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The Detailed Chemical and Biological Analysis of Ziziphora clinopodioides Lam. Species Growing in Cultural and Natural Environments

Year 2024, Volume: 27 Issue: Ek Sayı 2 (Suppl 2), 316 - 326, 31.12.2024

Mehmet Çavuşoğlu , Serkan Yiğitkan , İsmail Yener , Mehmet Veysi Çağlayan , Barış Reşitoğlu , Mehmet Akdeniz , Eda Çavuş Kaya , Fethullah Tekin , Mustafa Abdullah Yılmaz , Abdulselam Ertaş

https://doi.org/10.18016/ksutarimdoga.vi.1585656

Abstract

The Lamiaceae family is an important resource for the pharmaceutical, food, cosmetic, and perfumery sectors. The species Ziziphora clinopodioides Lam., belonging to the Lamiaceae family, has been used in folk medicine since ancient times. The aim of the present study was to determine the total phenolic and flavonoid contents, antioxidant, cytotoxic and enzyme (AChE, BChE, tyrosinase, urease, elastase, collagenase and ACE) inhibition activities of ethanol extracts of the aerial parts of natural and cultivated samples of the species Z. clinopodioides. In addition, the aroma contents of the species were determined by GC-MS/FID, and the phytochemical composition of the ethanol extracts was determined by LC-MS/MS. According to the aroma analysis results, the major components of the culture sample of the Z. clinopodioides species were determined as pulegone (39.83%), cis-menthone (21.36%), trans-menthone (16.64%), while the major components of the natural sample were determined as pulegone (62.42%), neoisomenthol (5.93%) and cis-pulegone oxide (5.47%). According to LC-MS/MS results, quinic acid (25.841, 15.694 mg analyte g-1 extract, respectively), rosmarinic acid (6.804, 25.523), and acacetin (6.115, 10.764) were detected as major compounds in cultured and natural samples of the species. Also, hesperidin (5.725) was higher in culture sample. According to the enzyme activity results, it was determined that cultured and natural samples of the species showed moderate butyrylcholinesterase enzyme inhibition activity (inhibition %: 45.14±1.40; 43.57±0.73, respectively). In urease enzyme inhibition activity, it was determined that culture sample showed moderate activity (inhibition %: 43.64±0.39) but natural sample did not show activity, and culture sample showed high antihypertensive activity (inhibition %: 81.6±1.19). When the results were evaluated in general, it was determined that the cultured sample of the species showed higher antioxidant, butyrylcholinesterase, urease, and antihypertensive activity compared to natural sample.

