Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 May 19;5(21):12568-12572.
doi: 10.1021/acsomega.0c01672. eCollection 2020 Jun 2.

First Total Synthesis and in Vitro Cytotoxicities of Flavesines G and J

Juris Pelss  1 , Gints Smits  1
Affiliations

First Total Synthesis and in Vitro Cytotoxicities of Flavesines G and J

Juris Pelss et al. ACS Omega. .

Abstract

The first total synthesis of flavesines G and J, natural products exhibiting antiviral activity against hepatitis B virus, is described. A robust, protecting-group-free route starting from commercially available natural product 9-azajulolidine allowed us to obtain the title compounds in a four- and five-step sequence accordingly. Flavesines G and J exhibit micromolar cytotoxicity in A549, MCF-7, HepG2, PANC-1, and HL-60 cancer cell lines.

PubMed Disclaimer

Conflict of interest statement

The authors declare no competing financial interest.

Figures

Figure 1
Figure 1
Flavesines A–J (1–10) and matrine (11).
Scheme 1
Scheme 1. Total Synthesis of Flavesines G (7) and J (10)
See this image and copyright information in PMC

Similar articles

See all similar articles

References

    1. Zhang Y.-B.; Luo D.; Yang L.; Cheng W.; He L.-J.; Kuang G.-K.; Li M.-M.; Li Y.-L.; Wang G.-C. Matrine-Type Alkaloids from the Roots of Sophora flavescens and Their Antiviral Activities against the Hepatitis B Virus. J. Nat. Prod. 2018, 81, 2259–2265. 10.1021/acs.jnatprod.8b00576. - DOI - PubMed
    1. Zhang Y.-B.; Zhan L.-Q.; Li G.-Q.; Wang F.; Wang Y.; Li Y.-L.; Ye W.-C.; Wang G.-C. Dimeric Matrine-Type Alkaloids from the Roots of Sophora flavescens and Their Anti-Hepatitis B Virus Activities. J. Org. Chem. 2016, 81, 6273–6280. 10.1021/acs.joc.6b00804. - DOI - PubMed
    1. He X.; Fang J.; Huang L.; Wang J.; Huang X. Sophora flavescens Ait.: Traditional usage, phytochemistry and pharmacology of an important traditional Chinese medicine. J. Ethnopharmacol. 2015, 172, 10–29. 10.1016/j.jep.2015.06.010. - DOI - PubMed
    1. Chinese Pharmacopoeia Commission . Chinese pharmacopoeia, 2010; Vol. 1, 172.
    1. Rashid H. u.; Xu Y.; Muhammad Y.; Wang L.; Jiang J. Research advances on anticancer activities of matrine and its derivatives: An updated overview. Eur. J. Med. Chem. 2019, 161, 205–238. 10.1016/j.ejmech.2018.10.037. - DOI - PubMed