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Plant Profiler

Anise (Pimpinella anisum)


Pimpinella anisum
Synonyms / Common Names / Related Terms
Anace, anason, aneys, anice, anis, anís, aniseed, anise seed, anisi, anisi fructus, anisi vulgaris, anison (Greek), anissame, anisu, anisum (Latin), anisun, anisur, anis vert (French), anny, annyle, anysum (Arabic), Apiaceae (family), fruto de anis (Spanish), fructus anisi, graines d'anis (French), p-anisaldehyde, Pimpinella anisetum, Pimpinella anisum, saunf, sconio, semi d'Aniso (Italian), simiente de anis (Spanish), sompf, souf, sweet Alice, sweet cumin, Tut-te See-Hau.




Mechanism of Action

Pharmacology:

  • Constituents: The major constituent of anise is anethole.7,2,8 Other constituents include gamma-himachalene (2-4%), p-anisaldehyde (<1%), methylchavicol (0.9-1.5%), cis-pseudoisoeugenyl 2-methylbutyrate (approximately 3%), and trans-pseudoisoeugenyl 2-methylbutyrate (approximately 1.3%).8 Pimpinella essential oils also contain mono-, sesqui- and trinorsesquiterpenoids, propenylphenols, and pseudoisoeugenols.9
  • Flavonoids isolated from anise include quercetin 3-glucuronide, rutin, luteolin 7-glucoside, isoorientin, isovitexin, apigenin 7-glucoside and a luteolin glycoside10,11
  • From the fruit of anise, eight glycosides of 2-C-methyl-D-erythritol were found.12
  • Sesquiterpenes isolated from the essential oil of anise (fruits and shoots) include gamma-himachalene and the diterpene neophytadiene.13
  • Studies indicate that anethole is not produced in the root of the plant; however the predominant phenolic precursor to anethole epoxypseudoisoeugenol-2-methylbutyrate (EPB) and phenolics were highest in root cultures.7
  • Anise has also been shown to contain aflatoxin, a mycotoxin.14
  • Anise also contains acetaldehyde, alpha-pinene, alpha-terpineol, alpha-zingiberene, anisaldehyde, anisic-acid, anisyl-alcohol, ar-curcumene, ascorbic-acid, bergapten, beta-bisabolene, beta-pinene, boron, caffeic-acid, calcium, camphene, chlorogenic-acid, choline, copper, d-carvone, dianethole , estragole, eugenol, fiber, furfural, hydroquinone, imperatorin, iron, isoorientin, isovitexin, limonene, linalool, magnesium, manganese, mannitol, methyl-chavicol, myristicin, p-cresol, phellandrene, phosphorus, potassium, rutin, scoparone, scopoletin, seselin, squalene, stigmasterol, trans-anethole, umbelliferone, zinc.
  • Anticoagulant effects: Coumarin derivatives and sterols have been reported in the tissue cultures of anise roots.6
  • Anti-diuretic effects: Aniseed, when added to the drinking water of rats, reduced the volume of urine produced and increased the activity of the renal Na+-K+ ATPase, even at low concentrations.5 It is proposed that the anti-diuretic effects are caused by a stimulation of the Na+-K+ pump in the kidney, which increases tubular sodium reabsorption and osmotic water movement. However, it was found that aniseed oil had no effect on water absorption from the colon and did not affect the activity of colonic Na+-K+ ATPase.
  • Antifungal effects: The essential oil of anise completely inhibited Aspergillus flavus, A. parasiticus, A. ochraceus and Fusarium moniliforme at concentrations <500ppm.15
  • Bronchodilatory effects: In an in vitro study using guinea pig bronchial cells, Boskabady et al. determined that the relaxant effect of aqueous and ethanol extracts of anise essential oil were due to inhibitory effects on muscarinic receptors.16
  • Estrogenic effects: Anise essential oil contains anethole, a phytoestrogen with estrogenic effects.2 Preliminary research has shown that anethole may not be the only constituent of anise with estrogenic effects; however more research in this area is needed before any conclusions can be made. An aqueous extract of anise has shown antiestrogenic effects on breast cancer cells without any proliferative effects on cervical adenocarcinoma cells in vitro.4 The presence of estradiol reduced the antiestrogenic effect which implies an estrogen receptor-related mechanism.
  • Glucose absorption effects: Aniseed oil has been shown to enhance glucose absorption in the jejunum of rats.5 It also has increased the Na+-K+ ATPase activity in a jejunal homogenate in a dose dependent manner. Aniseed oil is thought to increase glucose absorption by increasing the activity of the Na+-K+ ATPase thereby increasing the sodium gradient needed for the glucose transport.
  • Insecticide effects: Anise contains many phenylpropanoids which have shown insecticidal and acaricidal activities.17,3,1
  • Metabolic pathway: The genus Pimpinella contains pseudoisoeugenold, which are phenylpropanoids with a 2,5-dioxy substitution on the phenyl ring. The metabolic pathway of these pseudoisoeugeonld was determined by Reichling et al. as follows: L-phenylalanine is converted to (E)-cinnamic acid by phenylalanine ammonia lyase and that (E)-cinnamic acid is converted to p-coumaric acid by cinnamic acid 4-hydroxylase. L-2-aminooxy-3-phenylpropionic acid, an analogue of L-phenylalanine, inhibited the incorporation of L-[3'-13C] phenylalanine into epoxy- pseudoisoeugenol-(2-methylbutyrate).18 Up to 2% of the precursor DL-[3'-13C] phenyl lactate was incorporated into epoxy-pseudoisoeugenol-(2-methylbutyrate).
  • Muscle relaxant effects: Anise oil has demonstrated an increase in resting force of guinea pig tracheal smooth muscle. Anethole may be responsible for the positive inotropic effect.19
  • Neurological effects: In a study done in mice, it appeared that the essential oil of anise may reduce the morphine preference via a GABAergic mechanism.20 Some spices traditionally used in winter cooking, including anise, nutmeg, cinnamon and clove, contain two groups of chemicals, the allybenzenes and their isomers, propenylbenzenes, which are thought to acts as metabolic precursors of amphetamines.21

