Journal
JOURNAL OF NATURAL PRODUCTS
Volume 81, Issue 8, Pages 1884-1891Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jnatprod.8b00411
Keywords
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Funding
- JSPS KAKENHI [25293024]
- NIH from the National Cancer Institute [CA177584]
- Eshelman Institute for Innovation, Chapel Hill, North Carolina
- National Cancer Institute, National Institutes of Health (NIH) [HHSN261200800001E]
- NIH, National Cancer Institute, Center for Cancer Research
- Grants-in-Aid for Scientific Research [25293024] Funding Source: KAKEN
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Alangium longiflorum is currently in extinction crisis, which will likely severely hamper further phytochemical investigation of this plant species from new collections. A crude extract of leaves of A. longiflorum (N33539), collected for the U.S. National Cancer Institute in 1989, showed potent cancer cell line antiproliferative activity. A phytochemical study resulted in the isolation of 17 secondary metabolites, including two new tetrahydroisoquinoline alkaloids, 8-hydroxytubulosine (1) and 2'-O-trans-sinapoylisoalangiside (2), as well as a new sinapolyloxylupene derivative (3). Using in-house assays and NCI-60 panel screening, compound 1 displayed broad-spectrum inhibitory activity at submicromolar levels against most tested tumor cell lines, except for drug-transporter-overexpressing cells. Compound 1 caused accumulation of sub-GI cells with no effect on cell cycle progression, suggesting that this substance is an apoptosis inducer.
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