Cytotoxic Alkaloids from Leaves of Pilea aff. martinii

Ai Doan Thi Thuy; Van Trinh Thi Thanh; Huong Doan Thi Mai; Huyen Tram Le; Marc Litaudon; Van Hung Nguyen; Van Minh Chau; Van Cuong Pham

doi:10.1055/a-0826-0483

Planta Medica, Table of Contents

Planta Med 2019; 85(06): 496-502
DOI: 10.1055/a-0826-0483

Natural Product Chemistry and Analytical Studies

Original Papers

Georg Thieme Verlag KG Stuttgart · New York

Cytotoxic Alkaloids from Leaves of Pilea aff. martinii

Authors

Ai Doan Thi Thuy

¹Advanced Center for Bioorganic Chemistry, Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam

²National University of Agriculture, Trau Quy, Hanoi, Vietnam
Van Trinh Thi Thanh

¹Advanced Center for Bioorganic Chemistry, Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam
Huong Doan Thi Mai

¹Advanced Center for Bioorganic Chemistry, Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam
Huyen Tram Le

³Hanoi University of Science and Technology (HUST), Hanoi, Vietnam
Marc Litaudon

⁴Institut de Chimie des Substances Naturelles, CNRS-ICSN, UPR 2301, Université Paris-Sud, Paris, France
Van Hung Nguyen

¹Advanced Center for Bioorganic Chemistry, Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam
Van Minh Chau

¹Advanced Center for Bioorganic Chemistry, Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam
Van Cuong Pham

¹Advanced Center for Bioorganic Chemistry, Institute of Marine Biochemistry of the Vietnam Academy of Science and Technology (VAST), Hanoi, Vietnam

Abstract

Two new phenanthroquinolizidine alkaloids (1 and 2) and a new piperidine derivative (3) were isolated from the leaves of Pilea aff. martinii together with 3 known alkaloids: julandine (4), cryptopleurine (5), and 1,3,6,6-tetramethyl-5,6,7,8-tetrahydro-isoquinolin-8-one (6). Their structures were determined by spectral data analyses including mass spectrometry and 2-dimensional nuclear magnetic resonance data. The absolute configurations of 1–3 were established by comparison of their experimental circular dichroism data with the calculated electronic circular dichroism spectra. The isolated compounds were evaluated for their cytotoxicity against 4 cancer cell lines: KB (mouth epidermal carcinoma cells), HepG-2 (human liver hepatocellular carcinoma cells), LU-1 (human lung adenocarcinoma cells), and MCF-7 (human breast cancer cells). The new phenanthroquinolizidine pileamartine D (2) showed strong and selective proliferation inhibition toward KB and HepG-2 cells with IC₅₀ values of 25 and 27 nM, respectively. Pileamartine C (1), julandine (4), and cryptopleurine (5) exhibited cytotoxicity against 4 tested cancer cell lines with IC₅₀ values less than 1 µM.

Key words

Pilea aff. martinii - Urticaceae - pileamartine - cytotoxic - alkaloid - pileamartine - phenanthroquinolizidine

Full Text

References

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