Carnosic Acid and Carnosol, Two Major Antioxidants of Rosemary, Act through Different Mechanisms
Open accessAbstract
Carnosic acid, a phenolic diterpene specific to the Lamiaceae family, is highly abundant in rosemary (Rosmarinus officinalis). Despite numerous industrial and medicinal/pharmaceutical applications of its antioxidative features, this compound in planta and its antioxidant mechanism have received little attention, except a few studies of rosemary plants under natural conditions. In vitro analyses, using high-performance liquid chromatography-ultraviolet and luminescence imaging, revealed that carnosic acid and its major oxidized derivative, carnosol, protect lipids from oxidation. Both compounds preserved linolenic acid and monogalactosyldiacylglycerol from singlet oxygen and from hydroxyl radical. When applied exogenously, they were both able to protect thylakoid membranes prepared from Arabidopsis (Arabidopsis thaliana) leaves against lipid peroxidation. Different levels of carnosic acid and carnosol in two contrasting rosemary varieties correlated with tolerance to lipid peroxidation. Upon reactive oxygen species (ROS) oxidation of lipids, carnosic acid was consumed and oxidized into various derivatives, including into carnosol, while carnosol resisted, suggesting that carnosic acid is a chemical quencher of ROS. The antioxidative function of carnosol relies on another mechanism, occurring directly in the lipid oxidation process. Under oxidative conditions that did not involve ROS generation, carnosol inhibited lipid peroxidation, contrary to carnosic acid. Using spin probes and electron paramagnetic resonance detection, we confirmed that carnosic acid, rather than carnosol, is a ROS quencher. Various oxidized derivatives of carnosic acid were detected in rosemary leaves in low light, indicating chronic oxidation of this compound, and accumulated in plants exposed to stress conditions, in parallel with a loss of carnosic acid, confirming that chemical quenching of ROS by carnosic acid takes place in planta.
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Antioxidants play a crucial role in neutralizing free radicals, which are involved in the development of these conditions.
“Antioxidants play a crucial role in neutralizing free radicals, which are involved in the development of these conditions [33,57,67,68].”
From Comparative Analysis of Infusions and Ethanolic Extracts of Annona muricata Leaves from Colima, Mexico: Phytochemical Profile and Antioxidant Activity (2024) · cites this paper as [68]
The Discussion (page not specified in our copy) says carnosic acid scavenges free radicals and helps protect rosemary leaves from photooxidative stress. It also says carnosol protects lipids by a different mechanism, without directly quenching ROS. The paper does not establish that free radicals contribute to the development of the unspecified “conditions” in the citing sentence. (LLM, conf=0.84)
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Cites
Erkan, N., Ayrancı, G., & Ayrancı́, E. (2008) · Food Chemistry · doi:10.1016/j.foodchem.2008.01.058 · Cited by 734 · see citing works
Singlet Oxygen Is the Major Reactive Oxygen Species Involved in Photooxidative Damage to Plants
Triantaphylidès, C., Krischke, M., Hoeberichts, F. A., et al. (2008) · PLANT PHYSIOLOGY · doi:10.1104/pp.108.125690 · Cited by 602 · see citing works
Cuvelier, M., Richard, H. M. J., & Berset, C. (1996) · Journal of the American Oil Chemists Society · doi:10.1007/bf02518121 · Cited by 588 · see citing works
Antioxidant and pro-oxidant properties of active rosemary constituents: carnosol and carnosic acid
Aruoma, O. I., Halliwell, B. B., Aeschbach, R., & Löligers, J. (1992) · Xenobiotica · doi:10.3109/00498259209046624 · Cited by 514 · see citing works
Characterization of Phenolic Composition in Lamiaceae Spices by LC-ESI-MS/MS
Hossain, M. B., Rai, D. K., Brunton, N. P., Martín‐Diana, A. B., & Barry‐Ryan, C. (2010) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf102042g · Cited by 447 · see citing works
