Dear Friends,

What’s the difference between a flavanol and a flavonol? It almost looks the same, but the difference in their molecular structure and functions is critically important. Lets learn together.

After this week’s Forward Thinking we’ll definitely know

what flavanols are, and their powerful health benefits. Next week we’ll bring into the picture the flavonols.

Flavanols are also called flavan-3-ols.  They’re flavonoids that use the 2-phenyl-3, 4-dihydro-2H-chromen-3-ol skeleton.  There are five basic molecules that form the building blocks for this class of flavonoids:  catchin, epicatechin, epigallocatechin, epicatechin gallate and epigallocatechin gallate (EGCG).  These are called monomers.  When two of the five flavan-3-ols are joined together they are called dimers; and when two to five are linked they are called proanthocyanidins (OPCs).

The molcule to the right is a catechin.  An epicatechin has a OH at the R1 place on this molecule instead of an H like the catechin actually has.  Epigallocatechin and epicatechin gallate and EGCG have the same basic structures with changes at the R1 and OH location on the middle phenolic molecule. Each of these structural differences provides our bodies with a variety of differing molecular functions for the preservation of our good health.

Finally, when the monomeric flavan-3-ols are joined together as 6 or more units, they are called tannins.  If you refer back to my Phytochemical Flow Diagram from a couple of newsletters ago you will see that I put the tannins and the OPCs in the wrong place. They should appear as a subgrouping within the Flavonoids category, and placed under the Flavanols in the following succession:  catechins to OPCs to tannins.  OK, now that that’s all cleared up, let’s look at some health benefits of the Flavanols.

Health Benefits of the Flavanols

Flavan-3-ols exhibit several health beneficial effects by acting as antioxidants, anticarcingens, cardiopreventives, antimicrobials, antivirals and neuro-protective agents.  Flavanols are found in fruits, green tea, wine and cocoa.  Their presence in food also affects quality parameters such as astringency, bitterness ,sourness, sweet-ness and aroma.

Epicatechins:  There has been a wide amount of research on the beneficial effects of the abundance of epicatchins in natural cocoa.  In a very interesting study regarding the healthful Kuna Indians who live on the San Blas islands off the coast of Panama, high blood pressure and other signs of cardiovascular disease are rare.  The research found that epicatechins are directly linked to improved circulation and other hallmarks of cardiovascular health.  The Kuna consume large amounts of flavanol-rich cocoa—three to four cups a day.  They also showed in old age very little cognitive dysfunction.  Their cocoa boosted blood flow to key areas of the brain.  Flavanols have been shown to increase the formation of endothelial nitric oxide, which promotes vasodilation and consequently increases blood flow and lowers blood pressure.

EGCG:  Epigallocatechin gallate is a profound anti-oxidant, found mostly in green tea. On average a cup of green tea will have roughly 100 mg per 8 ounces.  Of course, the amount varies with the variety of tea, the age of the leave, and the amount of brewing time.  High levels of EGCG is believed to be responsible for much of green tea’s promise in the prevention of cardiovascular disease, obesity, Alzheimer’s disease, cancer and periodontal disease.

EGCG and related catechins have the ability to bind to the signaling  molecules that either block or activate transcription factors.  For example, they can block NF-kB, and thereby stop the expression of pro-inflammatory cytokines and chemokines; and they can upregulate the Antioxidant Defense System by binding to transcription factor NRF2.

Proanthocyanidins (OPCs):  Chief among the benefits of OPCs is antioxidant protection against heart disease and cancer.  Proanthocyanidins are found in many woody plants, the two most common sources are grape seeds and white pine.  OPCs are also abundant in apples, berries ,barley, bean hulls, chocolate, ruhbarb, rosehips and sorghum.

Epidemiological research leads us to believe that proanthocyanidins may help explain the French Paradox.  Red wine could be considered an alcohol tincture of several potent flavonoids, including proanthocyanidins from grape seed.

Next week we’ll talk about the Flavonols, also called Flavonoids (not to be confused with the larger category of Phenols also called the Flavonoid).  I’ll explain this next week.
Sincerely yours,

Seann Bardell

BioImmersion.com

Clinical Note:

Cinnamon contains a variety of phytonutrients, including the flavan-3-ols similiar to those found in grapes, berries, cocoa and green tea (OPCs and catechins).  This class of antioxidants boosts the stablilizing effect of insulin on blood sugar.  At the same time, these antioxidants inhibit insulin resistance.  Just a few of the benefits of these phytonutrients are as follows:

