comme réactifs sensibles des alcaloïdes, Anal. Chim. Acta, 1957, vol. 16, p. 201. https://doi.org/10.1016/S0003-2670(00)89913-4
Maghssoudi, R.H. and Fawzi, A.B., Direct spectrophotometric determination of thebaine in Arya II population capsules of Papaver bracteatum Lindi, J. Pharm. Sci. (Philadelphia, PA, U. S.), 1978, vol. 67, p. 32. https://doi.org/10.1002/jps.2600670109
Li, L., Long, W., Wan, X., Ding, Q., Zhang, F., and Wan, D., Studies on quantitative determination of total alkaloids and berberine in five origins of crude medicine “Sankezhen”, J. Chromatogr. Sci., 2015, vol. 53, p. 307. https://doi.org/10.1093/chromsci/bmu060
Liu, Y. and Liu, C., Determination of total alkaloids in different parts of Actinidia arguta by spectrophotography, Proc. International Conference on Materials, Environmental and Biological Engineering, Guilin, 2015, p. 127. https://doi.org/10.2991/mebe-15.2015.31
Patel, R.K., Patel, J.B., and Trivedi, P.D., Spectrophotometric method for the estimation of total alkaloids in the Tinospora cordifolia M. and its herbal formulations, Int. J. Pharm. Pharm. Sci., 2015, vol. 7, p. 249.
Shamsa, F., Monsef, H. R., Ghamooshi, R., Verdian, R.M.R., Spectrophotometric determination of total alkaloids in Peganum harmala L. using bromocresol green, Res. J. Phytochem., 2007, vol. 1, p. 79.
Szewczyk, A., Marino, A., Molinari, J., Ekiert, H., and Miceli, N., Phytochemical characterization, and antioxidant and antimicrobial properties of agitated cultures of three Rue species: Ruta chalepensis, Ruta corsica, and Ruta graveolens, Antioxidants, 2022, vol. 11, p. 592. https://doi.org/10.3390/antiox11030592
Kamal, L.Z.M., Adam, M.A.A., Shahpudin, S.N. Mohd., Shuib, A.N., Sandai, R., Hassan, N.M., Tabana, Y., Basri, D.F., Than, L.T.L., and Sandai, D., Identification of alkaloid compounds arborinine and graveoline from Ruta angustifolia (L.) Pers for their antifungal potential against isocitrate lyase (ICL1) gene of Candida albicans, Mycopathologia, 2021, vol. 186, p. 221. https://doi.org/10.1007/s11046-020-00523-z
Wolters, B. and Eilert, U., Antimicrobial substances in callus cultures of Ruta graveolens, Planta Med., 1981, vol. 43, p. 166. https://doi.org/10.1055/s-2007-971494
Adamska-Szewczyk, A., Glowniak, K., and Baj, T., Furochinoline alkaloids in plants from Rutaceae family—a review, Curr. Issues Pharm. Med. Sci., 2016, vol. 29, p. 33. https://doi.org/10.1515/cipms-2016-0008
Kaur, R. and Kumar, K., Synthetic and medicinal perspective of quinolines as antiviral agents, Eur. J. Med. Chem., 2021, vol. 215, p. 113220. https://doi.org/10.1016/j.ejmech.2021.113220
Ghosh, S., Bishayee, K., and Khuda-Bukhsh, A.R., Graveoline isolated from ethanolic extract of Ruta graveolens triggers apoptosis and autophagy in skin melanoma cells: A novel apoptosis-independent autophagic signaling pathway: Graveoline induces apoptosis and autophagy in A375 cells, Phytother. Res., 2014, vol. 28, p. 1153. https://doi.org/10.1002/ptr.5107
Yadav, T. T., Murahari, M., Peters, G. J., and Yc, M., A comprehensive review on acridone based derivatives as future anti-cancer agents and their structure activity relationships, Eur. J. Med. Chem., 2022, vol. 239, p. 114527. https://doi.org/10.1016/j.ejmech.2022.114527
Misawa, M., Plant Issue Culture: An Alternative for Production of Useful Metabolites, Rome: FAO, 1994.
Murashige, T. and Skoog, F., A revised medium for rapid growth and bio assays with tobacco tissue cultures, Physiol. Plant, 1962, vol. 15, p. 473. https://doi.org/10.1111/j.1399-3054.1962.tb08052.x
Wagner, H. and Bladt, S., Plant Drug Analysis: A Thin Layer Chromatography Atlas, Berlin; New York: Springer, 1996, 2nd ed.
Orlita, A., Sidwa-Gorycka, M., Kumirska, J., Malinski, E., Siedlecka, E.M., Gajdus, J., Lojkowska, E., and Stepnowski, P., Identification of Ruta graveolens L. metabolites accumulated in the presence of abiotic elicitors, Biotechnol. Prog., 2008, vol. 24, p. 128.
