The discovery, synthesis and antimalarial evaluation of natural product-based polyamine alkaloids

Vanida Choomuenwai; Brett D. Schwartz; Karren D. Beattie; Katherine T. Andrews; Shahan Khokhar; Rohan A. Davis

doi:10.1016/j.tetlet.2013.07.058

The discovery, synthesis and antimalarial evaluation of natural product-based polyamine alkaloids

Vanida Choomuenwai
, Brett D. Schwartz
, Karren D. Beattie
, Katherine T. Andrews
, Shahan Khokhar
, Rohan A. Davis

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

21 Citations (Scopus)

Abstract

Bioassay-guided fractionation of an antimalarial extract derived from the fungus Ramaria subaurantiaca afforded the known polyamine alkaloid, pistillarin. Nine pistillarin analogues were synthesised via EDC-mediated chemistry and these compounds along with the previously reported natural product polyamines, ianthelliformisamines A-C and spermatinamine, were evaluated against Plasmodium falciparum (3D7) parasites and a normal human cell line to determine parasite-specific activity. Spermatinamine (IC50 0.23 Î¼M) and pistillarin (IC50 1.9 Î¼M) were the two most potent antimalarials identified during these studies.

Original language	English
Pages (from-to)	5188-5191
Number of pages	4
Journal	Tetrahedron Letters
Volume	54
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2013.07.058
Publication status	Published - 2013

UN SDGs

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

SDG 3 Good Health and Well-being

Keywords

Australia
alkaloids
antimalarials
fungi
natural products
polyamines

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10.1016/j.tetlet.2013.07.058

Cite this

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title = "The discovery, synthesis and antimalarial evaluation of natural product-based polyamine alkaloids",

abstract = "Bioassay-guided fractionation of an antimalarial extract derived from the fungus Ramaria subaurantiaca afforded the known polyamine alkaloid, pistillarin. Nine pistillarin analogues were synthesised via EDC-mediated chemistry and these compounds along with the previously reported natural product polyamines, ianthelliformisamines A-C and spermatinamine, were evaluated against Plasmodium falciparum (3D7) parasites and a normal human cell line to determine parasite-specific activity. Spermatinamine (IC50 0.23 {\^I}¼M) and pistillarin (IC50 1.9 {\^I}¼M) were the two most potent antimalarials identified during these studies.",

keywords = "Australia, alkaloids, antimalarials, fungi, natural products, polyamines",

author = "Vanida Choomuenwai and Schwartz, \{Brett D.\} and Beattie, \{Karren D.\} and Andrews, \{Katherine T.\} and Shahan Khokhar and Davis, \{Rohan A.\}",

year = "2013",

doi = "10.1016/j.tetlet.2013.07.058",

language = "English",

volume = "54",

pages = "5188--5191",

journal = "Tetrahedron Letters",

issn = "0040-4039",

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number = "38",

}

TY - JOUR

T1 - The discovery, synthesis and antimalarial evaluation of natural product-based polyamine alkaloids

AU - Choomuenwai, Vanida

AU - Schwartz, Brett D.

AU - Beattie, Karren D.

AU - Andrews, Katherine T.

AU - Khokhar, Shahan

AU - Davis, Rohan A.

PY - 2013

Y1 - 2013

N2 - Bioassay-guided fractionation of an antimalarial extract derived from the fungus Ramaria subaurantiaca afforded the known polyamine alkaloid, pistillarin. Nine pistillarin analogues were synthesised via EDC-mediated chemistry and these compounds along with the previously reported natural product polyamines, ianthelliformisamines A-C and spermatinamine, were evaluated against Plasmodium falciparum (3D7) parasites and a normal human cell line to determine parasite-specific activity. Spermatinamine (IC50 0.23 Î¼M) and pistillarin (IC50 1.9 Î¼M) were the two most potent antimalarials identified during these studies.

AB - Bioassay-guided fractionation of an antimalarial extract derived from the fungus Ramaria subaurantiaca afforded the known polyamine alkaloid, pistillarin. Nine pistillarin analogues were synthesised via EDC-mediated chemistry and these compounds along with the previously reported natural product polyamines, ianthelliformisamines A-C and spermatinamine, were evaluated against Plasmodium falciparum (3D7) parasites and a normal human cell line to determine parasite-specific activity. Spermatinamine (IC50 0.23 Î¼M) and pistillarin (IC50 1.9 Î¼M) were the two most potent antimalarials identified during these studies.

KW - Australia

KW - alkaloids

KW - antimalarials

KW - fungi

KW - natural products

KW - polyamines

UR - http://handle.uws.edu.au:8081/1959.7/uws:34158

U2 - 10.1016/j.tetlet.2013.07.058

DO - 10.1016/j.tetlet.2013.07.058

M3 - Article

SN - 0040-4039

VL - 54

SP - 5188

EP - 5191

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 38

ER -

The discovery, synthesis and antimalarial evaluation of natural product-based polyamine alkaloids

Abstract

UN SDGs

Keywords

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