• Cinnamon acts as a powerful anti-inflammatory.  It inhibits the release of the inflamma-tory fatty acid arachidonic acid from platelet membranes.  It also reduces the production of an inflammatory prostaglandin called thromboxane A2.
• Its essential oil inhibits the growth of bacteria and fungi.
• It functions as a strong antioxidant.
• Its strong, fragrant aroma boosts cognitive processing in the brain, improving memory and attention span.
• Cinnamon also exhibits strong epigenetic effects by blocking NFkB and enhancing NRF2. (Forever Young by Nicholas Perricone, 2010)

The Last Quiz Answer:

This is our friend from a couple of weeks ago, close up, the Kudu.  Couldn’t pass up showing you this beautiful creature once again.  Greater kudu may be active throughout the 24-hour day.  The large ears are extremely sensitive to noise, making these shy antelope difficult to approach.  Under normal circumstance, kudu will sneak away and hide from potential enemies.  When startled, however, they flee with large jumps with their tails rolled upwards and forwards.  Kudu often stop and look back after a running for a short distance - a frequently fatal habit. Despite their large size, kudu are accomplished jumpers, with records of heights of over 2.5 meters / 8.25 feet being cleared with ease. (ultimateungulate.com/…/Tragelaphus_strepsiceros)

In a new rat study published in Molecular Nutrition and Food Research, the flavonoids in cocoa have shown protection effect against colon cancer onset. Here is a link to NutraIngredients discussion of this recent research.

Dear Friends,

Let’s talk about color in food!  The greens, reds, yellows, blues and purples… how do these colors heal us?  We’ve been talking about phytochemicals in the past several weeks, specifically the structures of the different flavonoids.  This week we will focus on the powerful benefits derived from one of the subgroups of flavonoids—the anthocyanins.

Anthocyanins fall into the category of phytochemicals called pigments. They bring in the spectrum colors ranging from crimson and magenta to violet and indigo.  The major anthocyanins are the following:  delphinidin, cyanidin, petunidin, peonidin and malvidin.  For example, the reason blueberries contain the blueish purple color is because of the delphinidin and petunidin—these two pigments are deep blue/purple.  If we go to red raspberries they don’t make those pigments at all.  They make almost exclusively cyanidin.  They might make a little peonidin which is pink, but they make mostly cyanadin which is a reddish pigment. In raspberries that are very dark they just have a higher concentration of different cynadin glycosides that make different derivatives.

As long as we are talking about pigments, the other major class of phytochemicals that are plant pigments are the carotenoids, which are part of the Terpenoid, a first level sub-grouping of phytochemicals (see the flow chart from last week).  The carotenoids are yellow, orange, and some red hues as in carrots, squash and tomatoes.  The carotenoids are one of the largest and most important classes of plant pigments.

Chemically they are sorted into two classes, the carotenes and the xanthophylls—each with unique biological activity.  Carotenoids, such as beta-carotene on the left, are void of any oxygen species are referred to as the carotenes, while those containing oxygen are know as the xanthophylls, on the right.

The long conjugated chain is responsible for the orange color of beta-carotene.

Carotenoids, anthocyanins and chlorophyll are the major pigments in the plant world. Chlorophyll is the green pigment found in abundance in the leaves and stems—making photosynthesis possible.  In the Fall when the plant’s berry harvest has been completed, chlororphyll production is reduced and we see the leaves bleed through with reds and purples, as they are also loaded with anthocyanins or carotenoids.  Different colors mean different flavonoids, and just as the different structures account for the different colors, the different colors provide different health benefits, and our bodies are designed to take in all of these molecules.

Now let’s look at the health benefits of the anthocyanins.

Epidemeological studies suggest that consuming anthocyanins regularily can lower the risk of CVD, arthritis, diabetes and cancer due to their antioxidant and antiinflammatory capabilities.  Their phenolic structures laden with conjugated double bonds are responsible for their antioxidant capacity.  Their double bonds are able to scavenge free radicals (ROS) such as superoxide anion, singlet oxygen, peroxides and hydroxyl radicals. (Prior and Wu 2006)  That’s four out of five of the major free radical catagories that our bodies must control to maintain health.

In several in vitro studies using cell culture systems from colon, endothelial, liver, breast and luekemic cell lines, the anthocyanins displayed numerous antitoxic and anticarcenogenic effects based on their ability to scavenge ROS which stimulated the expression of Phase 2 Proteins and ultimately reducing oxidative adducts in DNA and hindering mutagenesis. (Wang and Stover, 2006).

