Paliasanines A-E, 3,4-Methylenedioxyquinoline Alkaloids Fused with a Phenyl-14-oxabicyclo[3.2.1]octane Unit from Melochia umbellata var. deglabrata.
Five new quinoline alkaloids, paliasanines A-E (1-5), and 17 known compounds (6-22) were isolated from a methanol extract of Melochia umbellata var. deglabrata leaves. Their chemical structures were elucidated by analysis of HRMS and 1D and 2D NMR spectroscopic data. Compounds 1-5 are the first naturally occurring 3,4-methylenedioxyquinolines incorporating an oxabicyclo[3.2.1]octane unit. Compounds 6 and 7 displayed selective cytotoxicity (IC50 5.9-8.4 μM) against A549 and MCF-7 cell lines, while compounds 1-5 were not active. Compounds 1-3 did not exhibit an anti-HIV effect in MT4 cells, although the related quinolone derivative waltherione A exhibited significant activity. These preliminary results indicate that the 3-methoxy-4-quinolone skeleton might be preferred for both antiproliferative and anti-HIV activities.
Duke Scholars
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- Quinolines
- Plant Extracts
- Medicinal & Biomolecular Chemistry
- Malvaceae
- Antineoplastic Agents, Phytogenic
- Alkaloids
- 4208 Traditional, complementary and integrative medicine
- 11 Medical and Health Sciences
- 06 Biological Sciences
- 03 Chemical Sciences
Citation
Published In
DOI
EISSN
Publication Date
Volume
Issue
Start / End Page
Location
Related Subject Headings
- Quinolines
- Plant Extracts
- Medicinal & Biomolecular Chemistry
- Malvaceae
- Antineoplastic Agents, Phytogenic
- Alkaloids
- 4208 Traditional, complementary and integrative medicine
- 11 Medical and Health Sciences
- 06 Biological Sciences
- 03 Chemical Sciences