Carnosic acid

Phytochemistry

Volumn 115, Issue 1, 2015, Pages 9-19

  Birtić, Simona ^a   Dussort, Pierre ^a   Pierre, François Xavier ^a   Bily, Antoine C ^a   Roller, Marc ^a  

^a Givaudan SA   (Switzerland)

Author keywords

Antimicrobial; Antioxidant; Carnosic acid; Labiatae; Lamiaceae; Oxidation; Photooxidation; Photoprotection; Rosemary; Rosmarinus officinalis; Sage; Salvia

Indexed keywords

LAMIACEAE; ROSMARINUS; ROSMARINUS OFFICINALIS; SALVIA;

ABIETANE DERIVATIVE; ANTIINFECTIVE AGENT; ANTIOXIDANT; CARNOSIC ACID; CARNOSOL;

ANIMAL; CHEMICAL STRUCTURE; CHEMISTRY; CLASSIFICATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; ISOLATION AND PURIFICATION; MOUSE; PLANT LEAF; RAT; ROSMARINUS; SALVIA; SHEEP;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTIOXIDANTS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DITERPENES, ABIETANE; HUMANS; MICE; MOLECULAR STRUCTURE; PLANT LEAVES; RATS; ROSMARINUS; SALVIA; SHEEP;

EID: 84934916818     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2014.12.026     Document Type: Short Survey

References (123)

1. Abreu, M.E., Muller, M., Alegre, L., Munné-Bosch, S., 2008. Phenolic diterpene and atocopherol contents in leaf extracts of 60 Salvia species. J. Sci. Food Agric. 88, 2648-2653.
2. Achour, S., Khelifi, E., Attia, Y., Ferjani, E., Noureddine Hellal, A., 2012. Concentration of antioxidant polyphenols from Thymus capitatus extracts by membrane process technology. J. Food Sci. 77, 703-709.
3. Aoyagi, Y., Takahashi, Y., Satake, Y., Takeya, K., Aiyama, R., Matsuzaki, T., Hashimoto, S., Kurihara, T., 2006. Cytotoxicity of abietane diterpenoids from Perovskia abrotanoides and of their semisynthetic analogues. Bioorg. Med. Chem. 14, 5285-5291.
4. Aruoma, O.I., Halliwell, B., Aeschbach, R., Loligers, J., 1992. Antioxidant and prooxidant properties of active rosemary constituents: carnosol and carnosic acid. Xenobiotica 22, 257-268.
5. Azad, N., Rasoolijazi, H., Joghataie, M.T., Soleimani, S., 2011. Neuroprotective effects of carnosic acid in an experimental model of Alzheimer's disease in rats. Cell J. (Yakhteh) 13, 39-44.
6. Baliga, M.S., Jimmy, R., Thilakchand, K.R., Sunitha, V., Bhat, N.R., Saldanha, E., Rao, S., Rao, P., Arora, R., Palatty, P.L., 2013. Ocimum Sanctum L. (Holy Basil or Tulsi) and its phytochemicals in the prevention and treatment of cancer. Nutr. Cancer 65, 26-35.
7. Barni, M.V., Carlini, M.J., Cafferata, E.G., Puricelli, L., Moreno, S., 2012. Carnosic acid inhibits the proliferation and migration capacity of human colorectal cancer cells. Oncol. Rep. 27, 1041-1048.
8. Bauer, J., Kuehnl, S., Rollinger, J.M., Scherer, O., Northoff, H., Stuppner, H., Werz, O., Koeberle, A., 2012. Carnosol and carnosic acids from Salvia officinalis inhibit microsomal prostaglandin E2 synthase-1. J. Pharmacol. Exp. Ther. 342, 169-176.
9. Bernardes, W.A., Lucarini, R., Tozatti, M.G., Souza, M.G., Silva, M.L., Filho, A.A., Martins, C.H., Crotti, A.E., Pauletti, P.M., Groppo, M., Cunha, W.R., 2010. Antimicrobial activity of Rosmarinus officinalis against oral pathogens: relevance of carnosic acid and carnosol. Chem. Biodivers. 7, 1835-1840.
10. Bick, J.A., Lange, B.M., 2003. Metabolic cross talk between cytosolic and plastidial pathways of isoprenoid biosynthesis: unidirectional transport of intermediates across the chloroplast envelope membrane. Arch. Biochem. Biophys. 415, 146-154.
