Biologically active compounds of the bidentis cernuae herba
https://doi.org/10.37493/2307-910X.2025.3.10
Abstract
Introduction. Essential oil and other biologically active compounds of Bidens cernua L. are of scientific interest due to their pronounced biological activity. Research is focused on studying the chemical composition, chemotaxonomic significance, and pharmacological potential of this species, particularly its essential oil, polyacetylenes, phenolic compounds, and polysaccharides. Materials and Methods. Studies were conducted on samples of the aerial parts of Bidens cernua collected from various geographical regions (Serbia, Belarus, Poland, Russia, China). Analytical methods included hydrodistillation, high-performance thin-layer chromatography (HPTLC), gas chromatography (GC), gas chromatography-mass spectrometry (GC-MS), and high-performance liquid chromatography (HPLC). Biological activities (antimicrobial, antifungal, hypoglycemic, antioxidant) were assessed using in vitro and in vivo tests on model organisms. Results and discussion. The essential oil of Bidens cernua was found to possess significant antibacterial and antifungal activity, largely attributed to its main component, the polyacetylene 1-phenylhepta-1,3,5-triyne. The chemical composition of the oil demonstrates geographical variability. A significant fungistatic potential of phenylheptatriyne was revealed, including in the context of overcoming antifungal resistance. The hypoglycemic activity of plant extracts, associated with the inhibition of α-glucosidase, was demonstrated. A diverse flavonoid composition was identified, and the accumulation dynamics of polysaccharides were studied. It was shown that the parameters of raw material drying critically affect the preservation of bioactive compounds. Conclusion. The obtained data confirm that Bidens cernua is a valuable source of bioactive compounds with a wide spectrum of pharmacological properties. Geographical and eco-climatic variability of the chemical composition, as well as the plant's developmental stage and post-harvest processing conditions, significantly influence its quality and biological activity. Identified chemotaxonomic markers, such as phenylheptatriyne, are important for species identification. The results substantiate the potential of using Bidens cernua for the development of new medicines with antimicrobial, antifungal, antidiabetic, and antioxidant effects.
About the Authors
A. M. Nasukhova
Dagestan State Medical University, Ministry of Health of the Russian Federation
Россия
Россия
Aida M. Nasukhova – an assistant professor at the Department of General and Biological Chemistry
Author ID: 1109548
1, Lenin Square, Makhachkala, 367000, Republic of Dagestan
D. A. Konovalov
Pyatigorsk Medical and Pharmaceutical Institute – branch of Volgograd State Medical University, Ministry of Health of the Russian Federation
Россия
Россия
Dmitry Alekseevich Konovalov – Doctor of Pharmaceutical Sciences, Professor, Head of the Department of Pharmacognosy, Botany and Technology of Phytopreparations
Scopus ID: 56436041900
Researcher ID: JFS-1647-2023
11, Kalinin Avenue, Pyatigorsk, 357532
References
1. In vitro antifungal activity of phenylheptatriyne from Bidens cernua L. against yeasts / N.P. Rybalchenko et al. Fitoterapia. 2010. Vol. 81, Is. 5. P. 336-338.
2. A new sesquiterpene phenol from Bidens cernua L. with antimicrobial activity / V.V. Smirnov et al. Rastitel'nye Resursy (Plant Resources). 1995. Vol. 31, Iss. 2. P. 31-37.
3. Smirnov V.V. Antifungal activity of components of the drug cerbiden of plant origin / V.V. Smirnov, A.S. Bondarenko, N.P. Hladun. Mikrobiol. Z. 2003. Vol. 65, No. 4. P. 17-22.
4. Description of the invention for patent No. 22895 A, Ukraine, IPC: 6 A61K35/78. Preparation Cerbiden for the treatment of dermatomycoses / V.V. Smirnov et al. Patent holder D.K. Zabolotny Institute of Microbiology and Virology of the NAS of Ukraine. Appl. 18.10.96. Publ. 15.06.2001. Bull. No. 5.
5. Composition of essential oil of Bidens cernua L., Asteraceae from Serbia / J.-C. Chalchat, S. Petrovicz, Z. Maksimovic, M. Gorunovic. J. Essent. Oil Res. 2009. Vol. 21, No. 1. P. 41-42.
6. Bondarenko A.S. Biological properties and chemical nature of the antibiotic from Bidens cernuus L. / A.S. Bondarenko, L.A. Bakina, E.M. Kleĭner et al. Antibiotiki. 1968. Vol. 13, No. 2. P. 167-171.
7. Chang M.H. The low polar constituents from Bidens pilosa L. var. minor (Blume) Sherff / M.H. Chang, G.J. Wang, Y.H. Kuo, C.K. Lee. Journal of the Chinese Chemical Society. 2000. Vol. 47, No. 5. P. 1131-1136.
8. Korozhan N.V. Comparative analysis of the component composition of essential oil from herbs of Bidens species / N.V. Korozhan, G.N. Buzuk. News of Pharmacy. 2015. No. 1 (67). P. 18-24.