Pharmacodynamics/Kinetics:

  • The major routes of elimination of anise are via urination and exhalation.22

References
  1. Lee, H. S. p-Anisaldehyde: acaricidal component of Pimpinella anisum seed oil against the house dust mites Dermatophagoides farinae and Dermatophagoides pteronyssinus. Planta Med 2004;70(3):279-281. 15114512
  2. Tabanca, N., Khan, S. I., Bedir, E., Annavarapu, S., Willett, K., Khan, I. A., Kirimer, N., and Baser, K. H. Estrogenic activity of isolated compounds and essential oils of Pimpinella species from Turkey, evaluated using a recombinant yeast screen. Planta Med 2004;70(8):728-735. 15368661
  3. Prajapati, V., Tripathi, A. K., Aggarwal, K. K., and Khanuja, S. P. Insecticidal, repellent and oviposition-deterrent activity of selected essential oils against Anopheles stephensi, Aedes aegypti and Culex quinquefasciatus. Bioresour Technol  2005;96(16):1749-1757. 16051081
  4. Kassi, E., Papoutsi, Z., Fokialakis, N., Messari, I., Mitakou, S., and Moutsatsou, P. Greek plant extracts exhibit selective estrogen receptor modulator (SERM)-like properties. J Agric Food Chem  11-17-2004;52(23):6956-6961. 15537303
  5. Kreydiyyeh, S. I., Usta, J., Knio, K., Markossian, S., and Dagher, S. Aniseed oil increases glucose absorption and reduces urine output in the rat. Life Sci 12-19-2003;74(5):663-673. 14623036
  6. Kartnig, V., Moeckel, H., and Maunz, B. [The occurrence of cumarins and sterols in tissue-cultures of roots of Anethum graveolens and Pimpinella anisum (author's transl)]. Planta Med 1975;27(1):1-13. 1161870
  7. Andarwulan, N. and Shetty, K. Phenolic content in differentiated tissue cultures of untransformed and Agrobacterium-transformed roots of anise (Pimpinella anisum L.). J Agric Food Chem  1999;47(4):1776-1780. 10564054
  8. Rodrigues, V. M., Rosa, P. T., Marques, M. O., Petenate, A. J., and Meireles, M. A. Supercritical extraction of essential oil from aniseed (Pimpinella anisum L) using CO2: solubility, kinetics, and composition data. J Agric Food Chem  3-12-2003;51(6):1518-1523. 12617576
  9. Tabanca, N., Demirci, B., Ozek, T., Kirimer, N., Baser, K. H., Bedir, E., Khan, I. A., and Wedge, D. E. Gas chromatographic-mass spectrometric analysis of essential oils from Pimpinella species gathered from Central and Northern Turkey. J Chromatogr A 6-9-2006;1117(2):194-205. 16616174
  10. Kunzemann, J. and Herrmann, K. [Isolation and identification of flavon(ol)-O-glycosides in caraway (Carum carvi L.), fennel (Foeniculum vulgare Mill.), anise (Pimpinella anisum L.), and coriander (Coriandrum sativum L.), and of flavon-C-glycosides in anise. I. Phenolics of spices (author's transl)]. Z Lebensm Unters Forsch  7-29-1977;164(3):194-200. 910554
