Plant Profiler

Sweet basil (Ocimum basilicum)


Synonyms / Common Names / Related Terms
Apigenin, basil, citral, common basil, estragole, eugenol, geraniol, Lamiaceae (family), linalol, linolen, methylchavikol, methylcinnamat, Ocimum, Ocimum basilicum, Ocimum basilicum var. citratum, rosmarinic acid, Thai basil, ursolic acid.






Mechanism of Action

Pharmacology:

  • Constituents: Based on one laboratory study, Ocimum basilicum L. contains linalol (54.95%), methylchavikol (11.98%), methylcinnamat (7.24%), and linolen (0.14%).15 Essential oil is also found in sweet basil16, along with rosmarinic acid17,4, citral, eugenol, and geraniol1.
  • Antibacterial activity: In a laboratory study, Ocimum basilicum var. citratum showed promising antibacterial activity against Salmonella spp., Escherichai coli O157, Campylobacter jejunii, and Clostridium perferingens.3 The essential oil of basil, obtained from the aerial parts of Ocimum basilicum L., also showed activity against multidrug resistant clinical isolates from the genera Staphylococcus, Enterococcus, and Pseudomonas.15 The minimum inhibitory concentrations (MICs) were reported between 0.0030% and 0.0007% (v/v).
  • Antimicrobial activity: Sweet basil has been studied for its antimicrobial effects in laboratory studies with good results.18,5 In India, sweet basil is used for dental ailments due to its proposed antimicrobial effects; the mechanism of action is unclear.11
  • Antioxidant activity: In a study of patients with chronic bronchitis, exposure to essential oils of basil caused lowering of plasma levels of dienic conjugates and ketons and activation of catalase in red cells characteristic of antioxidant effects.10 Niture et al. report that the extracts from sweet basil were able to raise O6-methylguanine-DNA- methyltransferase (MGMT) levels.9 Increased levels of MGMT mRNA accounted at least, in part, for the increased activity of the DNA repair protein. Sweet basil also increased glutathione S-transferase-pi (GSTP1) expression, albeit to a lesser extent than MGMT. The authors concluded that plant constituents upregulate human MGMT and raise the possibility of rational dietary approaches for attenuating alkylation-induced carcinogenesis. Further, they reveal the putative antioxidant responsiveness of the MGMT gene in human cells.
  • Antiproliferative activity: Sweet basil (Ocimum basilicum L.) oil had an IC50 value of 0.0362mg/mL (12.7 times less potent than 5-FU) in P388 cell lines.7
  • Antiviral activity: Several laboratory studies have been conducted investigating sweet basil's antiviral activity; however, each study posits different compounds responsible for its antiviral effects. Based on in vitro study, Ocimum basilicum cv "cinnamon" showed significant inhibitory effects against HIV-1 induced cytopathogenicity in MT-4 cells.12 The active components in the extract samples were found to be water-soluble polar substances, not nonpolar compounds such as essential oils. In addition, these aqueous extracts inhibited giant cell formation in co-culture of Molt-4 cells with and without HIV-1 infection and showed inhibitory activity against HIV-1 reverse transcriptase. In a second laboratory study, Chiang et al. found that crude aqueous and ethanolic extracts of Ocimum basilicum and components such as apigenin, linalool, and ursolic acid exhibit a broad spectrum of antiviral activity.6 Of these compounds, ursolic acid showed the strongest activity against herpes viruses (EC50=6.6mg/L; selectivity index (SI)=15.2), adenoviruses (EC50=4.2mg/L; SI=23.8), coxsackievirus B1 (EC50=0.4mg/L; SI=251.3), and enterovirus 71 (EC50=0.5mg/L; SI=201), whereas apigenin showed the highest activity against herpes viruses (EC50=9.7mg/L; SI=6.2), adenoviruses (EC50=11.1mg/L; SI=5.4), hepatitis B surface antigen (EC50=7.1mg/L; SI=2.3), and hepatitis B e antigen (EC50=12.8mg/L; SI=1.3), and linalool showed the strongest activity against AVD-II (EC50=16.9mg/L; SI=10.5). No activity was noted for carvone, cineole, beta-caryophyllene, farnesol, fenchone, geraniol, beta-myrcene, or alpha-thujone. The action of ursolic acid against CVB1 and EV71 was found to occur during the infection process and the replication phase. The authors concluded that with SI values greater than 200, the potential use of ursolic acid for treating infection with CVB1 and EV71 merits further investigation.
  • Cytoprotective effects: Rosmarinic acid is a natural phenolic compound contained in many Lamiaceae herbs, such as basil, that inhibits complement-dependent inflammatory processes.4 Based on in vitro study, rosmarinic acid was able to reduce radical oxygen species production, protein and DNA synthesis inhibition, and apoptosis caused by the two mycotoxins. Rosmarinic acid dose dependently attenuated radical oxygen species production and DNA and protein synthesis inhibition induced by both of the toxins. Similarly, apoptosis cell death was prevented, as demonstrated by reduction of DNA fragmentation and inhibition of caspase-3 activation (p<0.001).
  • Dermatologic effects: Sweet basil (Ocimum basilicum) has been studied in humans for acne vulgaris, although a mechanism of action is unclear.2
  • Endothelial membrane fluidity effects: Omegacoeur® (omega3, omega6, omega9 fatty acids, garlic, and basil) (0.1mM) increased Na,K-ATPase activity by 40% without changes in 5'-nucleotidase activity in laboratory study.8 Cells incubated with Omegacoeur® preferentially incorporated linoleic acid. The authors suggest that linoleic acid or other constituents of Omegacoeur® could be responsible for the stimulation of the Na,K-ATPase activity that might be related to changes in endothelial membrane fluidity.
  • Insecticidal effects: Culex pipiens is usually the most common pest mosquito in urban and suburban settings. Sweet basil has been studied for its repellent effects on Culex pipiens.19
  • Spermicidal effects: Based on a study of human spermatozoa in vitro, sweet basil has potent spermicidal action.13 In one study, it was found that oil of cinnamon showed the highest activity, followed by eugenol, clove oil, oil of basil, oil of ajowan, oil of peppermint, and dill.

