Synthesis of messagenin and platanic acid chalcone derivatives and their biological potential

Synthesis of messagenin and platanic acid chalcone derivatives and their biological potential Full article

Journal

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

Output data

Year: 2021, DOI: 10.1080/14786419.2021.1922904

Tags

Alpha-glucosidase; anticancer; antiviral; betulin; betulonic acid; chalcone; Claisen‒Schmidt reaction; messagenin; platanic acid

Authors

Khusnutdinova Elmira ¹ , Galimova Zarema ¹ , Lobov Alexander ¹ , Baikova Irina ¹ , Kazakova Oxana ¹ , Thu Ha Nguyen Thi ^2,3 , Tuyen Nguyen Van ^2,3 , Gatilov Yuri ⁴ , Csuk René ⁵ , Serbian Immo ⁵ , Hoenke Sophie ⁵

Affiliations

1	Ufa Institute of Chemistry UFRC RAS, Oktyabrya, Russian Federation
2	Vietnamese Academy of Science and Technology, Institute of Chemistry, Cau Giay Dist, Hanoi, Viet Nam
3	Graduate University of Sciences and Technology, Cau Giay Dist, Hanoi, Viet Nam
4	N.N.Vorozhtzov, Novosibirsk Institute of Organic Chemistry SB RAS, Novosibirsk, Russian Federation
5	Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Halle (Saale), Germany

The chalcone derivatives of 20-oxo-lupanes have been synthesised and screened for some types of biological activity. Ozonolysis of lupanes afforded 20-oxo-derivatives with the following condensation using different aromatic aldehydes by Claisen‒Schmidt reaction to the target compounds. The E configuration of 19-[3-(pyridin-3-yl)-prop-2-en-1-one]-fragment was established by X-ray analysis. Screening of cytotoxic activity against NCI-60 cancer cell line panel revealed, that messagenin derivative 9 has the highest activity with GI50 value ranged from 0.304 to 0.804 μM. A colorimetric SRB assay revealed for the 2,30-bis-furfurylidene derivative 11 and 30-bromo-20-oxo-29-nor-3,28-diacetoxy-betulin 16 cytotoxic activity against breast carcinoma MCF-7 and ovarian carcinoma A2780 cell lines. Compounds 11 and 13 acted also as inhibitors of the enzyme α-glucosidase (from S. saccharomyces) with IC50 values of 1.76 μM and 3.3 μM thus being 97- and 52-fold more active than standard acarbose. Antiviral potency of compounds 12 and 14 against HCMV, HSV-1 and HPV is also discussed. © 2021 Informa UK Limited, trading as Taylor & Francis Group.

Khusnutdinova E. , Galimova Z. , Lobov A. , Baikova I. , Kazakova O. , Thu H.N.T. , Tuyen N.V. , Gatilov Y. , Csuk R. , Serbian I. , Hoenke S.
Synthesis of messagenin and platanic acid chalcone derivatives and their biological potential
Natural Product Research. 2021. DOI: 10.1080/14786419.2021.1922904 WOS Scopus

Published online:

May 10, 2021

Web of science	WOS:000648769200001
Scopus	2-s2.0-85106321719
OpenAlex	W3162819754