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Astaxanthin, Cell Membrane Nutrient with Diverse Clinical Benefits and Anti-Aging Potential Parris Kidd, Phd

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Astaxanthin, Cell Membrane Nutrient with Diverse Clinical Benefits and Anti-Aging Potential Parris Kidd, Phd Monograph amr Astaxanthin, Cell Membrane Nutrient with Diverse Clinical Benefits and Anti-Aging Potential Parris Kidd, PhD Abstract Introduction Astaxanthin, a xanthophyll carotenoid, is a nutrient with Astaxanthin is a carotenoid nutrient with unique cell membrane actions and diverse clinical benefits. molecular properties that precisely position it This molecule neutralizes free radicals or other oxidants by within cell membranes and circulating lipoproteins, either accepting or donating electrons, and without being thereby imbuing them with potent antioxidant and destroyed or becoming a pro-oxidant in the process. Its linear, anti-inflammatory actions.1,2 Astaxanthin also polar-nonpolar-polar molecular layout equips it to precisely effectively protects the double membrane system insert into the membrane and span its entire width. In this of mitochondria, to the point of boosting their position, astaxanthin can intercept reactive molecular species energy production efficiency.3 As a dietary supple- within the membrane’s hydrophobic interior and along its ment, astaxanthin demonstrates an exceptional hydrophilic boundaries. Clinically, astaxanthin has shown range of benefits, mostly at very modest dietary diverse benefits, with excellent safety and tolerability. In intakes (40 mg/day or less). The molecular struc- double-blind, randomized controlled trials (RCTs), astaxanthin ture of astaxanthin is illustrated in Figure 1. lowered oxidative stress in overweight and obese subjects and Humans do not make astaxanthin.4 Current in smokers. It blocked oxidative DNA damage, lowered human dietary intake is almost exclusively from C-reactive protein (CRP) and other inflammation biomarkers, seafood. Astaxanthin is produced by algae, bacteria, and boosted immunity in the tuberculin skin test. Astaxanthin and fungi, and concentrates higher up the food lowered triglycerides and raised HDL-cholesterol in another chain as these primary producers are consumed for trial and improved blood flow in an experimental microcircula- food.5 Its naturally intense red color brightens the tion model. It improved cognition in a small clinical trial and flesh, skin, or exoskeleton of animals, such as crabs, boosted proliferation and differentiation of cultured nerve crayfish, krill, lobsters, salmon, shrimp, and trout. stem cells. In several Japanese RCTs, astaxanthin improved It is also fed to farmed seafood for this coloring visual acuity and eye accommodation. It improved reproduc- purpose. Astaxanthin also occurs naturally in Parris M. Kidd, PhD – Cell tive performance in men and reflux symptoms in H. pylori flamingo feathers (where it is responsible for the biology; University of Califor- patients. In preliminary trials it showed promise for sports characteristic color) and the retinas of quail.6 nia, Berkeley; contributing editor, Alternative Medicine performance (soccer). In cultured cells, astaxanthin protected Although synthetic astaxanthin is available, it Review; health educator; the mitochondria against endogenous oxygen radicals, has a different molecular profile than the natural biomedical consultant to the conserved their redox (antioxidant) capacity, and enhanced material, as do certain manufactured astaxanthin dietary supplement industry. Correspondence address: their energy production efficiency. The concentrations used in esters. This review is therefore restricted to natural 847 Elm Street, El Cerrito, these cells would be attainable in humans by modest dietary astaxanthin, virtually all of which comes from CA 94530 intakes. Astaxanthin’s clinical success extends beyond commercial cultures of the single-celled alga Email: [email protected] protection against oxidative stress and inflammation, to Haematococcus pluvialis (H. pluvialis).7 demonstrable promise for slowing age-related functional The clinical and basic science research on decline. astaxanthin is considerable, although a number of (Altern Med Rev 2011;16(4):355-364) the clinical trials in circulation were not published 355 Alternative Medicine Review Volume 16, Number 4 Copyright © 2011 Alternative Medicine Review, LLC. All Rights Reserved. No Reprint Without Written Permission. amr Monograph in peer-reviewed journals and some were published Complex Three-Dimensional Chemistry Key words: astaxanthin, antioxidant, carotenoid, only in Japanese. However, the English-language, The bonding patterns of natural astaxanthin cardiovascular, cell mem- peer-reviewed publications sufficiently establish generate many different molecular forms (isomers), branes, cognition, CRP, DNA astaxanthin as a nutrient with broad-ranging each with its