Keywords

Lamiaceae GC-MS Pulegone Agricultural culture Antihypertensive

Project Number

ECZACILIK.24.007 ve TIP20.032

References

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  • Akdeniz, M., Yener, I., Yilmaz, M. A., Kandemir, S. I., Tekin, F., & Ertas, A. (2021). A potential species for cosmetic and pharmaceutical industries: Insight to chemical and biological investigation of naturally grown and cultivated Salvia multicaulis Vahl. Industrial Crops and Products, 168, 113566. https://doi.org/10.1016/j.indcrop.2021.113566
  • Aliakbarlu, J., & Shameli, F. (2013). In vitro antioxidant and antibacterial properties and total phenolic contents of essential oils from Thymus vulgaris, T. kotschyanus, Ziziphora tenuior and Z. clinopodioides. Turkish Journal of Biochemistry, 38(4). 450. https://doi.org/10.5505/tjb.2013.58070
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  • Apak, R., Güçlü, K., Özyürek, M., & Karademir, S. E. (2004). 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. Journal of Agricultural and Food Chemistry, 52(26), 7970-7981. https://doi.org/10.1021/jf048741x
  • Behravan, J., Ramezani, M., Hassanzadeh, M. K., Eskandari, M., Kasaian, J., & Sabeti, Z. (2007). Composition, antimycotic and antibacterial activity of Ziziphora clinopodioides Lam. essential oil from Iran. Journal of Essential Oil Bearing Plants, 10(4), 339-345. https://doi.org/ 10.1080/0972060X.2007.10643565
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  • Ellman, G. L., Courtney, K. D., Andres Jr, V., & Featherstone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7(2), 88-95. https://doi.org/10.1016/0006-2952(61)90145-9
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  • Hearing, V. J., & Jiménez, M. (1987). Mammalian tyrosinase the critical regulatory control point in melanocyte pigmentation. International Journal of Biochemistry, 19(12), 1141-1147. https://doi.org/ 10.1016/0020-711X(87)90095-4
  • Karayel, H. B. (2019). Kütahya (Gediz) yöresinde yetiştirilen tıbbi adaçayı (Salvia officinalis L.) türünün tohum ve yaprağında uçucu yağ bileşenlerin değerlendirilmesi. KSÜ Tarım ve Doğa Dergisi, 22, 1-5. https://doi.org/10.18016/ ksutarimdoga.vi.555167
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  • Kwon, Y. I. I., Vattem, D. A., & Shetty, K. (2006). Evaluation of clonal herbs of Lamiaceae species for management of diabetes and hypertension. Asia Pacific Journal of Clinical Nutrition, 15(1), 107.
  • Meral, G. E., Konyalioglu, S., & Ozturk, B. (2002). Essential oil composition and antioxidant activity of endemic Ziziphora taurica subsp. cleonioides. Fitoterapia, 73(7-8), 716-718. https://doi.org/ 10.1016/S0367-326X(02)00244-7
  • Mojarrab, M., Lagzian, M. S., Emami, S. A., Asili, J., & Tayarani-Najaran, Z. (2013). In vitro anti-proliferative and apoptotic activity of different fractions of Artemisia armeniaca. Revista Brasileira de Farmacognosia, 23(5), 783-788. https://doi.org/10.1590/S0102-695X2013000500010
  • Moreno, M. I. N., Isla, M. I., Sampietro, A. R., & Vattuone, M. A. (2000). Comparison of the free radical-scavenging activity of propolis from several regions of Argentina. Journal of Ethnopharmacology, 71(1-2), 109-114. https:// doi.org/10.1016/S0378-8741(99)00189-0
  • Oğan Y, & Cömert M. (2022). Artvin yöre gastronomisinde tıbbi ve aromatik bitkiler. Aydın Gastronomy, 6(1), 29-38. https://doi.org/ 10.17932/ iau.gastronomy.2017.016/gastronomy_v06i1003
  • Ozdemir, A., Turkoglu, V., & Demir, H. (2013). In vitro effect of some plant extracts on acetylcholinesterase enzyme in human erythrocytes and serum. Fresenius Environmental Bulletin, 22, 2510-5.
  • Ozturk, S., & Ercisli, S. (2007). Antibacterial activity and chemical constitutions of Ziziphora clinopodioides. Food Control, 18(5), 535-540. https://doi.org/10.1016/j.foodcont.2006.01.002
  • Özkan, E. E., Boğa, M., Yılmaz, M. A., Kara, E. M., & Yeşil, Y. (2020). LC-MS/MS analyses of Ziziphora clinopodioides Lam. from Turkey: Antioxidant, anticholinesterase, antimicrobial and, anticancer activities. İstanbul Journal of Pharmacy, 50(1), 33-41. https://doi.org/10.26650/IstanbulJPharm.2019. 0064
  • Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9-10), 1231-1237. https://doi.org/ 10.1016/S0891-5849(98)00315-3
  • Sahakyan, N., & Petrosyan, M. (2022). Possible preventive effect of Ziziphora clinopodioides Lam. essential oil on some neurodegenerative disorders. OBM Neurobiology, 6(4), 1-17. https://doi.org/ 10.21926/obm.neurobiol.2204140
  • Salehi, P., Sonboli, A., Eftekhar, F., Nejad-Ebrahimi, S., & Yousefzadi, M. (2005). Essential oil composition, antibacterial and antioxidant activity of the oil and various extracts of Ziziphora clinopodioides subsp. rigida (BOISS.) RECH. f. from Iran. Biological and Pharmaceutical Bulletin, 28(10), 1892-1896. https://doi.org/10.1248/ bpb.28.1892
  • Senejoux, F., Demougeot, C., Kerram, P., Aisa, H. A., Berthelot, A., Bévalot, F., & Girard-Thernier, C. (2012). Bioassay-guided isolation of vasorelaxant compounds from Ziziphora clinopodioides Lam.(Lamiaceae). Fitoterapia, 83(2), 377-382. https://doi.org/10.1016/j.fitote.2011.11.023
  • Slinkard, K., & Singleton, V. L. (1977). Total phenol analysis: automation and comparison with manual methods. American Journal of Enology and Viticulture, 28(1), 49-55. https://doi.org/10.5344/ ajev.1977.28.1.49
  • Taheri, A., Ganjeali, A., Arefi-Oskouie, A., Cirak, C., & Cheniany, M. (2023). The variability of phenolic constituents and antioxidant properties among wild populations of Ziziphora clinopodioides Lam. Physiology and Molecular Biology of Plants, 29(2), 221-237. https://doi.org/10.1007/s12298-023-01283-y
  • Tekin, F., Efe, A., Çınar, O., Özbek, O., Kılınç, E., Akpolat, N., Özcan, N., Özek, T., Avcioglu B., & Karakas, O. (2017). Güneydoğu Anadolu Bölgesi'ndeki tıbbi ve aromatik bitkilerin genetik kaynaklarının araştırılması. GAP Uluslararası Tarımsal Araştırma ve Eğitim Merkezi, Proje numarası: TAGEM/17/A07/P09/013.
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Ziziphora clinopodioides Lam. Türünün Kültür İle Doğal Ortamlarda Yetişen Örneklerinin Kimyasal ve Biyolojik Yönden Detaylı İncelenmesi