del Baño, M. J., Lorente, J., Castillo, J., Benavente-García, O., del Rı́o, J. A., Ortuño, A. M., Quirin, K., & Gerard, D. (2003) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf0300745 · Cited by 368 · see citing works
Birtić, S., Dussort, P., Pierre, F., Bily, A. C., & Roller, M. (2015) · Phytochemistry · doi:10.1016/j.phytochem.2014.12.026 · Cited by 340 · see citing works
Self-citationZhang, Y., Yang, L., Zu, Y., Chen, X., Wang, F., & Liu, F. (2009) · Food Chemistry · doi:10.1016/j.foodchem.2009.05.038 · Cited by 316 · see citing works
Membrane Transport, Sensing and Signaling in Plant Adaptation to Environmental Stress
Conde, A., Chaves, M. M., & Gerós, H. (2011) · Plant and Cell Physiology · doi:10.1093/pcp/pcr107 · Cited by 303 · see citing works
Carotenoids, tocopherols and thiols as biological singlet molecular oxygen quenchers
Mascio, P. D., Devasagayam, T. P. A., Kaiser, S., & Sies, H. (1990) · Biochemical Society Transactions · doi:10.1042/bst0181054 · Cited by 282 · see citing works
Pérez-Fons, L., GarzÓn, M. T., & Micol, V. (2009) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf9026487 · Cited by 273 · see citing works
Cifra, M., & Pospı́šil, P. (2014) · Journal of Photochemistry and Photobiology B Biology · doi:10.1016/j.jphotobiol.2014.02.009 · Cited by 271 · see citing works
Wijeratne, S. S. K., Cuppett, S. L., & Schlegel, V. (2005) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf0512003 · Cited by 264 · see citing works
The Ascorbate-glutathione-α-tocopherol Triad in Abiotic Stress Response
Szarka, A., Tomasskovics, B., & Bánhegyi, G. (2012) · International Journal of Molecular Sciences · doi:10.3390/ijms13044458 · Cited by 248 · see citing works
Chauvin, A., Caldelari, D., Wolfender, J., & Farmer, E. E. (2012) · New Phytologist · doi:10.1111/nph.12029 · Cited by 240 · see citing works
Liebler, D. C., Kling, D., & Reed, D. J. (1986) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)67210-2 · Cited by 228 · see citing works
Zhang, Y., Smuts, J. P., Dodbiba, E., Rangarajan, R., Lang, J. C., & Armstrong, D. W. (2012) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf302179c · Cited by 222 · see citing works
Munné‐Bosch, S., & Alegre, L. (2003) · PLANT PHYSIOLOGY · doi:10.1104/pp.102.019265 · Cited by 169 · see citing works
Haraguchi, H., Saito, T., Okamura, N., & Yagi, A. (1995) · Planta Medica · doi:10.1055/s-2006-958094 · Cited by 168 · see citing works
Hopia, A., Huang, S., Schwarz, K., et al. (1996) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf950777p · Cited by 164 · see citing works
Munné‐Bosch, S., Schwarz, K., & Alegre, L. (1999) · PLANT PHYSIOLOGY · doi:10.1104/pp.121.3.1047 · Cited by 158 · see citing works
Wang, H., Liu, F., Yang, L., Zu, Y., Wang, H., Qu, S., & Zhang, Y. (2011) · Food Chemistry · doi:10.1016/j.foodchem.2011.02.082 · Cited by 152 · see citing works
The upstream oxylipin profile of Arabidopsis thaliana: a tool to scan for oxidative stresses
Montillet, J., Cacas, J., Garnier, L., et al. (2004) · The Plant Journal · doi:10.1111/j.1365-313x.2004.02223.x · Cited by 151 · see citing works
Munné‐Bosch, S., & Alegre, L. (2001) · PLANT PHYSIOLOGY · doi:10.1104/pp.125.2.1094 · Cited by 135 · see citing works
Wellwood, C. R. L., & Cole, R. A. (2004) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf035335p · Cited by 131 · see citing works
Carnosic acid biosynthesis elucidated by a synthetic biology platform
Ignea, C., Athanasakoglou, A., Ioannou, E., Georgantea, P., Trikka, F. A., Loupassaki, S., Roussis, V., Makris, A. M., & Kampranis, S. C. (2016) · Proceedings of the National Academy of Sciences · doi:10.1073/pnas.1523787113 · Cited by 123 · see citing works
Christopher, S., Foote, Ching, T., & Geller, G. G. (1974) · Photochemistry and Photobiology · doi:10.1111/j.1751-1097.1974.tb06611.x · Cited by 121 · see citing works
Ksas, B., Bécuwe, N., Chevalier, A., et al. (2015) · Scientific Reports · doi:10.1038/srep10919 · Cited by 111 · see citing works
Antioxidant Activity of Carnosic Acid and Methyl Carnosate in Bulk Oils and Oil-in-Water Emulsions
Huang, S., Frankel, E. N., Schwarz, K., Aeschbach, R., & German, J. B. (1996) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf960068r · Cited by 109 · see citing works