11. Brieskorn, C.H., Dumling, H.J., 1969. Carnosolsaure, der wichtige antioxydativ wirksame Inhaltsstoff des Rosmarin-und Salbeiblattes. Eur. Food Res. Tech. Z. Lebensm. Unters. Forsch. 141, 10-16.
12. Brieskorn, C.H., Fuchs, A., 1962. Über die Inhaltsstoffe von Salvia off L., XIII. Die Struktur des Pikrosalvins, eines Diterpen-o-diphenol-lactons aus dem Salbeiblatt. Chem. Ber. 95, 3034-3041.
13. Brieskorn, C.H., Fuchs, A., Bredenberg, J.B., McChesney, J.D., Wenkert, E., 1964. The structure of carnosol. J. Org. Chem. 29, 2293-2298.
14. Brkner, K., Božić, D., Manzano, D., Papaefthimiou, D., Pateraki, I., Scheler, U., Ferrer, A., de Vos, R.C., Tissier, A., 2014. Characterization of two genes for the biosynthesis of abietane-type diterpenes in rosemary Rosmarinus officinalis glandular trichomes. Phytochemistry 101, 52-64.
15. Bruno, M., Savona, G., Piozzi, F., de la Torre, M.C., Rodriguez, B., Marlier, M., 1991. Abietane diterpenoids from Lepechinia meyeni and Lepechinia hastata. Phytochemistry 30, 2339-2343.
16. Calabrese, V., Scapagnini, G., Catalano, C., Dinotta, F., Geraci, D., Morganti, P., 2000. Biochemical studies of a natural antioxidant isolated from rosemary and its application in cosmetic dermatology. Int. J. Tissue React. 22, 5-13.
17. Campo, J.D., Amiot, M.J., 2000. Antimicrobial effect of rosemary extracts. J. Food Prot. 63, 1359-1368.
18. Campo, J.D., Sergent, M., Amiot, M.J., 2003. Determination of the most bioactive phenolic compounds from rosemary against Listeria monocytogenes: influence of concentration, pH, and NaCl. J. Food Sci. 68, 2066-2071.
19. Cao, R., Zhang, Y., Mann, F.M., Huang, C., Mukkamala, D., Hudock, M.P., Mead, M.E., Prisic, S., Wang, K., Lin, F.Y., Chang, T.K., Peeters, R.J., Oldfield, E., 2010. Diterpene cyclases and the nature of the isoprene fold. Proteins Struct. Funct. Bioinf. 78, 2417-2432.
20. Costa, S., Utan, A., Speroni, E., Cervellati, R., Piva, G., Prandini, A., Guerra, M.C., 2007. Carnosic acid from rosemary extracts: a potential chemoprotective agent against aflatoxin B1. An in vitro study. J. Appl. Toxicol. 27, 152-159.
21. Cowan, M.M., 1999. Plant products as antimicrobial agents. Clin. Microbiol. Rev. 12, 564-582.
22. Cuvelier, M.E., Berset, C., Richard, H., 1994. Antioxidant constituents in sage (Salvia officinalis). J. Agric. Food Chem. 42, 665-669.
23. Danilenko, M., Studzinski, G.P., 2004. Enhancement by other compounds of the anticancer activity of vitamin D(3) and its analogs. Exp. Cell Res. 298, 339-358.
24. del Bano, M.J., Lorente, J., Castillo, J., Benavente-Garcia, O., del Rio, J.A., Ortuno, A., Quirin, K.W., Gerard, D., 2003. Phenolic diterpenes, flavones, and rosmarinic acid distribution during the development of leaves, flowers, stems, and roots of Rosmarinus officinalis. Antioxidant activity. J. Agric. Food Chem. 51, 4247-4253.
25. DellaPenna, D., 1999. Carotenoid synthesis and function in plants: insights from mutant studies in Arabidopsis thaliana. Adv. Photosynth. 8, 21-37.
26. Dickmann, L.J., VandenBrink, B.M., Lin, Y.S., 2012. In vitro hepatotoxicity and cytochrome P450 induction and inhibition characteristics of carnosic acid, a dietary supplement with antiadipogenic properties. Drug Metab. Dispos. 40, 1263-1267.
27. Djarmati, Z., Jankov, R.M., Schwirtlich, E., Djulinac, B., Djordjevic, A., 1991. High antioxidant activity of extracts obtained from sage by supercritical CO2 extraction. J. Am. Oil Chem. Soc. 68, 731-734.
