Marchantin A, a macrocyclic bisbibenzyl ether, isolated from the liverwort Marchantia polymorpha, inhibits protozoal growth in vitro

Sophie Jensen; Sesselja Omarsdottir; Angela Gono Bwalya; Morten Agertoug Nielsen; Deniz Tasdemir; Elin Soffia Olafsdottir

doi:10.1016/j.phymed.2012.07.011

Marchantin A, a macrocyclic bisbibenzyl ether, isolated from the liverwort Marchantia polymorpha, inhibits protozoal growth in vitro

Sophie Jensen, Sesselja Omarsdottir, Angela Gono Bwalya, Morten Agertoug Nielsen, Deniz Tasdemir, Elin Soffia Olafsdottir

Faculty of Pharmaceutical Sciences

University of Iceland

Research output: Contribution to journal › Article › peer-review

Abstract

In vitro anti-plasmodial activity-guided fractionation of a diethyl ether extract of the liverwort species Marchantia polymorpha, collected in Iceland, led to isolation of the bisbibenzyl ether, marchantin A. The structure of marchantin A (1) was confirmed by NMR and HREIMS. Marchantin A inhibited proliferation of the Plasmodium falciparum strains, NF54 (IC₅₀ = 3.41 μM) and K1 (IC₅₀ = 2.02 μM) and showed activity against other protozoan species Trypanosoma brucei rhodesiense, T. cruzi and Leishmania donovani with IC₅₀ values 2.09, 14.90 and 1.59 μM, respectively. Marchantin A was tested against three recombinant enzymes (PfFabI, PfFabG and PfFabZ) of the PfFAS-II pathway of P. falciparum for malaria prophylactic potential and showed moderate inhibitory activity against PfFabZ (IC ₅₀ = 18.18 μM). In addition the cytotoxic effect of marchantin A was evaluated. This is the first report describing the inhibitory effects of the liverwort metabolite marchantin A against these parasites in vitro.

Original language	English
Pages (from-to)	1191-1195
Number of pages	5
Journal	Phytomedicine
Volume	19
Issue number	13
DOIs	https://doi.org/10.1016/j.phymed.2012.07.011
Publication status	Published - 15 Oct 2012

Bibliographical note

Funding Information: The authors are grateful to Sigridur Jonsdottir, Science Institute, University of Iceland, for recording the NMR spectra, Dr. Nils Nyberg and Dorte Brix, Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, for HREIMS and anti-plasmodial measurements. Financial support by The Icelandic Research Fund , The University of Iceland Research Fund – Doctoral grant , Bergthora and Thorsteinn Scheving Thorsteinsson Fund are gratefully acknowledged. Angela Gono Bwalya thanks the Commonwealth Scholarship Commission for financial support.

Other keywords

Malaria
Marchantia
Marchantin A
PfFAS-II
Plasmodium
Protozoa

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.phymed.2012.07.011

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title = "Marchantin A, a macrocyclic bisbibenzyl ether, isolated from the liverwort Marchantia polymorpha, inhibits protozoal growth in vitro",

abstract = "In vitro anti-plasmodial activity-guided fractionation of a diethyl ether extract of the liverwort species Marchantia polymorpha, collected in Iceland, led to isolation of the bisbibenzyl ether, marchantin A. The structure of marchantin A (1) was confirmed by NMR and HREIMS. Marchantin A inhibited proliferation of the Plasmodium falciparum strains, NF54 (IC50 = 3.41 μM) and K1 (IC50 = 2.02 μM) and showed activity against other protozoan species Trypanosoma brucei rhodesiense, T. cruzi and Leishmania donovani with IC50 values 2.09, 14.90 and 1.59 μM, respectively. Marchantin A was tested against three recombinant enzymes (PfFabI, PfFabG and PfFabZ) of the PfFAS-II pathway of P. falciparum for malaria prophylactic potential and showed moderate inhibitory activity against PfFabZ (IC 50 = 18.18 μM). In addition the cytotoxic effect of marchantin A was evaluated. This is the first report describing the inhibitory effects of the liverwort metabolite marchantin A against these parasites in vitro.",

keywords = "Malaria, Marchantia, Marchantin A, PfFAS-II, Plasmodium, Protozoa",

author = "Sophie Jensen and Sesselja Omarsdottir and Bwalya, \{Angela Gono\} and Nielsen, \{Morten Agertoug\} and Deniz Tasdemir and Olafsdottir, \{Elin Soffia\}",

