Discovery of Monolaurin

Shortly after arriving (1957) at University of Detroit (Dept. of Chemistry), I began placing undergraduate students into research projects. In the summer of 1960 a young student working for Sister Mary Stanislause (Mercy College, Detroit) was studying the nutritional needs of a protozoa, single-celled organisms, called Tetrahymena Pyriformis. Because of my interest in the structure-function of lipids, Sister and I decided to examine the nutritional affects of fatty acids, which were readily available in pure form. The results of the summer experiments indicated that a fatty acid with a 12-carbon chain acid as opposed to the other shorter or longer fatty acids was toxic to this organism. While interesting, I felt it necessary to repeat the experiments with another student the following year (1961). The first experiment was confirmed but its significance was not obvious. The reports of the toxicity of hexachlorophene (circa 1965) in nursery uses made me reevaluate the potential uses of lipids as non-toxic antimicrobial agents. This began a retrospective examination of older literature. It was therefore no surprise to learn about lauric acid being reported to be toxic to a variety of microorganisms. Following our initial results and literature survey my students and I began an active program of measuring the modification of lipid structure on antimicrobial activity.

Over the years my students, colleagues, and I examined a wide variety of other lipids hoping to improve on nature. During this period we screened some 300 lipids and other comparable structures for antimicrobial activity. These seminal studies indicated that certain fatty acids and monoglycerides (a single fatty acid attached to glycerol) obtained from mother’s milk or lauric oils had extraordinary antimicrobial properties. We were not able to improve on nature and therefore returned to a certain monoglyceride derivative (monolaurin) obtained from coconut and palm kernel oils and indeed mother’s milk. To have a clearer understanding of what a monoglyceride is the following graphic picture may be helpful.

Structurally a fat or triglyceride has a glycerol backbone bearing three fatty acid (R) “arms”. These fatty acids occupy three positions of the glycerol molecule labeled sn1, sn2, or sn3. Diglycerides have two fatty acids attached while the fatty acid of a synthesized monoglyceride preferably occupies the only the sn1 position. The sn 3 position being similar to the sn 1 position

H2-C---OH sn1
H2-C----- OH sn2
H2-C---OH sn1 (3)
Glycerol + Lauric Acid ---> Monolaurin (Glycerol monolaurate, GML)

Kabara (1968) was the first to patent that certain fatty acids (MCFAs) (e.g., medium-chain- fatty acids) and their derivatives (e.g., monoglycerides (MGs)) can have adverse effects on various microorganisms. While nontoxic and approved as a food additive by the FDA, monolaurin adversely affects bacteria, yeast, molds fungi, and enveloped viruses. Kabara et al determined for the first time that the monoglyceride of lauric acid was more effective than the fatty acid itself. The monoglycerides are active; diglycerides and triglycerides (fats in general and even those with lauric acid) are inactive. In chemical nomenclature monoglycerides are classified as lipids while fats are designate as triglycerides. Of the saturated fatty acids lauric acid has greater antimicrobial activity than caprylic acid (C-8), capric acid (C-10), or myristic acid (C-14).

This highly purified monoglyceride is commercially known as Lauricidin® rather than simply monolaurin since the usual commercial monolaurin is only 45-55% pure and has no antimicrobial properties. Lauricidin® as a Nutriceutical is 95±1-% pure 1-monolaurin with no additives, preservatives or inactive ingredients.

Fatty acids and monoglycerides produce their killing/inactivating effect by perturbing the plasma membrane lipid bilayer surrounding microorganisms. The antiviral action attributed to monolaurin is that of fluidizing the lipids and phospholipids in the envelope of the virus, causing the disintegration of the microbial membrane. This may not be the only mechanism. Recent studies indicate that one antimicrobial effect in bacteria is related to monolaurin's interference with signal transduction/toxin formation (Projan et al 1994), and another antimicrobial effect in viruses is due to lauric acid's interference with virus assembly and viral maturation (Hornung et al 1994). In addition, it is suspected that saturated Lauricidin® increase the immune response to infection since it is well documented that polyunsaturated fats lower our immune system.

Hierholzer and Kabara (1982) initially reported recognition of the antiviral aspects of the antimicrobial activity of the monoglyceride of lauric acid (monolaurin). They showed virucidal effects of monolaurin on enveloped RNA and DNA viruses. This work was done at the Center for Disease Control of the U.S. Public Health Service. These studies involved selected virus prototypes or recognized representative strains of human viruses. Viruses that have a lipid membrane are especially vulnerable to lauric acid and its derivative monolaurin. Further research has shown that enveloped viruses are inactivated in both human and bovine milk by added fatty acids and monoglycerides (Isaacs et al 1991), Kabara’s original statements concerning structure-function relationships for antimicrobial activity have been confirmed by others (Isaacs et al 1986, 1990,1991, 1992; Thormar et al 1987).