28. Doolaege, E.H., Raes, K., De Vos, F., Verhé R., De Smet, S., 2011. Absorption, distribution and elimination of carnosic acid, a natural antioxidant from Rosmarinus officinalis, in rats. Plant Food Hum. Nutr. 66, 196-202.
29. Einbond, L.S., Wu, H.a., Kashiwazaki, R., He, K., Roller, M., Su, T., Wang, X., Goldsberry, S., 2012. Carnosic acid inhibits the growth of ER-negative human breast cancer cells and synergizes with curcumin. Fitoterapia 83, 1160-1168.
30. Erkan, N., Ayranci, G., Ayranci, E., 2009. A kinetic study of oxidation development in sunflower oil under microwave heating: effect of natural antioxidants. Food Res. Int. 42, 1171-1177.
31. Fukuzawa, K., Inokami, Y., Tokumura, A., Terao, J., Suzuki, A., 1998. Rate constants for quenching singlet oxygen and activities for inhibiting lipid peroxidation of carotenoids and a-tocopherol in liposomes. Lipids 33, 751-756.
32. Gao, W., Hillwig, M.L., Huang, L., Cui, G., Wang, X., Kong, J., Yang, B., Peters, R.J., 2009. A functional genomics approach to tanshinone biosynthesis provides stereochemical insights. Org. Lett. 11, 5170-5173.
33. Gómez-García, F.J., López-Jornet, M.P., Álvarez-Sánchez, N., Castillo-Sánchez, J., Benavente-García, O., Vicente Ortega, V., 2013. Effect of the phenolic compounds apigenin and carnosic acid on oral carcinogenesis in hamster induced by DMBA. Oral Dis. 19, 279-286.
34. Guerrero, I.C., Andres, L.S., Leon, L.G., Machin, R.P., Padron, J.M., Luis, J.G., Delgadillo, J., 2006. Abietane diterpenoids from Salvia pachyphylla and S. clevelandii with cytotoxic activity against human cancer cell lines. J. Nat. Prod. 69, 1803-1805.
35. Guo, J., Zhou, Y.J., Hillwig, M.L., Shen, Y., Yang, L., Wang, Y., Zhang, X., Liu, W., Peters, R.J., Chen, X., 2013. CYP76AH1 catalyzes turnover of miltiradiene in tanshinones biosynthesis and enables heterologous production of ferruginol in yeasts. Proc. Natl. Acad. Sci. USA 110, 12108-12113.
36. Hadad, N., Levy, R., 2012. The synergistic anti-inflammatory effects of lycopene, lutein, b-carotene, and carnosic acid combinations via redox-based inhibition of NF-jB signaling. Free Radical Biol. Med. 53, 1381-1391.
37. Havaux, M., 1998. Carotenoids as membrane stabilizers in chloroplasts. Trends Plant Sci. 3, 147-151.
38. Hill, R.A., Connoly, J.D., 2013. Triterpenoids. Nat. Prod. Rep. 30, 1028-1065.
39. Hopia, A.I., Huang, S.W., Schwarz, K., German, J.B., Frankel, E.N., 1996. Effect of different lipid systems on antioxidant activity of rosemary constituents carnosol and carnosic acid with and without a-tocopherol. J. Agric. Food Chem. 44, 2030-2036.
40. Horiuchi, K., Shiota, S., Kuroda, T., Hatano, T., Yoshida, T., Tsuchiya, T., 2007. Potentiation of antimicrobial activity of aminoglycosides by carnosol from Salvia officinalis. Biol. Pharm. Bull. 30, 287-290.
41. Hossain, M.B., Rai, D.K., Brunton, N.P., Martin-Diana, A.B., Barry-Ryan, C., 2010. Characterization of phenolic compounds in marjoram (Origanum majorana L.) by LC-ESI-MS/MS. International Conference of Food Innovation (Food Innova 2010). Universidad Politecnica de Valencia, pp. 25-29.
42. Houlihan, C.M., Ho, C.T., Chang, S.S., 1984. Elucidation of the chemical structure of a novel antioxidant, rosmaridiphenol, isolated from rosemary. J. Am. Oil Chem. Soc. 61, 1036-1039.
43. Huang, S.W., Frankel, E.N., Schwarz, K., Aeschbach, R., German, J.B., 1996. Antioxidant activity of carnosic acid and methyl carnosate in bulk oils and oil-in-water emulsions. J. Agric. Food Chem. 44, 2951-2956.