Pharmacodynamics/Kinetics:

  • Metabolism: Iyer et al. reported that estragole (4-allyl-1-methoxybenzene), a natural constituent of sweet basil, and its metabolite, 1'-hydroxyestragole (1'-HE), are hepatocarcinogens in rodent models.14 Laboratory study has shown that glucuronidation of 1'-HE is a major detoxification pathway for estragole and 1'-HE, accounting for as much as 30% of urinary metabolites of estragole in rodents. The formation of the glucuronide of 1'-HE (1'-HEG) followed atypical kinetics and the data best fit to a Hill equation, resulting in apparent kinetic parameters of Km=1.45mM, Vmax=164.5pM/min/mg protein, and N=1.4. There was a significant intersubject variation in 1'-HE glucuronidation in 27 human liver samples, with a CV of 42%. A screen of cDNA expressed UGT isoforms indicated that UGT2B7 (83.94 ± 0.188pM/min/mg), UGT1A9 (51.36 ± 0.72 pM/min/mg), and UGT2B15 (8.18 ± 0.037 pM/min/mg) were responsible for 1'-HEG formation. Glucuronidation of 1'-HE was not detected in cells expressing UGT1A1, UGT1A3, UGT1A4, UGT1A6, UGT1A7, UGT1A8, and UGT1A10. 1'-HE glucuronidation in 27 individual human liver samples significantly (p<0.05) correlated with the glucuronidation of other UGT2B7 substrates (morphine and ibuprofen). The authors conclude that these results imply that concomitant chronic intake of therapeutic drugs and dietary components that are UGT2B7 and/or UGT1A9 substrates may interfere with estragole metabolism.

