Maslinic acid

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Structural formula
Structural formula of maslinic acid
General
Surname Maslinic acid
other names
  • (4a S , 6a R , 6a S , 6b R , 8a R , 10 R , 11 R , 12a R , 14b S ) -10,11-dihydroxy-2,2,6a, 6b, 9,9,12a-heptamethyl -1,3,4,5,6,6a, 7,8,8a, 10,11,12,13,14b-tetradecahydropicen-4a-carboxylic acid ( IUPAC )
  • 2 α- hydroxyoleanolic acid
  • 2 α , 3 β -dihydroxyolean-12-en-28-carboxylic acid
  • Crataegolic acid
Molecular formula C 30 H 48 O 4
Brief description

colorless crystals

External identifiers / databases
CAS number 4373-41-5
EC number 610-137-3
ECHA InfoCard 100.128.873
PubChem 73659
ChemSpider 66312
Wikidata Q1907191
properties
Molar mass 472.70 g mol −1
Physical state

firmly

solubility
  • poor in water (0.3 g / l at 25 ° C)
  • good in DMSO (20 g / l)
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 .

Maslinic acid is a pentacyclic triterpene made up of five cyclohexane rings . Maslinic acid is a natural component of olive oil .

Occurrence

Olives and olive leaves contain maslinic acid

Maslinic acid is found as a waxy protective layer on the leaves and fruits of the olive tree . The content of maslinic acid in olives is between about 700 and 1000 mg per kg. With increasing maturation, the content decreases. Up to 250 mg maslinic acid can be contained per kilogram of virgin olive oil. The maslinic acid content is significantly lower in refined oil. The press and centrifuge residues from olive oil production are an important source for the recovery of maslinic acid and other related pentacyclic triterpenes such as oleanolic acid . The triterpenes can be obtained from these residues by extraction with solvents .

Also in the Japanese clove root ( Geum japonicum ), the queen flower ( Lagerstroemia speciosa ) of the small brown elk ( Prunella vulgaris ), the Asian dogwood ( Cornus kousa ), the Siberian elm ( Ulmus pumila ), in the Chinese grass ( Boehmeria nivea ) and one Maslinic acid has been detected and isolated in a number of other plants.

Properties and pharmacological potential

Maslinic acid is cytotoxic . Although it is not able to intercept free radicals , it does protect the DNA against oxidation . In in-vitro experiments, maslinic acid was able to demonstrate an antiproliferative and apoptosis-inducing effect. Maslinic acid activates caspase-3 , an enzyme that is important for apoptosis . The compound also appears to inhibit the formation of new blood vessels ( angiogenesis ) and the enzyme cyclooxygenase-2 (COX-2). An anti-diabetic effect could be demonstrated in model organisms .

An anti- carcinogenic effect has been demonstrated in various cancer cell lines - especially colon cancer cells . It is assumed that the comparatively low colon risk of the Mediterranean population, known from epidemiological data, is related to the comparatively high consumption of olive oil and olives, and that one of the causes is the olive constituent maslinic acid. The intake of maslinic acid is around 62 mg per person and day. In addition, cardioprotective properties of maslinic acid could be demonstrated.

Compared with parasitic pathogens such as Plasmodium ( Plasmodium falciparum or Toxoplasma gondii ), or protozoa such as Eimeria tenella , maslinic shows an anti- parasitic effect.

Maslinic acid inhibits enzymes that the HI virus needs.

