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The flu
Posted on: January 19, 2015

Essential oils and Influenza virus

Briefly… about the virus…
Influenza A is a virus with many subtypes that are identified and categorized by differences in two proteins, hemagglutinin (H) and neuraminidase (N). Differences are due to the rapid mutation of the virus. The scientific community has learned quite a bit about Influenza A virus, but the fact remains that we are unable to know what we don’t know and the virus mutates rapidly, becoming something new and challenging very quickly. Antiviral drugs do not eliminate the virus; they inhibit the replication of the virus. Learning more about the life-cycle of a virus has lead to the development of anti-viral strategies that target the virus at different stages in that cycle.
We should all be using common sense in protecting and taking care of ourselves and our families. I won’t use this as a pulpit for my position on things that are related and responsible in varied degree. This is some information about plant materials that are easily obtained and that you may want to have to arm and educate yourself.

Essential oils and viral replication

All essential oils are anti-microbial to a degree. In this application, microbes refer to fungi, bacteria and viruses. Some are broad spectrum anti-viral. Because we just don’t know HOW they affect a virus in most cases, they very well may affect the Influenza virus as well. There is a tremendous amount of anecdotal, cultural and historical information that tells us certain plants are effective against certain aliments.
Tea Tree –(Melaleuca alternifolia) A study conducted by the European Society of Clinical Microbiology and Infectious Diseases revealed that replication of a strain of influenza was severely inhibited if the Tea Tree eo was introduced within 2 hours of infection. This suggests that Tea Tree eo interferes in an early stage of replication but after viral adsorption. Tea Tree eo is inexpensive and is pretty stable.
Wasabi (Wasabia japonica) Published in the Journal of the Science of Food and Agriculture. Apparently the summer leaves are discarded as inappropriate for making wasabi food preparations and there is development of a use for summer leaves. Anti-influenza virus activity is being investigated. Extracts of leaves harvested in July exhibited a high replication inhibition rate (98% or higher) in both the type A and B strain.

Licorice root (Glycyrrhiza glabra) Specifically glycyrrhizin. An animal trial showed that an injection of glycyrrhizin into the abdominal cavity completely protected a group of mice infected with an otherwise lethal influenza virus. Poor mice… The conclusion is that the glycyrrhizin stimulates the production of gamma-interferon.

St. Johns Wort (Hypericum perforatum) Evidently this has been researched since the 1980’s as an AIDS retro-viral. I did not know that. In the lab it significantly inhibits the replication of several viruses, including HIV, influenza A, cytomegalovirus, Herpes simplex 1 and 2, and Epstein-Barr virus. The challenge is that these results are only possible in the presence of light. The effective compound is either bound to or is a polycyclic anthrone, which have photosynthesizing properties.

Coconut oil – not an essential oil but worth mentioning. About 50% of the fatty acid in Coconut oil is Lauric acid, the most essential fatty acid for the building of an immune system. In the body, it is converted to monolaurin, a powerful monoglyceride that destroys lipid-coated viruses (such as cytomegalovirus, HIV, herpes, and influenza) as well as pathogenic bacteria. I use this on the skin and in the kitchen. The smell and taste of organic raw coconut oil are just fabulous.
Quercetin – also worth of mention. Quercetin is a flavonoid and is available as a supplement and in foods. Animal studies show that exercise stress increases the susceptibility to infection of Influenza A (H1Ni in the study) and that feedings of quercetin offset the increase of susceptibility. Eat your apples and onions!

Oregano oil – (Oreganum vulgare) A study cited in Annals of Clinical Microbiology and Antimicrobials 2009, 8:8 indicate that Oregano eo has inhibitory effects the replication of the Yellow Fever virus. Apparently the presence of O. vulgare essential oil in the culture medium at 11.1 ug/mL produced a 100% reduction of virus yield. (A Ug is a microgram, 1/1000000 of a gram or 1/1000 of a milligram.) Oregano eo seems to be effective because of direct inactivation of the virus rather than being effective only at a stage in the life cycle of the virus.
Mugwort (Artemisia vulgaris) was also tested in the above referenced study and produced similar striking results. Mugwort is very high in ketones and should be only used by the experienced.