Year 2024, Volume: 27 Issue: Ek Sayı 2 (Suppl 2), 316 - 326, 31.12.2024

Mehmet Çavuşoğlu , Serkan Yiğitkan , İsmail Yener , Mehmet Veysi Çağlayan , Barış Reşitoğlu , Mehmet Akdeniz , Eda Çavuş Kaya , Fethullah Tekin , Mustafa Abdullah Yılmaz , Abdulselam Ertaş

https://doi.org/10.18016/ksutarimdoga.vi.1585656

Abstract

Lamiaceae familyası ilaç, gıda, kozmetik ve parfümeri sektörleri için önemli bir kaynaktır. Lamiaceae familyasına ait olan Ziziphora clinopodioides Lam. türü çok eski zamanlardan beri halk hekimliğinde kullanılmaktadır. Mevcut çalışmada Z. clinopodioides türünün doğal ve kültür örneklerinin toprak üstü kısımlarının etanol ekstrelerinin toplam fenolik ve flavonoid içeriği, antioksidan, sitotoksik ve enzim (AChE, BChE, tirozinaz, üreaz, elastaz, kolajenaz ve ACE) inhibisyon aktivitelerinin belirlenmesi amaçlanmaktadır. Ayrıca türün aroma içerikleri GC-MS/FID ile belirlenip, etanol ekstrelerinin fitokimyasal bileşimi LC-MS/MS ile tespit edilmiştir. Aroma analizi sonuçlarına göre Z. clinopodioides türünün kültür örneğinin majör bileşenleri pulegon (%39.83), cis-menton (%21.36), trans-menton (%16.64), doğal örneğin majör bileşenleri ise pulegon (%62.42), neoizomentol (%5.93) ve cis-pulegon oksit (%5.47) olarak tespit edilmiştir. LC-MS/MS sonuçlarına göre türün kültür ve doğal örneklerinde kinik asit (sırasıyla, 25.841, 15.694 mg analit g-1 ekstre), rosmarinik asit (6.804, 25.523) ve asasetin (6.115, 10.764) majör bileşenler olarak tespit edilmiştir. Ayrıca kültür örneğinde hesperidin (5.725) daha yüksek olduğu tespit edilmiştir. Enzim aktivitesi sonuçlarına göre türün kültür ve doğal örneklerinin orta düzeyde bütirilkolinesteraz enzim inhibisyon aktivitesi (sırasıyla, % inhibisyon: 45.14±1.40; 43.57±0.73) gösterdiği belirlenmiştir. Üreaz enzim inhibisyon aktivitesinde ise kültür örneğinin orta düzeyde aktvite gösterdiği (% inhibisyon: 43.64±0.39) fakat doğal örneğin aktivite göstermediği, ayrıca kültür örneğinin yüksek antihipertansif (% inhibisyon: 81.6±1.19) aktivite gösterdiği belirlenmiştir. Sonuçlar genel olarak değerlendirildiğinde türün kültür örneğinin doğal örneğe kıyasla yüksek antioksidan, bütürilkolinesteraz, üreaz ve antihipertansif aktivite gösterdiği belirlenmiştir.

