142449-89-6
Chemical Structure
Vitisin A
Synonym(s): (+)-Vitisin A
- CAS No.: 142449-89-6
- Formula:C56H42O12
- Molecular Weight:906.93
IUPAC Name: (1S,6R,7S,11bS)-6-(5-((E)-2-((2S,3S)-3-(3,5-dihydroxyphenyl)-6-hydroxy-2-(4-hydroxyphenyl)-2,3-dihydrobenzofuran-4-yl)vinyl)-2-hydroxyphenyl)-1,7-bis(4-hydroxyphenyl)-1,6,7,11b-tetrahydrobenzo[6,7]cyclohepta[1,2,3-cd]benzofuran-4,8,10-triol
InChIKey: XAXVWWYPKOGXSY-DBHYGPPCSA-N
SMILES: OC1=CC2=C(C3=C1)[C@]([C@@H](C(C=C4)=CC=C4O)O3)([H])C5=CC(O)=CC(O)=C5[C@H](C(C=C6)=CC=C6O)[C@H]2C7=CC(/C=C/C8=C9[C@H](C%10=CC(O)=CC(O)=C%10)[C@@H](C(C=C%11)=CC=C%11O)OC9=CC(O)=C8)=CC=C7O
Biological Activity: Vitisin A ((+)-Vitisin A) is an orally active natural product with multiple pharmacological activities including anti-inflammatory, anti-tumor, anti-oxidant, anti-pathogenic microorganism, hypoglycemic and lipid-regulating, anti-osteoporotic, neuroprotective and cardiovascular protective effects. Vitisin A exhibits inhibitory effects on human AChE and MAO-B with IC50 values of 1.29 µM and 4.94 µM, respectively. Vitisin A inhibits the ERK, MAPK, NF-κB, STAT1, HMGCR and TRAF6 pathways, downregulates the related phosphorylation and protein expression, while activates the Nrf2/HO-1 pathway and upregulates p21 expression. Vitisin A induces tumor cell apoptosis and cell cycle arrest, inhibits adipogenesis and lipid accumulation, while alleviates oxidative stress, suppresses inflammatory responses, blocks hepatic fibrosis, Cuproptosis and cholesterol synthesis, and increases the expression levels of central BDNF and TrkB. Vitisin A can be used in the research of tumors, infectious diseases, metabolic diseases, bone and joint diseases, liver diseases, skin injuries, as well as neurodegenerative and cognitive dysfunction-related diseases[1][2][3][4][5].
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Vitisin A | 96% | Vitisin A ((+)-Vitisin A) is an orally active natural product with multiple pharmacological activities including anti-inflammatory, anti-tumor, anti-oxidant, anti-pathogenic microorganism, hypoglycemic and lipid-regulating, anti-osteoporotic, neuroprotective and cardiovascular protective effects. Vitisin A exhibits inhibitory effects on human AChE and MAO-B with IC50 values of 1.29 µM and 4.94 µM, respectively. Vitisin A inhibits the ERK, MAPK, NF-κB, STAT1, HMGCR and TRAF6 pathways, downregulates the related phosphorylation and protein expression, while activates the Nrf2/HO-1 pathway and upregulates p21 expression. Vitisin A induces tumor cell apoptosis and cell cycle arrest, inhibits adipogenesis and lipid accumulation, while alleviates oxidative stress, suppresses inflammatory responses, blocks hepatic fibrosis, Cuproptosis and cholesterol synthesis, and increases the expression levels of central BDNF and TrkB. Vitisin A can be used in the research of tumors, infectious diseases, metabolic diseases, bone and joint diseases, liver diseases, skin injuries, as well as neurodegenerative and cognitive dysfunction-related diseases. | ||||||||||||||||||||
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- [1]. Bakrim S., et al. Vitisin a and B: Natural sources, chemistry, metabolism, pharmacological properties, and health benefits – A comprehensive review. Journal of Functional Foods, 2025, 127: 106774.
- [2]. Ding S, et al. Vitisin A inhibits liver fibrosis by promoting Nrf2/HO-1 pathway and inhibiting Cuproptosis. Sci Rep. 2025;15(1):44186. Published 2025 Dec 19. [Content Brief]
- [3]. Kim S.-h., et al. Vitisin A inhibits adipocyte differentiation through cell cycle arrest in 3T3-L1 cells. Biochemical and Biophysical Research Communications, 2008, 372(1): 108-113.
- [4]. Mi Jeong Sung, et al. Vitisin A suppresses LPS-induced NO production by inhibiting ERK, p38, and NF-kappaB activation in RAW 264.7 cells. Int Immunopharmacol. 2009;9(3):319-323. [Content Brief]
- [5]. Chen LG, et al. Vitisin A, a Resveratrol Tetramer, Improves Scopolamine-Induced Impaired Learning and Memory Functions in Amnesiac ICR Mice. Biomedicines. 2022;10(2):273. Published 2022 Jan 26. [Content Brief]
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