44. Hussein, A.A., Meyer, J.J.M., Jimeno, M.L., Rodriguez, B., 2007. Bioactive diterpenes from Orthosiphon labiatus and Salvia africana-lutea. J. Nat. Prod. 70, 293-295.
45. Ibarra, A., Cases, J., Roller, M., Chiralt-Boix, A., Coussaert, A., Ripoll, C., 2011. Carnosic acid-rich rosemary (Rosmarinus officinalis L.) leaf extract limits weight gain and improves cholesterol levels and glycaemia in mice on a high-fat diet. Br. J. Nutr. 106, 1182-1189.
46. Jayasinghe, C., Gotoh, N., Aoki, T., Wada, S., 2003. Phenolics composition and antioxidant activity of sweet basil (Ocimum basilicum L.). J. Agric. Food Chem. 51, 4442-4449.
47. Jordán, M.J., Castillo, J., Bañón, S., Martínez-Conesa, C., Sotomayor, J.A., 2014. Relevance of the carnosic acid/carnosol ratio for the level of rosemary diterpene transfer and for improving lamb meat antioxidant status. Food Chem. 151, 212-218.
48. Kamatou, G.P.P., Viljoen, A.M., Steenkamp, P., 2009. Antioxidant, antiinflammatory activities and HPLC analysis of South African Salvia species. Food Chem. 119, 684-688.
49. Klančnik, A., Guzej, B., Hadolin Kolar, M., Abramovič, H., Možina, S.S., 2009. In vitro antimicrobial and antioxidant activity of commercial rosemary extract formulations. J. Food Protect. 72, 1744-1752.
50. Klančnik, A., Piskernik, S., Jeršek, B., Možina, S.S., 2010. Evaluation of diffusion and dilution methods to determine the antibacterial activity of plant extracts. J. Microbiol. Methods 81, 121-126.
51. K?sal, M., Hu, H., Coates, R.M., Peters, R.J., Christianson, D.W., 2011. Structure and mechanism of the diterpene cyclase ent-copalyl diphosphate synthase. Nat. Chem. Biol. 7, 431-433.
52. Kontogianni, V.G., Tomic, G., Nikolic, I., Nerantzaki, A.A., Sayyad, N., Stosic-Grujicic, S., Stojanovic, I., Gerothanassis, I.P., Tzakos, A.G., 2013. Phytochemical profile of Rosmarinus officinalis and Salvia officinalis extracts and correlation to their antioxidant and anti-proliferative activity. Food Chem. 136, 120-129.
53. Kosaka, K., 2012. Anti-ageing effect of rosemary by the biophylaxis mechanism: activation of Nrf2 biophylaxis mechanism and suppression of the glycation stress. Food Style 21 (16), 46-49.
54. Kuhlmann, A., Roehl, C., 2006. Phenolic antioxidant compounds produced by in vitro cultures of rosemary (Rosmarinus officinalis) and their anti-inflammatory effect on lipopolysaccharide-activated microglia. Pharm. Biol. 44, 401-410.
55. Kuo, C.F., Su, J.D., Chiu, C.H., Peng, C.C., Chang, C.H., Sung, T.Y., Huang, S.H., Lee, W.C., Chyau, C.C., 2011. Anti-inflammatory effects of supercritical carbon dioxide extract and its isolated carnosic acid from Rosmarinus officinalis leaves. J. Agric. Food Chem. 59, 3674-3685.
56. Kuzmenko, A.I., Morozova, R.P., Nikolenko, I.A., Donchenko, G.V., Richheimer, S.L., Bailey, D.T., 1999. Chemiluminescence determination of the in vivo and in vitro antioxidant activity of RoseOx® and carnosic acid. J. Photochem. Photobiol., B 48, 63-67.
57. Lee, J.J., Jin, Y.R., Lee, J.H., Yu, J.Y., Han, X.H., Oh, K.W., Hong, J.T., Kim, T.J., Yun, Y.P., 2007. Antiplatelet activity of carnosic acid, a phenolic diterpene from Rosmarinus officinalis. Planta Med. 73, 121-127.
58. Linde, H., 1964. Ein neues Diterpen aus Salvia officinalis L. und eine Notiz zur Konstitution von Pikrosalvin. Helv. Chim. Acta 47, 1234-1239.
