BIOLOGICALLY ACTIVE COMPOUNDS IN SPECIES OF CARLINA L. GENUS OF FLORA OF UKRAINE

O. V. Soroka, M. Z. Prokopiak, L. R. Hrytsak, N. M. Drobyk

Abstract


The review analyzes literature on the biologically active compounds synthesized in the underground and aboveground parts of medicinal plants of the Carlina L. genus. Various phytochemicals have been identified in these species, including flavonoids, essential oils, terpenes and terpenoids, saponins, alkaloids, polysaccharides, tannins, resins, glycosides, ketones, polyacetylenes, and aldehydes.
According to modern research, the highest concentration of inulin polysaccharide (up to 12–22 %) has been found in the roots of Carlina plants. Inulin is an effective prebiotic widely used in medicine due to its ability to reduce glucose and low-density lipoprotein (LDL) levels, making it beneficial for treating diabetes, atherosclerosis, and obesity. Additionally, inulin exhibits anticoagulant, immunomodulatory, antitumor, and anti-inflammatory properties.
Essential oil (1–5 %) is extracted from the roots of Carlina plants using the hydrodistillation method. This oil contains a variety of terpene components, including β-sesquifellandrene, α-zingiberene, β-farnesene, ar-curcumin, γ-curcumin, and β-bisabolene. These constituents are responsible for the antimicrobial, antifungal, anti-inflammatory, anti-ulcer, and antioxidant activities of the oil and also function as acetylcholinesterase inhibitors.
The roots and aerial parts of Carlina plants are also rich sources of chlorogenic acid (1.94 %), triterpene saponins, alkaloids, and flavonoids. Alkaloids are typically found in plants as salts of organic acids or in glycosidic form. In medical applications, plant materials containing these compounds are used for their anti-inflammatory, sedative, tonic, and diuretic properties.
Flavonoids, one of the most abundant groups of phenolic compounds in the aboveground organs of Carlina plants, exhibit potent antimicrobial activity against a broad range of microorganisms. The predominant flavonoids found in the leaves include glycoside flavones such as orientin, homoorientin, and vitexin, which possess antioxidant, antiviral, antibacterial, and analgesic properties. Additionally, the leaves contain apigenin, a biologically active compound that interacts with molecular targets in the body, exerting anti-inflammatory, antioxidant, and neuroprotective effects.
Carlina plants serve as the basis for various herbal medicines, including diuretic, anthelmintic, sedative, expectorant, anti-inflammatory, analgesic, diaphoretic, antihemorrhoidal, and antimicrobial formulations. Phytopreparations derived from Carlina plants are used to treat digestive disorders and are also applied topically to manage skin infections and purulent rashes.

Keywords


species of Carlina L. genus; biologically active compounds; inulin; essential oil; triterpenes; terpenoids; saponins; flavonoids; xanthones

References


Kolisnyk Kh. M., Prokopiak M. Z., Hrytsak L. R., Drobyk N. M. Khorolohiia ta bioekolohichni osoblyvosti vydiv rodu Carlina L. flory Ukrainy. Naukovi zapysky Ternopilskoho natsionalnoho pedahohichnoho universytetu imeni Volodymyra Hnatiuka. Seriia Biolohiia. 2024. T. 83, No 3–4. S. 48–57. https://doi.org/10.25128/2078-2357.23.3-4.6. [in Ukrainian]

Sabat M. Ya., Iskra R. Ya. Fruktany: khimichna struktura, biolohichni vlastyvosti ta metabolizm kyshkovoiu mikrofloroiu. Biolohichni studii. 2016. T. 10, No 2. S. 203–214. https://doi.org/10.30970/sbi.1002.486. [in Ukrainian]

Chervona knyha Ukrainy. Roslynnyi svit / za red. Ya. P. Didukha. K. : Hlobalkonsaltynh, 2009. 900 s. [in Ukrainian]

Akhtar N., Mohammed A. A. S., Khan R. A., Yusuf M., Singh V., Mohammed H. A., Al-Omar M. S., Abdellatif A. A. H., Naz M., Khadri H. Self-Generating nano-emulsification techniques for alternatively-routed, bioavailability enhanced delivery, especially for anti-cancers, anti-diabetics, and miscellaneous drugs of natural, and synthetic origins. Journal of Drug Delivery Science and Technology. 2020. Vol. 58. P. 101808. https://doi.org/10.1016/j.jddst.2020.101808.