Helping to prevent and even reverse cancer, heart disease, diabetes, and arthritis—not bad, but there is more.  Anthocyanins can even protect and enhance the cognitive functioning of the brain!  Protect against dementia and Alzheimer’s.  Who wouldn’t want to consume foods rich in anthocyanins.  This is what led us in the quest for foods with anthocyanins as a big part of their high actives.  This is why we chose the Wild Blueberry as one of our Therapeutic Foods.
Sincerely yours,

Seann Bardell

BioImmersion.com

Clinical Note:

In some fruits you’ll find three, four, perhaps five types of anthocyanins.  Wild blueberries can have as many as twenty-five or thirty. (Wilhelmina Kalt, PhD food chemist for Agriculture and Agri-Food Canada, the Canadian equivalent of our USDA).

As James Joseph PhD, past Chief Nueroscientist at Tufts University and past head of the USDA Anti-Aging Center at Tufts, said, It’s not that the individual anthocyanins in blueberries are stronger than those in others fruits.  It’s that blueberries have so darn many types and in such large concentrations. In ORAC tests by the USDA wild blueberries had the highest score of any fruit in North America.

The awesome antioxidant power of blueberries comes from two main souces.  One is chlorogenic acid which is among the cancer fighters in tomatoes and bell peppers. Chlorogenic acid is found in large quantities in blueberries.  And the other is in the anthocyanins. (Wilhemina Kalt, cited in The Color Code by Joseph)

In our Wild Blueberry Extract Therapeutic Foods supplement, we have concentrated the phenolics.  A typical C of A results show 65% total phenolics, 19% anthocyanins and 5.8% chlorogenic acid with an ORAC of 7000 umole/gram.  It takes us one cup and one-quarter of the Nova Scotia wild blueberries to fill one 500 mg capsule.  The color is so blue that it is almost black.  It provide much antioxidant, antiinflammatory, neuro-regenerative punch as documented over the years by our doctors with their patients.  A side note:  I hear quite frequently from our clients that they have tried the product on their animals with amazing results.  After all it was, in part, the therapeutic success in animal research that made the case for possible successful outcomes for us humans.

Here is the link to our monograph on this product.  You will be inspired.  It is a very profound product—the Wild Blueberry Monograph. (When in, click on Blueberry dossier) Print it out so that your patients can read it.

The Last Quiz Answer:

This beauty is a Kobus ellipsprymnus—a Waterbuck. While the Blue Duikers from last week’s newsletter are not much taller than a jack rabbit, the waterbuck is a large antelope with a height of around 54 inches at the shoulder and a weight of up to 600 pounds. Their body is heavy set and their legs are strong and muscular. Even though they are called waterbucks they really only go into the water to escape preditors—lions, leopards, hyenas and Cape wild dogs, otherwise they prefer to stay out of the water.  They have a wide distribution from sub-Saharan West Africa to most of East Africa.

OK guys, here we go!!!  This is a fight we must face together.  Click on this link and add at least your voice to the issue.  We all need to carefully watch how this is playing out, the court date is set:  January 31st, 2012:         Small Family Farmers verses Monsanto.

Dear Friends,

What is becoming a renaissance of awareness within the practice of medicine is the acknowledgement that colorful fruits and vegetables have much to offer for health building and disease prevention.  It is all available to us through their multitude of phytochemicals.

Last week I diagramed the various categories within phytochemicals.  This week I want to deepen our understanding of these categories.  Remembering that function follows structure, I will set the stage for our functional discussions (next week) of the individual phytochemical by first looking at their structure.

Below are the molecular structures for the Flavonoids, a subgroup within the Phenols.  Notice their structural similarities and differences.  We will see how these structures affect their biological performances as antioxidants, gene modifiers, or other functional attributes.

But first, I must make a correction in last weeks Forward Thinking’s Phytochemical Diagram, where in the first subdivision I put as one of the groups- Polyphenols.  I should have put instead- Phenols, as the group designation.  I have done so below.

Phenolics are compounds possessing one or more aromatic rings with one or more hydroxyl groups.  They are broadly distributed in the plant kingdom and are the most abundant secondary metabolites of plants, with more that 8,000 phenolic structures currently known, ranging from simple molecules such as phenolic acids to highly polymerized substances such as tannins. (Jin Dai and Russell Mumper 2010)

What are secondary metabolites?

Secondary metabolites are organic compounds that are not directly involved in normal growth, development or reproduction of an organism.  Unlike primary metabolites, absence of secondary metabolites does not result in immediate death, but rather long-term impairment of the organisms survivability and fecundity [ability to reproduce]. (Wikipedia)

Long term impairment, sounds familiar?  Isn’t that what we are all concern about in  today’s diseases of diabetes, obesity, heart disease, arthritis, Alzheimer’s, Parkinson’s, IBD, autoimmune disorders, and cancer—all diseases with multifactoral etiologies with a large mediating dose of oxidative stress (inflammation).