59. Lopez-Jimenez, A., Garcia-Caballero, M., Medina, M.A., Quesada, A.R., 2013. Antiangiogenic properties of carnosol and carnosic acid, two major dietary compounds from rosemary. Eur. J. Nutr. 52, 85-95.
60. Luis, J.C., Johnson, C.B., 2005. Seasonal variations of rosmarinic and carnosic acids in rosemary extracts. Analysis of their in vitro antiradical activity. Span. J. Agric. Res. 3, 106-112.
61. Luis, J.G., Quinones, W., Grillo, T.A., Kishi, M.P., 1994. Diterpenes from the aerial part of Salvia columbariae. Phytochemistry 35, 1373-1374.
62. Luis, J.G., 1991. Chemistry, biogenesis, and chemotaxonomy of the diterpenoids of Salvia. In: Harborne, J.B., Tomas-Barberan, F.A. (Eds.), Ecological Chemistry and Biochemistry of Plant Terpenoids. Clarendon Press, Oxford. UK, pp. 63-82.
63. Masuda, T., Oyama, Y., Arata, T., Inaba, Y., Takeda, Y., 2002. Cytotoxic activity of quinone derivatives of phenolic diterpenes from sage (Salvia officinalis). ITE Lett. Batt. New Technol. Med. 3, 39-42.
64. Mengoni, E.S., Vichera, G., Rigano, L.A., Rodriguez-Puebla, M.L., Galliano, S.R., Cafferata, E.E., Pivetta, O.H., Moreno, S., Vojnov, A.A., 2011. Suppression of COX-2, IL-1b and TNF-a expression and leukocyte infiltration in inflamed skin by bioactive compounds from Rosmarinus officinalis L. Fitoterapia 82, 414-421.
65. Molnar, V., Garai, J., 2005. Plant-derived anti-inflammatory compounds affect MIF tautomerase activity. Int. Immunopharmacol. 5, 849-856.
66. Morán, L., Andrés, S., Bodas, R., Prieto, N., Giráldez, F.J., 2012. Meat texture and antioxidant status are improved when carnosic acid is included in the diet of fattening lambs. Meat Sci. 91, 430-434.
67. Moreno, S., Scheyer, T., Romano, C.S., Vojnov, A.A., 2006. Antioxidant and antimicrobial activities of rosemary extracts linked to their polyphenol composition. Free Radical Res. 40, 223-231.
68. Munné-Bosch, S., Alegre, L., 2000. Changes in carotenoids, tocopherols and diterpenes during drought and recovery, and the biological significance of chlorophyll loss in Rosmarinus officinalis plants. Planta 210, 925-931.
69. Munné-Bosch, S., Alegre, L., 2001. Subcellular compartmentation of the diterpene carnosic acid and its derivatives in the leaves of rosemary. Plant Physiol. 125, 1094-1102.
70. Munné-Bosch, S., Alegre, L., 2003. Drought-induced changes in the redox state of atocopherol, ascorbate and the diterpene carnosic acid in chloroplasts of Labiatae species differing in carnosic acid contents. Plant Physiol. 131, 1816-1825.
71. Munné-Bosch, S., Schwarz, K., Alegre, L., 1999. Enhanced formation of a-tocopherol and highly oxidized abietane diterpenes in water-stressed rosemary plants. Plant Physiol. 121, 1047-1052.
72. Nabekura, T., Yamaki, T., Hiroi, T., Ueno, K., Kitagawa, S., 2010. Inhibition of anticancer drug efflux transporter P-glycoprotein by rosemary phytochemicals. Pharmacol. Res. 61, 259-263.
73. Nakamura, A., Yoshida, R., Maeda, H., Corredig, M., 2006. The stabilizing behaviour of soybean soluble polysaccharide and pectin in acidified milk beverages. Int. Dairy J. 16, 361-369.
74. Nakatani, N., Inatani, R., 1984. Two antioxidative diterpenes from rosemary (Rosmarinus officinalis L.) and a revised structure for rosmanol. Agric. Biol. Chem. 48, 2081-2085.
75. Ngo, S.N.T., Williams, D.B., Head, R.J., 2011. Rosemary and cancer prevention: preclinical perspectives. Crit. Rev. Food Sci. Nutr. 51, 946-954.
76. Nieto, G., Díaz, P., Bañón, S., Garrido, M.D., 2010. Dietary administration of ewe diets with a distillate from rosemary leaves Rosmarinus officinalis L.: influence on lamb meat quality. Meat Sci. 84, 23-29.
