Glycation and Skin Aging: A Review

Jun 1, 2011 | Contact Author | By: Zoe Diana Draelos, MD, Dermatology Consulting Services; and Peter T. Pugliese, MD
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Title: Glycation and Skin Aging: A Review
advanced glycation end productsx sugar chemistryx glucosex Maillard reactionx
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Keywords: advanced glycation end products | sugar chemistry | glucose | Maillard reaction

Abstract: The present article, adapted from Draelos and Pugliese*, provides a review of the chemistry involved in the glycation process to assist formulators in developing topical or nutricosmetic solutions for mature skin care.

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ZD Draelos and PT Pugliese, Glycation and Skin Aging: A Review, Cosm & Toil>/em> 126(6) 438 (2011)

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Editor’s note: Glycation has previously been addressed1 in terms of its impact on skin aging, and several ingredients as well as finished products making anti-glycation related claims have since appeared on the market.2–5 The present article, adapted from Draelos and Pugliese*, provides a review of the chemistry involved in the glycation process to assist formulators in developing topical or nutricosmetic solutions for mature skin care.

Glycation fortunately does not occur largely in the dermis before age 35 but once it begins, along with intrinsic aging, it progresses rapidly. These long-lived tissues are the target of advanced glycation end products (AGEs) that bind tenaciously to collagen and elastin, more avidly to elastin, which can be seen in the upper dermis in the realm of elastin. In fact, a paper by Mizutari et al. showed a section of a skin biopsy from the face of a 91-year-old revealing tangled masses of elastotic material in the upper dermis.6 Elastotic material consists of abnormal elastin fibers and protein and is usually associated with sun damage. It does not function like normal elastin and is quite stiff.

Many of the fine processes involved in glycation remain to be discovered. However, it is known that glucose and other simple sugars combine with proteins as a first step, and that sugars combine with amino acids and other compounds to initiate the process. As an example, fructoselysine, formed by glycation of the amino acid lysine, can be oxidatively cleaved to form smaller reactive compounds such as carboxy-methyl lysine (CML) and pentosidine.7

As consumers age they have a greater risk of glycation-initiated damage and their glucose level is the major culprit in initiating the formation of AGEs and glycation. Glucose, in its common closed-ring form, D-glucopyranose, is a rather unreactive molecule that is an important cellular fuel. It is the only sugar that circulates in abundance and although it is relatively harmless, as noted, it can become harmful through its transformation into an AGE by an intricate random process that occurs in animals and vegetables. This “browning” action requires no enzymes but depends merely upon temperature and an abundance of reactants.

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Figure 1. D-glucose

Figure 1. D-glucose

Figure 1 shows the structure of a simple sugar, glucose. It has six carbon atoms in a straight chain but can spontaneously react to make a circular form, shown in Figure 2, which occurs when it is placed in water.

Figure 2. Cyclic form of β-D-glucose

Figure 2. Cyclic form of β-D-glucose

Figure 1 shows the structure of a simple sugar, glucose. It has six carbon atoms in a straight chain but can spontaneously react to make a circular form, shown in Figure 2, which occurs when it is placed in water.

Figure 3. Glucosidic bond

Figure 3. Glucosidic bond

When a glucosidic linkage is found through an oxygen molecule, it is called an O-glucan, whereas a glucosidic linkage found through a nitrogen molecule is called an N-glucan. Figure 3 shows this relationship.

Figure 4. Steps in Maillard reaction

Figure 4. Steps in Maillard reaction

Figure 4 shows the steps of the Maillard reaction, which follow several pathways depending on the type of reactants or ingredients, the temperature and the pH.

Figure 5. Early stages of glycation

Figure 5. Early stages of glycation

The reaction in Figure 5 outlines the process using basic reaction groups.

Figure 6. Strecker reaction

Figure 6. Strecker reaction

Consider the Strecker degradation pathway (see Figure 6).

Figure 7. Glyoxal and methlglyoxal produced from glucose without the Maillard reaction

Figure 7. Glyoxal and methlglyoxal produced from glucose without the Maillard reaction

Figure 7 shows how both glyoxal and methylglyoxal can be produced from glucose without going through the whole Maillard reaction.

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