Brückner, K., Božić, D., Manzano, D., et al. (2014) · Phytochemistry · doi:10.1016/j.phytochem.2014.01.021 · Cited by 106 · see citing works
Using spontaneous photon emission to image lipid oxidation patterns in plant tissues
Birtić, S., Ksas, B., Genty, B., Mueller, M. J., Triantaphylidès, C., & Havaux, M. (2011) · The Plant Journal · doi:10.1111/j.1365-313x.2011.04646.x · Cited by 101 · see citing works
Self-citationNakatani, N., & Inatani, R. (1984) · Agricultural and Biological Chemistry · doi:10.1271/bbb1961.48.2081 · Cited by 101 · see citing works
Romo‐Vaquero, M., Garcı́a-Villalba, R., Larrosa, M., et al. (2013) · Molecular Nutrition & Food Research · doi:10.1002/mnfr.201300052 · Cited by 100 · see citing works
Plastochromanol-8: Fifty years of research
Kruk, J., Szymańska, R., Cela, J., & Munné‐Bosch, S. (2014) · Phytochemistry · doi:10.1016/j.phytochem.2014.09.011 · Cited by 98 · see citing works
Autoluminescence imaging: a non-invasive tool for mapping oxidative stress
Havaux, M., Triantaphylidès, C., & Genty, B. (2006) · Trends in Plant Science · doi:10.1016/j.tplants.2006.08.001 · Cited by 97 · see citing works
Self-citationChloroplast Membrane Photostability in chlPTransgenic Tobacco Plants Deficient in Tocopherols
Havaux, M., Lütz, C., & Grimm, B. (2003) · PLANT PHYSIOLOGY · doi:10.1104/pp.102.017178 · Cited by 95 · see citing works
Self-citationLuis, J., & Johnson, C. B. (2005) · Spanish Journal of Agricultural Research · doi:10.5424/sjar/2005031-130 · Cited by 91 · see citing works
Antioxidant properties of phenolic diterpenes from Rosmarinus officinalis.
Zeng, H. H., Tu, P., Zhou, K., et al. (2001) · PubMed · Cited by 81 · see citing works
Božić, D., Papaefthimiou, D., Brückner, K., et al. (2015) · PLoS ONE · doi:10.1371/journal.pone.0124106 · Cited by 77 · see citing works
Maheswarappa, N. B., Vaithiyanathan, S., Muthukumar, M., et al. (2013) · Meat Science · doi:10.1016/j.meatsci.2013.04.043 · Cited by 77 · see citing works
Membranes as Structural Antioxidants
Schmid‐Siegert, E., Stepushenko, O., Glauser, G., & Farmer, E. E. (2016) · Journal of Biological Chemistry · doi:10.1074/jbc.m116.729921 · Cited by 77 · see citing works
Pearson, D. A., Frankel, E. N., Aeschbach, R., et al. (1997) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf9603893 · Cited by 76 · see citing works
Pérez-Fons, L., Aranda, F. J., Guillén, J., Villalaı́n, J., & Micol, V. (2006) · Archives of Biochemistry and Biophysics · doi:10.1016/j.abb.2006.07.004 · Cited by 76 · see citing works
Determination of the Carnosic Acid Content in Wild and Cultivated Rosmarinus officinalis
Hidalgo, P. J., Ubera, J. L., Tena, M. T., et al. (1998) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf970974j · Cited by 67 · see citing works
Wijeratne, S. S. K., & Cuppett, S. L. (2007) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf063089m · Cited by 61 · see citing works
Thylakoid membrane stability in drought-tolerant and drought-sensitive plants
Schwab, K. B., & Heber, U. (1984) · Planta · doi:10.1007/bf00951458 · Cited by 57 · see citing works
Jordán, M. J., Castillo, J., Bañón, S., Conesa, C. M., & Sotomayor, J. A. (2013) · Food Chemistry · doi:10.1016/j.foodchem.2013.11.068 · Cited by 57 · see citing works
Nakatani, N., & Inatani, R. (1984) · Agricultural and Biological Chemistry · doi:10.1080/00021369.1984.10866436 · Cited by 55 · see citing works
Function of isoprenoid quinones and chromanols during oxidative stress in plants
Kruk, J., Szymańska, R., Nowicka, B., et al. (2016) · New Biotechnology · doi:10.1016/j.nbt.2016.02.010 · Cited by 54 · see citing works
Role of plastoglobules in metabolite repair in the tocopherol redox cycle
Piller, L. E. (2014) · Frontiers in Plant Science · doi:10.3389/fpls.2014.00298 · Cited by 50 · see citing works
Song, Y., Yan, H., Chen, J., et al. (2013) · Journal of Pharmaceutical and Biomedical Analysis · doi:10.1016/j.jpba.2013.11.001 · Cited by 40 · see citing works
Martini, D., Iacazio, G., Ferrand, D., et al. (1994) · Biocatalysis · doi:10.3109/10242429409034376 · Cited by 39 · see citing works
