Withanoside V 

Withanoside V is a blood-brain barrier-permeable withanolide derivative. Withanoside V binds strongly to Sudlow I (domain IIA) of human serum albumin (HSA) to form a stable complex and alter the secondary structure of albumin, thereby increasing helix content and reducing β-sheet and random coil. Withanoside V binds to Aβ (1-42) to block the interaction between monomers and subsequent aggregation. Withanoside V inhibits the viability of neuroblastoma cells, reduces the number of apoptotic cells induced by Aβ (1-42), and decreases ROS production. Withanoside V inhibits SARS-CoV-2 M_pro. Withanoside V can be used for research on Alzheimer's disease and coronavirus disease 2019^[1][2][3][4].

Withanoside V binds tightly to human serum albumin with a K_s of 5.33 × 10⁴ M^-1, and binds to Sudlow's site I (domain IIA) of human serum albumin with a K_s of 4.8 × 10⁴ M^-1, inducing conformational changes in human serum albumin^[1].
Withanoside V (100 μM; 6-72 h) inhibits the aggregation of Aβ (1-42) in vitro and reduces the formation of β-sheet-rich oligomers and fibrils over an incubation period of up to 72 h^[2].
Withanoside V (10-100 μM; 24-48 h) inhibits the viability of SK-N-SH cells with an IC₅₀ of 30.14 μM, and protects SK-N-SH cells from Aβ (1-42)-induced cytotoxic damage^[2].
Withanoside V (15.07 μM; 24 h) increases the proportion of early apoptotic cells in human SK-N-SH neuroblastoma cells while maintaining a high overall cell viability^[2].
Compared with cells treated with Aβ (1-42), Withanoside V (15.07 μM; 24 h) reduces the level of DNA fragmentation and the number of apoptotic cells in human SK-N-SH neuroblastoma cells^[2].
Withanoside V (15.07 μM; 24 h) significantly reduces Aβ (1-42)-induced intracellular ROS production in human SK-N-SH neuroblastoma cells^[2].
Withanoside V is a SARS-CoV-2 M_pro inhibitor with a binding affinity of -8.96 kcal/mol. It forms stable hydrogen bonds at the active site of this enzyme, and its mechanism of action is similar to that of the natural N3 inhibitor^[4].

MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.

766.91

C₄₀H₆₂O₁₄

256520-90-8

Solid

White to off-white

C[C@]1(CC2)[C@](CC[C@]1([H])[C@@H]([C@@](OC3=O)([H])CC(C)=C3C)C)([H])[C@@](CC=C4C[C@H]5O[C@@H]([C@@H]([C@H]6O)O)O[C@@H]([C@H]6O)CO[C@@H]([C@@H]([C@H]7O)O)O[C@@H]([C@H]7O)CO)([H])[C@@]2([H])[C@]4([C@H](C5)O)C

Room temperature in continental US; may vary elsewhere.

• [1]. Dubey S, et al. Elucidating the active interaction mechanism of phytochemicals withanolide and withanoside derivatives with human serum albumin. PLoS One. 2018;13(11):e0200053. Published 2018 Nov 7.  [Content Brief]

  [2]. Dubey S, et al. Improving the inhibition of β-amyloid aggregation by withanolide and withanoside derivatives. Int J Biol Macromol. 2021;173:56-65.  [Content Brief]

  [3]. Matsuda H, et al. Structures of withanosides I, II, III, IV, V, VI, and VII, new withanolide glycosides, from the roots of Indian Withania somnifera DUNAL. and inhibitory activity for tachyphylaxis to clonidine in isolated guinea-pig ileum. Bioorg Med Chem. 2001 Jun;9(6):1499-507.  [Content Brief]

  [4]. Choe J, et al. The Efficacy of Traditional Medicinal Plants in Modulating the Main Protease of SARS-CoV-2 and Cytokine Storm. Chem Biodivers. 2022;19(11):e202200655.  [Content Brief]