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(-)-Neocaryachine, an Antiproliferative Pavine Alkaloid from Cryptocarya laevigata, Induces DNA Double-Strand Breaks

  1. Author:
    Suzuki, Yuki
    Saito, Yohei
    Goto, Masuo
    Newman, Dave
    O'Keefe, Barry
    Lee, Kuo-Hsiung
    Nakagawa-Goto, Kyoko

  2. Author Address

    Kanazawa Univ, Sch Pharmaceut Sci, Coll Med Pharmaceut & Hlth Sci, Kanazawa, Ishikawa 9201192, Japan.Univ North Carolina Chapel Hill, UNC Eshelman Sch Pharm, Nat Prod Res Labs, Chapel Hill, NC 27599 USA.NCI, Nat Prod Branch, Dev Therapeut Program, Div Canc Treatment & Diag, Frederick, MD 21702 USA.NCI, Mol Targets Lab, Ctr Canc Res, Frederick, MD 21702 USA.Univ North Carolina Chapel Hill, Lineberger Comprehens Canc Ctr, Chapel Hill, NC 27599 USA.China Med Univ & Hosp, Chinese Med Res & Dev Ctr, 2 Yuh Der Rd, Taichung 40447, Taiwan.
    1. Year: 2017
    2. Date: Jan 27
  2. Journal: JOURNAL OF NATURAL PRODUCTS
  3. AMER CHEMICAL SOC,
    1. 80
    2. 1
    3. Pages: 220-224
  5. Type of Article: Article
  6. ISSN: 0163-3864
  1. Abstract:

    Twelve benzylisoquinoline alkaloids, including pavine and phenanthroindolizidine types, were isolated from a MeOH/CH2Cl2 extract of Cryptocarya laevigata (stem bark) through bioactivity-guided fractionation for antitumor effects. Selected compounds were evaluated for antiproliferative activity against five human tumor cell lines, including a multidrug-resistant subline. Since more common 2,3,8,9-tetrasubstituted pavine alkaloids, such as crychine (3), exhibit very mild or no cytotoxicity, this compound type has not been well investigated for antitumor activity. Thus, this report is the first discovery of a 7-hydroxylated pavine alkaloid, (-)-neocaryachine (1), to demonstrate strong antiproliferative activity, with IC50 values of 0.06 to 0.41 mu M against five tested tumor cell lines, including an MDR subline. Further mechanism of action studies revealed that 1 impacts the cellular S-phase by inducing DNA double-strand breaks.

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External Sources

  1. View Full Text
  2. DOI: 10.1021/acs.jnatprod.6b01153
  3. PMID: 28099003
  4. View record in Web of Science®
  5. WOS: 000393089600031

Library Notes

  1. Fiscal Year: FY2016-2017
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