Calendula (Calendula officinalis)

Pharmacology:

• General: The essential oils of Calendula micrantha were shown in one study to resemble hormones of the Mediterranean fruit fly
  Ceratitis capitata, and the oils suppressed their reproductive potential.¹¹
• Constituents: The principal identified constituents of calendula are triterpenoids and flavonoids.^12,13 At least eight bioactive triterpendiol monoesters have been identified in the extracts of dried calendula flowers: faradiol-3-O-palmitate, faradiol-3-O-myristate, faradiol-3-O-laurate, arnidiol-3-O-palmitate, arnidiol-3-O-myristate, arnidiol-3-O-laurate, calenduladiol-3-O-palmitate, and calenduladiol-3-O-myristate.¹⁴ The flavonoids, particularly patulitrin and patuletin, may be used as dyes.¹⁵ The saponin fractions isolated from Calendula officinalis flower include oleanolic acid (205.53mg/g dry weight) and ursolic acid.¹⁶ Calendasaponins A, B, C, and D, two additional ionone glucosides (officinosides A and B), and two sesquiterpene oligoglycosides (officinosides C and D) have been isolated from the flowers of Egyptian Calendula officinalis.¹⁷ Various pharmacological properties have been attributed in preclinical research to various constituents, including anti-inflammatory, immunostimulating, antibacterial, antiviral, antiprotozoal, and antineoplastic properties. The mechanisms underlying these possible effects are poorly understood. Two homologous cDNAs, CoFad2 and CoFac2, were isolated from a Calendula officinalis developing seed by polymerase chain reaction.¹⁸
• Antibacterial effects: Hydroacetonic extract from fresh plants inhibited the growth of Staphylococcus aureus at a concentration of 1mg/mL in vitro.⁵ Calendula extract was tested on biofilms of infant dentifrices and did not demonstrate antimicrobial effects against A. viscosus, C. albicans, L. casei, S. mitis, S. mutans, S. oralis, S. sanguis, or S. sobrinus.⁶
• Anti-inflammatory effects: The active components of calendula's anti-inflammatory activity are thought to be the triterpenoids, particularly faradiol monoester. Free ester faradiol is the most active and exhibits the same effects as an equimolar dose of indomethacin.^7,19,20 In one study, the aromatic moieties of the triterpenes were chemically modified to increase anti-inflammatory activity in vivo.²¹ Calendula's glycosides have also inhibited lipooxygenase activity in vitro.²²
• Antioxidant effects: Extracts of Calendula officinalis have anti-oxidant activity and demonstrate strong abilities to scavenge reactive oxygen species.²³ Plants of the genus Calendula are natural sources of betacarotene²⁴, which may contribute to potential antioxidant effects. Nineteen carotenoids have been identified in extracts of Calendula officinalis petals, including flavoxanthin and isomers of lycopene, carotene, and rubixanthin²⁵.
• Antiprotozoal effects: Oxygenated terpene alcohols and terpene lactones from calendula have been observed to possess trichomonacidal activity.⁹
• Antiproliferative effects: In a mouse model, dietary lutein derived from calendula extract has been found to suppress mammary tumor growth, increase tumor latency, and enhance lymphocyte proliferation.²⁶ Saponins isolated from calendula express in vitro antimutagenic and tumor cell cytotoxic activity.^27,28 C. officinalis does not exert a direct mitogenic effect on human lymphocytes in vitro and exhibits inhibitory effects on lymphocyte. proliferation²⁹ A preparation of several herbs (Calendula officinalis, echinacea, Scorzonera humilis, and Aconitum moldavicum) has been associated with the "normalization" of pathologic enzyme activity by rat hepatocytes affected by carcinoma.³⁰
• Antispasmodic and spasmogenic effects: Crude extracts of Calendula officinalis flowers have been shown to contain both spasmolytic and spasmogenic constituents in rabbit jejunum.³¹
• Antiviral effects: Anti-HIV activity of calendula has been demonstrated in vitro¹⁰ specifically involving the inhibition of HIV-1 (IIIB) induced cytopathogenicity in CD4+ lymphocytic Molt-4 clone 8 cells. Triterpenoid saponins from Calendula arvensis have inhibited multiplication of vesicular stomatitis virus and rhinovirus in vitro.³² Triterpene and flavonol glycosides isolated from calendula have also demonstrated inhibitory activity against Epstein-Barr virus activation.³³