77. Offord, E.A., Gautier, J.C., Avanti, O., Scaletta, C., Runge, F., Kramer, K., Applegate, L.A., 2002. Photoprotective potential of lycopene, beta-carotene, vitamin E, vitamin C and carnosic acid in UVA-irradiated human skin fibroblasts. Free Radic. Biol. Med. 32, 1293-1303.
78. Oh, J., Yu, T., Choi, S.J., Yang, Y., Baek, H.S., An, S.A., Kwon, L.K., Kim, J., Rho, H.S., Shin, S.S., Choi, W.S., Hong, S., Cho, J.Y., 2012. Syk/Src pathway-targeted inhibition of skin inflammatory responses by carnosic acid. Mediators Inflammation 2012, 1-13.
79. Ojeda-Sana, A.M., Repetto, V., Moreno, S., 2013. Carnosic acid is an efflux pumps modulator by dissipation of the membrane potential in Enterococcus faecalis and Staphylococcus aureus. World J. Microbiol. Biotechnol. 29, 137-144.
80. Oluwatuyi, M., Kaatz, G.W., Gibbons, S., 2004. Antibacterial and resistance modifying activity of Rosmarinus officinalis. Phytochemistry 65, 3249-3254.
81. Otto, A., White, J.D., Simoneit, B.R., 2002. Natural product terpenoids in Eocene and Miocene conifer fossils. Science 297, 1543-1545.
82. Park, M.Y., Mun, S.T., 2013. Dietary carnosic acid suppresses hepatic steatosis formation via regulation of hepatic fatty acid metabolism in high-fat diet-fed mice. Nutr. Res. Pract. 7, 294-301.
83. Peñuelas, J., Munné-Bosch, S., 2005. Isoprenoids: an evolutionary pool for photoprotection. Trends Plant Sci. 10, 166-169.
84. Peters, R.J., 2010. Two rings in them all: the labdane-related diterpenoids. Nat. Prod. Rep. 27, 1521-1530.
85. Poeckel, D., Greiner, C., Verhoff, M., Rau, O., Tausch, L., Hoernig, C., Steinhilber, D., Schubert-Zsilavecz, M., Werz, O., 2008. Carnosic acid and carnosol potently inhibit human 5-lipoxygenase and suppress pro-inflammatory responses of stimulated human polymorphonuclear leukocytes. Biochem. Pharmacol. 76, 91-97.
86. Posadas, S.J., Caz, V., Largo, C., De la Gándara, B., Matallanas, B., Reglero, G., De Miguel, E., 2009. Protective effect of supercritical fluid rosemary extract Rosmarinus officinalis, on antioxidants of major organs of aged rats. Exp. Gerontol. 44, 383-389.
87. Rajasekaran, D., Manoharan, S., Silvan, S., Vasudevan, K., Baskaran, N., Palanimuthu, D., 2013. Proapoptotic, anti-cell proliferative, anti-inflammatory and antiangiogenic potential of carnosic acid during 7,12 dimethylbenz[a]anthraceneinduced hamster buccal pouch carcinogenesis. Afr. J. Tradit. Complement. Altern. Med. 10, 102-112.
88. Rasoolijazi, H., Azad, N., Joghataie, M.T., Kerdari, M., Nikbakht, F., Soleimani, M., 2013. The protective role of carnosic acid against beta-amyloid toxicity in rats. Sci. World J. 2013, 1-5.
89. Rau, O., Wurglics, M., Dingermann, T., Abdel-Tawab, M., Schubert-Zsilavecz, M., 2006a. Screening of herbal extracts for activation of the human peroxisome proliferator-activated receptor. Pharmazie 61, 952-956.
90. Rau, O., Wurglics, M., Paulke, A., Zitzkowski, J., Meindl, N., Bock, A., Dingermann, T., Abdel-Tawab, M., Schubert-Zsilavecz, M., 2006b. Carnosic acid and carnosol, phenolic diterpene compounds of the labiate herbs rosemary and sage, are activators of the human peroxisome proliferator-activated receptor gamma. Planta Med. 72, 881-887.
91. Reuter, J., Jocher, A., Hornstein, S., Mönting, J.S., Schempp, C.M., 2007. Sage extract rich in phenolic diterpenes inhibits ultraviolet-induced erythema in vivo. Planta Med. 73, 1190-1191.