9. Flavonoids and Essential Oil of Bidens cernua of Polish Origin and in vitro Antimicrobial Activity of the Oil / M. Tomczykowa et al. Rec. Nat. Prod. 2017. Vol. 11, No. 5. P. 468-473.
10. Nasukhova A.M. Composition of the essential oil of nodding bur-marigold (Bidens cernua) from different growing locations / A.M. Nasukhova, K.K. Orynbasarova. Modern Science and Innovations. 2016. No. 4 (16). P. 203-206.
11. Vinogradova Yu.K. Taxa of the genus Bidens L. in Central Russia (variability and heritability of biomorphological traits) / Yu.K. Vinogradova, M.A. Galkina. Bulletin of Udmurt University. Series "Biology. Earth Sciences". 2016. No. 1. P. 53-62.
12. Korozhan N.V. Pharmacognostic substantiation of the use of a new source of bur-marigold herb and a combined agent based on it: abstract of thesis ... candidate of pharmaceutical sciences: 14.04.01. Vitebsk, 2016. 23 p.
13. Nasukhova A.M. Composition of essential oil of Bidens cernua L. / A.M. Nasukhova, D.A. Konovalov. Bulletin of the Volgograd State Medical University. 2015. No. 1(53). P. 50-52.
14. Christensen L.P. Acetylenes and related compounds in Heliantheae / L.P. Christensen, J. Lam. Phytochemistry. 1991. Vol. 30, No. 1. P. 11-49.
15. Konovalov D.A. Polyacetylene compounds in species of the genus Bidens / D.A. Konovalov, A.M. Nasukhova. Farmatsiya i Farmakologiya (Pharmacy and Pharmacology). 2014. Vol. 2, No. 2(3). P. 34-65.
16. Polyacetylenes in Hawaiian Bidens / Y.Y. Marchant et al. Biochemical Systematics and Ecology. 1984. Vol. 12, No. 2. P. 167-178.
17. Konovalov D.A. Aromatic polyacetylene compounds from the Asteraceae family and their chemotaxonomic importance / D.A. Konovalov. Rastitel'nye Resursy (Plant Resources). 1996. Vol. 32, No. 4. P. 84-98.
18. Natural polyacetylene compounds with anti-tuberculosis activity / A.M. Nasukhova et al. Medical News of the North Caucasus. 2016. Vol. 11, No. 4. P. 595-599.
19. Christensen L.P. Biological activities of naturally occurring acetylenes and related compounds from higher plants / L.P. Christensen. Recent Res. Devel. Phytochem. 1998. Vol. 2. P. 227-257.
20. Dembitsky V.M. Anticancer activity of natural and synthetic acetylenic lipids / V.M. Dembitsky. Lipids. 2006. Vol. 41, No. 10. P. 883-924.
21. Kagan J. Phenylheptatriyne: occurrence, synthesis, biological properties, and environmental concerns / J. Kagan. Chemosphere. 1987. Vol. 16, No. 10-12. P. 2405-2416.
22. Kumari P. A promising anticancer and antimalarial component from the leaves of Bidens pilosa / P. Kumari, K. Misra, B.S. Sisodia et al. Planta Medica. 2009. Vol. 75, No. 1. P. 59-61.
23. Sanglard D. Resistance of Candida species to antifungal agents: molecular mechanisms and clinical consequences / D. Sanglard, F.C. Odds. The Lancet Infectious Diseases. 2002. Vol. 2, No. 2. P. 73-85.
24. Nasukhova A.M. Study of the antibacterial activity of the essential oil of Bidens cernua L. herb / A.M. Nasukhova, D.A. Konovalov, N.M. Alieva. In: Pharmacy of Dagestan: integration of science, education and medicine. Collection of scientific works of the All-Russian Scientific and Practical Conference. Makhachkala, 2022. P. 73-76.
25. Ansari P. Pharmacologically active phytomolecules isolated from traditional antidiabetic plants and their therapeutic role for the management of diabetes mellitus / P. Ansari et al. Molecules. 2022. Vol. 27, No. 13. Art. 4278.
26. Anti-hyperglycemic effects and mechanism of Bidens pilosa water extract / Y.J. Hsu et al. Journal of Ethnopharmacology. 2009. Vol. 122, No. 2. P. 379-383.
27. Konovalov D.A. Biological and pharmacological properties of polyacetylene compounds of higher plants / D.A. Konovalov, V.N. Orobinskaya, A.M. Nasukhova. Modern Science and Innovations. 2017. No. 3 (19). P. 177-191.
28. Evaluation of the effectiveness of internal use of antidiabetic collection for the treatment and prevention of diabetes mellitus / A.M. Nasukhova et al. Modern Science and Innovations. 2016. No. 1 (13). P. 153-159.
29. Konovalov D.A. Composition possessing antidiabetic action / D.A. Konovalov, V.V. Kozlova, I.V. Pshukova, N.M. Nasukhova, A.M. Nasukhova. Patent for invention RU 2611353, 21.02.2017. Application No. 2015128738 dated 14.07.2015.
