Pharmacological properties of the ubiquitous natural product betulin

Sami Alakurtti, Taru Mäkelä, Salme Koskimies, Jari Yli-Kauhaluoma (Corresponding Author)

Research output: Contribution to journalReview ArticleScientificpeer-review

407 Citations (Scopus)

Abstract

Betulin (lup-20(29)-ene-3β,28-diol) is an abundant naturally occurring triterpene and it is found predominantly in bushes and trees forming the principal extractive (up to 30% of dry weight) of the bark of birch trees. Presently, there is no significant use for this easily isolable compound, which makes it a potentially important raw material for polymers and a precursor of biologically active compounds. Betulin can be easily converted to betulinic acid, which possesses a wide spectrum of biological and pharmacological activities. Betulinic acid has antimalarial and anti-inflammatory activities. Betulinic acid and its derivatives have especially shown anti-HIV activity and cytotoxicity against a variety of tumor cell lines comparable to some clinically used drugs. A new mechanism of action has been confirmed for some of the most promising anti-HIV derivatives, which makes them potentially useful additives to the current anti-HIV therapy. Betulinic acid is specifically cytotoxic to several tumor cell lines by inducing apoptosis in cells. Moreover, it is non-toxic up to 500 mg/kg body weight in mice. The literature concerning derivatization of betulin for structure–activity relationship (SAR) studies and its pharmacological properties is reviewed.

Original languageEnglish
Pages (from-to)1-13
Number of pages13
JournalEuropean Journal of Pharmaceutical Sciences
Volume29
Issue number1
DOIs
Publication statusPublished - 2006
MoE publication typeA2 Review article in a scientific journal

Fingerprint

Biological Products
Pharmacology
HIV
Tumor Cell Line
Plant Bark
Betula
Triterpenes
Antimalarials
Polymers
Anti-Inflammatory Agents
Body Weight
Apoptosis
Weights and Measures
betulinic acid
betulin
Pharmaceutical Preparations
Therapeutics

Keywords

  • betulin
  • betulinic acid
  • birch bark
  • betulin derivatives
  • natural products
  • betula sp.
  • medicinal chemistry
  • health
  • Health-effects
  • bark
  • cytotoxic

Cite this

Alakurtti, Sami ; Mäkelä, Taru ; Koskimies, Salme ; Yli-Kauhaluoma, Jari. / Pharmacological properties of the ubiquitous natural product betulin. In: European Journal of Pharmaceutical Sciences. 2006 ; Vol. 29, No. 1. pp. 1-13.
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abstract = "Betulin (lup-20(29)-ene-3β,28-diol) is an abundant naturally occurring triterpene and it is found predominantly in bushes and trees forming the principal extractive (up to 30{\%} of dry weight) of the bark of birch trees. Presently, there is no significant use for this easily isolable compound, which makes it a potentially important raw material for polymers and a precursor of biologically active compounds. Betulin can be easily converted to betulinic acid, which possesses a wide spectrum of biological and pharmacological activities. Betulinic acid has antimalarial and anti-inflammatory activities. Betulinic acid and its derivatives have especially shown anti-HIV activity and cytotoxicity against a variety of tumor cell lines comparable to some clinically used drugs. A new mechanism of action has been confirmed for some of the most promising anti-HIV derivatives, which makes them potentially useful additives to the current anti-HIV therapy. Betulinic acid is specifically cytotoxic to several tumor cell lines by inducing apoptosis in cells. Moreover, it is non-toxic up to 500 mg/kg body weight in mice. The literature concerning derivatization of betulin for structure–activity relationship (SAR) studies and its pharmacological properties is reviewed.",
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Pharmacological properties of the ubiquitous natural product betulin. / Alakurtti, Sami; Mäkelä, Taru; Koskimies, Salme; Yli-Kauhaluoma, Jari (Corresponding Author).

In: European Journal of Pharmaceutical Sciences, Vol. 29, No. 1, 2006, p. 1-13.

Research output: Contribution to journalReview ArticleScientificpeer-review

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T1 - Pharmacological properties of the ubiquitous natural product betulin

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AU - Koskimies, Salme

AU - Yli-Kauhaluoma, Jari

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N2 - Betulin (lup-20(29)-ene-3β,28-diol) is an abundant naturally occurring triterpene and it is found predominantly in bushes and trees forming the principal extractive (up to 30% of dry weight) of the bark of birch trees. Presently, there is no significant use for this easily isolable compound, which makes it a potentially important raw material for polymers and a precursor of biologically active compounds. Betulin can be easily converted to betulinic acid, which possesses a wide spectrum of biological and pharmacological activities. Betulinic acid has antimalarial and anti-inflammatory activities. Betulinic acid and its derivatives have especially shown anti-HIV activity and cytotoxicity against a variety of tumor cell lines comparable to some clinically used drugs. A new mechanism of action has been confirmed for some of the most promising anti-HIV derivatives, which makes them potentially useful additives to the current anti-HIV therapy. Betulinic acid is specifically cytotoxic to several tumor cell lines by inducing apoptosis in cells. Moreover, it is non-toxic up to 500 mg/kg body weight in mice. The literature concerning derivatization of betulin for structure–activity relationship (SAR) studies and its pharmacological properties is reviewed.

AB - Betulin (lup-20(29)-ene-3β,28-diol) is an abundant naturally occurring triterpene and it is found predominantly in bushes and trees forming the principal extractive (up to 30% of dry weight) of the bark of birch trees. Presently, there is no significant use for this easily isolable compound, which makes it a potentially important raw material for polymers and a precursor of biologically active compounds. Betulin can be easily converted to betulinic acid, which possesses a wide spectrum of biological and pharmacological activities. Betulinic acid has antimalarial and anti-inflammatory activities. Betulinic acid and its derivatives have especially shown anti-HIV activity and cytotoxicity against a variety of tumor cell lines comparable to some clinically used drugs. A new mechanism of action has been confirmed for some of the most promising anti-HIV derivatives, which makes them potentially useful additives to the current anti-HIV therapy. Betulinic acid is specifically cytotoxic to several tumor cell lines by inducing apoptosis in cells. Moreover, it is non-toxic up to 500 mg/kg body weight in mice. The literature concerning derivatization of betulin for structure–activity relationship (SAR) studies and its pharmacological properties is reviewed.

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