1H-qNMR as a Tool for the Quantitative and Qualitative Evaluation of Abietane-Type Diterpenes in Lamiaceae Species Cultivated in Greece
Source abstract
Abstract
This study aimed to quantitatively and qualitatively evaluate the content of carnosic acid (CA), 12-O-methyl-carnosic acid (12MCA), carnosol (CS), rosmanol (RO) and 7-O-methyl-epi-rosmanol (7MER) in 61 Lamiaceae plants growing in Greece, using 1H-qNMR spectroscopy as a simple, rapid and direct method without sample deterioration. For this purpose, methanol extracts from 18 genera (e.g., Salvia, Mentha, Melissa, Ocimum) were analyzed using isolated and fully characterized metabolites, previously identified by our group, as standards. At least one of the target compounds was detected in 22 species, predominantly belonging to the genus Salvia. Notably, 7MER and RO were not detected in any extract. CA, CS and 12MCA were exclusively found in Salvia species, with S. somalensis, S. officinalis and S. fruticosa emerging as the richest sources of these diterpenes. Among them, S. somalensis showed the highest concentration of CA (>30 mg/g), while 12MCA was most abundant in S. microphylla. These results highlight Salvia as the most promising genus for the accumulation of bioactive abietane-type diterpenes. The implementation of 1H-qNMR for such chemical profiling provides a reliable approach toward the phytochemical standardization of plant extracts, supporting their further use in nutraceutical or pharmaceutical formulations.
Source: crossref · Quality: baseline
Research context
OpenAlex topics: Biological Activity of Diterpenoids and Biflavonoids · Natural product bioactivities and synthesis · Phytochemistry and Biological Activities
SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.
Affiliations
Laboratory of Pharmacognosy & Chemistry of Natural Products, Department of Pharmacy, National & Kapodistrian University of Athens, University Campus, 15771 Zografou, Greece
Department of Food Science and Technology, University of West Attica, Egaleo Park Campus, Ag. Spyridonos, 12243 Egaleo, Greece
Institute of Chemical Biology, National Hellenic Research Foundation, Vas. Constantinou Ave., 11635 Athens, Greece
Institute of Biosciences & Applications, National Centre for Scientific Research “Demokritos”, Agia Paraskevi, 15310 Attikis, Greece
References (33)
Show source-provided references
1. Aromatic abietane diterpenoids: Their biological activity and synthesis10.1039/C4NP00110A ↗
2. On the evolution and distribution in Labiatae
3. Rosmarinus officinalis L: An update review of its phytochemistry and biological activity10.4155/fsoa-2017-0124 ↗
4. Kallimanis, P., Chinou, I., Panagiotopoulou, A., Soshilov, A.A., He, G., Denison, M.S., and Magiatis, P. (2022). Rosmarinus officinalis L. Leaf Extracts and Their Metabolites Inhibit the Aryl Hydrocarbon Receptor (AhR) Activation In Vitro and in Human Keratinocytes: Potential Impact on Inflammatory Skin Diseases and Skin Cancer. Molecules, 27.10.3390/molecules27082499 ↗
5. Kallimanis, P., Magiatis, P., Panagiotopoulou, A., Ioannidis, K., and Chinou, I. (2024). Extraction Optimization and Qualitative/Quantitative Determination of Bioactive Abietane-Type Diterpenes from Three Salvia Species (Common Sage, Greek Sage and Rosemary) by 1H-qNMR. Molecules, 29.10.3390/molecules29030625 ↗
6. Mantzourani, C., Tarantilis, P.A., and Kokotou, M.G. (2023). Carnosic Acid and Carnosol: Analytical Methods for Their Determination in Plants, Foods and Biological Samples. Separations, 10.10.3390/separations10090481 ↗
7. Sun, S., Jin, M., Zhou, X., Ni, J., Jin, X., Liu, H., and Wang, Y. (2017). The Application of Quantitative 1H-NMR for the Determination of Orlistat in Tablets. Molecules, 22.10.3390/molecules22091517 ↗
8. Structure activity relationship of phenolic diterpenes from Salvia officinalis as activators of the nuclear factor E2-related factor 2 pathway10.1016/j.bmc.2013.02.019 ↗
