Allobetulone rearrangement to l8αH, 19βH-ursane triterpenoids with antiviral activity. Issue 13 (1st July 2022)

• Record Type: Journal Article
• Authors: Babaev, Marat; Khusnutdinova, Elmira; Lobov, Alexander; Galimova, Zarema; Petrova, Anastasiya; Rybalova, Tatyana; Nguyen, Ha Thi Thu; Meyers, Craig; Prichard, Mark; Kazakova, Oxana
• Is Part Of: Natural product research. Volume 36:Issue 13(2022)
• Page Start: 3286
• Page End: 3296
• Publication Date: 2022-07-01
• Subjects: Triterpenoids -- betulin -- allobetulin -- lupane -- ursane -- skeleton rearrangement -- antiviral activity -- NCI-60 -- α-glucosidase; Natural products -- Periodicals; Natural products -- Research -- Periodicals; Biological Factors -- Periodicals; Biological Products -- Periodicals; 547
• DOI: 10.1080/14786419.2020.1855159
• Languages: English
• ISSNs: 1478-6419

Abstract

Abstract: Allobetulone E-ring rearrangement under treating with HClO4 in Ac2 O under reflux afforded new triterpenoids: 3, 28-diacetoxy-21-acetyl-2(3), 20(21)-18α, 19βH-ursandiene 3 and 3, 28-diacetoxy-2(3), 18(19)-oleandiene 4 . 18α, 19βH-Ursanes were transformed at A- and E-rings into indolo- and bis-furfurylidene 7 derivatives. Structure elucidation was performed using COSY, NOESY, HSQC and HMBC experiments, and X-Ray analysis for 3 . The potential of newly obtained 18α, 19βH-ursanes was evaluated against HCMV and HPV-11, the NCI-60 cancer cell panel and inhibition of α-glucosidase. All of the compounds have shown viral inhibition towards HCMV compared to standard drug Acyclovir. 3β-Acetoxy-21β-acetyl-20β, 28-epoxy-18α, 19βН-ursane 1 showed moderate activity (EC50 4.87 μM) towards the HCMV-resistant isolate (GDGr K17) compared to standard drug Cidofovir and was four times more potent than Ganciclovir. Compound 7 inhibited the cell growth of the three melanoma and one colon cancer cell. 3-Oxo-21β-acetyl-20β, 28-epoxy-18α, 19βН-ursane 5 and compound 7 inhibited α-glucosidase with IC50 28.0 µM and 4.0 µM being from 6 to 44 times more active than acarbose. Graphical Abstract: UF0001