further reading

  • X. Wen, H. Sun, J. Liu, K. Cheng, P. Zhang, L. Zhang, J. Hao, L. Zhang, P. Ni, among others: Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies. In: Journal of Medicinal Chemistry Volume 51, Number 12, June 2008, pp. 3540-3554, doi : 10.1021 / jm8000949 . PMID 18517260 .
  • C. Li, Z. Yang, Z. Li, Y. Ma, L. Zhang, C. Zheng, W. Qiu, X. Wu, ao: Maslinic acid suppresses osteoclastogenesis and prevents ovariectomy-induced bone loss by regulating RANKL-mediated NF-κB and MAPK signaling pathways. In: Journal of Bone and Mineral Research Volume 26, Number 3, March 2011, pp. 644-656, doi : 10.1002 / jbmr.242 . PMID 20814972 .
  • C. Li, Z. Yang, C. Zhai, W. Qiu, D. Li, Z. Yi, L. Wang, inter alia: Maslinic acid potentiates the anti-tumor activity of tumor necrosis factor alpha by inhibiting NF-kappaB signaling pathway . In: Molecular Cancer Volume 9, 2010, p. 73, doi : 10.1186 / 1476-4598-9-73 . PMID 20367887 . PMC 2907730 (free full text).
  • LY Mooi, NA Wahab, NH Lajis, AM Ali: Chemopreventive properties of phytosterols and maslinic acid extracted from Coleus tuberosus in inhibiting the expression of EBV early-antigen in Raji cells. In: Chemistry & biodiversity Volume 7, Number 5, May 2010, pp. 1267-1275, doi : 10.1002 / cbdv.200900193 . PMID 20491082 .
  • WW Qiu, Q. Shen, F. Yang, B. Wang, H. Zou, JY Li, J. Li, J. Tang: Synthesis and biological evaluation of heterocyclic ring-substituted maslinic acid derivatives as novel inhibitors of protein tyrosine phosphatase 1B . In: Bioorganic & medicinal chemistry letters Volume 19, Number 23, December 2009, pp. 6618-6622, doi : 10.1016 / j.bmcl.2009.10.017 . PMID 19846303 .
  • T. Guan, Y. Li, H. Sun, X. Tang, Y. Qian: Effects of maslinic acid, a natural triterpene, on glycogen metabolism in cultured cortical astrocytes. In: Planta Medica Volume 75, Number 10, August 2009, pp. 1141-1143, doi : 10.1055 / s-0029-1185481 . PMID 19291614 .