Here is our corrected chart from last week.  As you can see from Phenols we go down to Flavonoids and have highlighted the Flavonoids.  Take a moment to notice how subtle the structural differences are.

Anthocyanins:  Anthocyanins fall within the category called pigments.   They bring in the spectrum colors ranging from crimson and magenta to violet and indigo.  Anthrocyanins are widely distributed in cherries, plums, red currants, blackberries and blueberries.  There are more than 70 different kinds of anthocyanins that have been indentified in fruits—with names such as pelagonidins, cyanidins, delphinidin, petunidins,  malvidins, etc.

With the generic anthocyanin molecule on the right notice the R1 and R2 locations on the molecule. It’s at these locations where the differences in the forementioned anthocyanins occur:  Pelagonidin: R1=H, R2=H; Cyanidin: R1=OH, R2=H; Delphinidin: R1=OH, R2=OH; Petunidin: R1=OCH3, R2=OH; and Malvidin: R1=OCH3, R2=OCH3.

Isoflavones: found in abundance is soybeans, soy foods and legumes.  They are a class of phytoestrogens.  Three of the isoflavones are genistein, daidzein and glycitein.  To the right is genistein.  Here’s the molecular differences between the three:

Daidzein does not have an OH on top of the left hand phenol, otherwise it is exactly the same as genistein.  Glycitein has no OH like Daidzein but has a H3CO coming off the left phenolic.

Flavanols:  catechin, epicatechin, epigallocatechin, epicatechin gallate, and epigallocatechin gallate (EGCG) are all monomers.  These are teas particularly green and white, chocolate, grapes, berries and apples.  Then there are the dimers:  Theaflavins, thearubigins.  These are black and oolong teas.  And, there are polymers:  proanthocyanidins.  These are in chocolate, apples, berries, red grapes, red wine.

The molecule to the right is a catechin.  An epicatechin has a OH at the R1 place on this molecule instead of an H like the catechin actually has.  Epigallocatechin and epicatechin gallate and EGCG have the same basic structures with changes at the R1 and OH location on the middle phenolic molecule.

Flavanones:  are represented by the citrus family of fruits, ie lemons, grapefruits, and oranges.  There of the flavanones are hesperetin (in oranges), naringenin (in grapefruit) and eriodictyol (in lemons).

Regarding the generic flavanone are the right.  If it is Naringenin the R1=H and the R2=OH.  If it is Eriodictyol, then the R1=OH and the R2=OH.  And, if it is Hesperetin, then the R1=OH and the R2=OCH3.

Flavonols:  are widely distributed in yellow onions, scallions, kale, broccoli, apples, berries and teas.  Some of them are kaempferol, quercetin, muricetin and isorhamnetin.

In the flavonol on the right Kaempferol has R1=H and R2=H.  Quercetin has R1=OH and R2=H.  Myricetin has R1=OH and R2-OH.  And, Isorhamnetin has R1=OCH3 and R2=H.

There are so many benefits that can  be derived from the consumption of flavonols.  Quercitin for example is an antihistamine, thereby fighting against inflammation.  It reduces blood pressure and reduces LDL cholesterol.  Rutin another flavonol improves blood circulation, strengthens capillaries, and keeps the eyes healthy.  Flavonols can fight cancers, strengthen the immune system, reduce inflammation.

Flavones: Apigenin, Luteolin.  Parsley, thyme, celery, hot peppers.  Two of the flavones are apigenin and luteolin.  Regarding the molecular structure of Apigenin the R1=H.  With Luteolin the R1=OH.

In recent years, scientific and public interest in flavones has grown enormously due to their beneficial effects against atheroscherosis, osteoporosis, diabetes mellitis and cancers.

Flavonoids are the most abundant polyphenols in our diet.  The basic flavonoid structure is the flavan nucleus, containing 15 carbons arranged in three rings (C6-C3-C6), and as you can see from the above, this basic skeleton can have numerous substituents, and these differences account for their differing therapeutic benefits for human health.

Next week we will look at these benefits.

Sincerely yours,

Seann Bardell

BioImmersion.com

Clinical Note:

What makes our Therapeutic Foods therapeutic?  Quite simply it is the bringing together of nature and technology.  In order to create products that naturally have high actives, we paintakenly source our raw produce from areas of the world where the environment and farming methods allow for exceptionally high active levels of the phytochemicals we are looking for; we harvest them at just the right time to maximun yields of the actives; we intelligently use the highest quality technological in processing of the raw material to preserve what has been captured and we follow-up with our clients as to their good results.

