How A Lipid Garnered Two Academy Awards

Posted on April 15, 2022

Website Tiolein Preview

The Oscar winning film “Lorenzo’s Oil” garnering two Academy Awards, the olive oil sitting on your kitchen counter, Avanti Polar Lipids, and Croda – what do these all have in common? The answer is triolein.

Triolein is a symmetric triglyceride that makes up anywhere from 4-30% of olive oil, depending on its origin. You can also find this chemical compound at Avanti and in METLIN’s spectral database. We’ll get to how these all tie in with a critically acclaimed film a little later.

A triglyceride is a glycerol backbone with three fatty acid chains. Most triglycerides are asymmetrical and in human and plant biology contain fatty acid chains with an even number of carbons (i.e. 16, 18, 20) due to the acetyl CoA building block that contains two carbon atoms. Triglycerides can also differ in saturation. Some triglycerides are saturated such as those containing 16:0 or 18:0 fatty acid chains. And others are considered unsaturated due to the presence of at lease one double bond in the fatty acid chain like those containing 18:1 or 20:1 fatty acid chains.

The simplest form of triglyceride has three of the same fatty acid tails, but simple does not mean they are common. Most triglycerides are composed of different fatty acid chains and are called “mixed” triglycerides. Triolein is a triglyceride composed of three identical unsaturated 18-carbon long fatty acid chains. This also means that triolein is considered a rare triglyceride due to its perfect symmetry.

One of the most common occurrences of triolein is in olive oil. Interestingly, olive oil is composed of various amounts of triolein dependant upon the area which it originated. Italian olive oils typically have about 5% of triolein compared to Palestinian olive oils which contain about 30% of triolein.

And how do the film, Croda/Avanti, and olive oil tie together? Triolein has also been investigated as a potential therapy for adrenoleukodystrophy (ALD). In the 1980s, a young boy, Lorenzo, was diagnosed with ALD at the age of six after he began showing symptoms of neurological problems. At the time, ALD which had progressed to signs of neurological problems carried with it a death sentence and a life span of no more than a few years after the signs began to show.

Lorenzo’s parents, unwilling to let their child die without a fight, began searching for potential treatments. They combed through scientific literature and experimental data and even put together a meeting of the world’s most prominent ALD researchers. The meeting featured a presentation revealing oleic acid as a potential therapy for ALD. So, they set out to find someone to isolate and formulate a therapy similar to oleic acid. After calling nearly 100 scientists and laboratories, they finally found someone willing to accept the challenge. Dr. Don Suddaby, working with Croda International at the time, distilled and formulated a 4:1 mixture of triolein and trierucate. This formula was given to Lorenzo, and he lived 20 years longer than the doctors predicted, to see his 30th birthday before passing away.

In 1992, a critically acclaimed feature film, Lorenzo’s Oil, was produced and garnered two Academy Awards for Best Actress in a Leading Role (Susan Sarandon) and Best Original Screenplay (George Miller and Nick Enright).

Interested in conducting some of your own research on Triolein? Get it from Avanti Polar Lipids. If you want to see MS/MS, ion mobility, or neutral loss data of Triolein, visit METLIN’s website. Who knew something you use to cook with could be used to treat a rare disease?