• Cytotoxic effects: A novel laser-activated calendula extract is reported to activate lymphocytes and cytotoxicity in vitro, and may have important anti-tumor effects in vivo.⁸
• Deodorant effects: The components of marigold and other medicinal plants may act as oral deodorants by inhibiting salivary protein putrification.³⁴
• Hepatic effects: Calendula officinalis extracts have been shown to have both protective and cytotoxic effects in rat hepatocyte cultures.³⁵ Calendula extracts have also been shown to reduce hepatocytolysis and steatosis in CCl₄-intoxicated liver in Wistar rats.³⁶
• Hypoglycemic effects: Hypoglycemic, gastric emptying inhibitory, and gastroprotective properties have been attributed to calendasaponins A, B, C, and D, two additional ionone glucosides (officinosides A and B), and two sesquiterpene oligoglycosides (officinosides C and D).³⁷
• Wound-healing effects: It has been proposed that Calendula officinalis extract may aid in wound healing by promoting epithelial growth and by enhancing immune responses.⁴ Rao et al. observed a reduction of epithelialization time, an increase in wound strength, and improvement of wound contraction in rats with experimental incision wounds that were topically treated with calendula.³⁸ The effects may also be mediated by the stimulation of phagocytosis, by increased granulation³, and via effects on metabolism of glycoproteins, nucleoproteins, and collagen proteins in tissue regeneration¹.
• Other effects: In vitro, calendula exhibited moderate "uterotonic" effects in isolated rabbit and guinea pig uterine tissues.³⁹ In early (1964) animal studies, high doses of calendula preparations were reported to act as sedatives and hypotensive agents².

Pharmacodynamics/Kinetics:

• Bioavailability: To investigate whether digestive processes could affect the antioxidant properties of plant extracts, Gladine et al. examined the bioavailability of polyphenols in ruminants.⁴⁰ Sheep were infused with linseed oil to increase susceptibility to lipid peroxidation and then given a single dose of plant polyphenol extract (rosemary grape, citrus, or marigold) directly into the rumen. Marigold extract, in particular, significantly reduced plasma lipoperoxidation. This study suggested that ruminant digestive processes do not abolish the antioxidant properties of marigold polyphenols.
• Extracts of Calendula officinalis were tested in cell-free systems for inhibitory activity of 5-lipoxygenase (5-LO) and cyclooxygenase-2 (COX-2), key enzymes in inflammatory pathways.⁴¹

1. Klouchek-Popova, E., Popov, A., Pavlova, N., and Krusteva, S. Influence of the physiological regeneration and epithelialization using fractions isolated from Calendula officinalis. Acta Physiol Pharmacol Bulg  1982;8(4):63-67. 7185264
2. Bojadjiev C. On the sedative and hypotensive effect of preparations from the plant Calendula officinalis. Nauch Trud Visshi Med Inst Sof 1964;43:15-20.
3. Dietz V. Calendula preparations to treat cutaneous infections. Alt Med Alert 1998;1(12):140-142.
4. Duran, V., Matic, M., Jovanovc, M., Mimica, N., Gajinov, Z., Poljacki, M., and Boza, P. Results of the clinical examination of an ointment with marigold (Calendula officinalis) extract in the treatment of venous leg ulcers. Int J Tissue React  2005;27(3):101-106. 16372475
5. Dumenil, G., Chemli, R., Balansard, C., Guiraud, H., and Lallemand, M. [Evaluation of antibacterial properties of marigold flowers (Calendula officinalis L.) and other homeopathic tinctures of C. officinalis L. and C. arvensis L. (author's transl)]. Ann Pharm Fr  1980;38(6):493-499. 7283346
6. Modesto, A., Lima, K. C., and de Uzeda, M. Effects of three different infant dentifrices on biofilms and oral microorganisms. J Clin Pediatr Dent 2000;24(3):237-243. 11314149
7. Della Loggia R. and et al. Topical anti-inflammatory activity of Calendula officinalis extracts. Planta Med 1990;56:658.