Ana B. Ramos-Hryb, Mauricio P. Cunha, Manuella P. Kaster, Ana Lúcia S Rodrigues. Natural Polyphenols and Terpenoids for Depression Treatment: Current Status. Studies in Natural Products Chemistry. 2018. P. 181–221. https://doi.org/10.1016/b978-0-444-64068-0.00006-1.

Atanasov A. G., Zotchev S. B., Dirsch, V. M., Supuran C. T. Natural products in drug discovery: advances and opportunities. Nature Reviews Drug Discovery. 2021. Vol. 20, No 3. P. 200–216. https://doi.org/10.1038/s41573-020-00114-z.

Ayeleso T., Matumba M. Oleanolic Acid and Its Derivatives: Biological Activities and Therapeutic Potential in Chronic Diseases. Molecules. 2017. Vol. 22, No 11. P. 1915. https://doi.org/10.3390/molecules22111915.

Benelli G., Pavela R., Petrelli R., Nzekoue F. K., Cappellacci L., Lupidi G., Quassinti L., Bramucci M., Sut S., Dall’Acqua S., Canale A., Maggi F. Carlina oxide from Carlina acaulis root essential oil acts as a potent mosquito larvicide. Industrial Crops and Products. 2019. Vol. 137. P. 356–366. https://doi.org/10.1016/j.indcrop.2019.05.037.

Benelli G., Rizzo R., Zeni V., Govigli A., Samková A., Sinacori M., Verde L. G., Pavela R., Cappellacci L., Petrelli R., Spinozzi E., Morshedloo M. R., Maggi Filippo, Canale A. Carlina acaulis and Trachyspermum ammi essential oils formulated in protein baits are highly toxic and reduce aggressiveness in the medfly, Ceratitis capitata. Industrial Crops and Products. 2021. Vol. 161. P. 113191. https://doi.org/10.1016/j.indcrop.2020.113191.

Biesalski H.-K., Dragsted L. O., Elmadfa I., Grossklaus R., Müller M., Schrenk D., Walter P., Weber P. Bioactive compounds: Definition and assessment of activity. Nutrition. 2009. Vol. 25, No. 11–12. P. 1202–1205. https://doi.org/10.1016/j.nut.2009.04.023.

Bohlmann F., Schuster A., Meusel H. A carlina oxide derivative from Carlina diae. Phytochemistry. 1981. Vol. 20, No. 4. P. 823–824. https://doi.org/10.1016/0031-9422(81)85186-2.

Carlina oxide Structure. Mol-Instincts. https://www.molinstincts.com/structure/Carlina-oxide-cstr-CT1000773185.html (Last accessed: 12.09.2024).

Chaachouay N., Zidane L. Plant-Derived Natural Products: A Source for Drug Discovery and Development. Drugs and Drug Candidates. 2024. Vol. 3, No. 1. P. 184–207. https://doi.org/10.3390/ddc3010011.

Dar R. A., Shahnawaz M., Ahanger M. A., Majid ul I. Exploring the Diverse Bioactive Compounds from Medicinal Plants: A Review. The Journal of Phytopharmacology. 2023. Vol. 12, No. 3. P. 189–195. https://doi.org/10.31254/phyto.2023.12307.

Djordjevic S., Petrovic S., Ristic, D. M. Composition of Carlina acanthifolia Root Essential Oil. Chemistry of Natural Compounds. 2005. Vol. 41, No. 4. P. 410–412. https://doi.org/10.1007/s10600-005-0163-2.

Đorđević S., Petrović S., Dobrić S., Milenković M., Vučićević D., Žižić S., Kukić J. Antimicrobial, anti-inflammatory, anti-ulcer and antioxidant activities of Carlina acanthifolia root essential oil. Journal of Ethnopharmacology. 2007. Vol. 109, No. 3. P. 458–463. https://doi.org/10.1016/j.jep.2006.08.021.

Ferreira B. A., Ferreira R. S., de Moura F. B. R., Narduchi C. T., Deconte S. R., Sartorelli P., Tomiosso T. C., Lago J. H. G., Araújo F. de A. α-zingiberene, a sesquiterpene from essential oil from leaves of Casearia sylvestris, suppresses inflammatory angiogenesis and stimulates collagen deposition in subcutaneous implants in mice. Natural Product Research. 2021. С. 1–5. https://doi.org/10.1080/14786419.2021.2019729.

Herbal & Natural Medicine. herbal-organic.com. URL: http://www.herbal-organic.com (Last accessed: 09.06.2024).