92. Richheimer, S.L., Bernart, M.W., King, G.A., Kent, M.C., Beiley, D.T., 1996. Antioxidant activity of lipid-soluble phenolic diterpenes from rosemary. J. Am. Oil Chem. Soc. 73, 507-514.
93. Richhelmer, S.L., Bailey, D.T., Bernart, M.W., Kent, M., Vininski, J.V., Anderson, L.D., 1999. Antioxidant activity and oxidative degradation of phenolic compounds isolated from rosemary. In: Pandalai, S.G. (Ed.), Recent Research Developments in Oil Chemistry, vol. 3. Transworld Research Network, Trivandrum, pp. 45-58.
94. Romano, C.S., Abadi, K., Repetto, V., Vojnov, A.A., Moreno, S., 2009. Synergistic antioxidant and antibacterial activity of rosemary plus butylated derivatives. Food Chem. 115, 456-461.
95. Romo Vaquero, M., García Villalba, R., Larrosa, M., Yázez-Gascón, M.J., Fromentin, E., Flanagan, J., Roller, M., Tomas-Barberan, F.A., Espin, J.C., García-Conesa, M.T., 2013. Bioavailability of the major bioactive diterpenoids in a rosemary extract: metabolic profile in the intestine, liver, plasma, and brain of Zucker rats. Mol. Nutr. Food Res. 57, 1834-1846.
96. Romo-Vaquero, M., Selma, M.V., Larrosa, M., Obiol, M., García-Villalba, R., González-Barrio, R., García-Conesa, M.T., 2014. A rosemary extract rich in carnosic acid selectively modulates caecum microbiota and inhibits β-glucosidase activity, altering fiber and short chain fatty acids fecal excretion in lean and obese female rats. PLoS ONE 9, 1-12.
97. Rozman, T., Jersek, B., 2009. Antimicrobial activity of rosemary extracts (Rosmarinus officinalis L.) against different species of Listeria. Acta Agric. Slov. 93, 51-58.
98. Ruzicka, L., 1953. The isoprene rule and the biogenesis of terpenic compounds. Experientia 9, 357-367.
99. Schwarz, K., Ternes, W., 1992. Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis. I. Determination of phenolic diterpenes with antioxidative activity amongst tocochromanols using HPLC. Eur. Food Res. Tech. Z. Lebensm. Unters. Forsch. 195, 95-98.
100. Schwarz, K., Ternes, W., Schmauderer, E., 1992. Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis. III. Stability of phenolic diterpenes of rosemary extracts under thermal stress as required for technological processes. Z. Lebensm. Unters. Forsch. 195, 104-107.
101. Schwarz, K., Huang, S.W., German, J.B., Tiersch, B., Hartmann, J., Frankel, E.N., 2000. Activities of antioxidants are affected by colloidal properties of oil-in-water and water-in-oil emulsions and bulk oils. J. Agric. Food Chem. 48, 4874-4882.
102. Sharabani, H., Izumchenko, E., Wang, Q., Kreinin, R., Steiner, M., Barvish, Z., Kafka, M., Sharoni, Y., Levy, J., Uskokovic, M., Studzinski, G.P., Danilenko, M., 2006. Cooperative antitumor effects of vitamin D3 derivatives and rosemary preparations in a mouse model of myeloid leukemia. Int. J. Cancer 118, 3012-3021.
103. Shayma'a, J.A., Khaleel, I.R., Ranin, K.A.-A., Marwa, M.A.-K., 2011. Study of the antimicrobial activity of rosemary (Rosmarinus officinalis L.) callus extract and selected types of antibiotics against some bacterial species. Al-TAaqani 24, 128-138.
104. Souza, A.B., de Souza, M.G.M., Moreira, M.A., Furtado, N.A.J.C., Martins, C.H.G., Bastos, J.K., dos Santos, R.A., Heleno, V.C.G., Ambrosio, S.R., Veneziani, R.C.S., 2011. Antimicrobial evaluation of diterpenes from Copaifera langsdorffii oleoresin against periodontal anaerobic bacteria. Molecules 16, 9611-9619.
105. Steiner, M., Priel, I., Giat, J., Levy, J., Sharoni, Y., Danilenko, M., 2001. Carnosic acid inhibits proliferation and augments differentiation of human leukemic cells induced by 1,25-dihydroxyvitamin D3 and retinoic acid. Nutr. Cancer 41, 135-144.
106. Tashmukhamedova, M.A., Khushbaktova, Z.A., Syrov, V.N., 1988. Hypoglycemic activity of salvin and salvicin. Dokl. Akad. Nauk UzSSR, 43-45.
