Anti-leishmanial activity of betulin derivatives

Sami Alakurtti, N. Sacerdoti-Sierra, C. L. Jaffe, Salme Koskimies, Jari Yli-Kauhaluoma

Research output: Contribution to journalArticleScientificpeer-review

Abstract

Betulin (lup-20(29)-ene-3ß,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. Betulin and its derivatives such as betulinic acid have many interesting pharmacological properties, such as cytotoxic activity against many tumour cell lines and anti-HIV activity with a new mechanism of action. Several synthetic betulin derivatives that have been chemically modified at the positions C-3 and C-28 of the lupane skeleton were produced, and the anti-leishmanial inhibition activity of compounds was evaluated at 50 µM against Leishmania donovani and Leishmania tropica. Betulonic acid had the best anti-leishmanial activity with remarkable 98% inhibition at 50 µM giving a GI50 value of 14.6 µM. In conclusion, carbonyl or carboxyl groups seem to have beneficial effect in anti-leishmanial inhibition activity, and these compounds represent important leads for further optimization.
Original languageEnglish
Pages (from-to)S37-S37
JournalEuropean Journal of Pharmaceutical Sciences
Volume34
Issue number1, Supplement
DOIs
Publication statusPublished - 2008
MoE publication typeA1 Journal article-refereed
Event19th Helsinki Drug Research 2008 - Helsinki, Finland
Duration: 9 Jun 200811 Jun 2008

Fingerprint

Leishmania tropica
Plant Bark
Leishmania donovani
Betula
Triterpenes
Tumor Cell Line
Skeleton
HIV
Pharmacology
Weights and Measures
betulin
lupane
betulonic acid
betulinic acid

Keywords

  • betulin
  • betulin derivatives
  • betulinic acid
  • cytotoxic
  • tumours
  • anti-leishmanial
  • Leishmania donovani
  • Leishmania tropica

Cite this

Alakurtti, S., Sacerdoti-Sierra, N., Jaffe, C. L., Koskimies, S., & Yli-Kauhaluoma, J. (2008). Anti-leishmanial activity of betulin derivatives. European Journal of Pharmaceutical Sciences, 34(1, Supplement), S37-S37. https://doi.org/10.1016/j.ejps.2008.02.105
Alakurtti, Sami ; Sacerdoti-Sierra, N. ; Jaffe, C. L. ; Koskimies, Salme ; Yli-Kauhaluoma, Jari. / Anti-leishmanial activity of betulin derivatives. In: European Journal of Pharmaceutical Sciences. 2008 ; Vol. 34, No. 1, Supplement. pp. S37-S37.
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abstract = "Betulin (lup-20(29)-ene-3{\ss},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. Betulin and its derivatives such as betulinic acid have many interesting pharmacological properties, such as cytotoxic activity against many tumour cell lines and anti-HIV activity with a new mechanism of action. Several synthetic betulin derivatives that have been chemically modified at the positions C-3 and C-28 of the lupane skeleton were produced, and the anti-leishmanial inhibition activity of compounds was evaluated at 50 µM against Leishmania donovani and Leishmania tropica. Betulonic acid had the best anti-leishmanial activity with remarkable 98{\%} inhibition at 50 µM giving a GI50 value of 14.6 µM. In conclusion, carbonyl or carboxyl groups seem to have beneficial effect in anti-leishmanial inhibition activity, and these compounds represent important leads for further optimization.",
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Alakurtti, S, Sacerdoti-Sierra, N, Jaffe, CL, Koskimies, S & Yli-Kauhaluoma, J 2008, 'Anti-leishmanial activity of betulin derivatives', European Journal of Pharmaceutical Sciences, vol. 34, no. 1, Supplement, pp. S37-S37. https://doi.org/10.1016/j.ejps.2008.02.105

Anti-leishmanial activity of betulin derivatives. / Alakurtti, Sami; Sacerdoti-Sierra, N.; Jaffe, C. L.; Koskimies, Salme; Yli-Kauhaluoma, Jari.

In: European Journal of Pharmaceutical Sciences, Vol. 34, No. 1, Supplement, 2008, p. S37-S37.

Research output: Contribution to journalArticleScientificpeer-review

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T1 - Anti-leishmanial activity of betulin derivatives

AU - Alakurtti, Sami

AU - Sacerdoti-Sierra, N.

AU - Jaffe, C. L.

AU - Koskimies, Salme

AU - Yli-Kauhaluoma, Jari

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N2 - Betulin (lup-20(29)-ene-3ß,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. Betulin and its derivatives such as betulinic acid have many interesting pharmacological properties, such as cytotoxic activity against many tumour cell lines and anti-HIV activity with a new mechanism of action. Several synthetic betulin derivatives that have been chemically modified at the positions C-3 and C-28 of the lupane skeleton were produced, and the anti-leishmanial inhibition activity of compounds was evaluated at 50 µM against Leishmania donovani and Leishmania tropica. Betulonic acid had the best anti-leishmanial activity with remarkable 98% inhibition at 50 µM giving a GI50 value of 14.6 µM. In conclusion, carbonyl or carboxyl groups seem to have beneficial effect in anti-leishmanial inhibition activity, and these compounds represent important leads for further optimization.

AB - Betulin (lup-20(29)-ene-3ß,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. Betulin and its derivatives such as betulinic acid have many interesting pharmacological properties, such as cytotoxic activity against many tumour cell lines and anti-HIV activity with a new mechanism of action. Several synthetic betulin derivatives that have been chemically modified at the positions C-3 and C-28 of the lupane skeleton were produced, and the anti-leishmanial inhibition activity of compounds was evaluated at 50 µM against Leishmania donovani and Leishmania tropica. Betulonic acid had the best anti-leishmanial activity with remarkable 98% inhibition at 50 µM giving a GI50 value of 14.6 µM. In conclusion, carbonyl or carboxyl groups seem to have beneficial effect in anti-leishmanial inhibition activity, and these compounds represent important leads for further optimization.

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Alakurtti S, Sacerdoti-Sierra N, Jaffe CL, Koskimies S, Yli-Kauhaluoma J. Anti-leishmanial activity of betulin derivatives. European Journal of Pharmaceutical Sciences. 2008;34(1, Supplement):S37-S37. https://doi.org/10.1016/j.ejps.2008.02.105