Some of the viruses inactivated by these lipids are the measles virus, herpes simplex virus-1 (HSV-1) and virus-2(HSV-2), herpes family members (HIV, hepatitis , vesicular, stomatitis virus (VSV), visna virus, and cytomegalovirus (CMV). Many of the pathogenic organisms inactivated by monolaurin are those known to be responsible for opportunistic infections in HIV-positive individuals. For example, concurrent infection with cytomegalovirus is recognized as a serious complication for HIV positive individuals (Macallan et al 1993).

Thus, it would appear to be important to investigate the practical aspects and the potential benefit of using Lauricidin® for nutritional support for microbial infected individuals. Until now no one in the mainstream nutrition community seems to have recognized the added potential of antimicrobial lipids in the treatment of infected patients. The lipid-coated (envelope) viruses, bacteria and other microorganisms are dependent on host lipids for their lipid constituents. The variability of fatty acids in the foods of individuals as well as the variability from de novo synthesis accounts for the variability of fatty acids in their membranes. Putting special lipids into our diet may have adverse effects on parasitic organisms.

Most important monolaurin does not appear to have an adverse effect on desirable gut bacteria, but rather on only potentially pathogenic microorganisms. For example, Isaacs et al (1991) reported major inactivation of Hemophilus influenza, Staphylococcus epidermidis and Group B gram positive Streptococcus. by monolaurin. The other potentially pathogenic bacteria inactivated by monolaurin include Listeria monocytogenes, Staphylococcus aureus, Streptococcus agalactiae, gram-positive organisms, and some gram-negative organisms (Vibrio parahaemolyticus and Helicobacter pylori). Monolaurin rapidly inactivate the latter organism causing gastric ulcers (Petschow et al,1996)

Decreased growth of Staphylococcus aureus and decreased production of toxic shock syndrome toxin-1 was shown with 150-mg monolaurin per liter (Holland et al 1994). Monolaurin was 5000 times more inhibitory against Listeria monocytogenes, a pathogen found in dairy products, than ethanol (Oh & Marshall 1993). Helicobacter pylori which A number of fungi, yeast, and protozoa are inactivated or killed by monolaurin. The fungi include several species of ringworm (Isaacs et al 1991). The yeast reported is Candida albicans (Isaacs et al 1991). The protozoan parasite Giardia lamblia, responsible for diarrhea in babies, is killed by monoglycerides from hydrolyzed human milk (Hernell et al 1986, Reiner et al 1986, Crouch et al 1991, Isaacs et al 1991). Chlamydia trachomatis is also inactivated by (Bergsson et al 1998), and hydrogels containing monocaprin/monolaurin are potent in vitro inactivators of sexually transmitted viruses such as HSV-2 and HIV-1and bacteria such as Neisseria gonorrhea (Thormar 1999).

Most important and different from drug antibiotics is the fact that there appears to be very little development of resistance in organisms to the bactericidal effects of these natural antimicrobial lipids (Petschow et al 1996). In fact monolaurin has been shown to reduce or prevent resistance of organisms to certain antibiotics.

Lauricidin® As A Nutriceutical

By definition a nutriceutical is a functional food that has both nutritional/caloric value and pharmacological (drug) effects. Hippocrates (Greek physician, circa 460-377 B.C.) recognized this truism when he declared “Let thy food be your medicine and your medicine thy food”. The monolaurin found in mother’s milk must be considered the first nutriceutical we ingest following birth. Mother’s milk not only provides the newborn with important nutrients for growth and development but also contains substances, which have antimicrobial, antiviral and other protective properties.

This concept of human milk having sanitizing effects was recognized early in Ayurveda medicine (circa 600 BC). In the history of cataract, surgery that extends back at least 3000 years, the translation of Hindu manuscripts gives detailed methods of the great surgeon Susruta. He described principles of surgery based on anatomic dissection. He practiced asepsis (fumigated the operating room with sweet vapors) and gave an excellent account of his technique of couching (depression of the lens into the vitreous) as well as an outline of postoperative care. After couching the milk of a nursing mother would be sprinkled into the conjunctive sac much in the way antiseptics are used presently after an operation to reduce infection.

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