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Furanoheliangolides from Centratherum punctatum and a General Approach for Stereochemical Assignment of Flexible Chiral Side Chains

  1. Author:
    Khong,Quan
    Marron,Lindsay
    Huang, Shar-Yin Naomi
    Dalilian, Masoumeh
    Saha, Sourav
    Goncharova,Ekaterina
    Woldemichael, Girma M
    Pommier, Yves
    O'Keefe,Barry [ORCID]
    Wilson,Brice [ORCID]
    Du,Lin [ORCID]

  2. Author Address

    Molecular Targets Program, Center for Cancer Research, National Cancer Institute, Frederick, Maryland 21702, United States., Laboratory of Molecular Pharmacology, Center for Cancer Research, National Cancer Institute, Bethesda, Maryland 20892, United States., Advanced Biomedical Computational Science, Frederick National Laboratory for Cancer Research, Frederick, Maryland 21701, United States., Leidos Biomedical Res., Frederick National Laboratory for Cancer Research, Frederick, Maryland 21701, United States., Natural Products Branch, Developmental Therapeutics Program, Division of Cancer Treatment and Diagnosis, National Cancer Institute, Frederick, Maryland 21701, United States.,
    1. Year: 2025
    2. Date: May 22
    3. Epub Date: 2025 05 22
  2. Journal: Journal of Natural Products
  4. Type of Article: Article
  1. Abstract:

    Human topoisomerase 3ß (TOP3B) is a potential molecular therapeutic target for cancer and viral infections. A high-throughput differential cell viability assay using colon cancer cell lines was developed to identify natural product modulators of TOP3B-associated cancer cell viability. The assay identified an organic extract of the plant Centratherum punctatum as having cytotoxic activity. Seven new furanoheliangolides, centratherolides A-G (1-7), along with two known analogues (2,3-epoxybutyryloxy)-goyazensolanolide (8) and goyazensolide (9), were isolated. Compounds 1, 8, and 9 exhibited selective cytotoxic activities against the TOP3B-knockout (TOP3B-KO) human colon carcinoma HCT116 cells compared with the wild-type HCT116 cells (TOP3B-WT). The challenging absolute configuration determination of the flexible chiral side chains in selected analogues (1-4 and 8) was resolved by combined approaches, including synthesis of chemical standards, DFT ECD calculation, and chiral HPLC analysis. Application of this elucidation methodology to a commercial sesquiterpene lactone clarified a contradiction in the stereochemical assignments reported for centaurepensin/chlorohyssopifolin A and 17-epi-chlorohyssopifolin A.

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External Sources

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  2. DOI: 10.1021/acs.jnatprod.5c00329
  3. PMID: 40402310

Library Notes

  1. Fiscal Year: FY2024-2025
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