9. Semisynthesis of rosmanol and its derivatives. Easy access to abietatriene diterpenes isolated from the genus Salvia with biological activities10.1021/np010565o ↗
10. de Macedo, L.M., dos Santos, E.M., Militão, L., Tundisi, L.L., Ataide, J.A., Souto, E.B., and Mazzola, P.G. (2020). Rosemary (Rosmarinus officinalis L., syn Salvia rosmarinus Spenn.) and Its Topical Applications: A Review. Plants, 9.10.3390/plants9050651 ↗
11. Habtemariam, S. (2023). Anti-Inflammatory Therapeutic Mechanisms of Natural Products: Insight from Rosemary Diterpenes, Carnosic Acid and Carnosol. Biomedicines, 11.10.3390/biomedicines11020545 ↗
12. Carnosic acid10.1016/j.phytochem.2014.12.026 ↗
13. Karagianni, K., Pettas, S., Kanata, E., Lioulia, E., Thune, K., Schmitz, M., Tsamesidis, I., Lymperaki, E., Xanthopoulos, K., and Sklaviadis, T. (2022). Carnosic acid and carnosol display antioxidant and anti-prion properties in in vitro and cell-free models of prion diseases. Antioxidants, 11.10.3390/antiox11040726 ↗
14. Phenolic diterpene and α-tocopherol contents in leaf extracts of 60 Salvia species10.1002/jsfa.3384 ↗
15. Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis. II. Isolation of carnosic acid and formation of other phenolic diterpenes10.1007/BF01201766 ↗
16. Antioxidative activity and phenolic composition of pilot-plant and commercial extracts of sage and rosemary10.1007/BF02518121 ↗
17. Phytochemical composition of fractions isolated from ten Salvia species by supercritical carbon dioxide and pressurized liquid extraction methods10.1016/j.foodchem.2016.12.047 ↗
18. HPLC fingerprint of important phenolic compounds in some Salvia L. species from Iran10.25135/rnp.72.18.02.228 ↗
19. Supercritical carbon dioxide extraction of antioxidant fractions from selected Lamiaceae herbs and their antioxidant capacity10.1016/j.ifset.2009.08.013 ↗
20. Application of principal component and hierarchical cluster analysis to classify different spices based on in vitro antioxidant activity and individual polyphenolic antioxidant compounds10.1016/j.jff.2011.03.010 ↗
21. Optimization of ultrasound assisted extraction of antioxidant compounds from marjoram (Origanum majorana L.) using response surface methodology10.1016/j.ultsonch.2011.11.001 ↗
22. Antioxidant effect rosemary (Rosmarinus officinalis L.) and oregano (Origanum vulgare L.) extracts on TBARS and colour of model raw pork batters10.1016/j.meatsci.2008.09.004 ↗
23. Phenolic and triterpenoid antioxidants from Origanum majorana L. herb and extracts obtained with different solvents10.1021/jf048777p ↗
24. Contamination during micropropagation: Analysis of the bacterial lines and treatment with sage extract10.17660/ActaHortic.2012.961.7 ↗
25. Degradation pathway of carnosic acid in methanol 24 through isolation and structural identification of its degradation products10.1007/s00217-013-2035-5 ↗
26. Solvent extraction study of antioxidants from Balm (Melissa officinalis L.) leaves10.1016/S0308-8146(02)00382-5 ↗
27. Phenolics composition and antioxidant activity of sweet basil (Ocimum basilicum L.)10.1021/jf034269o ↗
28. Koutsoulas, A., Čarnecká, M., Slanina, J., Tóth, J., and Slaninová, I. (2019). Characterization of Phenolic Compounds and Antiproliferative Effects of Salvia pomifera and Salvia fruticose Extracts. Molecules, 24.10.3390/molecules24162921 ↗
29. Constituents of Salvia microphylla10.1080/14786410500462843 ↗
30. Profiling of essential oils and polyphenolics of Salvia argentea and evaluation of its by-products antioxidant activity10.1016/j.indcrop.2013.02.007 ↗
31. Kamatou, G. (2006). Indigenous Salvia Species−an Investigation of Their Pharmacological Activities and Phytochemistry. [Ph.D. Thesis, University of the Witwatersrand].
32. First Report of Phoma Strasseri as a Pathogen of Stachys officinalis in Bulgaria10.1094/PDIS.2002.86.6.699B ↗
33. Total Content of Kaurene Diterpenes in Annona vepretorum Stems via 1H qNMR: A Method for Speeding the Identification of Bioactive Extracts10.1002/pca.2792 ↗