References
  1. Lalko, J. and Api, A. M. Investigation of the dermal sensitization potential of various essential oils in the local lymph node assay. Food Chem Toxicol 2006;44(5):739-746. 16324777
  2. Balambal, R., Thiruvengadam, K. V., Kameswarant, L., Janaki, V. R., and Thambiah, A. S. Ocimum basilicum in acne vulgaris--a controlled comparison with a standard regime. J Assoc Physicians India 1985;33(8):507-508. 2932427
  3. Wannissorn, B., Jarikasem, S., Siriwangchai, T., and Thubthimthed, S. Antibacterial properties of essential oils from Thai medicinal plants. Fitoterapia 2005;76(2):233-236. 15752638
  4. Renzulli, C., Galvano, F., Pierdomenico, L., Speroni, E., and Guerra, M. C. Effects of rosmarinic acid against aflatoxin B1 and ochratoxin-A-induced cell damage in a human hepatoma cell line (Hep G2). J Appl Toxicol 2004;24(4):289-296. 15300717
  5. Yano, Y., Satomi, M., and Oikawa, H. Antimicrobial effect of spices and herbs on Vibrio parahaemolyticus. Int J Food Microbiol 8-15-2006;111(1):6-11. 16797760
  6. Chiang, L. C., Ng, L. T., Cheng, P. W., Chiang, W., and Lin, C. C. Antiviral activities of extracts and selected pure constituents of Ocimum basilicum. Clin Exp Pharmacol Physiol 2005;32(10):811-816. 16173941
  7. Manosroi, J., Dhumtanom, P., and Manosroi, A. Anti-proliferative activity of essential oil extracted from Thai medicinal plants on KB and P388 cell lines. Cancer Lett 4-8-2006;235(1):114-120. 15979235
  8. Duran, M. J., Sabatier, F., Pieroni, G., Gerber, G., Sampol, J., and Maixent, J. M. Omegacoeur, a Mediterranean nutritional complement, stimulates Na,K-ATPase activity in human endothelial cells. Cell Mol Biol (Noisy.-le-grand) 2001;47(2):313-318. 11355006
  9. Niture, S. K., Rao, U. S., and Srivenugopal, K. S. Chemopreventative strategies targeting the MGMT repair protein: augmented expression in human lymphocytes and tumor cells by ethanolic and aqueous extracts of several Indian medicinal plants. Int J Oncol 2006;29(5):1269-1278. 17016661
  10. Siurin, S. A. [Effects of essential oil on lipid peroxidation and lipid metabolism in patients with chronic bronchitis]. Klin Med (Mosk) 1997;75(10):43-45. 9490339
  11. Patel, V. K. and Venkatakrishna-Bhatt, H. Folklore therapeutic indigenous plants in periodontal disorders in India (review, experimental and clinical approach). Int J Clin Pharmacol Ther Toxicol 1988;26(4):176-184. 3042642
  12. Yamasaki, K., Nakano, M., Kawahata, T., Mori, H., Otake, T., Ueba, N., Oishi, I., Inami, R., Yamane, M., Nakamura, M., Murata, H., and Nakanishi, T. Anti-HIV-1 activity of herbs in Labiatae. Biol Pharm Bull 1998;21(8):829-833. 9743251
  13. Buch, J. G., Dikshit, R. K., and Mansuri, S. M. Effect of certain volatile oils on ejaculated human spermatozoa. Indian J Med Res 1988;87:361-363. 3169889
  14. Iyer, L. V., Ho, M. N., Shinn, W. M., Bradford, W. W., Tanga, M. J., Nath, S. S., and Green, C. E. Glucuronidation of 1'-hydroxyestragole (1'-HE) by human UDP-glucuronosyltransferases UGT2B7 and UGT1A9. Toxicol Sci 2003;73(1):36-43. 12657745
  15. Opalchenova, G. and Obreshkova, D. Comparative studies on the activity of basil--an essential oil from Ocimum basilicum L.--against multidrug resistant clinical isolates of the genera Staphylococcus, Enterococcus and Pseudomonas by using different test methods. J Microbiol. Methods 2003;54(1):105-110. 12732427
  16. Satoh, T. and Sugawara, Y. Effects on humans elicited by inhaling the fragrance of essential oils: sensory test, multi-channel thermometric study and forehead surface potential wave measurement on basil and peppermint. Anal Sci 2003;19(1):139-146. 12558038
  17. Rady, M. R. and Nazif, N. M. Rosmarinic acid content and RAPD analysis of in vitro regenerated basil (Ocimum americanum) plants. Fitoterapia 2005;76(6):525-533. 16112496
  18. Suciu, G., Hodisan, V., Ban, I., Chiorean, V., and Pop, D. [Pharmaceutical preparations from plant products employed in stomatologic diseases]. Rev Chir Oncol Radiol O.R.L. Oftalmol Stomatol Ser Stomatol 1988;35(3):191-194. 2978706
  19. Erler, F., Ulug, I., and Yalcinkaya, B. Repellent activity of five essential oils against Culex pipiens. Fitoterapia 2006;77(7-8):491-494. 16890387




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