note = "Funding Information: The authors are grateful to Sigridur Jonsdottir, Science Institute, University of Iceland, for recording the NMR spectra, Dr. Nils Nyberg and Dorte Brix, Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, for HREIMS and anti-plasmodial measurements. Financial support by The Icelandic Research Fund , The University of Iceland Research Fund – Doctoral grant , Bergthora and Thorsteinn Scheving Thorsteinsson Fund are gratefully acknowledged. Angela Gono Bwalya thanks the Commonwealth Scholarship Commission for financial support.",

year = "2012",

month = oct,

day = "15",

doi = "10.1016/j.phymed.2012.07.011",

language = "English",

volume = "19",

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T1 - Marchantin A, a macrocyclic bisbibenzyl ether, isolated from the liverwort Marchantia polymorpha, inhibits protozoal growth in vitro

AU - Jensen, Sophie

AU - Omarsdottir, Sesselja

AU - Bwalya, Angela Gono

AU - Nielsen, Morten Agertoug

AU - Tasdemir, Deniz

AU - Olafsdottir, Elin Soffia

N1 - Funding Information: The authors are grateful to Sigridur Jonsdottir, Science Institute, University of Iceland, for recording the NMR spectra, Dr. Nils Nyberg and Dorte Brix, Department of Medicinal Chemistry, Faculty of Pharmaceutical Sciences, University of Copenhagen, for HREIMS and anti-plasmodial measurements. Financial support by The Icelandic Research Fund , The University of Iceland Research Fund – Doctoral grant , Bergthora and Thorsteinn Scheving Thorsteinsson Fund are gratefully acknowledged. Angela Gono Bwalya thanks the Commonwealth Scholarship Commission for financial support.

PY - 2012/10/15

Y1 - 2012/10/15

N2 - In vitro anti-plasmodial activity-guided fractionation of a diethyl ether extract of the liverwort species Marchantia polymorpha, collected in Iceland, led to isolation of the bisbibenzyl ether, marchantin A. The structure of marchantin A (1) was confirmed by NMR and HREIMS. Marchantin A inhibited proliferation of the Plasmodium falciparum strains, NF54 (IC50 = 3.41 μM) and K1 (IC50 = 2.02 μM) and showed activity against other protozoan species Trypanosoma brucei rhodesiense, T. cruzi and Leishmania donovani with IC50 values 2.09, 14.90 and 1.59 μM, respectively. Marchantin A was tested against three recombinant enzymes (PfFabI, PfFabG and PfFabZ) of the PfFAS-II pathway of P. falciparum for malaria prophylactic potential and showed moderate inhibitory activity against PfFabZ (IC 50 = 18.18 μM). In addition the cytotoxic effect of marchantin A was evaluated. This is the first report describing the inhibitory effects of the liverwort metabolite marchantin A against these parasites in vitro.

AB - In vitro anti-plasmodial activity-guided fractionation of a diethyl ether extract of the liverwort species Marchantia polymorpha, collected in Iceland, led to isolation of the bisbibenzyl ether, marchantin A. The structure of marchantin A (1) was confirmed by NMR and HREIMS. Marchantin A inhibited proliferation of the Plasmodium falciparum strains, NF54 (IC50 = 3.41 μM) and K1 (IC50 = 2.02 μM) and showed activity against other protozoan species Trypanosoma brucei rhodesiense, T. cruzi and Leishmania donovani with IC50 values 2.09, 14.90 and 1.59 μM, respectively. Marchantin A was tested against three recombinant enzymes (PfFabI, PfFabG and PfFabZ) of the PfFAS-II pathway of P. falciparum for malaria prophylactic potential and showed moderate inhibitory activity against PfFabZ (IC 50 = 18.18 μM). In addition the cytotoxic effect of marchantin A was evaluated. This is the first report describing the inhibitory effects of the liverwort metabolite marchantin A against these parasites in vitro.

KW - Malaria

KW - Marchantia

KW - Marchantin A

KW - PfFAS-II

KW - Plasmodium

KW - Protozoa

UR - https://www.scopus.com/pages/publications/84866729527

U2 - 10.1016/j.phymed.2012.07.011

DO - 10.1016/j.phymed.2012.07.011

M3 - Article

C2 - 22951393

SN - 0944-7113

VL - 19

SP - 1191

EP - 1195

JO - Phytomedicine

JF - Phytomedicine

IS - 13

ER -

Marchantin A, a macrocyclic bisbibenzyl ether, isolated from the liverwort Marchantia polymorpha, inhibits protozoal growth in vitro

Abstract

Bibliographical note

Other keywords

UN SDGs

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