In vitro antimalarial activity of hyperforin, a prenylated acylphloroglucinol. A structure-activity study

Luisella Verotta; Giovanni Appendino; Ezio Bombardelli; Reto Brun

doi:10.1016/j.bmcl.2006.12.100

In vitro antimalarial activity of hyperforin, a prenylated acylphloroglucinol. A structure-activity study

Luisella Verotta
, Giovanni Appendino
, Ezio Bombardelli
, Reto Brun

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

Abstract

The antimalarial activity of hyperforin, a phenol-like compound that can be easily absorbed orally, and a series of derivatives variously modified on the cyclohexatrienone system was investigated. Hyperforin was active against Plasmodium falciparum with an IC₅₀ value in the micromolar range, and the activity was not critically dependent on either its phenol-like sensitivity to autooxidation or the presence of unsaturation on the prenyl residues. Related phloroglucinols like the hop β-acids and the enantiomers of usnic acid showed only marginal activity, suggesting that hyperforin is a new antimalarial chemotype.

Original language	English
Pages (from-to)	1544-1548
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	6
DOIs	https://doi.org/10.1016/j.bmcl.2006.12.100
Publication status	Published - 15 Mar 2007
Externally published	Yes

Keywords

Antiprotozoal
Hyperforin derivatives
Phloroglucinols
Plasmodium falciparum

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10.1016/j.bmcl.2006.12.100

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title = "In vitro antimalarial activity of hyperforin, a prenylated acylphloroglucinol. A structure-activity study",

abstract = "The antimalarial activity of hyperforin, a phenol-like compound that can be easily absorbed orally, and a series of derivatives variously modified on the cyclohexatrienone system was investigated. Hyperforin was active against Plasmodium falciparum with an IC50 value in the micromolar range, and the activity was not critically dependent on either its phenol-like sensitivity to autooxidation or the presence of unsaturation on the prenyl residues. Related phloroglucinols like the hop β-acids and the enantiomers of usnic acid showed only marginal activity, suggesting that hyperforin is a new antimalarial chemotype.",

keywords = "Antiprotozoal, Hyperforin derivatives, Phloroglucinols, Plasmodium falciparum",

author = "Luisella Verotta and Giovanni Appendino and Ezio Bombardelli and Reto Brun",

note = "Funding Information: The present work supported by MIUR of Italy and EEC (Contract No. 018834: Antimal).",

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TY - JOUR

T1 - In vitro antimalarial activity of hyperforin, a prenylated acylphloroglucinol. A structure-activity study

AU - Verotta, Luisella

AU - Appendino, Giovanni

AU - Bombardelli, Ezio

AU - Brun, Reto

N1 - Funding Information: The present work supported by MIUR of Italy and EEC (Contract No. 018834: Antimal).

PY - 2007/3/15

Y1 - 2007/3/15

N2 - The antimalarial activity of hyperforin, a phenol-like compound that can be easily absorbed orally, and a series of derivatives variously modified on the cyclohexatrienone system was investigated. Hyperforin was active against Plasmodium falciparum with an IC50 value in the micromolar range, and the activity was not critically dependent on either its phenol-like sensitivity to autooxidation or the presence of unsaturation on the prenyl residues. Related phloroglucinols like the hop β-acids and the enantiomers of usnic acid showed only marginal activity, suggesting that hyperforin is a new antimalarial chemotype.

AB - The antimalarial activity of hyperforin, a phenol-like compound that can be easily absorbed orally, and a series of derivatives variously modified on the cyclohexatrienone system was investigated. Hyperforin was active against Plasmodium falciparum with an IC50 value in the micromolar range, and the activity was not critically dependent on either its phenol-like sensitivity to autooxidation or the presence of unsaturation on the prenyl residues. Related phloroglucinols like the hop β-acids and the enantiomers of usnic acid showed only marginal activity, suggesting that hyperforin is a new antimalarial chemotype.

KW - Antiprotozoal

KW - Hyperforin derivatives

KW - Phloroglucinols

KW - Plasmodium falciparum

UR - https://www.scopus.com/pages/publications/33847215470

U2 - 10.1016/j.bmcl.2006.12.100

DO - 10.1016/j.bmcl.2006.12.100

M3 - Article

SN - 0960-894X

VL - 17

SP - 1544

EP - 1548

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 6

ER -

In vitro antimalarial activity of hyperforin, a prenylated acylphloroglucinol. A structure-activity study

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Keywords

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