Keywords

Lamiaceae GC-MS Pulegon Tarımsal kültür Antihipertansif

Ethical Statement

Bu çalışma, sadece bitkisel örneklerin toplanması ve bitkisel bileşiklerin kimyasal analizlerinin yapılması üzerine odaklanmıştır. İnsan ya da hayvan denekleri kullanılmadığı ve herhangi bir etik müdahale gerektiren deneysel süreç gerçekleştirilmediği için, etik kurul izni gerektirmemektedir.

Supporting Institution

Dicle Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi Koordinatörlüğü’ne (Proje Numarası: Eczacılık 24.007 ve Tıp 20.032)

Project Number

ECZACILIK.24.007 ve TIP20.032

Thanks

Yazarlar bu çalışmada Dicle Üniversitesi Bilimsel Araştırma Projeleri Koordinasyon Birimi Koordinatörlüğü’ne (Proje Numarası: Eczacılık 24.007 ve Tıp 20.032) teşekkür etmektedirler. Ayrıca yazarlar türün doğal örneklerini teşhis eden Dr. Mehmet Fırat’a teşekkür eder.

References

  • Acıbuca, V., & Budak, D. B. (2018). Dünya’da ve Türkiye'de tıbbi ve aromatik bitkilerin yeri ve önemi. Çukurova Tarım ve Gıda Bilimleri Dergisi, 33(1), 37-44.
  • Akdeniz, M., Yener, I., Yilmaz, M. A., Kandemir, S. I., Tekin, F., & Ertas, A. (2021). A potential species for cosmetic and pharmaceutical industries: Insight to chemical and biological investigation of naturally grown and cultivated Salvia multicaulis Vahl. Industrial Crops and Products, 168, 113566. https://doi.org/10.1016/j.indcrop.2021.113566
  • Aliakbarlu, J., & Shameli, F. (2013). In vitro antioxidant and antibacterial properties and total phenolic contents of essential oils from Thymus vulgaris, T. kotschyanus, Ziziphora tenuior and Z. clinopodioides. Turkish Journal of Biochemistry, 38(4). 450. https://doi.org/10.5505/tjb.2013.58070
  • Alp, S., Ercisli, S., Dogan, H., Temim, E., Leto, A., Zia-Ul-Haq, M., Handıabulic, A., & Aladag, H. (2016). Chemical composition and antioxidant activity Ziziphora clinopodioides ecotypes from Turkey. Romanian Biotechnological Letters, 21(2), 11298-11303.
  • Apak, R., Güçlü, K., Özyürek, M., & Karademir, S. E. (2004). 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. Journal of Agricultural and Food Chemistry, 52(26), 7970-7981. https://doi.org/10.1021/jf048741x
  • Behravan, J., Ramezani, M., Hassanzadeh, M. K., Eskandari, M., Kasaian, J., & Sabeti, Z. (2007). Composition, antimycotic and antibacterial activity of Ziziphora clinopodioides Lam. essential oil from Iran. Journal of Essential Oil Bearing Plants, 10(4), 339-345. https://doi.org/ 10.1080/0972060X.2007.10643565
  • Blois, M.S. (1958). Antioxidant determination by the use of a stable free radical, Nature, 181, 1199-1200. Ding, W., Yang, T., Liu, F., & Tian, S. (2014). Effect of different growth stages of Ziziphora clinopodioides Lam. on its chemical composition. Pharmacognosy Magazine, 10(Suppl 1), 1-5. https://doi.org/ 10.4103/0973-1296.127329
  • Ellman, G. L., Courtney, K. D., Andres Jr, V., & Featherstone, R. M. (1961). A new and rapid colorimetric determination of acetylcholinesterase activity. Biochemical Pharmacology, 7(2), 88-95. https://doi.org/10.1016/0006-2952(61)90145-9
  • Göktaş, Ö., & Gıdık, B. (2019). Tıbbi ve aromatik bitkilerin kullanım alanları. Bayburt Üniversitesi Fen Bilimleri Dergisi, 2(1), 145-151.
  • Hayta, S., & Bagcı, E. (2016). The essential oil composition of Ziziphora clinopodiodies Lam.(Lamiaceae) from Turkey. Turkish Journal of Science and Technology, 11(1), 17-19.
  • Hearing, V. J., & Jiménez, M. (1987). Mammalian tyrosinase the critical regulatory control point in melanocyte pigmentation. International Journal of Biochemistry, 19(12), 1141-1147. https://doi.org/ 10.1016/0020-711X(87)90095-4
  • Karayel, H. B. (2019). Kütahya (Gediz) yöresinde yetiştirilen tıbbi adaçayı (Salvia officinalis L.) türünün tohum ve yaprağında uçucu yağ bileşenlerin değerlendirilmesi. KSÜ Tarım ve Doğa Dergisi, 22, 1-5. https://doi.org/10.18016/ ksutarimdoga.vi.555167
  • Kazeminia, M., Gandomi, H., Koohi, M. K., Noori, N., Khanjari, A., & Ehterami, A. (2024). Optimization of Ziziphora clinopodioides L. essential oil nanoencapsulation in chitosan nanocomplex by response surface methodology. International Journal of Biological Macromolecules, 265, 131114. https://doi.org/10.1016/j.ijbiomac.2024.131114