8. Jimenez-Medina, E., Garcia-Lora, A., Paco, L., Algarra, I., Collado, A., and Garrido, F. A new extract of the plant Calendula officinalis produces a dual in vitro effect: cytotoxic anti-tumor activity and lymphocyte activation. BMC Cancer 2006;6:119. 16677386
9. Gracza L. Oxygen-containing terpene derivatives from Calendula officinalis. Planta Med 1987;53:227.
10. Kalvatchev, Z., Walder, R., and Garzaro, D. Anti-HIV activity of extracts from Calendula officinalis flowers. Biomed Pharmacother  1997;51(4):176-180. 9207986
11. Hussein, K. T. Suppressive effects of Calendula micrantha essential oil and gibberelic acid (PGR) on repro ductive potential of the Mediterranean fruit fly Ceratitis capitata Wied. (Diptera: Tephritidae). J Egypt Soc Parasitol  2005;35(2):365-377. 16083052
12. Yoshikawa, M., Murakami, T., Kishi, A., Kageura, T., and Matsuda, H. Medicinal flowers. III. Marigold. (1): hypoglycemic, gastric emptying inhibitory, and gastroprotective principles and new oleanane-type triterpene oligoglycosides, calendasaponins A, B, C, and D, from Egyptian Calendula officinalis. Chem Pharm Bull (Tokyo) 2001;49(7):863-870. 11456093
13. Vidal-Ollivier E, Elias R, Faure F, and et al. Flavonol glycosides from Calendula officinalis flowers. Planta Med 1989;55:73-74.
14. Neukirch, H., D'Ambrosio, M., Dalla, Via J., and Guerriero, A. Simultaneous quantitative determination of eight triterpenoid monoesters from flowers of 10 varieties of Calendula officinalis L. and characterisation of a new triterpenoid monoester. Phytochem Anal  2004;15(1):30-35. 14979524
15. Guinot, P., Gargadennec, A., Valette, G., Fruchier, A., and Andary, C. Primary flavonoids in marigold dye: extraction, structure and involvement in the dyeing process. Phytochem Anal  2008;19(1):46-51. 17654539
16. Kowalski, R. Studies of selected plant raw materials as alternative sources of triterpenes of oleanolic and ursolic acid types. J Agric Food Chem 2-7-2007;55(3):656-662. 17263457
17. Marukami, T., Kishi, A., and Yoshikawa, M. Medicinal flowers. IV. Marigold. (2): Structures of new ionone and sesquiterpene glycosides from Egyptian Calendula officinalis. Chem Pharm Bull (Tokyo) 2001;49(8):974-978. 11515588
18. Qiu, X., Reed, D. W., Hong, H., MacKenzie, S. L., and Covello, P. S. Identification and Analysis of a Gene from Calendula officinalis Encoding a Fatty Acid Conjugase. Plant Physiol 2001;125(2):847-855. 11161042
19. Della, Loggia R., Tubaro, A., Sosa, S., Becker, H., Saar, S., and Isaac, O. The role of triterpenoids in the topical anti-inflammatory activity of Calendula officinalis flowers. Planta Med 1994;60(6):516-520. 7809203
20. Zitterl-Eglseer, K., Sosa, S., Jurenitsch, J., Schubert-Zsilavecz, M., Della, Loggia R., Tubaro, A., Bertoldi, M., and Franz, C. Anti-oedematous activities of the main triterpendiol esters of marigold (Calendula officinalis L.). J Ethnopharmacol  1997;57(2):139-144. 9254116
21. Neukirch, H., D'Ambrosio, M., Sosa, S., Altinier, G., Della, Loggia R., and Guerriero, A. Improved anti-inflammatory activity of three new terpenoids derived, by systematic chemical modifications, from the abundant triterpenes of the flowery plant Calendula officinalis. Chem Biodivers  2005;2(5):657-671. 17192009
22. Bezakova, L., Masterova, I., Paulikova, I., and Psenak, M. Inhibitory activity of isorhamnetin glycosides from Calendula officinalis L. on the activity of lipoxygenase. Pharmazie 1996;51(2):126-127. 8720810
23. Herold, A., Cremer, L., Calugaru, A., Tamas, V., Ionescu, F., Manea, S., and Szegli, G. Antioxidant properties of some hydroalcoholic plant extracts with antiinflammatory activity. Roum Arch Microbiol Immunol 2003;62(3-4):217-227. 16008145