Diamond, D., Lau, K. T., Brady, S., and Cleary, J., Integration of analytical measurements and wireless communications—Current issues and future strategies, Talanta, 2008, vol. 75, p. 606. https://doi.org/10.1016/j.talanta.2007.11.022
Saad, B., Ion-association method for the spectrophotometric determination of the antitussive drug noscapine, Talanta, 1997, vol. 44, p. 53. https://doi.org/10.1016/S0039-9140(96)02009-7
Zhu, S.-C., Shi, M.-Z., Yu, Y.-L., Jiao, Y.-H., Zheng, H., Liu, F.-M., and Cao, J., In-situ formation of ion pair assisted liquid-liquid microextraction of natural alkaloids by response surface methodology, Microchem. J., 2021, vol. 171, p. 106813. https://doi.org/10.1016/j.microc.2021.106813
Gainza, A.H., Reaction of halogenated hydrocarbon solvents with tertiary amines: Spectrophotometric and conductimetric study, Int. J. Chem. Kinet., 2004, vol. 36, p. 500. https://doi.org/10.1002/kin.20022
Shamsa, F., Monsef, H. R., Ghamooshi, R., and Verdian-rizi, R., Spectrophotometric determination of total alkaloids in some Iranian medicinal plants, Thai J. Pharm. Sci., 2008, vol. 32, p. 17.
Gaínza, A.H., Associations of ajmaline and homatropine with bromocresol green and bromophenol blue in dichloromethane: Thermodynamic and kinetic parameters, Can. J. Chem., 1987, vol. 65, p. 1279. https://doi.org/10.1139/v87-215
Sakai, T., Ohno, N., Sasaki, H., Hyuga, T., Extraction-spectrophotometric determination of berberine in crude drugs by the formation of a new ion associate, Anal. Sci., 1991, vol. 7, p. 39. https://doi.org/10.2116/analsci.7.39
Baumert, A., Maier, W., Schumann, B., and Gröger, D., Increased accumulation of acridone alkaloids by cell suspension cultures of Ruta graveolens in response to elicitors, J. Plant Physiol., 1991, vol. 139, p. 224. https://doi.org/10.1016/S0176-1617(11)80612-7
Eilert, U., Acridones (Ruta Alkaloids), Phytochemicals in Plant Cell Cultures, Friedrich, L. and Vasil, I.K., Eds., Amsterdam: Elsevier. 1988, p. 419. https://doi.org/10.1016/B978-0-12-715005-5.50031-5
Kuzovkina, I.N., Specific accumulation and revised structures of acridone alkaloid glucosides in the tips of transformed roots of Ruta graveolens, Phytochemistry, 2004, vol. 65, p. 1095. https://doi.org/10.1016/j.phytochem.2004.03.003
Kuzovkina, I.N., Chernysheva, T.P., and Alterman, I.E., Characteristics of a strain of callus tissue of Ruta aromatica producing rutacridone, Russ. J. Plant Physiol., 1979, vol. 26, p. 492.
Ramawat, K.G., Rideau, M., and Chenieux, J.-C., Growth and quaternary alkaloid production in differentiating and non-differentiating strains of Ruta graveolens, Phytochemistry, 1985, vol. 24, p. 441. https://doi.org/10.1016/S0031-9422(00)80743-8
Zhang, N., Wang, M., Li, Y., Zhou, M., Wu, T., and Cheng, Z., TLC–MS identification of alkaloids in Leonuri herba and Leonuri fructus aided by a newly developed universal derivatisation reagent optimised by the response surface method: 3, Phytochem. Anal., 2021, vol. 32, p. 242. https://doi.org/10.1002/pca.2970
Kuzovkina, I.N., Senderei, K., Rosa, S., Raisch, I., Composition of alkaloids in isolated roots, callus tissues and cell suspensions of Ruta graveolens L., Rast. Res., 1980, vol. 16, p. 112.
Funding
The study was carried out with the financial support of the Ministry of Science and Higher Education of the Russian Federation within the framework of state assignments carried out by the Kazan Institute of Biochemistry and Biophysics, Federal Research Center Kazan Scientific Center, Russian Academy of Sciences (state registration no. 122011800137-0).
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
CONFLICT OF INTEREST
The authors of this work declare that they have no conflicts of interest.
ETHICS APPROVAL AND CONSENT TO PARTICIPATE
This work does not contain any studies involving human and animal subjects.
Additional information
Publisher’s Note.
Pleiades Publishing remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Abbreviations: BCG—bromocresol green; ultrasound—U/S.
Supplementary Information
Rights and permissions
About this article
Cite this article
Valieva, A.I., Akulov, A.N. Application of Bromocresol Green for Spectrophotometric Determination of Alkaloid Content Using the Example of Ruta graveolens. Russ J Plant Physiol 71, 33 (2024). https://doi.org/10.1134/S1021443724604336
Received:
Revised:
Accepted:
Published:
DOI: https://doi.org/10.1134/S1021443724604336