Bioactive Polyacetylenes: What’s the Deal?

Posted on 21 December 2009 by sie

Recently, my posts have illuminated the importance of other molecules in plants we can benefit from besides essential nutrients. With my recent find of the molecule falcarinol, I wanted to learn more about it’s chemical family from where to find it to more detail about the bioactivity of the polyacetylene group.  I found an excellent paper to provide me with back filler on the bioactive polyacetylene group, and wanted to fill y’all in too.

Bioactive polyacetylenes in food plants of the
Apiaceae family: Occurrence, bioactivity and analysis
published January 2006 in the Journal of Pharmaceutical and Biomedical Analysis

Introduction to Bioactive Polyacetylenes
In the search for the reason behind many plants’ health promoting effects, researchers have begun to investigate some of the molecules that act as natural pesticides and are part of the plant’s defense system. These bioactive compounds were initially thought to be harmful because they are toxic in large doses, but recent studies have shown that in low doses these “toxins” may be the reason for many of the heath benefiting properties of some edible plants.

Polyacetylenes are one example of these beneficial “toxins”. Most of these molecules are found in the Apiaceae plant family which includes (but is not limited to) carrots, celery, fennel, parsnip, dill, and parsley. Over 1400 different polyacetylenes have been isolated from plants in the Apiaceae family, and almost all of the polyacetylenes in the edible parts of these plants are of the falcarinol type.

Bioactivity of Polyacetylenes in Edible Apiaceae Plants
1) Anti-Fungal: Both falcarinol and falcarindiol are known anti-fungal compounds via spore germination inhibition. They mostly act as a preventative anti-fungal, but some observations have recorded an increase in their production in response to an infection.

2) Neurotoxicity: Some water hemlock plants contain the acetylenes oenanthotoxin and cicutoxin that are extremely poisonous. Falcarioldiol has not demonstrated any acute neurological effects. Falcarinol has shown similar effects to the acetylenes in the hemlocks, but only in extremely high doses.

3) Allerginicity: Most of these bioactive polyacetylenes have caused skin irritation. Falcarinol is the most common offender, but related molecules falcarindiol and falcarinone do not show the same irritant properties. It is thought that these allergenic properties of falcarinol are what gives it its bioactivity.

4) Anti-Inflammatory, Anti-Platelet-Aggregatory, and Anti-bacterial Effects: Both Falcarinol and falcarindiol have shown anti-inflammatory and anti-platelet-aggregatory effects which do occur as non-toxic levels.

5) Cytotoxicity: Cytotoxic polyactylenes include falcarinol, panaxydol, and panaxytriol which have shown high activity against many different cancer cell types. Of all the bioactive polyacetylenes, falcarinol has tested the most active against cancer cells both in vitro and in vivo.

Falcarinol and Health Benefits:
Until recently, both alpha-carotene and beta-carotene were thought to by the primary reason behind carrot’s health benefits. Recent studies have shown that falcariol, not beta-carotene, could explain carrot’s health promoting properties. Falcarinol has shown a significant ability to inhibit cancer cell growth, both in vitro and in vivo.

To verify falcarinol’s bioavailability in humans, a study looked at levels of falcarinol in serum after ingestion of carrot juice and found that falcarinol was indeed rapidly adsorbed.

Authors’ Conclusions:
The author’s report that the traditional view of food polyacetylenes as toxins needs to be revised as they could prove to be very beneficial nutraceuticals, particularly the falcarinol type polyacetylenes. The authors feel it is only a matter of time before these compounds are being extracted on large scales to further verify their beneficial bioactive properties leading to the conduction of clinical trials. (Note that the paper I discussed in the previous post was published in 2009 by this same lead author)

Leave a Reply