C-glycosylation invented by Pr Lubineau’s team: a key-reaction for innovation in cosmetics - Carbohydrate Chemistry: Chemical and Biological Approaches - page 7

4 Biological activities of synthesized C -glycosyl
derivatives: major interest of a C - b -xylosyl compound
The interest of synthesized C-glycosyl derivatives as potential activators
of the biosynthesis of GAGs was evaluated using human fibroblast
cultures and assessed by the incorporation of the D -[6-H3]-glucosamine
within the GAG fraction. 15 The main results, reported in Table 4, highlight
the better activity of compound 18.
This evaluation confirms the interest of xylose unit in the biosynthesis
of GAGs. 16 It also confirms that the C-xylosyl structure and the reduction
of the exocyclic ketone are essential to obtain the best results. Moreover,
further studies gave evidence that the b anomer was crucial to maintain
activity, as compared to the a anomer.

5 From a biomimetic approach to an industrial
development of a new eco-friendly active ingredient in
cosmetics
These results show the interest of our approach based upon biomimicry
and green chemistry to select a new active ingredient of high perform-
ance in skin anti-ageing strategy. Compound 18 selected as the best ac-
tivator of the biosynthesis of GAGs in vitro, was further confirmed also
very active in vivo in a clinical trial when topically applied. Introduced in
cosmetic skin care products, 17 it has been marketed under the trade

name Pro-Xylane t .

Table 4 Activity of C-glycosyl derivatives on the D -(6-H3)-glucosamine incorporation in
the GAG fraction by human fibroblasts (P evaluates the reproducibility of the results).

Compound [C] % P

None - 100 -

Transforming Growth Factor-b
(TGF-b) (positive control)

10 ng/mL 348 o 0.01

Xylose 0.5 mM 52 o 0.01

0.1 mM 85 W0.05

0.02 mM 106 W0.05

Lyxose 2.0 mM 86 W0.05

0.4 mM 102 W0.05

0.08 mM 90 W0.05

Compound 2 10.0 mM 161 o 0.01

o 0.01

2.0 mM 141

0.4 mM 110 W0.05

Compound 4 10.0 mM 99 W0.05

3.0 mM 119 W0.05

1.0 mM 136 o 0.01

Compound 18 3.0 mM 218 o 0.01

1.0 mM 169 o 0.01

0.3 mM 139 W0.05

Compound 10 1.0 mM 95 W0.05

0.3 mM 102 W0.05

0.1 mM 120 W0.05