Wijeratne, S. S. K., & Cuppett, S. L. (2006) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf060475v · Cited by 32 · see citing works
Tavadyan, L. A., Khachoyan, A. A., Martoyan, G. A., et al. (2007) · Chemistry and Physics of Lipids · doi:10.1016/j.chemphyslip.2007.03.002 · Cited by 29 · see citing works
Masuda, T., Kirikihira, T., & Takeda, Y. (2005) · Journal of Agricultural and Food Chemistry · doi:10.1021/jf050685s · Cited by 25 · see citing works
Antioxidant Capacity of Abietanes from Sphacele Salviae
Escuder, B., Torres, R., Lissi, E. A., et al. (2002) · Natural product letters · doi:10.1080/10575630290020631 · Cited by 19 · see citing works
Direct Detection of Free Radicals and Reactive Oxygen Species in Thylakoids
Hideg, É., Kálai, T., & Hideg, K. (2010) · Methods in molecular biology · doi:10.1007/978-1-60761-925-3_16 · Cited by 18 · see citing works
Masuda, T., Kirikihira, T., Takeda, Y., et al. (2004) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.1836 · Cited by 12 · see citing works
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Gao, Y., Zhuang, H., Yeh, H.-Y., Bowker, B., & Zhang, J. (2019) · Innovative Food Science & Emerging Technologies · doi:10.1016/j.ifset.2019.05.007 · Cited by 71 · see citing works
Hernandez-Fuentes, G. A., Delgado-Enciso, O. G., Larios-Cedeño, E. G., Sánchez-Galindo, J. M., Ceballos-Magaña, S. G., Pineda-Urbina, K., Alcalá-Pérez, M. A., Magaña-Vergara, N. E., Delgado-Enciso, J., Díaz-Llerenas, U., et al. (2024) · Life · doi:10.3390/life14121702 · Cited by 15 · see citing works
Hernández-Rangel, A. E., Cabrera-Licona, A., Hernandez-Fuentes, G. A., Beas-Guzmán, O. F., Martínez-Martínez, F. J., Alcalá-Pérez, M. A., Montes-Galindo, D. A., Rodriguez-Sanchez, I. P., Martinez-Fierro, M. L., Casarez-Price, J. C., et al. (2024) · Biomedicines · doi:10.3390/biomedicines12081804 · Cited by 7 · see citing works
- Authors
- Loussouarn, M., Krieger-Liszkay, A., Svilar, L., Bily, A., Birtić, S., & Havaux, M.
- Affiliations
- Commissariat à l’Energie Atomique et aux Energies Alternatives Cadarache, Centre National de la Recherche Scientifique, Unité Mixte de Recherche 7265 Biologie Végétale et Microbiologie Environnementales, Aix Marseille Université, Laboratoire d’Ecophysiologie Moléculaire des Plantes, F-13108 Saint-Paul-lez-Durance, France
- Institut de Biologie Intégrative de la Cellule, Centre National de la Recherche Scientifique, Commissariat à l’Energie Atomique et aux Energies Alternatives Saclay, Institut de Biologie et de Technologie de Saclay, Université Paris-Sud, 91191 Gif-sur-Yvette, France
- Inserm (FR)
- Naturex (France) (FR)
- Centre National de la Recherche Scientifique (FR)
- Venue
- PLANT PHYSIOLOGY
- Publisher
- Oxford University Press (OUP)
- Published
- 2017-09-15
- Volume
- 175
- Issue
- 3
- Pages
- 1381-1394
- ISSN
- 0032-0889 (ISSN-L)
- 1532-2548
- PMC
- PMC5664485
- OpenAlex
- W2755455639
- Cited by
- 234
- References
- 58
- Citations by year
- 2026: 30 · 2025: 44 · 2024: 38 · 2023: 27 · 2022: 33 · 2021: 25 · 2020: 21 · 2019: 11 · 2018: 4 · 2017: 1
- FWCI
- 6.32
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Locations
- PLANT PHYSIOLOGY (publishedVersion, cc-by)
- PubMed Central (publishedVersion)
- PubMed (publishedVersion)
- HAL (submittedVersion, other-oa)
- Funders
- French National Association for Research and Technology
- Topics
- Health Sciences › Medicine › Biochemistry › Phytochemicals and Antioxidant Activities
- Health Sciences › Medicine › Biochemistry › Antioxidant Activity and Oxidative Stress
- Physical Sciences › Chemistry › Organic Chemistry › Edible Oils Quality and Analysis
- Keywords
- carnosic acid, carnosol, Rosmarinus officinalis, antioxidant defense, lipid peroxidation, reactive oxygen species quenching, singlet oxygen, hydroxyl radicals, thylakoid membranes, linolenic acid, monogalactosyldiacylglycerol, phenolic diterpenes, oxidative stress resistance, spin probes, electron spin resonance
- MeSH terms
- Antioxidants, Intracellular Membranes, Lipids, Oxidation-Reduction, Time Factors, Lipid Peroxidation, Reactive Oxygen Species, Plant Leaves, Thylakoids, alpha-Tocopherol, Rosmarinus, Abietanes
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