  11. Gebhardt, Y., Witte, S., Forkmann, G., Lukacin, R., Matern, U., and Martens, S. Molecular evolution of flavonoid dioxygenases in the family Apiaceae. Phytochemistry 2005;66(11):1273-1284. 15913674
  12. Kitajima, J., Ishikawa, T., Fujimatu, E., Kondho, K., and Takayanagi, T. Glycosides of 2-C-methyl-D-erythritol from the fruits of anise, coriander and cumin. Phytochemistry 2003;62(1):115-120. 12475627
  13. Burkhardt, G., Reichling, J., Martin, R., and Becker, H. Terpene hydrocarbons in Pimpinella anisum L. Pharm Weekbl Sci 6-20-1986;8(3):190-193. 3737372
  14. El Kady, I. A., El Maraghy, S. S., and Eman, Mostafa M. Natural occurrence of mycotoxins in different spices in Egypt. Folia Microbiol (Praha) 1995;40(3):297-300. 8919936
  15. Soliman, K. M. and Badeaa, R. I. Effect of oil extracted from some medicinal plants on different mycotoxigenic fungi. Food Chem Toxicol  2002;40(11):1669-1675. 12176092
  16. Boskabady, M. H. and Ramazani-Assari, M. Relaxant effect of Pimpinella anisum on isolated guinea pig tracheal chains and its possible mechanism(s). J Ethnopharmacol  2001;74(1):83-88. 11137352
  17. Reichling, J., Merkel, B., and Hofmeister, P. Studies on the biological activities of rare phenylpropanoids of the genus Pimpinella. J Nat Prod  1991;54(5):1416-1418. 1800640
  18. Reichling, J., Kemmerer, B., and Sauer-Gurth, H. Biosynthesis of pseudoisoeugenols in tissue cultures of Pimpinella anisum. Phenylalanine ammonia lyase and cinnamic acid 4-hydroxylase activities. Pharm World Sci 7-28-1995;17(4):113-119. 7581216
  19. Reiter, M. and Brandt, W. Relaxant effects on tracheal and ileal smooth muscles of the guinea pig. Arzneimittelforschung  1985;35(1A):408-414. 4039178
  20. Sahraei, H., Ghoshooni, H., Hossein, Salimi S., Mohseni, Astani A., Shafaghi, B., Falahi, M., and Kamalnegad, M. The effects of fruit essential oil of the Pimpinella anisum on acquisition and expression of morphine induced conditioned place preference in mice. J Ethnopharmacol  2002;80(1):43-47. 11891086
  21. Idle, J. R. Christmas gingerbread (Lebkuchen) and Christmas cheer--review of the potential role of mood elevating amphetamine-like compounds formed in vivo and in furno. Prague Med Rep  2005;106(1):27-38. 16007907
  22. Caldwell, J. and Sutton, J. D. Influence of dose size on the disposition of trans-[methoxy-14C]anethole in human volunteers. Food Chem Toxicol  1988;26(2):87-91. 3366415




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