A new lipophilic pro-vitamin C, tetra-isopalmitoyl ascorbic acid (VC-IP), prevents UV-induced skin pigmentation through its anti-oxidative properties.
BACKGROUND
Vitamin C, which is a strong anti-oxidant, plays an important role in maintaining physiological states. In dermatology, Vitamin C is used for treatment of various skin problems such as de-pigmentation of hyperpigmented spots. However, Vitamin C has limited stability and permeability, and development of a Vitamin C derivative with improved properties is needed.


OBJECTIVE
We evaluated the effect of a lipophilic Vitamin C derivative, tetra-isopalmitoyl ascorbic acid (VC-IP), on ultraviolet (UV)-induced skin pigmentation, to determine its potential as a more effective form of Vitamin C.


METHODS
The release of Vitamin C from VC-IP was examined using a reconstructed skin model following topical application of VC-IP. Anti-oxidative and anti-inflammatory activities of VC-IP were tested in cultured human keratinocytes. Subsequently, clinical test was done to clarify the effect of VC-IP on UVB-induced skin pigmentation.


RESULTS
VC-IP released Vitamin C in physiological conditions and worked as pro-Vitamin C. In subsequent experiments, we found that VC-IP suppressed the elevation of intracellular peroxide after UVB irradiation, and enhanced cellular tolerance against UVB and reactive oxygen species such as hydrogen peroxide and tert-butyl hydroperoxide. Furthermore, VC-IP reduced the production of interleukin-1alpha and prostaglandin E2 in UVB-irradiated keratinocytes and suppressed melanocyte proliferation in conditioned culture medium prepared from UVB-irradiated keratinocytes. Finally, in a clinical study, topical application of a 3% VC-IP cream for 3 weeks suppressed pigmentation after UVB irradiation.


CONCLUSIONS
These results demonstrate that VC-IP is a precursor of Vitamin C, and effectively suppresses UVB-induced skin pigmentation, possibly through its anti-oxidative activity.
Ochiai
Yasunobu
Y
Cosmos Technical Center Co., Ltd., 3-24-3, Hasune, Itabashi-Ku, Tokyo 174-0046, Japan. ochiai@ns-cosmos.co.jp
Kaburagi
Satoko
S
Obayashi
Kei
K
Ujiie
Nobuyuki
N
Hashimoto
Satoru
S
Okano
Yuri
Y
Masaki
Hitoshi
H
Ichihashi
Masamitsu
M
Sakurai
Hiromu
H
D000328:Adult; D000975:Antioxidants / Q000008:administration & dosage* / Q000737:chemistry / Q000493:pharmacokinetics; D001205:Ascorbic Acid / Q000008:administration & dosage / Q000031:analogs & derivatives* / Q000737:chemistry / Q000378:metabolism / Q000493:pharmacokinetics; D002455:Cell Division; D002461:Cell Line, Transformed; D015232:Dinoprostone / Q000378:metabolism; D005260:Female; D006017:Glycolipids / Q000008:administration & dosage* / Q000737:chemistry / Q000493:pharmacokinetics; D006801:Humans; D053582:Interleukin-1alpha / Q000378:metabolism; D015603:Keratinocytes / Q000166:cytology / Q000187:drug effects* / Q000528:radiation effects; D008297:Male; D008544:Melanocytes / Q000187:drug effects / Q000378:metabolism / Q000528:radiation effects; D018384:Oxidative Stress / Q000187:drug effects; D012880:Skin Pigmentation / Q000187:drug effects* / Q000528:radiation effects; D013400:Sugar Acids; D014466:Ultraviolet Rays
D000975:Antioxidants; D006017:Glycolipids; D053582:Interleukin-1alpha; D013400:Sugar Acids; C515144:tetra-isopalmitoyl ascorbic acid; C011491:provitamin C; D015232:Dinoprostone; D001205:Ascorbic Acid