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

Jensen, S.; Ómarsdóttir, Sesselja; Bwalya, Angela Gono; Nielsen, Morten A.; Taşdemir, Deniz; Ólafsdóttir, Elín Soffia

doi:10.1016/j.phymed.2012.07.011

Cited by 31 publications

(33 citation statements)

References 32 publications

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“…The cytotoxicity against BMDM mirrors those against the macrophages J774.1. With regard to antileishmanial activity cinnamic acid menthyl (20) and thymyl ester (19) show good activities combined with low cytotoxicity. Again the cinnamic acid bornyl ester (15) is the most active compound.…”

Section: Amastigote Resultsmentioning

confidence: 99%

“…The toxicity is an attribute of all meta and para dihydroxylated cinnamic acid derivatives (7, 10, 12) and has been reported in the literature for similar compounds [14,18,19]. The catechol moiety is prone to oxidation resulting in an o-quinone which can easily react with amino groups of proteins [20].…”

Section: The Catechol Moietymentioning

confidence: 95%

“…Substituting borneol with a less sterically demanding alcohol e.g., cyclohexanol (23) or eugenol (24) gives IC 50 values higher than 100 µM (L. major). Using thymol (10,11,19), menthol (12,13,20) or other bulky substituents like naphthol (22) or adamantol (21) preserves the activity. A similar pattern is found with L. donovani promastigotes.…”

Section: Influence Of the Bornyl Moietymentioning

confidence: 99%

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Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

et al. 2014

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Bioassay-guided fractionation of a chloroform extract of Valeriana wallichii (V. wallichii) rhizomes lead to the isolation and identification of caffeic acid bornyl ester (1) as the active component against Leishmania major (L. major) promastigotes (IC 50 = 48.8 µM). To investigate the structure-activity relationship (SAR), a library of compounds based on 1 was synthesized and tested in vitro against L. major and L. donovani promastigotes, and L. major amastigotes. Cytotoxicity was determined using a murine J774.1 cell line and bone marrow derived macrophages (BMDM). Some compounds showed antileishmanial activity in the concentration range of pentamidine and miltefosine which are the standard drugs in use. In the L. major amastigote assay compounds 15, 19 and 20 showed good activity with relatively low cytotoxicity against BMDM, resulting in acceptable selectivity indices. Molecules with adjacent phenolic hydroxyl groups exhibited elevated cytotoxicity against murine cell lines J774.1 and BMDM. The Michael system seems not to be essential for antileishmanial activity. Based on the results compound 27 can be regarded as new lead structure for further structure optimization.

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Section: Amastigote Resultsmentioning

confidence: 99%

Section: The Catechol Moietymentioning

confidence: 95%

Section: Influence Of the Bornyl Moietymentioning

confidence: 99%

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Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

et al. 2014

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“…Of those compounds with reported biological activity, marchantin A, which is found in this liverwort, possesses antibacterial (Jensen et al . ) and antifungal properties (Friederich et al . ).…”

Section: Discussionmentioning

confidence: 99%

“…; Jensen et al . ), although fungal activity on the leaf surface is poorly understood. The destruction of KRCP‐4N fungal structures is not likely due to compounds such as marchantin A because these would have no marked specificity for KTP‐02 and KRCP‐4N.…”

Section: Discussionmentioning

confidence: 99%

Targeted destruction of fungal structures of Erysiphe trifoliorum on flat leaf surfaces of Marchantia polymorpha

et al. 2013

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In this study, we observed the germination behaviour of airborne conidia from powdery mildews that settle on thalloid surfaces. We inoculated thalli (flat, sheet-like leaf tissues) and gemmae (small, flat, sheet-like leaf tissues that propagate asexually via bud-like structures) of the common liverwort (Marchantia polymorpha) with conidia from tomato powdery mildew (Oidium neolycopersici; KTP-02) and red clover powdery mildew (Erysiphe trifoliorum; KRCP-4N) and examined their germination and subsequent appressorium formation under a high-fidelity digital microscope. Conidial bodies and germ tubes of the inoculated KRCP-4N conidia were destroyed on both the thalli and gemmae. The destruction of these fungal structures was observed only for KRCP-4N conidia inoculated onto M. polymorpha on both leaf surfaces. No differences in destruction of the KRCP-4N fungal structures between thalli and gemmae were observed. At 4 h post-inoculation, destruction of the germ tube tip was observed when it reached the gemmae leaf surface. At 6 h post-inoculation, the conidial bodies and germ tubes were destroyed. In contrast, KTP-02 conidia were not destroyed and formed normal, well-lobed appressoria on the surface of M. polymorpha gemmae.

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Bioactive Compounds from Bryophytes

Das

Kityania²,

Nath³

et al. 2022

Reference Series in Phytochemistry

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

Cited by 31 publications

References 32 publications

Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

Antileishmanial Lead Structures from Nature: Analysis of Structure-Activity Relationships of a Compound Library Derived from Caffeic Acid Bornyl Ester

Targeted destruction of fungal structures of Erysiphe trifoliorum on flat leaf surfaces of Marchantia polymorpha

Bioactive Compounds from Bryophytes

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