Betulinic acid

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Structural formula
Structure of betulinic acid
General
Surname Betulinic acid
other names
  • Mairin
  • 3 α- Hydroxymethyl-1-isopropenyl-5 α , 5 β , 8,8,11 α -pentamethyl-icosahydro-cyclopenta [ a ] chrysen-9-acid
  • 3 β- hydroxylup-20 (29) -en-28-acid
Molecular formula C 30 H 48 O 3
Brief description

colorless crystals

External identifiers / databases
CAS number 472-15-1
EC number 207-448-8
ECHA InfoCard 100.006.773
PubChem 64971
DrugBank DB12480
Wikidata Q384111
properties
Molar mass 456.71 g mol −1
Physical state

firmly

Melting point

295–298 ° C (decomposition)

safety instructions
GHS labeling of hazardous substances
no GHS pictograms
H and P phrases H: no H-phrases
P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Betulinic acid is a pentacyclic triterpene - carboxylic acid (in the subgroup of lupanes ) used as secondary plant substance ( phytoalexin found) mainly in the bark of many different plants.

Occurrence and manufacture

Betulinic acid is found in many plant species, especially the bark of trees from the plane tree , birch and ebony families , e.g. B. with about 2.5 percent in the bark of plane trees ( Platanus acerifolia ) and a small percentage in the dried bark sap of birch trees (Latin Betula , hence the name). It can either be produced oxidatively from betulin or by extraction and multiple crystallization from plane tree bark. Particular advantages of the extraction from plane trees are the lack of contamination with other terpenes and a relatively low energy consumption. Biosolutions Halle GmbH has a patent for the manufacturing process . The patent for the extraction process has since been bought up by the pharmaceutical manufacturer Boehringer Ingelheim .

use

In laboratory tests, betulinic acid has an inhibitory effect on melanoma cells (by initiating the cell death program ) and HIV viruses (by inhibiting reverse transcriptase ). It forms the starting substance for further developed AIDS drugs such as Bevirimat (PA-457), which is currently being clinically tested. The effectiveness of betulinic acid against dermatophytes and plasmodia indicates the substance's original use against fungal and plasmodia infestation of the plant. However , the required dose and its side effects are too high for medical use against malaria . Betulinic acid is said to have a liver-protective and anti-inflammatory effect, as well as an apoptosis-inducing mechanism. In the latter, betulinic acid acts on the mitochondria in such a way that they lose their membrane potential and release proapoptotic factors (AIF, Endo G, Cyt c , SMAC), which in turn activate caspase n and ultimately cause apoptosis . This anti-tumor potential is currently the subject of research.

Episalvan is approved by the EMA as a phytotherapeutic agent. It is a highly enriched birch bark extract (72–88% betulin ) that is applied locally to wounds and accelerates the healing of the upper layers of the skin.

literature

  • Simone Fulda, Irmela Jeremias, Hans H. Steiner, Torsten Pietsch, Klaus-Michael Debatin: Betulinic acid: A new cytotoxic agent against malignant brain-tumor cells . In: International Journal of Cancer . tape 82 , no. 3 , July 30, 1999, p. 435 , PMID 10399962 .
  • Donglei Yu, Susan L Morris-Natschke, Kuo-Hsiung Lee: New developments in natural products-based anti-AIDS research . In: Medicinal Research Reviews . tape 27 , no. 1 , January 2007, p. 108-132 , doi : 10.1002 / med.20075 , PMID 16888749 .
  • IC Sun, JK Shen, HK Wang, LM Cosentino, KH Lee: Anti-AIDS agents. 32. Synthesis and anti-HIV activity of betulin derivatives . In: Bioorganic & Medicinal Chemistry Letters . tape 8 , no. 10 , May 19, 1998, pp. 1267-1272 , PMID 9871747 .
  • S. Dathe, U. Paasch, S. Grunewald, H.-J. Glander: Mitochondrial damage to human sperm caused by the oncotherapeutic agent betulinic acid . In: The dermatologist . tape 56 , no. 8 , August 2005, p. 768-772 , doi : 10.1007 / s00105-005-0951-4 .
  • JC Steele, DC Warhurst, GC Kirby, MS Simmonds: In vitro and in vivo evaluation of betulinic acid as an antimalarial . In: Phytotherapy Research : PTR . tape 13 , no. 2 , March 1999, p. 115-119 , doi : 10.1002 / (SICI) 1099-1573 (199903) 13: 2 <115 :: AID-PTR404> 3.0.CO; 2-1 , PMID 1673251 .
  • Hanne L. Ziegler, Trine Staalsø, Jerzy W. Jaroszewski: Loading of erythrocyte membrane with pentacyclic triterpenes inhibits Plasmodium falciparum invasion . In: Planta Medica . tape 72 , no. 7 , June 2006, p. 640-642 , doi : 10.1055 / s-2006-931575 , PMID 17128435 .
  • Jules-Roger Kuiate, Simplice Mouokeu, Hypolyte K. Wabo, Pierre Tane: Antidermatophytic triterpenoids from Syzygium jambos (L.) Alston (Myrtaceae) . In: Phytotherapy Research: PTR . tape 21 , no. 2 , February 2007, p. 149-152 , doi : 10.1002 / ptr.2039 , PMID 10190183 .
  • Sebastian Jäger, Karin Winkler, Uwe Pfüller, Armin Scheffler: Solubility Studies of Oleanolic Acid and Betulinic Acid in Aqueous Solutions and Plant Extracts of Viscum album L. In: Planta Medica . tape 73 , no. 2 , February 2007, p. 157-162 , doi : 10.1055 / s-2007-967106 .

Web links

Individual evidence

  1. ^ Chemical Society (Great Britain): Journal of the Chemical Society . 1877, p. 96 ( limited preview in Google Book search).
  2. a b c Datasheet Betulinic acid from Sigma-Aldrich , accessed on February 13, 2019 ( PDF ).
  3. Andreas Bechthold, Robert Fürst, Angelika Vollmar: Biogenic medicinal substances . 1st edition. Wissenschaftliche Verlagsgesellschaft Stuttgart, Stuttgart 2019, ISBN 978-3-8047-3623-8 , pp. 225 .