24. Karadas, F., Grammenidis, E., Surai, P. F., Acamovic, T., and Sparks, N. H. Effects of carotenoids from lucerne, marigold and tomato on egg yolk pigmentation and carotenoid composition. Br Poult Sci 2006;47(5):561-566. 17050099
25. Kishimoto, S., Maoka, T., Sumitomo, K., and Ohmiya, A. Analysis of carotenoid composition in petals of calendula (Calendula officinalis L.). Biosci Biotechnol Biochem 2005;69(11):2122-2128. 16306694
26. Chew, B. P., Wong, M. W., and Wong, T. S. Effects of lutein from marigold extract on immunity and growth of mammary tumors in mice. Anticancer Res 1996;16(6B):3689-3694. 9042242
27. Elias, R., De Meo, M., Vidal-Ollivier, E., Laget, M., Balansard, G., and Dumenil, G. Antimutagenic activity of some saponins isolated from Calendula officinalis L., C. arvensis L. and Hedera helix L. Mutagenesis 1990;5(4):327-331. 2204784
28. Quetin-Leclercq, J., Elias, R., Balansard, G., Bassleer, R., and Angenot, L. Cytotoxic activity of some triterpenoid saponins. Planta Med 1992;58(3):279-281. 1409985
29. Amirghofran, Z., Azadbakht, M., and Karimi, M. H. Evaluation of the immunomodulatory effects of five herbal plants. J Ethnopharmacol  2000;72(1-2):167-172. 10967468
30. Marchenko, M. M., Kopyl'chuk, H. P., and Hrygor'ieva, O. V. [Activity of cytoplasmic proteinases from rat liver in Heren's carcinoma during tumor growth and treatment with medicinal herbs]. Ukr Biokhim Zh 2000;72(3):91-94. 11200483
31. Bashir, S., Janbaz, K. H., Jabeen, Q., and Gilani, A. H. Studies on spasmogenic and spasmolytic activities of Calendula officinalis flowers. Phytother Res 2006;20(10):906-910. 16906636
32. De Tommasi, N., Conti, C., Stein, M. L., and Pizza, C. Structure and in vitro antiviral activity of triterpenoid saponins from Calendula arvensis. Planta Med 1991;57(3):250-253. 1654576
33. Ukiya, M., Akihisa, T., Yasukawa, K., Tokuda, H., Suzuki, T., and Kimura, Y. Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers. J Nat Prod 2006;69(12):1692-1696. 17190444
34. Sterer, N. and Rubinstein, Y. Effect of various natural medicinals on salivary protein putrefaction and malodor production. Quintessence Int 2006;37(8):653-658. 16922026
35. Barajas-Farias, L. M., Perez-Carreon, J. I., Arce-Popoca, E., Fattel-Fazenda, S., Aleman-Lazarini, L., Hernandez-Garcia, S., Salcido-Neyoy, M., Cruz-Jimenez, F. G., Camacho, J., and Villa-Trevino, S. A dual and opposite effect of Calendula officinalis flower extract: chemoprotector and promoter in a rat hepatocarcinogenesis model. Planta Med 2006;72(3):217-221. 16534725
36. Rusu, M. A., Tamas, M., Puica, C., Roman, I., and Sabadas, M. The hepatoprotective action of ten herbal extracts in CCl4 intoxicated liver. Phytother Res 2005;19(9):744-749. 16220565
37. Marukami, T., Kishi, A., and Yoshikawa, M. Medicinal flowers. IV. Marigold. (2): Structures of new ionone and sesquiterpene glycosides from Egyptian Calendula officinalis. Chem Pharm Bull (Tokyo) 2001;49(8):974-978. 11515588
38. Rao, SG, Udupa, AL, Udupa SL, and et al. Calendula and Hypericum: Two homeopathic drugs promoting wound healing in rats. Fitoterapia 1991;62(6):508-510.
39. Shipochliev, T. [Uterotonic action of extracts from a group of medicinal plants]. Vet Med Nauki 1981;18(4):94-98. 7314446
40. Gladine, C., Rock, E., Morand, C., Bauchart, D., and Durand, D. Bioavailability and antioxidant capacity of plant extracts rich in polyphenols, given as a single acute dose, in sheep made highly susceptible to lipoperoxidation. Br J Nutr 2007;98(4):691-701. 17475083
41. Herold, A., Cremer, L., Calugaru, A., Tamas, V., Ionescu, F., Manea, S., and Szegli, G. Hydroalcoholic plant extracts with anti-inflammatory activity. Roum Arch Microbiol Immunol 2003;62(1-2):117-129. 15493372

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