Individual evidence

  1. ^ Hager's Handbook of Pharmaceutical Practice. Drugs E-O , 5th edition, Springer, 1993, ISBN 978-3-642-63427-7 , p. 938.
  2. ↑ a b c d data sheet maslinic acid from Sigma-Aldrich , accessed on September 2, 2016 ( PDF ).
  3. ↑ Maslinic Acid. Cayman Chemicals, dated December 8, 2009.
  4. ^ A b F.J. Reyes-Zurita, G. Pachón-Peña, D. Lizárraga, EE Rufino-Palomares, M. Cascante, JA Lupiáñez: The natural triterpene maslinic acid induces apoptosis in HT29 colon cancer cells by a JNK-p53-dependent mechanism . In: BMC Cancer Volume 11, 2011, p. 154, doi : 10.1186 / 1471-2407-11-154 . PMID 21524306 . PMC 3103477 (free full text).
  5. ↑ A. Guinda, M. Rada, T. Delgado, P. Gutiérrez-Adánez, JM Castellano: Pentacyclic triterpenoids from olive fruit and leaf. In: Journal of Agricultural and Food Chemistry Volume 58, Number 17, September 2010, pp. 9685-9691, doi : 10.1021 / jf102039t . PMID 20712364 .
  6. ↑ a b H. Schmandke : Triterpenoids in olives. (PDF; 283 kB) In: Ernahrung Umschau 2, 2009, pp. 92–95.
  7. ^ A. Parra, PE Lopez, A. Garcia-Granados: Bioactive compounds with added value prepared from terpenes contained in solid wastes from the olive oil industry. In: Chemistry & biodiversity Volume 7, Number 2, February 2010, pp. 421-439, doi : 10.1002 / cbdv.200900023 . PMID 20151391 .
  8. ↑ a b H. X. Xu, FQ Zeng, M. Wan, KY Sim: Anti-HIV triterpene acids from Geum japonicum. In: Journal of Natural Products Volume 59, Number 7, July 1996, pp. 643-645, doi : 10.1021 / np960165e . PMID 8759159 .
  9. ↑ W. Hou, Y. Li, Q. Zhang, X. Wei, A. Peng, L. Chen, Y. Wei: Triterpene acids isolated from Lagerstroemia speciosa leaves as alpha-glucosidase inhibitors. In: Phytotherapy Research  : PTR Volume 23, Number 5, May 2009, pp. 614-618, doi : 10.1002 / ptr.2661 . PMID 19107840 .
  10. ↑ IK Lee, do Kim, SY Lee, KR Kim, SU Choi, JK Hong, JH Lee, YH Park, KR Lee: Triterpenoic acids of Prunella vulgaris var. Lilacina and their cytotoxic activities in vitro. In: Archives of Pharmacal Research Volume 31, Number 12, December 2008, pp. 1578-1583, doi : 10.1007 / s12272-001-2154-6 . PMID 19099227 .
  11. ^ N. Sultana, NH Lee: Antielastase and free radical scavenging activities of compounds from the stems of Cornus kousa. In: Phytotherapy research: PTR Volume 21, Number 12, December 2007, pp. 1171-1176, doi : 10.1002 / ptr.2230 . PMID 17661332 .
  12. ↑ D. Wang, M. Xia, Z. Cui: New triterpenoids isolated from the root bark of Ulmus pumila L. In: Chemical & pharmaceutical bulletin Volume 54, Number 6, June 2006, pp. 775-778, PMID 16755042 .
  13. ↑ Q. Xu, G. Chen, J. Fan, M. Zhang, X. Li, S. Yang, X. Li: [Chemical constituents of roots of Boehmeria nivea]. In: Zhongguo Zhong yao za zhi Volume 34, Number 20, October 2009, pp. 2610-2612, PMID 20069903 .
  14. ↑ Y. Allouche, F. Warleta, M. Campos, C. Sánchez-Quesada, M. Uceda, G. Beltrán, JJ Gaforio: antioxidant, antiproliferative, and pro-apoptotic capacities of pentacyclic triterpenes found in the skin of olives on MCF -7 human breast cancer cells and their effects on DNA damage. In: Journal of agricultural and food chemistry Volume 59, Number 1, January 2011, pp. 121-130, doi : 10.1021 / jf102319y . PMID 21142067 .
  15. ↑ ME Juan, JM Planas, V. Ruiz-Gutierrez, H. Daniel, U. Wenzel: Antiproliferative and apoptosis-inducing effects of maslinic and oleanolic acids, two pentacyclic triterpenes from olives, on HT-29 colon cancer cells. In: The British journal of nutrition Volume 100, number 1, July 2008, pp. 36-43, doi : 10.1017 / S0007114508882979 . PMID 18298868 .
  16. ↑ CC Lin, CY Huang, MC Mong, CY Chan, MC Yin: Antiangiogenic potential of three triterpenic acids in human liver cancer cells. In: Journal of agricultural and food chemistry Volume 59, Number 2, January 2011, pp. 755-762, doi : 10.1021 / jf103904b . PMID 21175131 .
  17. ↑ YW Hsum, WT Yew, PL Hong, KK Soo, LS Hoon, YC Chieng, LY Mooi: Cancer chemopreventive activity of maslinic acid: suppression of COX-2 expression and inhibition of NF-? B and AP-1 activation in Raji cells . In: Planta medica Volume 77, Number 2, January 2011, pp. 152-157, doi : 10.1055 / s-0030-1250203 . PMID 20669087 .
  18. ↑ J. Liu, H. Sun, W. Duan, D. Mu, L. Zhang: Maslinic acid reduces blood glucose in KK-Ay mice. In: Biological and Pharmaceutical Bulletin Volume 30, Number 11, November 2007, pp. 2075-2078, PMID 17978478 .
  19. Jump up ↑ Y. Allouche, G. Beltrán, JJ Gaforio, M. Uceda, MD Mesa: Antioxidant and antiatherogenic activities of pentacyclic triterpenic diols and acids. In: Food and Chemical Toxicology Volume 48, Number 10, October 2010, pp. 2885-2890, doi : 10.1016 / j.fct.2010.07.022 . PMID 20650302 .
  20. ↑ C. Moneriz, P. Marín-García, A. García-Granados, JM Bautista, A. Diez, A. Puyet: Parasitostatic effect of maslinic acid. I. Growth arrest of Plasmodium falciparum intraerythrocytic stages. In: Malaria Journal Volume 10, 2011, p. 82, doi : 10.1186 / 1475-2875-10-82 . PMID 21477369 . PMC 3087696 (free full text).
  21. ↑ C. Moneriz, P. Marín-García, JM Bautista, A. Diez, A. Puyet: Parasitostatic effect of maslinic acid. II. Survival increase and immune protection in lethal Plasmodium yoelii-infected mice. In: Malaria journal Volume 10, 2011, p. 103, doi : 10.1186 / 1475-2875-10-103 . PMID 21518429 . PMC 3107817 (free full text).
  22. Jump up ↑ LM De Pablos, G. González, R. Rodrigues, A. García Granados, A. Parra, A. Osuna: Action of a pentacyclic triterpenoid, maslinic acid, against Toxoplasma gondii. In: Journal of natural products Volume 73, Number 5, May 2010, pp. 831-834, doi : 10.1021 / np900749b . PMID 20441162 .
  23. ↑ LM De Pablos, MF dos Santos, E. Montero, A. Garcia-Granados, A. Parra, A. Osuna: Anticoccidial activity of maslinic acid against infection with Eimeria tenella in chickens. In: Parasitology research Volume 107, Number 3, August 2010, pp. 601-604, doi : 10.1007 / s00436-010-1901-3 . PMID 20499099 .
  24. ↑ J. Zittlau: Olive oil can damage blood vessels. In: Die Welt from January 24, 2008.

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