Jit B. P., Pattnaik S., Arya R., Dash R., Sahoo S. S., Pradhan B., Bhuyan P. P., Behera P. K., Jena M., Sharma A., Agrawal P. K., Behera R. K. Phytochemicals: A potential next generation agent for radioprotection. Phytomedicine. 2022. P. 154188. https://doi.org/10.1016/j.phymed.2022.154188.

Kavallieratos N. G., Nika Erifili P., Skourti A., Spinozzi E., Ferrati M., Petrelli R., Maggi F., Benelli G. Carlina acaulis essential oil: a candidate product for agrochemical industry due to its pesticidal capacity. Industrial Crops and Products. 2022. Vol. 188. P. 115572. https://doi.org/10.1016/j.indcrop.2022.115572.

Kumar A., Ahmad F., Zaidi S. Importance of Bioactive Compounds Present in Plant Products and Their Extraction – A Review. Agricultural Reviews. 2019. Vol. 40, No. 04. https://doi.org/10.18805/ag.r-1926.

Lahlou M. Screening of natural products for drug discovery. Expert Opinion on Drug Discovery. 2007. Vol. 2, No. 5. P. 697–705. https://doi.org/10.1517/17460441.2.5.697.

Liu K., Zhang X., Xie L., Deng M., Chen H., Song J., Long J., Li X., Luo J. Lupeol and its derivatives as anticancer and anti-inflammatory agents: Molecular mechanisms and therapeutic efficacy. Pharmacological Research. 2021. Vol. 164. P. 105373. https://doi.org/10.1016/j.phrs.2020.105373.

Marinho L. de F., Sganzerla W. G., Ferreira V. C., Moreno J. A. J., Rostagno M. A., Forster-Carneiro T. Advances in green extraction methods, biological properties, and applications of betanin and vitexin: An updated review and bibliometric analysis. Biocatalysis and Agricultural Biotechnology. 2023. P. 102744. https://doi.org/10.1016/j.bcab.2023.102744.

Moldoveanu S. C. Analytical pyrolysis of polymeric carbohydrates. Analytical Pyrolysis of Natural Organic Polymers. 2021. P. 111–269. https://doi.org/10.1016/b978-0-12-818571-1.00004-2.

Muktar B., Bello I., Sallau M. Isolation, characterization and antimicrobial study of lupeol acetate from the root bark of Fig-Mulberry Sycamore (Ficus sycomorus LINN). Journal of Applied Sciences and Environmental Management. 2018. Vol. 22, No. 7. P. 1129. https://doi.org/10.4314/jasem.v22i7.21.

NCATS Inxight Drugs – Benzaldehyde. Inxight Drugs. URL: https://drugs.ncats.io/drug/TA269SD04T (Last accessed: 03.09.2024).

Nuutinen T. Medicinal properties of terpenes found in Cannabis sativa and Humulus lupulus. European Journal of Medicinal Chemistry. 2018. Vol. 157. P. 198–228. https://doi.org/10.1016/j.ejmech.2018.07.076.

Pavela R., Maggi F., Petrelli R., Cappellacci L., Buccioni M., Palmieri A., Canale A., Benelli G. Outstanding insecticidal activity and sublethal effects of Carlina acaulis root essential oil on the housefly, Musca domestica, with insights on its toxicity on human cells. Food and Chemical Toxicology. 2020. Vol. 136. P. 111037. https://doi.org/10.1016/j.fct.2019.111037.

Qin Y.-Q., Wang L.-Y., Yang X.-Y., Xu Y.-J., Fan G., Fan Y.-G., Ren J.-N., An Q., Li X. Inulin: Properties and health benefits. Food & Function. 2023. https://doi.org/10.1039/d2fo01096h.

Rani K. Cyclisation of farnesyl pyrophosphate into sesquiterpenoids in ginger rhizomes (Zingiber officinale). Fitoterapia. 1999. Vol. 70, No. 6. P. 568–574. https://doi.org/10.1016/s0367-326x(99)00090-8.

Safitri E., Purnobasuki H., Al-Anshori A. A., Lestari T. D., Utama S., Yimer N. Honey-derived phytochemicals: Implications for stem cell activation and health benefits. Journal of Functional Foods. 2024. Vol. 114. P. 106058. https://doi.org/10.1016/j.jff.2024.106058.

Saleem M. Lupeol, a novel anti-inflammatory and anti-cancer dietary triterpene. Cancer Letters. 2009. Vol. 285, No. 2. P. 109–115. https://doi.org/10.1016/j.canlet.2009.04.033.

