What is Di-esterified 3S, 3'S Astaxanthin?

Astaxanthin, nature's most powerful antioxidant, was created 700M years ago by single cell lifeforms struggling to deal with reactive oxygen species (ROS) generated by their mitochondria. 

However, not all astaxanthin is created equally. 

This blog covers three topics: what form of astaxanthin works best, where should astaxanthin reside to properly function and how do you we get it there.   We also compare other astaxanthin sources to see if they work. 

(To learn more about astaxanthin and reactive oxygen species (ROS) click here)

What form of astaxanthin works best? 

Astaxanthin comes in three shapes called stereoisomers.  Two of the three shapes (3S. 3'R, 3R, 3'R)  are toxic to animal health flesh orange. More on that later.

The third stereoisomer,  3S, 3’S, is the one we want to feed fish and the one responsible for the deep color of wild salmon. 

There is another nuance. The best form of the 3S, 3’S astaxanthin comes with ‘hooks” (ester groups)  on either end that help capture ROS.  When attached to a 3S, 3’S stereoisomer,  the hooks provide the maximum antioxidant benefit. 

The ideal and most powerful form of astaxanthin is therefore esterified 3S, 3’S stereoisomer,  aka “the good stuff.”

No coincidence.  Copepods, Krill, Shrimp and other low order animals make the Good Stuff.  Higher order animals including salmonoids evolved to bypass astaxanthin production entirely. Salmon get astaxanthin in their diets by eating astaxanthin producing animals or other fish that did. 

Where should astaxanthin reside?

To function as a powerful antioxidant, we need to get the good stuff into the cell and mitochondria plasma membrane. 

Location matters.  ROS is produced by the mitochondria and being close to the source improves efficiency.  Here is a picture of what it looks like: 

How do you deliver the good stuff to the right place? 

Esterified 3S, 3’S Astaxanthin is a complex structure.  Parts of the structure loves water and therefore dissolves in blood (hydrophilic) and parts hate water/blood *hydrophobic”). 

To get into the cell and mitochondria plasma membrane it needs help. 

When wild salmon dine on shrimp,  the astaxanthin is very small,  <10 nanometers, 1500 smaller than the width of human hair.  The astaxanthin is not directly soluble in blood.  That is where fatty acids and lipids in the shrimp flesh come into play.  These fatty acids and lipids loosely bind with astaxanthin forming blood -soluble envelopes called micelles and liposomes forming a delivery system that "hides" astaxanthin inside, allowing it to pass through the digestive track and bloodstream.  

The final trick is where the envelop deposits astaxanthin.    The two tail ends of diesterified 3S, 3'S isomer are attracted to the hydrophobic heads that form the inner and outer layer of the cell and mitochondria plasma membrane.  

The "R" forms are flipped in orientation and are the wrong angle to get into the cell/mitochondria membrane. These compounds form loose bonds with the fatty tissues in the muscle mass. 

Now that we know the right form, the right place and how the delivery system works, let’s compare astaxanthin supplements.

Synthetic Astaxanthin

Synthetic astaxanthin is made from petrochemical feedstock. The majority of the astaxanthin in synthetic material is the "R" form.  Salmon farmers use synthetic astaxanthin to tint salmon flesh orange.  Synthetic astaxanthin will kill a baby fish.  Small amounts are legally allowed for coloring adult fish and shellfish. 

 "Natural Astaxanthin" from Bacteria

Bacteria instead of petroleum?  Sounds more natural. Unfortunately, these little guys don't have mitochondria producing ROS to worry about. Some bacteria strains did, however, evolve to make the "R" forms of astaxanthin to protect them from ROS generated by UV induced photooxidation. 

"Natural Astaxanthin" from Yeast

Yeast have relatively few mitochondria (circa 34/cell) wheres a mature animals can have upwards of thousands in a cell or hundreds of thousands in a yolk.   

Given the low ROS load some yeast evolved to make the "R" forms of astaxanthin but never had to develop the chemistry and enzymes needed make the 3S, 3'S compound.  

Algae derived "Natural Astaxanthin"

The freshwater algae Haematococcus pluvialis (HP) makes lots of the good stuff when it hibernates to survive the winter.  It protects the astaxanthin and other compounds by enclosing everything in a hard outer shell called a cyst about the  thickness of a human hair.

If a hungry fish swallows the cyst, it is way too big to hide in a blood soluble envelope.  This cysts passes out the back end unscathed by the digestive tract. Neat survival trick.

Astaxanthin supplement providers are fully aware that this material is too big and attempt to break the cyst apart using pressure, temperature and super critical carbon dioxide as a solvent.

Right idea but wrong outcome. 

This process makes material that is 30 times bigger than what a salmon gets from krill, shrimp and other feed fish.   Still too big to form stable envelopes. We tested this material in fish and found 99% of what went in the front comes out the back. The supercritical carbon dioxide process doesn't produce the ester "hooks" that turbocharge astaxanthin's ability to mitigate ROS nor does it supply the fatty acids and liposomes needed to form the blood soluble envelopes.  

Introducing Amplifeed Topcoat 

We also use HP as our source, but instead of carbon dioxide and pressure we use high mechanical forces to break apart the cyst into its nano-sized elements.  We retain the fatty acids and lipids in the algae to form the blood-soluble envelope.  The fatty acids also form the ester groups that turbocharge the antioxidant function.

Amplifeed Topcoat:  The right form of astaxanthin with the delivery chemistry needed to deliver astaxanthin to the right place.