unique three-dimensional shape. The damage, eye accommoda- tion, free radicals, H. pylori, efficacy and safety. intricacies of astaxanthin’s isomer array are beyond inflammation, immunity, the scope of this review. Pertaining to its use as a male fertility, mitochondria, Biochemistry dietary supplement, virtually all commercially oxidative stress, redox, vision, The Unique Molecular Layout of Astaxanthin available natural astaxanthin is predominantly in xanthophyll Astaxanthin (3,3’-dihydroxy-beta,beta-carotene- the all-trans geometric form 3S,3S’ Astaxanthin, as 4,4’-dione) belongs to the xanthophyll subclass of occurs in H. pluvialis and as illustrated in Figure 1. carotenoids. It has oxygen in its molecular struc- This is the predominant natural astaxanthin used ture, which sets it apart from beta-carotene and in all clinical trials to date. other molecules of the carotene subclass.5 The Another complication in the chemistry of natural astaxanthin molecule has an extended shape, with astaxanthin is that the molecule in its free form is a polar structure at either end of the molecule and relatively uncommon within the various organisms a nonpolar zone in the middle (Figure 1). The polar that produce it. Instead, most of this astaxanthin is structures are ionone rings that have potent either conjugated with proteins or esterified with capacity for quenching free radicals or other one or two fatty acids (as astaxanthin acyl monoes- oxidants, primarily in an aqueous environment, ters or diesters).11 Acyl esters make up more than but possibly also in the absence of water.8,9 99 percent of the astaxanthin from H. pluvialis and Figure 1. Molecular Layout of All-trans Astaxanthin, the Major Molecular Species in Natural Foods and Dietary Supplements O OH HO O all-trans astaxanthin Note the polar ionone rings at the ends and the non-polar zone of conjugated carbon-carbon bonds in the middle. The nonpolar middle segment of the astaxanthin approximately 80 percent of astaxanthin in molecule is a series of carbon-carbon double bonds, krill.11,12 Thus, acyl monoester and diester forms which alternate with carbon-carbon single bonds make up virtually all the astaxanthin currently – termed “conjugated.” This series of conjugated available in dietary supplements. double bonds gives the molecule a further antioxi- dant dimension, with a capacity to remove high- Metabolism: Absorption and Tissue energy electrons from free radicals and “delocalize” Distribution their electronic energy via the carbon-carbon chain In pharmacokinetic studies, after ingestion of – analogous to a lightning rod on the molecular esterified natural astaxanthin, only unesterified level (Figure 2).10 This polar-nonpolar-polar layout astaxanthin appears in the blood.13 This is most also allows the astaxanthin molecule to take a likely due to breaking the ester bonds by digestive transmembrane orientation, making a precise fit enzymes via their hydrolytic activity. Absorption into the polar-nonpolar-polar span of the cell into the intestinal lining cells (enterocytes) is membrane. thought to occur by passive diffusion and is Copyright © 2011 Alternative Medicine Review, LLC. All Rights Reserved. No Reprint Without Written Permission. Volume 16, Number 4 Alternative Medicine Review 356 Monograph amr Figure 2. Transverse Cell Membrane Orientation of 3S,3S’ Astaxanthin, the Major Molecular Form from H. pluvialis10 Vitamin C 3S, 3S’ Astaxanthin OH Extracellular e- e- O Space HO Oxidized O phospholipid HO OH HO OH O O Polar Heads (Hydrophilic) e- e- e- CholesterolCholesterol Bi-layer e- Membrane Fatty Acids Tails e- (Hydrophobic) O O Polar Heads OH (Hydrophilic) HO e- ROS Cytoplasm e- e- e- 3S, 3S’ Astaxanthin The polar end groups overlap the polar boundary zones of the membrane, while the nonpolar middle ts the membrane’s nonpolar interior. The dashed red line speculatively indicates “lightning-rod” conduction of electrons along the astaxanthin molecule, possibly to vitamin C or other antoxidants located outside the membrane. From: Pashkow FJ, Watumull DG, Campbell CL. Astaxanthin: a novel potential treatment for oxidative stress and inammation in cardiovascular disease. Am J Cardiol 2008;101(suppl):58D-68D. Used with permission. facilitated in the presence of fat or other lipids.14 When astaxanthin is fed to human subjects, The enterocytes then incorporate the unesterified detailed pharmacokinetic data are difficult to astaxanthin into chylomicrons, which transport it obtain for single doses of less than 10 mg, due to to the liver.13 The liver does not convert this limitations of assay precision.13 However, there is molecule to vitamin A or otherwise biochemically good data to indicate a single 10-mg dose can transform it.4 Instead it becomes incorporated into persist in the blood for 24 hours and a 100-mg low-density lipoprotein (LDL) and high-density dose for 76 hours.13 Doses as low as 1
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