There is a difference in BioImmersion products.

The Last Quiz Answer:

Blue duikers are among the smallest antelope in the world.  Not much taller than a jack rabbit, they live in south Afirica’s southern forests.  They can be spotted at dawn and dusk looking for fallen fruits, flowers, fresh leaves and even bird eggs.  Duikers means ‘diver’ in Afrikaans, and refers to this small antelope’s habit of leaping into undergrowth to escape.

How many of your patients are dealing with toxic mercury fillings.  This little video should convince them that these amalgums must go!

Dear Friends,

My goal in this Forward Thinking Newsletter is to help you get a hold of, or get your mind around, a class of nutrients called the phytochemicals. I know, I know, sounds boring, we’ve been there and have done that. But read on.

Over the past several decades these molecules have immerged as a major focus for medical researchers and are now seen as key players in the restoration of human health around the world. Phytochemicals are now viewed as foundational deterrents against the plagues of cancer, CVD, diabetes, obesity and chronic degerative disease patterns worldwide.

Historically, when we taught good nutrition in our schools, the focus was on proteins, fats, carbohydrates, fibers, vitamins and minerals.  We used to call flavonoids vitamin P; cabbage factors (glucosinolates and indoles) were called vitamin U; and ubiquinone was vitamin Q.  However, the vitamin designation for P, U, and Q was dropped because specific deficiency symptoms could not be established. The three vitamins were then all lumped into one huge category that we call phytonutrients or phytochemicals.  Today, phytochemicals like vitamins Q, P, and U are in, and it is critically important that we understand them.

With all this health promoting power, phytochemicals are the most exciting thing happening in nutrition today. For years, we’ve known about vitamins, minerals and fiber. Those are all good substances but now we know there’s even more to a healthy diet than vitamins and minerals. There’s also the disease-busting strength of phytochemicals. This is a revolution in nutrition. (Joseph, Nadeau, & Underwood, 2002)

And there are so many of them!  It can be quite daunting and confusing, I readily admit, to grasp and remember how and why they all fit together to make a sound nutritional picture.  For example, can you arrange the following important phytochemicals into some relevant diagram:  lignans, anthocyanins, carotenoids, terpenes, delphinidin, quercitin, catechins, malvidin, isoflavones, glucosinolates, flavonoids, lipoic acid, polyphenols, limonoids, thiols, phytosterols,indoles, proanthocyanidin, resveratrol, hesperetin?

To help with our future discussions on phytochemicals I’ve create the following flow diagram, and in next week’s newsletter I will continue in this prediscussion foundation building by showing you molecular models for several key categories of phytochemicals.

Sincerely yours,

Seann Bardell

BioImmersion.com

Clinical Note:

Our new Energy Sustain Complex can provide a great base for a wonderful morning meal.  In case you haven’t tried Energy Sustain, it contains organic amaranth, chia, quinoa, buckwheat and millet. The first four are true seeds with the millet being a true grain.  They are all especially milled (like our Beta Glucan), through a patented heating process, where they are cooked enough to crach the crack the endosperm of each, liberating their soluble fibers, yet not destroying the vitamin content.  The powder has a wonderful mouth feel to it like our Beta Glucan Synbiotic Formula.  There is no gluten in the Energy Sustain.

Take one scoop of the Energy Sustain and add a scoop of rice protein (or other pure protein sources), fresh or frozen berries, a little pomegranate juice (or other juices) and water.  You can also add the Orginal Synbiotic, Triple Berry Probiotic, or No. 7 Systemic Booster for added nutrients, good bacteria, and fiber.  It tastes great and really sustains our energy levels well until the afternoon!

The Last Quiz Answer:

Where do you think this beautiful creature comes from? Africa?  Excellent, good answer.  Is it an Impala or Wildebeast? Sable? Kudu, Oryx, Waterbuck, Eland, Springbok, Duiker?—there are many kinds of antelopes in Africa.  What is your guess?

This magnificent creature comes in two sizes, large and a little less large.  This may be a large one.  An adult male’s horn can be 6 feet long with 2 1/2 twists.  This one appears to have one twist, so it may be a young male.  Males max out at around 600 pounds.

Ok, the answer:  this is most likely a Greater Kudu (as apposed to the Lesser Kudu).

I love the Rocky Mountain Institute.  They really put the feet on the ground when it comes to putting programs in place to impliment a clean energy revolution.  Last year they came out with their important book, Reinventing Fire. I’ve linked you here to their 2012 new year’s message and a way for you to investigate them further.