Synthesis of betulin derivatives against intracellular pathogens

Sami Alakurtti

Tutkimustuotos: OpinnäyteVäitöskirja

Kuvaus

White birches (Betula spp.) are utilized in huge quantities in the forest industry in northern latitudes of the world and low-value side-stream birch bark is burnt for energy. Outer birch bark is rich in (up to 30% dry weight) triterpene betulin and it can be easily isolated by solvent extraction. Betulin could be used as such or as starting material for more valuable products, fine chemicals and pharmaceuticals.

In this work two sets of betulin derivatives were synthesized and screened as antiviral, antileishmanial and antibacterial agents. First set includes relatively easily synthesizable betulin derivatives, such as esters and various oxidation products. Second set includes novel heterocyclic betulin derivatives, where triazolo ring is fused by Diels-Alder reaction to the lupane skeleton of betulin.

In the biological assays against human pathogens Semliki Forest virus; L. donovani parasites, which cause tropical disease leishmaniasis; and Gram-negative bacteria Chlamydia pneumoniae, several betulin derivatives displayed low-micromolar 50% growth inhibition values in vitro. In addition, most of the derivatives showed low cytotoxicity against the host cell lines.

Alkuperäiskielienglanti
JulkaisupaikkaEspoo
Kustantaja
Painoksen ISBN978-951-38-8013-2
Sähköinen ISBN978-951-38-8014-9
TilaJulkaistu - 2013
OKM-julkaisutyyppiG5 Tohtorinväitöskirja (artikkeli)

Tieteenalat

  • 317 Farmasia

Lainaa tätä

Alakurtti, S. (2013). Synthesis of betulin derivatives against intracellular pathogens. Espoo: VTT Technical Research Centre of Finland.
Alakurtti, Sami . / Synthesis of betulin derivatives against intracellular pathogens. Espoo : VTT Technical Research Centre of Finland, 2013. 99 Sivumäärä
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abstract = "White birches (Betula spp.) are utilized in huge quantities in the forest industry in northern latitudes of the world and low-value side-stream birch bark is burnt for energy. Outer birch bark is rich in (up to 30{\%} dry weight) triterpene betulin and it can be easily isolated by solvent extraction. Betulin could be used as such or as starting material for more valuable products, fine chemicals and pharmaceuticals. In this work two sets of betulin derivatives were synthesized and screened as antiviral, antileishmanial and antibacterial agents. First set includes relatively easily synthesizable betulin derivatives, such as esters and various oxidation products. Second set includes novel heterocyclic betulin derivatives, where triazolo ring is fused by Diels-Alder reaction to the lupane skeleton of betulin. In the biological assays against human pathogens Semliki Forest virus; L. donovani parasites, which cause tropical disease leishmaniasis; and Gram-negative bacteria Chlamydia pneumoniae, several betulin derivatives displayed low-micromolar 50{\%} growth inhibition values in vitro. In addition, most of the derivatives showed low cytotoxicity against the host cell lines.",
keywords = "317 Pharmacy",
author = "Sami Alakurtti",
year = "2013",
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isbn = "978-951-38-8013-2",
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Synthesis of betulin derivatives against intracellular pathogens. / Alakurtti, Sami .

Espoo : VTT Technical Research Centre of Finland, 2013. 99 s.

Tutkimustuotos: OpinnäyteVäitöskirja

TY - THES

T1 - Synthesis of betulin derivatives against intracellular pathogens

AU - Alakurtti, Sami

PY - 2013

Y1 - 2013

N2 - White birches (Betula spp.) are utilized in huge quantities in the forest industry in northern latitudes of the world and low-value side-stream birch bark is burnt for energy. Outer birch bark is rich in (up to 30% dry weight) triterpene betulin and it can be easily isolated by solvent extraction. Betulin could be used as such or as starting material for more valuable products, fine chemicals and pharmaceuticals. In this work two sets of betulin derivatives were synthesized and screened as antiviral, antileishmanial and antibacterial agents. First set includes relatively easily synthesizable betulin derivatives, such as esters and various oxidation products. Second set includes novel heterocyclic betulin derivatives, where triazolo ring is fused by Diels-Alder reaction to the lupane skeleton of betulin. In the biological assays against human pathogens Semliki Forest virus; L. donovani parasites, which cause tropical disease leishmaniasis; and Gram-negative bacteria Chlamydia pneumoniae, several betulin derivatives displayed low-micromolar 50% growth inhibition values in vitro. In addition, most of the derivatives showed low cytotoxicity against the host cell lines.

AB - White birches (Betula spp.) are utilized in huge quantities in the forest industry in northern latitudes of the world and low-value side-stream birch bark is burnt for energy. Outer birch bark is rich in (up to 30% dry weight) triterpene betulin and it can be easily isolated by solvent extraction. Betulin could be used as such or as starting material for more valuable products, fine chemicals and pharmaceuticals. In this work two sets of betulin derivatives were synthesized and screened as antiviral, antileishmanial and antibacterial agents. First set includes relatively easily synthesizable betulin derivatives, such as esters and various oxidation products. Second set includes novel heterocyclic betulin derivatives, where triazolo ring is fused by Diels-Alder reaction to the lupane skeleton of betulin. In the biological assays against human pathogens Semliki Forest virus; L. donovani parasites, which cause tropical disease leishmaniasis; and Gram-negative bacteria Chlamydia pneumoniae, several betulin derivatives displayed low-micromolar 50% growth inhibition values in vitro. In addition, most of the derivatives showed low cytotoxicity against the host cell lines.

KW - 317 Pharmacy

M3 - Doctoral Thesis

SN - 978-951-38-8013-2

T3 - VTT Science

PB - VTT Technical Research Centre of Finland

CY - Espoo

ER -

Alakurtti S. Synthesis of betulin derivatives against intracellular pathogens. Espoo: VTT Technical Research Centre of Finland, 2013. 99 s. (VTT Science; 39).