107. Ternes, W., Schwarz, K., 1995. Antioxidative constituents of Rosmarinus officinalis and Salvia officinalis. Z. Lebensm. Unters. Forsch. 201, 548-550.
108. Tounekti, T., Munné-Bosch, S., 2012. Enhanced phenolic diterpenes antioxidant levels through non-transgenic approaches. Crit. Rev. Plant Sci. 31, 505-519.
109. Tounekti, T., Munné-Bosch, S., Vadel, A.M., Chtara, C., Khemira, H., 2010. Influence of ionic interactions on essential oil and phenolic diterpene composition of Dalmatian sage Salvia officinalis L.). Plant Physiol. Biochem. 48, 813-821.
110. Tounekti, T., Hernández, I., Müller, M., Khemira, H., Munné-Bosch, S., 2011. Kinetin applications alleviate salt stress and improve the antioxidant composition of leaf extracts in Salvia officinalis. Plant Physiol. Biochem. 49, 1165-1176.
111. Triantaphylides, C., Krischke, M., Hoeberichts, F.A., Ksas, B., Gresser, G., Havaux, M., Van Breusegem, F., Mueller, M.J., 2008. Singlet oxygen is the major reactive oxygen species involved in photooxidative damage to plants. Plant Physiol. 148, 960-968.
112. Tsai, C.W., Lin, C.Y., Wang, Y.J., 2011. Carnosic acid induces the NAD(P)H: quinone oxidoreductase 1 expression in rat clone 9 cells through the p38/nuclear factor erythroid-2 related factor 2 pathway. J. Nutr. 141, 2119-2125.
113. Wada, M., Kido, H., Ohyama, K., Kishikawa, N., Ohba, Y., Kuroda, N., Nakashima, K., 2004. Evaluation of quenching effects of non-water-soluble and water-soluble rosemary extracts against active oxygen species by chemiluminescent assay. Food Chem. 87, 261-267.
114. Wang, T., Takikawa, Y., Tabuchi, T., Satoh, T., Kosaka, K., Suzuki, K., 2012. Carnosic acid (CA) prevents lipid accumulation in hepatocytes through the EGFR/MAPK pathway. J. Gastroenterol. 47, 805-813.
115. Wellwood, C.R., Cole, R.A., 2004. Relevance of carnosic acid concentrations to the selection of rosemary, Rosmarinus officinalis (L.), accessions for optimization of antioxidant yield. J. Agric. Food Chem. 52, 6101-6107.
116. Wenkert, E., Fuchs, A., McChesney, J.D., 1965. Chemical artifacts from the family Labiatae. J. Org. Chem. 30, 2931-2934.
117. White, A.I., Jenkins, G.L., 1942. Salvia carnosa (Dougl.).-phytochemical study. J. Am. Pharm. Assoc. 31, 33-37.
118. Yanagitai, M., Itoh, S., Kitagawa, T., Takenouchi, T., Kitani, H., Satoh, T., 2012. Carnosic acid, a pro-electrophilic compound, inhibits LPS-induced activation of microglia. Biochem. Biophys. Res. Commun. 418, 22-26.
119. Yang, M.H., Blunden, G., XU, Y.X., Nagy, G., Mathe, I., 1996. Diterpenoids from Salvia species. Pharm. Pharmacol. Commun. 2, 69-71.
120. Yang, J., Zhao, G., Sun, Y., Zheng, Y., Jiang, X., Liu, W., Xian, M., 2012. Bio-isoprene production using exogenous MVA pathway and isoprene synthase in Escherichia coli. Bioresour. Technol. 104, 642-647.
121. Yesil-Celiktas, O., Sevimli, C., Bedir, E., Vardar-Sukan, F., 2010. Inhibitory effects of rosemary extracts, carnosic acid and rosmarinic acid on the growth of various human cancer cell lines. Plant Foods Hum. Nutr. 65, 158-163.
122. Yu, Y.M., Lin, C.H., Chan, H.C., Tsai, H.D., 2009. Carnosic acid reduces cytokineinduced adhesion molecules expression and monocyte adhesion to endothelial cells. Eur. J. Nutr. 48, 101-106.
123. Zi, J., Peters, R.J., 2013. Characterization of CYP76AH4 clarifies phenolic diterpenoid biosynthesis in the Lamiaceae. Org. Biomol. Chem. 11, 7650-7652.