IDENTIFICATION OF CHEMICAL CONSTITUENTS AND EVALUATION OF BIOLOGICAL ACTIVITIES OF Piper cubeba EXTRACTS

Year 2025, Volume: 11 Issue: 2, 127 - 134, 31.12.2025

Bihter Şahin , Emine Baştürk

https://doi.org/10.22531/muglajsci.1782879

Abstract

Piper cubeba L., commonly known as cubeb, is a medicinal plant known for its essential oil and phenolic compounds with various biological activities. In this study, fruits of P. cubeba collected from Gaziantep were analyzed for their chemical composition and bioactivity. The essential oil, obtained via hexane extraction and analyzed by GC-MS, contained 49 compounds, with Eudesma-3,7(11)-diene (31.00%) as the major component, followed by cubenol, β-cubebene, and others. Sequential solvent extraction (acetone, ethyl acetate, methanol, and water) was performed, and the phenolic profiles of the extracts were determined using HPLC-DAD. The major phenolics identified included 1,4-dichlorobenzene, curcumin, cynarin, and rutin. Antioxidant activities were evaluated using DPPH, ABTS, CUPRAC, and β-carotene-linoleic acid assays. The water extract (PC4) showed the strongest antioxidant capacity among all extracts. Acetylcholinesterase, butyrylcholinesterase, and tyrosinase inhibition assays revealed that the acetone extract (PC1) exhibited the highest enzyme inhibitory activity. This comprehensive study provides new insights into the chemical composition and biological potential of P. cubeba fruits collected from Turkey.

Keywords

Piper cubeba , Phenolic compounds , Chemical content , Enzyme inhibition activity

Supporting Institution

TUBITAK

Project Number

TUBITAK 2209A_Proje Numarası: 1919B012220708

Thanks

This study was financially supported by TUBITAK with the number 2209-A with the project numbered 1919B012220708 within the scope of the University Students Research Projects Support Program in the 2022/2. I would like to express my sincere thanks to Prof. Dr. Mehmet ÖZTÜRK and Assoc. Prof. Dr. Yusuf SICAK for their support and for allowing me to utilize their facilities during the course of this study.

Piper cubeba EKSTRELERININ KIMYASAL BILEŞENLERININ BELIRLENMESI VE BIYOLOJIK AKTIVITELERININ DEĞERLENDIRILMESI

Abstract

Piper cubeba L., yaygın olarak kebabe veya kebabiye olarak bilinen, uçucu yağı ve fenolik bileşikleriyle çeşitli biyolojik aktivitelere sahip tıbbi bir bitkidir. Bu çalışmada, Gaziantep’ten toplanan P. cubeba meyvelerinin kimyasal bileşimi ve biyolojik aktiviteleri incelenmiştir. Hekzan ekstraksiyonu ile elde edilen uçucu yağ, GC-MS ile analiz edilmiş ve Eudesma-3,7(11)-dien (%31,00) majör bileşik olarak tespit edilmiştir. Diğer önemli bileşikler arasında cubenol, β-cubebene ve τ-cadinol yer almaktadır. Aseton, etil asetat, metanol ve su ile sırasıyla yapılan ekstraksiyon sonucunda elde edilen ekstrelerin fenolik içerikleri HPLC-DAD ile analiz edilmiştir. Başlıca tespit edilen fenolik bileşikler arasında 1,4-diklorobenzen, kurkumin, sinarin ve rutin yer almaktadır. Antioksidan aktiviteler DPPH, ABTS, CUPRAC ve β-karoten-linoleik asit yöntemleriyle değerlendirilmiş; en yüksek antioksidan aktivite su ekstresinde (PC4) gözlemlenmiştir. Asetilkolinesteraz, bütirilkolinesteraz ve tirozinaz enzim inhibisyon testleri sonucunda ise en yüksek inhibitör etki aseton ekstresinde (PC1) belirlenmiştir. Bu çalışma, Türkiye'den toplanan P. cubeba meyvelerinin kimyasal ve biyolojik özelliklerini kapsamlı bir şekilde ortaya koyan ilk araştırmalardan biridir.

Keywords

Piper cubeba , Fenolik bileşikler , Kimyasal içerik , Enzim inhibisyon aktivite

Ethical Statement

Bu çalışma kapsamında etik kurul onayı gerektiren herhangi bir insan veya hayvan deneyi yapılmamıştır. Bu nedenle etik kurul izni alınmamıştır.

Supporting Institution

TUBITAK

Project Number

TUBITAK 2209A_Proje Numarası: 1919B012220708

Thanks

Bu çalışma 2022/2 yılında Üniversite Öğrencileri Araştırma Projelerini Destekleme Programı kapsamında 1919B012220708 nolu proje ile TÜBİTAK tarafından desteklenmiştir. Bu çalışmanın gerçekleşmesinde imkanlarını kullanmamıza destek olan Prof. Dr. Mehmet ÖZTÜRK'e ve Doç. Dr. Yusuf SICAK'a teşekkür ederim.