  • Kraunsoe, J. A., Claridge, T. D., & Lowe, G. (1996). Inhibition of human leukocyte and porcine pancreatic elastase by homologues of bovine pancreatic trypsin inhibitor. Biochemistry, 35(28), 9090-9096. https://doi.org/10.1021/bi953013b
  • Kwon, Y. I. I., Vattem, D. A., & Shetty, K. (2006). Evaluation of clonal herbs of Lamiaceae species for management of diabetes and hypertension. Asia Pacific Journal of Clinical Nutrition, 15(1), 107.
  • Meral, G. E., Konyalioglu, S., & Ozturk, B. (2002). Essential oil composition and antioxidant activity of endemic Ziziphora taurica subsp. cleonioides. Fitoterapia, 73(7-8), 716-718. https://doi.org/ 10.1016/S0367-326X(02)00244-7
  • Mojarrab, M., Lagzian, M. S., Emami, S. A., Asili, J., & Tayarani-Najaran, Z. (2013). In vitro anti-proliferative and apoptotic activity of different fractions of Artemisia armeniaca. Revista Brasileira de Farmacognosia, 23(5), 783-788. https://doi.org/10.1590/S0102-695X2013000500010
  • Moreno, M. I. N., Isla, M. I., Sampietro, A. R., & Vattuone, M. A. (2000). Comparison of the free radical-scavenging activity of propolis from several regions of Argentina. Journal of Ethnopharmacology, 71(1-2), 109-114. https:// doi.org/10.1016/S0378-8741(99)00189-0
  • Oğan Y, & Cömert M. (2022). Artvin yöre gastronomisinde tıbbi ve aromatik bitkiler. Aydın Gastronomy, 6(1), 29-38. https://doi.org/ 10.17932/ iau.gastronomy.2017.016/gastronomy_v06i1003
  • Ozdemir, A., Turkoglu, V., & Demir, H. (2013). In vitro effect of some plant extracts on acetylcholinesterase enzyme in human erythrocytes and serum. Fresenius Environmental Bulletin, 22, 2510-5.
  • Ozturk, S., & Ercisli, S. (2007). Antibacterial activity and chemical constitutions of Ziziphora clinopodioides. Food Control, 18(5), 535-540. https://doi.org/10.1016/j.foodcont.2006.01.002
  • Özkan, E. E., Boğa, M., Yılmaz, M. A., Kara, E. M., & Yeşil, Y. (2020). LC-MS/MS analyses of Ziziphora clinopodioides Lam. from Turkey: Antioxidant, anticholinesterase, antimicrobial and, anticancer activities. İstanbul Journal of Pharmacy, 50(1), 33-41. https://doi.org/10.26650/IstanbulJPharm.2019. 0064
  • Re, R., Pellegrini, N., Proteggente, A., Pannala, A., Yang, M., & Rice-Evans, C. (1999). Antioxidant activity applying an improved ABTS radical cation decolorization assay. Free Radical Biology and Medicine, 26(9-10), 1231-1237. https://doi.org/ 10.1016/S0891-5849(98)00315-3
  • Sahakyan, N., & Petrosyan, M. (2022). Possible preventive effect of Ziziphora clinopodioides Lam. essential oil on some neurodegenerative disorders. OBM Neurobiology, 6(4), 1-17. https://doi.org/ 10.21926/obm.neurobiol.2204140
  • Salehi, P., Sonboli, A., Eftekhar, F., Nejad-Ebrahimi, S., & Yousefzadi, M. (2005). Essential oil composition, antibacterial and antioxidant activity of the oil and various extracts of Ziziphora clinopodioides subsp. rigida (BOISS.) RECH. f. from Iran. Biological and Pharmaceutical Bulletin, 28(10), 1892-1896. https://doi.org/10.1248/ bpb.28.1892
  • Senejoux, F., Demougeot, C., Kerram, P., Aisa, H. A., Berthelot, A., Bévalot, F., & Girard-Thernier, C. (2012). Bioassay-guided isolation of vasorelaxant compounds from Ziziphora clinopodioides Lam.(Lamiaceae). Fitoterapia, 83(2), 377-382. https://doi.org/10.1016/j.fitote.2011.11.023
  • Slinkard, K., & Singleton, V. L. (1977). Total phenol analysis: automation and comparison with manual methods. American Journal of Enology and Viticulture, 28(1), 49-55. https://doi.org/10.5344/ ajev.1977.28.1.49
  • Taheri, A., Ganjeali, A., Arefi-Oskouie, A., Cirak, C., & Cheniany, M. (2023). The variability of phenolic constituents and antioxidant properties among wild populations of Ziziphora clinopodioides Lam. Physiology and Molecular Biology of Plants, 29(2), 221-237. https://doi.org/10.1007/s12298-023-01283-y
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There are 35 citations in total.

