Antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of Garcinia mckeaniana

© 2016 Elsevier Ltd The first phytochemical investigation of the leaf and branch extracts of Garcinia mckeaniana has led to the isolation and characterization of five new polyoxygenated and prenylated xanthones, mckeanianones A-E (1–5), and one new biflavone, mckeaniabiflavone (6), together with 13...

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Main Authors: Chiramet Auranwiwat, Surat Laphookhieo, Roonglawan Rattanajak, Sumalee Kamchonwongpaisan, Stephen G. Pyne, Thunwadee Ritthiwigrom
Format: Journal
Published: 2018
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http://cmuir.cmu.ac.th/jspui/handle/6653943832/55311
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spelling th-cmuir.6653943832-553112018-09-05T03:12:44Z Antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of Garcinia mckeaniana Chiramet Auranwiwat Surat Laphookhieo Roonglawan Rattanajak Sumalee Kamchonwongpaisan Stephen G. Pyne Thunwadee Ritthiwigrom Biochemistry, Genetics and Molecular Biology Chemistry Pharmacology, Toxicology and Pharmaceutics © 2016 Elsevier Ltd The first phytochemical investigation of the leaf and branch extracts of Garcinia mckeaniana has led to the isolation and characterization of five new polyoxygenated and prenylated xanthones, mckeanianones A-E (1–5), and one new biflavone, mckeaniabiflavone (6), together with 13 known compounds (7–19). The diprenylated pyrano-xanthones (1–3) and the biflavone (6) were isolated from the leaves while the monoprenylated xanthones (4 and 5) were isolated from the branches. The structures of all isolated compounds were elucidated based on spectroscopic methods and were evaluated for their antimalarial activities against the Plasmodium falciparum strains, TM4 (drug sensitive strain) and K1 (a multidrug resistant strain), and cytotoxicity against a Vero cell line (African green monkey kidney epithelial cells). The pyrano-xanthones (1–3, 7 and 8), having two isoprene units, were generally the most active compounds with IC50values in the range of 6.0±1.1_8.5±1.2 and 3.6±1.7_7.3±1.2 μM, respectively against the TM4 and K1 strains. Of these compounds 2, 3 and 8 were 2–5 times less cytotoxic against a Vero cell line (IC50values of 12.6±0.9, 29.5±3.9 and 13.2±4.6 μM, respectively) in comparison with their antiplasmodial activities. 2018-09-05T02:54:17Z 2018-09-05T02:54:17Z 2016-01-01 Journal 14645416 00404020 2-s2.0-84988835934 10.1016/j.tet.2016.09.018 https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84988835934&origin=inward http://cmuir.cmu.ac.th/jspui/handle/6653943832/55311
institution Chiang Mai University
building Chiang Mai University Library
country Thailand
collection CMU Intellectual Repository
topic Biochemistry, Genetics and Molecular Biology
Chemistry
Pharmacology, Toxicology and Pharmaceutics
spellingShingle Biochemistry, Genetics and Molecular Biology
Chemistry
Pharmacology, Toxicology and Pharmaceutics
Chiramet Auranwiwat
Surat Laphookhieo
Roonglawan Rattanajak
Sumalee Kamchonwongpaisan
Stephen G. Pyne
Thunwadee Ritthiwigrom
Antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of Garcinia mckeaniana
description © 2016 Elsevier Ltd The first phytochemical investigation of the leaf and branch extracts of Garcinia mckeaniana has led to the isolation and characterization of five new polyoxygenated and prenylated xanthones, mckeanianones A-E (1–5), and one new biflavone, mckeaniabiflavone (6), together with 13 known compounds (7–19). The diprenylated pyrano-xanthones (1–3) and the biflavone (6) were isolated from the leaves while the monoprenylated xanthones (4 and 5) were isolated from the branches. The structures of all isolated compounds were elucidated based on spectroscopic methods and were evaluated for their antimalarial activities against the Plasmodium falciparum strains, TM4 (drug sensitive strain) and K1 (a multidrug resistant strain), and cytotoxicity against a Vero cell line (African green monkey kidney epithelial cells). The pyrano-xanthones (1–3, 7 and 8), having two isoprene units, were generally the most active compounds with IC50values in the range of 6.0±1.1_8.5±1.2 and 3.6±1.7_7.3±1.2 μM, respectively against the TM4 and K1 strains. Of these compounds 2, 3 and 8 were 2–5 times less cytotoxic against a Vero cell line (IC50values of 12.6±0.9, 29.5±3.9 and 13.2±4.6 μM, respectively) in comparison with their antiplasmodial activities.
format Journal
author Chiramet Auranwiwat
Surat Laphookhieo
Roonglawan Rattanajak
Sumalee Kamchonwongpaisan
Stephen G. Pyne
Thunwadee Ritthiwigrom
author_facet Chiramet Auranwiwat
Surat Laphookhieo
Roonglawan Rattanajak
Sumalee Kamchonwongpaisan
Stephen G. Pyne
Thunwadee Ritthiwigrom
author_sort Chiramet Auranwiwat
title Antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of Garcinia mckeaniana
title_short Antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of Garcinia mckeaniana
title_full Antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of Garcinia mckeaniana
title_fullStr Antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of Garcinia mckeaniana
title_full_unstemmed Antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of Garcinia mckeaniana
title_sort antimalarial polyoxygenated and prenylated xanthones from the leaves and branches of garcinia mckeaniana
publishDate 2018
url https://www.scopus.com/inward/record.uri?partnerID=HzOxMe3b&scp=84988835934&origin=inward
http://cmuir.cmu.ac.th/jspui/handle/6653943832/55311
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