TY - JOUR
T1 - Allobetulone rearrangement to l8αH,19βH-ursane triterpenoids with antiviral activity
AU - Babaev, Marat
AU - Khusnutdinova, Elmira
AU - Lobov, Alexander
AU - Galimova, Zarema
AU - Petrova, Anastasiya
AU - Rybalova, Tatyana
AU - Nguyen, Ha Thi Thu
AU - Meyers, Craig
AU - Prichard, Mark
AU - Kazakova, Oxana
N1 - Funding Information:
This work was supported by the Russian Foundation for Basic Research (project no. 19-33-60083 for MSB) and the Federal program (Nº AAAA-A20-120012090029-0). The study of antiviral activity was funded in whole or in part with Federal funds from the National Institutes of Allergy and Infectious Diseases, National Institutes of Health, Department of Health and Human Services (contract HHSN272201100016I). We thank National Cancer Institute for the screening of cytotoxicity for compounds 3 and 7 . The study of α-glucosidase inhibitory activity was supported by National Foundation for Science and Technology Development of Vietnam QTRU01.05/20-21.
Publisher Copyright:
© 2020 Informa UK Limited, trading as Taylor & Francis Group.
PY - 2022
Y1 - 2022
N2 - Allobetulone E-ring rearrangement under treating with HClO4 in Ac2O 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.
AB - Allobetulone E-ring rearrangement under treating with HClO4 in Ac2O 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.
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U2 - 10.1080/14786419.2020.1855159
DO - 10.1080/14786419.2020.1855159
M3 - Article
C2 - 33287588
AN - SCOPUS:85097319749
SN - 1478-6419
VL - 36
SP - 3286
EP - 3296
JO - Natural Product Research
JF - Natural Product Research
IS - 13
ER -
