Synthesis of Ascorbic Acid Derivatives with Different Types of C8 Straight Acyl Chain and Their Neurite Outgrowth-Enhancing Activities.
J Nutr Sci Vitaminol (Tokyo)
; 68(3): 236-239, 2022.
Article
in En
| MEDLINE
| ID: mdl-35768255
ABSTRACT
We previously reported that 2-O-α-D-glucopyranosyl-6-O-octanoyl-L-ascorbic acid, having a C8 straight acyl chain, at a concentration of 100 µM remarkably enhanced nerve growth factor (NGF)-induced neurite outgrowth in PC12 cells after being metabolized to L-ascorbic acid (AA) as an active form by esterase and α-glucosidase. In this study, to examine the structure-activity relationship of 6-O-substituted AA derivatives with a C8 straight acyl chain for neurite outgrowth-promoting activity, we synthesized AA derivatives 1-4 and compared their activities for promoting NGF-induced neurite outgrowth in PC12 cells. AA derivatives 1-4 showed neurite outgrowth-enhancing activity at 100 µM, while AA derivative 2 also showed the enhancing activity at 3 µM. Furthermore, AA derivative 2 as well as AA enhanced NGF-induced neurite outgrowth after being incorporated into PC12 cells via sodium-dependent vitamin C transporter as an anion transporter. The results suggested that AA derivative 2 has neurite outgrowth-enhancing activity in its intact form at a low concentration (3 µM) and that AA derivatives 1-4 showed their activities in the form of AA, a metabolite of these derivatives, at a higher concentration (100 µM).
Key words
Full text:
1
Collection:
01-internacional
Database:
MEDLINE
Main subject:
Ascorbic Acid
/
Nerve Growth Factor
Limits:
Animals
Language:
En
Journal:
J Nutr Sci Vitaminol (Tokyo)
Year:
2022
Document type:
Article