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Comprehensive review on betulin as a potent anticancer agent.

Król SK, Kiełbus M, Rivero-Müller A, Stepulak A - Biomed Res Int (2015)

Bottom Line: Numerous plant-derived substances, and their derivatives, are effective antitumour and chemopreventive agents.Betulin (BE) is a pentacyclic triterpene and secondary metabolite of plants abundantly found in the outer bark of the birch tree Betulaceae sp.Although the antineoplastic mechanism of action of BE is not well understood yet, several interesting aspects of BE's interactions are coming to light.

View Article: PubMed Central - PubMed

Affiliation: The Chair and Department of Biochemistry and Molecular Biology, Medical University, 20-093 Lublin, Poland.

ABSTRACT
Numerous plant-derived substances, and their derivatives, are effective antitumour and chemopreventive agents. Yet, there are also a plethora of tumour types that do not respond, or become resistant, to these natural substances. This requires the discovery of new active compounds. Betulin (BE) is a pentacyclic triterpene and secondary metabolite of plants abundantly found in the outer bark of the birch tree Betulaceae sp. BE displays a broad spectrum of biological and pharmacological properties, among which the anticancer and chemopreventive activity attract most of the attention. In this vein, BE and its natural and synthetic derivatives act specifically on cancer cells with low cytotoxicity towards normal cells. Although the antineoplastic mechanism of action of BE is not well understood yet, several interesting aspects of BE's interactions are coming to light. This review will summarize the anticancer and chemopreventive potential of BE in vitro and in vivo by carefully dissecting and comparing the doses and tumour lines used in previous studies, as well as focusing on mechanisms underlying its activity at cellular and molecular level, and discuss future prospects.

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Chemical structure of betulin and lupane.
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fig2: Chemical structure of betulin and lupane.

Mentions: Betulin (BE, 3-lup-20(29)-ene-3β,28-diol), also known as betulinol, betuline, or betulinic alcohol [11], is a pentacyclic lupane-type triterpenoid (Figure 2) naturally distributed in many plants [12, 13]. BE was one of the first natural substances isolated from plants, by Lowitz in 1788, and its chemical structure was finally determined in 1952. Later, BE has been found in other plant species of the Betulaceae family, as a component of the outer bark of the birch species, Betula alba, B. pendula, B. pubescent, and B. platyphylla. BE has also been found in Diospyros leucomelas, Zizyphus mauritiana, Nelumbo nucifera, seeds of Ziziphus vulgaris var. spinosus, and in the bark of Trochodendron aralioides. BE is predominantly found in a content between 10 and 30% [14], through 34% of dry weight of bark from white birch [15] or even over 50% in the birch bark extract from B. pendula Roth [16] and yellow birch (B. alleghaniensis Britton) in the Quebec region in Canada [17]. Chemical composition of the birch bark extracts is strongly linked to preparation and purification methods used and influences the percentage of BE which can vary from 54% to 82% of dry weight [16].


Comprehensive review on betulin as a potent anticancer agent.

Król SK, Kiełbus M, Rivero-Müller A, Stepulak A - Biomed Res Int (2015)

Chemical structure of betulin and lupane.
© Copyright Policy
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4383233&req=5

fig2: Chemical structure of betulin and lupane.
Mentions: Betulin (BE, 3-lup-20(29)-ene-3β,28-diol), also known as betulinol, betuline, or betulinic alcohol [11], is a pentacyclic lupane-type triterpenoid (Figure 2) naturally distributed in many plants [12, 13]. BE was one of the first natural substances isolated from plants, by Lowitz in 1788, and its chemical structure was finally determined in 1952. Later, BE has been found in other plant species of the Betulaceae family, as a component of the outer bark of the birch species, Betula alba, B. pendula, B. pubescent, and B. platyphylla. BE has also been found in Diospyros leucomelas, Zizyphus mauritiana, Nelumbo nucifera, seeds of Ziziphus vulgaris var. spinosus, and in the bark of Trochodendron aralioides. BE is predominantly found in a content between 10 and 30% [14], through 34% of dry weight of bark from white birch [15] or even over 50% in the birch bark extract from B. pendula Roth [16] and yellow birch (B. alleghaniensis Britton) in the Quebec region in Canada [17]. Chemical composition of the birch bark extracts is strongly linked to preparation and purification methods used and influences the percentage of BE which can vary from 54% to 82% of dry weight [16].

Bottom Line: Numerous plant-derived substances, and their derivatives, are effective antitumour and chemopreventive agents.Betulin (BE) is a pentacyclic triterpene and secondary metabolite of plants abundantly found in the outer bark of the birch tree Betulaceae sp.Although the antineoplastic mechanism of action of BE is not well understood yet, several interesting aspects of BE's interactions are coming to light.

View Article: PubMed Central - PubMed

Affiliation: The Chair and Department of Biochemistry and Molecular Biology, Medical University, 20-093 Lublin, Poland.

ABSTRACT
Numerous plant-derived substances, and their derivatives, are effective antitumour and chemopreventive agents. Yet, there are also a plethora of tumour types that do not respond, or become resistant, to these natural substances. This requires the discovery of new active compounds. Betulin (BE) is a pentacyclic triterpene and secondary metabolite of plants abundantly found in the outer bark of the birch tree Betulaceae sp. BE displays a broad spectrum of biological and pharmacological properties, among which the anticancer and chemopreventive activity attract most of the attention. In this vein, BE and its natural and synthetic derivatives act specifically on cancer cells with low cytotoxicity towards normal cells. Although the antineoplastic mechanism of action of BE is not well understood yet, several interesting aspects of BE's interactions are coming to light. This review will summarize the anticancer and chemopreventive potential of BE in vitro and in vivo by carefully dissecting and comparing the doses and tumour lines used in previous studies, as well as focusing on mechanisms underlying its activity at cellular and molecular level, and discuss future prospects.

Show MeSH
Related in: MedlinePlus