Quite a bit of chemistry
Posted on: January 19, 2015

As you begin to use essential oils, reading and learning, you will encounter terms used to discuss their chemistry. Being familiar with these terms and knowing where to look for further definitions will enhance your experience with the essentials oils. Understanding some cursory chemistry will deepen your confidence and enable you to be better informed about the essential oils that you are using and those that you are interested in. An essential oil may contain upwards of 100 different chemical compounds, most of these being very low percentages. The synergy of those compounds makes each essential oil unique. The growing conditions, harvest and distillation can affect this already complex chemical signature. The material presented here is intended as an introduction, a brief view of some common categories and their generalities. It is by no means comprehensive.

There are 2 main types of chemical groups that make up most of the components of essential oils. Terpenes and their homologues and phenylpropane derivitaves, the latter are by products of amino acid metabolism and based on a ring structure, more about these phenylpropane derivitaves at another time.  Gattefosse categorized essential oils according to their functional groups; French aromatherapy is based on these distinctions.

Terpenes-

Isoprene (with 5 carbons) is the basic building block of terpenes. Terpenes are distinguished by the number of isoprene units. Syntheses within the plant cell takes isoprene to monoterpene and so on to larger and more complex molecules that aren’t mentioned here.

Monoterpenes- 10 carbons/2 isoprenes. Very common in essential oils. These oils tend to be clear, mobile and volatile. The names of terpenes end in –ene.

Sesquiterpenes-15 carbons/3 isoprenes. Less common in essential oils. These tend to be viscous, yellow or brown in color, and are usually used as fixatives and base notes. The names of sesquiterpenes also end in –ene.

Diterpenes- 20 carbons/4 isoprenes. These are resins, balsams and vitamin A.

Triterpenes- 30 carbons/6 isoprenes. These are resins, sterols, steroids and hormones.

Hydrocarbons- you may come across this term describing compounds in essential oils. A hydrocarbon contains only carbon and hydrogen, this term would apply to isoprenes, terpenes, monoterpenes etc…

 

Functional groups

Alcohols, esters, aldehydes, phenols, ketones, oxides…Just a little bit about organic chemistry…carbon needs to bond 4 times, this means that there are quite a bit of combinations possible. The carbon to carbon bond is the base of all organic molecules. Hydrogen slips into this equation very nicely. The carbon-carbon and carbon-hydrogen bond are typically very strong and being non-polar, makes hydrocarbons not very willing to react with other molecules, therefore very stable. Plants can add an oxygen to a hydrocarbon and make ‘oxygenated hydrocarbons’, structural elements of a molecule that are not the carbon-carbon or carbon-hydrogen. These oxygenated hydrocarbons are called functional groups. (acids, alcohols, aldehydes, ketones, esters, phenols, ethers, oxides, peroxides, furans and lactones). Because this carbon-oxygen bond is polar and therefore more reactive, chemical reactivity is greatly determined by ‘functional groups’. The smell, taste and effects of essential oils on living organisms is determined by these functional groups. In some essential oils, primarily the needle oils and the oils from citrus rind, hydrocarbons dominate, they are essentially monoterpenes without functional groups. These oils can leave a residue in diffusors that is very difficult to remove, the hydrocarbons can become attached like a plaque to the narrow glass tubing. I have threaded copper wire through this tubing many times to manually remove this.

Monoterpenes and functional groups.

alcohols- names end in –ol. They are generally mild, effective against micro-organisms, general tonics. The monoterpene alcohols are generally tolerated topically very well.

