2. Academic Validation
  3. Paliasanines A-E, 3,4-Methylenedioxyquinoline Alkaloids Fused with a Phenyl-14-oxabicyclo[3.2.1]octane Unit from Melochia umbellata var. deglabrata

Paliasanines A-E, 3,4-Methylenedioxyquinoline Alkaloids Fused with a Phenyl-14-oxabicyclo[3.2.1]octane Unit from Melochia umbellata var. deglabrata

  • J Nat Prod. 2020 Oct 23;83(10):2931-2939. doi: 10.1021/acs.jnatprod.0c00454.
Abdul Rahim 1 2,  Yohei Saito 1,  Shuichi Fukuyoshi 1,  Katsunori Miyake 3,  Masuo Goto 4,  Chin-Ho Chen 5,  Gemini Alam 2,  Kuo-Hsiung Lee 4 6,  Kyoko Nakagawa-Goto 1 4
Affiliations

Affiliations

  • 1 School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa, 920-1192, Japan.
  • 2 Department of Pharmacognosy-Phytochemistry, Faculty of Pharmacy, Hasanuddin University, Makassar, 90245, Indonesia.
  • 3 School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, Hachioji, Tokyo 192-0392, Japan.
  • 4 Division of Chemical Biology and Medicinal Chemistry, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill, North Carolina 27599-7568, United States.
  • 5 Duke University Medical Center, Durham, North Carolina 27710, United States.
  • 6 Chinese Medicine Research and Development Center, China Medical University and Hospital, Taichung 401, Taiwan.
PMID: 32946697 DOI: 10.1021/acs.jnatprod.0c00454
Abstract

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.

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