References

• Junqueira, A. P. F., Perazzo, F. F., Souza, G. H. B., and Maistro, E. L. “Clastogenicity of Piper cubeba (Piperaceae) seed extract in an in vivo mammalian cell system”, Genetics and Molecular Biology, 30(3), 656–663. 2007.
• Abdul-Jalil, T. Z. and Nasser, Z. A. “Piper cubeba: phytochemical and pharmacological review of a routinely used spices”, International Journal of Pharmaceutical Research, 1:761–8. 2020.
• Perazzo, F. F., Rodrigues, I. V., Maistro, E. L., Souza, S. M., Nanaykkara, N. P. D., Bastos, J. K., and de Souza, G. H. B. “Anti-inflammatory and analgesic evaluation of hydroalcoholic extract and fractions from seeds of Piper cubeba L. (Piperaceae)”, Pharmacognosy Journal, 5(1), 13–16. 2013.
• Carlis, De. P., Féboli, M. S., Laurentiz, A., C., de A. Filardi, da S., de Oliveira, R., A. H. P., e Silva, A., M. L., and da Silva de Laurentiz, R. “In vitro anthelmintic activity of the crude hydroalcoholic extract of Piper cubeba fruits and isolated natural products against gastrointestinal nematodes in sheep”, Veterinary Parasitology, 275, 108932. 2019.
• Rajalekshmi, D. S., Kabeer, F. A., Madhusoodhanan, A. R., Bahulayan, A. K., Prathapan, R., Prakasan, N., and Nair, M. S. “Anticancer activity studies of cubebin isolated from Piper cubeba and its synthetic derivatives”, Bioorganic & Medicinal Chemistry Letters, 26(7), 1767–1771. 2016.
• Choi, E.-M., and Hwang, J.-K. “Investigations of anti-inflammatory and antinociceptive activities of Piper cubeba, Physalis angulata and Rosa hybrida”, Journal of Ethnopharmacology, 89(1), 171–175. 2003.
• Luca, S.V., Minceva, M., Gertsch, J., and Skalicka-Woźniak, K. “LC-HRMS/MS-based phytochemical profiling of Piper spices: Global association of piperamides with endocannabinoid system modulation”, Food Research International, 141, 110123. 2021.
• Magalhães, L. G., Lima, T. C., de Paula, R. G., Morais, E. R., Aguiar, D. P., Gardinassi, L. G., and Silva, M.L.A. “Effects of (−)-6,6′-dinitrohinokinin on adult worms of Schistosoma mansoni: a proteomic analysis”, Revista Brasileira de Farmacognosia, 26(3), 334–341. 2016.
• Tokul Ölmez, Ö., Şahin, B., Çakır, C., & Öztürk, M. “Rapid and easy method for simultaneous measurement of widespread 27 compounds in natural products and foods”, Journal of Chemical Metrology. 1, 1-11. 2020.
• Blois, M. S. (1958) “Antioxidant determinations by the use of a stable free radical”, Nature, 181: 1199-1200.
• Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M. and Rice-Evans, C. “Antioxidant activity applying an improved ABTS radical cation decolorization assay”, Free Radical Biology & Medicine, 26: 1231-1237. 1989.
• Apak, R., Güçlü, K., Özyürek, M. and Karademir, S.E. “Novel total antioxidant capacity index for dietary polyphenols and vitamins C and E, Using their cupric ion reducing capability in the presence of neocuproine: CUPRAC Method”, J Agric Food Chem, 52: 7970–7981. 2004.
• Miller, H.M. “A simplified method for the evaluation of antioxidants”, JAm Oil Chem Soc.,48, 91. 1971.
• Ellman, G. L., Courtney, K. D., Andres, V., and Featherston, R. M. “A new and rapid colorimetric determination of acetylcholinesterase activity”. Biochemical Pharmacology, 7: 88–95. 1961.
• Hearing, V.J. “Mammalian monophenol monooxygenase (tyrosinase): purification, properties, and reactions catalyzed. Methods in Enzymology”, 142, In D. Kaufman (Ed.), New York, NY: Academic Press, pp. 154-165. 1987.
• Ullah, Z., Alia, S., Hussain, A., Ozturk, M., Ertaş, A., Alamzeba, M., Ur Rashide, M., Ullahe, H., Zamana, R. and Imtiaz, M. In vitro antioxidant, anticholinesterase, tyrosinase activity studies, and LC-MS/MS simultaneous determination of 37 bioactive compounds in Indigofera heterantha. South African Journal of Botany, 148: 537-545. 2022.
• Conde-Hernández, L. A. and Guerrero-Beltrán, J. Á. “Total phenolics and antioxidant activity of Piper auritum and Porophyllum ruderale.” Food Chemistry, 142: 455-460. 2014.
• Ranilla, L. G., Kwon, Y.-I., Apostolidis, E. and Shetty K. “Phenolic compounds, antioxidant activity and in vitro inhibitory potential against key enzymes relevant for hyperglycemia and hypertension of commonly used medicinal plants, herbs and spices in Latin America.” Bioresource Technology, 101,12: 4676-4689. 2010.
• Mustafa, A.M., Eldahmy, S.I., Caprioli, G., Bramucci, M., Quassinti, L., Lupidi, G., Beghelli, D., Vittori, S., Maggi, F., 2018. Chemical composition and biological activities of the essential oil from pulicaria undulata (L.) C. A. Mey. Growing wild in Egypt. Natural Products Res. 34 (16), 2358–2362. https://doi.org/10.1080/ 14786419.2018.1534107.