Linalol – Coriander, Rosewood, Petitgrain, Thyme linalool, Neroli, Clary sage, Palmarosa

citronellol- Geranium, rose

geraniol – Palmarosa

a terpinol – Eucalyptus radiata, MQV, Ravensare

terpinol 4 – Tea tree, Marjoram, Mastic

menthol – peppermint, spearmint

Alcohols easily react with acids to form esters. Acids are  just available hydrogen ions.

esters- names generally end in –yl –ate.

Strong fungicides, anti-spasmodic, this depends on the length of the acid chain.

(1c) Formic acid, found in Geranium, mildly antispasmodic

(2c) acetates, found in Inula, Rosemary verbenon, abies siberica, Bay laurel, Cardamom

(5c) Roman chamomile

(7c) Ylang, Mandarin petitgrain, very strongly anti spasmodic

aldehydes – names end in –aldehyde or -al

Best used in low concentrations, diffused or diluted. Antispasmodic

Citronellal tends to be sedative, anti-inflammatory. Found in Eucalyptus citriodora, Citronella, Lemongrass.

Citral found in Lemongrass,  Indian verbena (Andropogon citratus), Lemon verbena, Melissa.

phenols – names end in –ol. This makes it easy to mistake a phenols and alcohols.

Pure phenols are toxic. They are synthetic and carcinogenic, derived from mineral oil. Plant phenols have a hydroxyl group (OH) and a short carbon chain. Stimulating and irritating.

Anethole – is an irritant. Found in Anise seed, Star Anise seed, Fennel

Asarone – is a carcinogen, found in Calamus

Apiole – is an irritant, especially to mucous membrane. Found in Parsley

Eugenol – irritant, Allspice, Cinnamon leaf, Clove leaf, stem and bud, Pimento leaf, Savory.

Methyl chavicol – mucous membrane irritant, toxic, carcinogenic in animals. Basil, Bay, Marjoram, Tarragon.

Safrole – carcinogenic. Found in Sassafras, brown and yellow Camphor.

Thymol and carvacrol are the most common plant phenols, found in Thyme, Savory, Oregano and Ajowan.

ketones- names generally end in –one. Ketones may be able to cross the blood-brain barrier easily or more readily than other molecules. Ketones dissolve fats are and potentially neurotoxic, causing seizures, liver damage and fatality. However… ketones stimulate cell and tissue regeneration, and are mucolytic. Ketone containing essential oils should only be used by well informed individuals.

There are ketone containing essential oils that can be used safely.

Everlast and Rosemary verbenon are suitable for external use. Eucalyptus globulus and Vetiver do seem to be benign.

Yarrow, not for children. Rosemary ct.camphor, Peppermint, Atlas Cedar. Eucalyptus polybractea and dives can be redeered nontoxic by dilution.

Sage, does appear to be less toxic than it’s ketone levels would lead one to expect, not for children. Spike lavender, best if mixed with other essential oils, do not confuse with lavandula angustifolia. Camphor is a neurotoxin.

Rue, santolina, Mugwort, pennyroyal are all not suitable for any but the very experienced. Thuja, wormwood and Hyssop all have their place in aromatherapy, again…not for the inexperienced. Lavandula stoechas should not be mistaken for lavandula angustifolia.

oxides and ethers – names usually end in –oxide, -ether. Oxides and ethers are both compounds that have an oxygen atom located between two carbon atoms. Ethers have this series in a linear arrangement, oxides utilize an oxide that is within a ring.

The most common oxide is cineole aka eucalyptol. Very antiviral and expectorant, found in eucalyptus and melaleuca

linalool oxide- antiviral and expectorant, great for bronchial infections, found only in Hyssop decumbens

Sesquiterpene alcohols

The larger terpene molecule is less affected by the accompanying functional group. There is more variation within the chemical structure and the effect and therefore there are no categories as with the monoterpenes. Researched examples show that the sesquiterpene alcohols are antiallergenic, stimulating to the liver and glands. They are anti-inflammatory and reduce congestion in veins and the lymph system. They are moderately antimicrobial. Other functional groups effect sesquiterpenes in very different ways and we are not able to generalize here.