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

Presented by:

Annie Mancha & Jerry FuentesThe University of Texas-Pan American

1201 W. University Drive Edinburg, Texas 78539

OutlineOutline

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?

Background Information: MyristicinBackground 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

Where can you find Myristicin?Where can you find Myristicin?

Parsley Nutmeg Dill Carrots Broccoli Coffee

Background Information: ParsleyBackground 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

Constituents of ParsleyConstituents 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

Historical Uses of ParsleyHistorical 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

Background Information: NutmegBackground 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

Constituents of NutmegConstituents 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”

Historical Uses of NutmegHistorical 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

Current Uses of MyristicinCurrent Uses of Myristicin

Non-Medicinal Most commonly used culinary

herb in the United States Insecticidal agent Used to flavor cigarettesMedicinal Still used as a botanical remedy Chemopreventative hepatoprotective

Myristicin and CancerMyristicin 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.

Myristicin and the LiverMyristicin 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 injury induced in the lab

This study shows that nutmeg, particularly myristicin isolated from nutmeg, has a potent hepatoprotective activity

Myristicin in CigarettesMyristicin 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

Drawbacks of MyristicinDrawbacks 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.

Future Studies 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

Conclusion & QuestionsConclusion & Questions