30. Borisov M.I. Flavonoids of Bidens cernua / M.I. Borisov, T.I. Isakova, A.G. Serbin. Chemistry of Natural Compounds. 1979. Vol. 15, No. 2. P. 197-198.
31. Constituents from aerial parts of Bidens ceruna L. and their DPPH radical scavenging activity / N. Zhu et al. Chemical Research in Chinese Universities. 2009. Vol. 25, No. 3. P. 328-331.
32. Zhu N. Studies on flavonoid constituents and bioactivities of Bidens cernua L.: diss. ... of DPh. [Electronic resource]. Access mode: https://global.cnki.net/index/ (accessed 10.09.2021).
33. Kotova E.E. Study of chromatographic fingerprint of flavonoid compounds of the bur-marigold herb / E.E. Kotova, S.A. Kotov, A.G. Kotov. Scientific Study & Research. Chemistry & Chemical Engineering, Biotechnology, Food Industry. 2021. Vol. 22, No. 1. P. 65-79.
34. Korozhan N.V. Variability of the content of flavonoids and polysaccharides in the herb of Bidens cernua L. / N.V. Korozhan. Khimiya Rastitel'nogo Syr'ya (Chemistry of Plant Raw Material). 2020. No. 3. P. 197-206.
35. Korozhan N.V. Antianaphylactoid action of Bidens cernua L. herb / N.V. Korozhan. Materials of the international conference "Modern achievements of pharmaceutical science and practice", Vitebsk, Oct. 31, 2019. P. 232-233.
36. Constituents of Bidens parviflora / N. De Tommasi et al. Fitoterapia. 1992. Vol. 63, No. 5. P. 470.
37. Karicome H. New acetylated glucosides of chalcone from the leaves of Bidens frondosa / H. Karicome, K. Ogawa, Y. Sashida. Chemical & Pharmaceutical Bulletin. 1992. Vol. 40, No. 3. P. 689-691.
38. Romussi G. Constituents of Bidens frondosa L. / G. Romussi, F. Pagani. Bollettino Chimico Farmaceutico. 1970. Vol. 109, No. 7. P. 467-475.
39. Structural studies of 2-(3',4'-dihydroxyphenyl)-7-beta-D-glucopyranos-1-omikron-yl-8- hydroxychroman-4-one in the liquid and solid states by means of 2D NMR spectroscopy and DFT calculations / S. Olejniczak et al. Journal of the Chemical Society, Perkin Transactions 2. 2002. No. 6. P. 1059-1065.
40. Antioxidant activity of extracts and flavonoids from Bidens tripartite / M. Wolniak et al. Acta Poloniae Pharmaceutica. 2007. Vol. 64, No. 5. P. 441-447.
41. In vitro and in vivo antioxidant and antidiabetic activity studies on standardized extracts of two Bidens species / U.G. Icoz et al. Journal of Food Biochemistry. 2017. Vol. 41, No. 6. Art. e12429.
42. Polyphenols content, antioxidant and antimicrobial activities of Ampelocissus grantii (Baker) Planch. (Vitaceae): A medicinal plant from Burkina Faso / C. Zongo et al. International Journal of Pharmacology. 2010. Vol. 6, No. 6. P. 880-887.
43. Quantitative analysis of the flavonoids in raw propolis from northern Croatia / I. Kosalec, M. Bakmaz, S. Pepeljnjak, S. Vladimir-Knezevic. Acta Pharmaceutica (Zagreb, Croatia). 2004. Vol. 54, No. 1. P. 65-72.
44. Korozhan N.V. Comparative analysis of the component composition of alcoholic extracts from herbs of Bidens species by liquid chromatography / N.V. Korozhan, G.N. Buzuk. News of Pharmacy. 2013. No. 4. P. 49-56.
45. Chin S.K. Effect of drying on crude ganoderic acids and water-soluble polysaccharides content in Ganoderma lucidum / S.K. Chin, C.L. Law, P.G. Cheng. International Journal of Pharmacy and Pharmaceutical Sciences. 2011. Vol. 3, No. 1. P. 38-43.
46. Chin S.K. Optimization of Convective Hot Air Drying of Ganoderma lucidum Slices Using Response Surface Methodology / S.K. Chin, C.L. Law. International Journal of Scientific and Research Publications. 2012. Vol. 2, No. 5. P. 1-11.
47. Drying Characteristics and Water-soluble Polysaccharides Evaluation of Kidney Shape Ganoderma lucidum Drying in Air Circulation System / D.J. Prasetyo, T.H. Jatmiko, C.D. Poeloengasih, M. Kismurtono. IOP Conference Series: Earth and Environmental Science. 2017. Vol. 101. Art. 012012.
48. Effects of different drying methods on the physicochemical properties and antioxidant activities of isolated acorn polysaccharides / S. Ahmadi et al. LWT - Food Science and Technology. 2019. Vol. 100. P. 1-9.
Review
For citations:
Nasukhova A.M., Konovalov D.A. Biologically active compounds of the bidentis cernuae herba. Modern Science and Innovations. 2025;(3):100-115. (In Russ.) https://doi.org/10.37493/2307-910X.2025.3.10
Views:
12
JATS XML
Email this article 