2. Academic Validation
  3. 2-O-β-d-glucopyranosyl-l-ascorbic acid, a novel vitamin C derivative from Lycium barbarum, prevents oxidative stress

2-O-β-d-glucopyranosyl-l-ascorbic acid, a novel vitamin C derivative from Lycium barbarum, prevents oxidative stress

  • Redox Biol. 2019 Jun:24:101173. doi: 10.1016/j.redox.2019.101173.
Shen-Fei Wang 1,  Xin Liu 1,  Mo-Yu Ding 1,  Shuangcheng Ma 2,  Jing Zhao 3,  Ying Wang 4,  Shaoping Li 5
Affiliations

Affiliations

  • 1 Institute of Chinese Medical Sciences and State Key Laboratory of Quality Research in Chinese Medicine, University of Macau, Avenida da Universidade, Taipa, Macao SAR, China.
  • 2 Institute of Chinese Medical Sciences and State Key Laboratory of Quality Research in Chinese Medicine, University of Macau, Avenida da Universidade, Taipa, Macao SAR, China; National Institutes for Food and Drug Control, Beijing, 100050, China.
  • 3 Institute of Chinese Medical Sciences and State Key Laboratory of Quality Research in Chinese Medicine, University of Macau, Avenida da Universidade, Taipa, Macao SAR, China. Electronic address: [email protected].
  • 4 Institute of Chinese Medical Sciences and State Key Laboratory of Quality Research in Chinese Medicine, University of Macau, Avenida da Universidade, Taipa, Macao SAR, China. Electronic address: [email protected].
  • 5 Institute of Chinese Medical Sciences and State Key Laboratory of Quality Research in Chinese Medicine, University of Macau, Avenida da Universidade, Taipa, Macao SAR, China. Electronic address: [email protected].
PMID: 30903981 DOI: 10.1016/j.redox.2019.101173
Abstract

Reducing agents are crucial for the management of maladaptive inflammation-induced macrophage death and hematopoietic toxicity of chemotherapy. 2-O-β-d-glucopyranosyl-l-ascorbic acid (AA-2βG), a unique AA (or vitamin C) derivative identified in Lycium barbarum, exhibited enhanced free radical scavenging activity compared with AA and its synthetic derivative AA-2αG. AA-2βG protected hydrogen peroxide-induced cell death in murine macrophage RAW264.7 cells. Treatment with AA-2βG eliminated oxidative stress and the ratio of cellular glutathione to glutathione disulfide more effectively than AA and AA-2αG. AA-2βG also significantly reduced the fluorescent intensity of DCFH-DA triggered by chemotherapeutic agent camptotehcin-11 but not fluorouracil. AA, AA-2αG, and AA-2βG significantly decreased Keap-1expression, and increased the expression levels of nuclear factor E2-related factor 2 (Nrf2) and heme oxygenase-1. All compounds triggered the nuclear translocation of Nrf2, while the ability of AA-2βG to enhance the Nrf2-DNA binding affinity was approximately two fold as those of AA and AA-2αG. Sodium ascorbate cotransporters (SVCT) inhibitors, sulfinpyrazone, phloretin, and 3-O-methyglucose, potently abrogated the free radical scavenging activities of AA, AA-2αG, and AA-2βG. The cellular uptake efficacy of AA-2αG and AA-2βG was less than 10% of AA, while the inhibition of SVCT with sulfinpyrazone considerably diminished the uptake efficacy of these compounds. AA-2αG and AA-2βG are more stable in the Fenton reagents than AA. In summary, AA-2βG from L. barbarum with excellent free radical scavenging activity is a promising natural AA derivative for further pharmacological evaluation.

Keywords

2-O-β-d-glucopyranosyl-(l)-ascorbic acid (AA-2βG); Ascorbic acid; Lycium barbarum; Nuclear factor E2-related factor 2 (Nrf2); Oxidative stress.

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