Details

Primary Language Turkish
Subjects Plant Biochemistry
Journal Section RESEARCH ARTICLE
Authors

Mehmet Çavuşoğlu 0000-0002-8871-5646

Serkan Yiğitkan 0000-0002-6202-1515

İsmail Yener 0000-0002-0988-9462

Mehmet Veysi Çağlayan 0000-0002-9803-6444

Barış Reşitoğlu 0000-0003-2635-4395

Mehmet Akdeniz 0000-0002-4435-4826

Eda Çavuş Kaya 0000-0002-5359-8056

Fethullah Tekin 0000-0003-3710-1705

Mustafa Abdullah Yılmaz 0000-0002-4090-7227

Abdulselam Ertaş 0000-0002-2193-8386

Project Number ECZACILIK.24.007 ve TIP20.032
Early Pub Date December 26, 2024
Publication Date December 31, 2024
Submission Date November 14, 2024
Acceptance Date December 26, 2024
Published in Issue Year 2024Volume: 27 Issue: Ek Sayı 2 (Suppl 2)

Cite

APA Çavuşoğlu, M., Yiğitkan, S., Yener, İ., Çağlayan, M. V., et al. (2024). Ziziphora clinopodioides Lam. Türünün Kültür İle Doğal Ortamlarda Yetişen Örneklerinin Kimyasal ve Biyolojik Yönden Detaylı İncelenmesi. Kahramanmaraş Sütçü İmam Üniversitesi Tarım Ve Doğa Dergisi, 27(Ek Sayı 2 (Suppl 2), 316-326. https://doi.org/10.18016/ksutarimdoga.vi.1585656
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