Evaluation of the health beneficial properties of the aromatic ether Myristicin, a volatile oil derived from various pla

1. Presented by: Annie Mancha & Jerry Fuentes The University of Texas-Pan American 1201 W. University Drive Edinburg, Texas 78539 Evaluation of the health beneficial properties of the aromatic ether Myristicin, a volatile oil derived from various plants sources

2. Outline • Background Information • Where is myristicin found? • What are the historical uses of myristicin? • In what capacity is myristicin currently used? • Are there drawbacks to myristicin? • What are the future uses of myristicin?

3. Background Information: Myristicin • An aromatic ether extracted from nutmeg, parsley, and carrots • Molecular formula: C11H12O3 • IUPAC: 4-Methoxy-6-prop-2-enyl-benzo[1,3]dioxole • Other: 5-Allyl-1-methoxy-2,3-(methylenedioxy)benzene • Many historical uses such as a diuretic • Chemopreventative, hepatoprotective, can be psychotropic, can be toxic

4. Where can you find Myristicin? • Parsley • Nutmeg • Dill • Carrots • Broccoli • Coffee

5. Background Information: Parsley • Botanical Name: Carum petroselinum • Parts used: leaves, roots, and sometimes fruit • Habitat: Linnaeus stated its wild habitat to be Sardinia ; eastern mediterranean regions • Aromatic oils of parsley make it an ideal breath freshener • High in vitamins A and C; Contains iron, iodine, and copper • Two different varieties today: root parsley & leaf parsley • Many varieties such as plain-leaved, curled-leaved, Hamburg • Curled-leaf parsley (Petroselinum crispum) is used extensively for garnishing and seasoning foods

6. Constituents of Parsley • Many constituents; main is essential oil • Contains the volatile oils myristicin, apiole, beta-bisabolene, flavanoids such as apiin, apigenin, and luteolin, and furanocuoumarins such as psoralen • 10-30% (in leaves and roots) are myristicin, limonene, and menthatriene • Minor components are mono- and sesquiterpenes • Essential oil from fruits is dominated by myristicin (60-80%) • Curly varieties are higher in myristicin

7. Historical Uses of Parsley • Romans were first to use parsley as food and also as a garland • Greeks used parsley medicinally but did not eat it • Greek medicinal use of parsley spread to India where it was used in Ayurvedic medicine • Carminative • Diuretic • Emmenagogue • expectorant • Spread to the Americas in the 17th century

8. Background Information: Nutmeg • Botanical name: Myristica fragrans • Parts used: dried kernel of the seeds • Origin: Banda Islands, Malayan Archipelago, Molucca Islands, and cultivated in Sumatra, French Guiana • Nutmegs have a strong, peculiar and delightful fragrance and a very strong bitter warm aromatic taste • oil of nutmeg, often termed 'oil of mace' or 'nutmeg butter,' is made by bruising the nuts and treating them with steam • The seed or nutmeg is firm, fleshy, whitish, covered by red-brown veins and is abounding in oil

9. Constituents of Nutmeg Many constituents: • lignin, stearin, volatile oil (myristicin), starch, and gum • By submitting nutmegs and water to distillation, a volatile oil is obtained. • The powder of nutmegs, beaten to a pulp with water, then pressed between heated plates, gives from 10 to 30 per cent of orange colored scented concrete oil erroneously called “oil of mace”

10. Historical Uses of Nutmeg • Oil of Nutmeg is used to conceal the taste of various drugs • Oil was also used as local stimulant to the gastro-intestinal tract • Used for flatulence • Used to stop nausea and vomiting

11. Current Uses of Myristicin Non-Medicinal • Most commonly used culinary herb in the United States • Insecticidal agent • Used to flavor cigarettes Medicinal • Still used as a botanical remedy • Chemopreventative • hepatoprotective

12. Myristicin and Cancer • Parsley leaf oil exhibited high biological activity that warrants further study • Myristicin from Parsley leaf oil induces phase II enzymes allowing for detoxification of carcinogens • Glutathione S-transferase: A phase II enzyme that detoxifies xenobiotics and catalyzes the reaction of glutathione with electrophiles including activated carcinogens to form less toxic conjugates that are readily excreted. • NAD(P)H:Quinone oxidoreductase: Catalyzes the obligatory two electron reduction of quinones and thus shields the cells against the electrophilicity of quinones and oxidative stress.

13. Myristicin and the Liver • Limited information is available to systematically examine the effects of spices on liver injury • Screening of various compounds found potent activity of nutmeg • A single oral administration of myristicin at a dose of 50, 100, or 200 mg/kg dose prohibited elevations of serum ALT and AST activities in mice with liver injuryinduced in the lab • This study shows that nutmeg, particularly myristicin isolated from nutmeg, has a potent hepatoprotective activity

14. Myristicin in Cigarettes • Bidi cigarettes: small hand-rolled cigarettes produced primarily in India • Originated in India around 1905 as small unflavored cigarettes • Made popular in America because of flavors • Clove cigarettes: “kreteks” another highly flavored tobacco product that is popular in America • Flavor-related compounds were found in various brands at very high levels • Myristicin and elemicin showed consistent levels in many of the tobacco-containing bidis tested • Myristicin was also consistently present in mainstream smoke from bidis

15. Drawbacks of Myristicin • Nutmeg seeds have been used as hallucinogenic narcotic, and many reports have been issued on nutmeg poisoning. • Acute or chronic nutmeg or myristicin abuse has adverse effects on neuronal cells. • The accumulation of myristicin from decreased oxidation may cause psychopharmacological effects such as hallucination. • Myristicin has been shown to have anti-cholinergic and psychotropic effects. • 3-methoxy-4,5-methylenedioxyamphetamine (MMDA), one of the metabolites of myristicin, has a pronounced hallucinogenic effect resembling the inebriation induced by mescaline.

16. Future Studies • Myristicin against benzo[a]pyrene-induced cancer • Determine the hepatoprotective properties of myristicin • Determine whether myristicin induces phase II enzymes in a substrate-specific manner • Investigate which phase II enzymes myristicin can induce • Harfmul effects of inhalation of myristicin from cigarettes

17. Conclusion & Questions