Sansinenea E., Cabrera Vivas B. M., Ortiz A. A Natural Curcumene Bisabolane Sesquiterpene: Syntheses and Recent Applications. Current Organic Synthesis. 2015. Vol. 12, No. 4. P. 431–439. https://doi.org/10.2174/157017941204150522185129.

Seo D. Y., Lee S. R., Heo J.-W., No M.-H., Rhee B. D., Ko K. S., Kwak H.-B., Han J. Ursolic acid in health and disease. The Korean Journal of Physiology & Pharmacology. 2018. Vol. 22, No. 3. P. 235. https://doi.org/10.4196/kjpp.2018.22.3.235.

Shoaib M., Shehzad A., Omar M., Rakha A., Raza H., Sharif H. R., Shakeel A., Ansari A., Niazi S. Inulin: Properties, health benefits and food applications. Carbohydrate Polymers. 2016. Vol. 147. P. 444–454. https://doi.org/10.1016/j.carbpol.2016.04.020.

Sofowora A., Ogunbodede E., Onayade A. The role and place of medicinal plants in the strategies for disease prevention. African Journal of Traditional, Complementary and Alternative Medicines. 2013. Vol. 10, No. 5. https://doi.org/10.4314/ajtcam.v10i5.2.

Soucy N. V. Acetophenone. Encyclopedia of Toxicology. 2014. P. 43–45. https://doi.org/10.1016/b978-0-12-386454-3.01157-x.

Spinozzi E., Ferrati M., Cappellacci L., Caselli A., Perinelli D. R., Bonacucina G., Maggi F., Strzemski M., Petrelli R., Pavela R., Desneux N., Benelli G. Carlina acaulis L. (Asteraceae): biology, phytochemistry, and application as a promising source of effective green insecticides and acaricides. Industrial Crops and Products. 2023. Vol. 192. P. 116076. https://doi.org/10.1016/j.indcrop.2022.116076.

Strzemski M., Wójciak-Kosior M., Sowa I., Rutkowska E., Szwerc W., Kocjan R., Latalski M. Carlina species as a new source of bioactive pentacyclic triterpenes. Industrial Crops and Products. 2016. Vol. 94. P. 498–504. https://doi.org/10.1016/j.indcrop.2016.09.025.

Strzemski M., Wójciak-Kosior M., Sowa I., Załuski D., Verpoorte R. Historical and traditional medical applications of Carlina acaulis L. – A critical ethnopharmacological review. Journal of Ethnopharmacology. 2019. Vol. 239. P. 111842. https://doi.org/10.1016/j.jep.2019.111842.

The IUCN Red List of Threatened Species. IUCN Red List of Threatened Species. URL: https://www.iucnredlist.org/ (Last accessed: 10.08.2024).

Viet T. D., Xuan T. D., Anh L. H. α-Amyrin and β-Amyrin Isolated from Celastrus hindsii Leaves and Their Antioxidant, Anti-Xanthine Oxidase, and Anti-Tyrosinase Potentials. Molecules. 2021. Т. 26, No 23. Р. 7248. https://doi.org/10.3390/molecules26237248.

Vincken J.-P., Heng L., de Groot A., Gruppen H. Saponins, classification and occurrence in the plant kingdom. Phytochemistry. 2007. Vol. 68, No. 3. P. 275–297. https://doi.org/10.1016/j.phytochem.2006.10.008.

Wnorowski A., Wnorowska S., Wojas-Krawczyk K., Grenda A., Staniak M., Michalak A., Woźniak S., Matosiuk D., Biała G., Wójciak M., Sowa I., Krawczyk P., Strzemski M. Toxicity of Carlina Oxide–A Natural Polyacetylene from the Carlina acaulis Roots–In Vitro and in Vivo Study. Toxins. 2020. Vol. 12, No. 4. P. 239. https://doi.org/10.3390/toxins12040239.

Xiao L., Chen X.-J., Feng J.-K., Li W.-N., Yuan S., Hu Y. Natural products as the calcium channel blockers for the treatment of arrhythmia: Advance and prospect. Fitoterapia. 2023. P. 105600. https://doi.org/10.1016/j.fitote.2023.105600.

Zhang X., Gao Y., Zhou Y., Liu Z., Liu R. Pharmacological mechanism of natural drugs and their active ingredients in the treatment of arrhythmia via calcium channel regulation. Biomedicine & Pharmacotherapy. 2023. Vol. 160. P. 114413. https://doi.org/10.1016/j.biopha.2023.114413.




DOI: https://doi.org/10.25128/2078-2357.24.3-4.10

Refbacks

  • There are currently no refbacks.


Creative Commons Attribution 4.0 License