Allobetulone rearrangement to l8αH,19βH-ursane triterpenoids with antiviral activity

Allobetulone rearrangement to l8αH,19βH-ursane triterpenoids with antiviral activity Full article

Journal

Natural Product Research
ISSN: 1478-6419 , E-ISSN: 1478-6427

Output data

Year: 2020, DOI: 10.1080/14786419.2020.1855159

Tags

allobetulin; antiviral activity; betulin; lupane; NCI-60; skeleton rearrangement; Triterpenoids; ursane; α-glucosidase

Authors

Babaev Marat ¹ , Khusnutdinova Elmira ¹ , Lobov Alexander ¹ , Galimova Zarema ¹ , Petrova Anastasiya ¹ , Rybalova Tatyana ² , Nguyen Ha Thi Thu ³ , Meyers Craig ⁴ , Prichard Mark ⁵ , Kazakova Oxana ¹

Affiliations

1	Ufa Institute of Chemistry UFRC RAS, Ufa, Russian Federation
2	N.N. Vorozhtzov, Novosibirsk Institute of Organic Chemistry SB RAS, Novosibirsk, Russian Federation
3	Institute of Chemistry, Vietnamese Academy of Science and Technology, Cau Giay Dist, Hanoi, Viet Nam
4	Penn State College of Medicine, Hershey, PA, United States
5	University of Alabama at Birmingham, Birmingham, AL, United States

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. © 2020 Informa UK Limited, trading as Taylor & Francis Group.

Babaev M. , Khusnutdinova E. , Lobov A. , Galimova Z. , Petrova A. , Rybalova T. , Nguyen H.T.T. , Meyers C. , Prichard M. , Kazakova O.
Allobetulone rearrangement to l8αH,19βH-ursane triterpenoids with antiviral activity
Natural Product Research. 2020. DOI: 10.1080/14786419.2020.1855159 WOS Scopus

Published online:

Dec 8, 2020

Web of science	WOS:000597012200001
Scopus	2-s2.0-85097319749
OpenAlex	W3113202492