Maslinic acid

  • (4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-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-carbonsäure (IUPAC)
  • 2α - Hydroxyoleanolsäure

Crystalline solid

Poorly water (0.3 g / l at 25 ° C), good in DMSO (20 g / l)

Template: Infobox chemical / molecular formula search available

Maslinic is a pentacyclic triterpene, which is composed of five cyclohexane. The saponin Maslinic is a natural component of olive oil.

Occurrence

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

Also in Japanese Avens ( Geum japonicum), Queen Flower ( Lagerstroemia speciosa) of the Small (Prunella vulgaris), the Asian flowering dogwood (Cornus kousa ), the Siberian elm ( Ulmus pumila ), in ramie ( Boehmeria nivea ) and a number of other plants could be detected and isolated maslinic.

Pharmacological properties and potential

Maslinic is cytotoxic. Although it is not trap free radicals capable of, but provides protection against oxidation of DNA. In in vitro experiments, an anti-proliferative and apoptosis- inducing effect of Maslinic could be detected. Maslinic activated caspase -3, an important enzyme for apoptosis. The compound appears to inhibit angiogenesis in addition, the (angiogenesis) as well as the enzyme cyclooxygenase-2 (COX -2). An anti - diabetic activity could be demonstrated in model organisms.

At various cancer cell lines - especially in colon cancer cells - an anti -carcinogenic effect has been demonstrated. It is believed that the forth known from epidemiological data, relatively low risk of colon Mediterranean population related to the relatively high consumption of olive oil and olives, and one of the causes of the olive constituent is Maslinic. Per person and day is there admission to Maslinic at about 62 mg. In addition cardioprotective properties of Maslinic could be detected.

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

Maslinic inhibit enzymes required for the HIV virus.

Further Reading

  • X. Wen, H. Sun, J. Liu, K. Cheng, P. Zhang, L. Zhang, J. Hao, L. Zhang, P. Ni, including: 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, ISSN 0022-2623. doi: 10.1021/jm8000949. PMID 18,517,260th
  • C. Li, Z. Yang, Z. Li, Y. Ma, L. Zhang, C. Zheng, W. Qiu, X. Wu, including: maslinic acid Suppresses osteoclastogenesis and ovariectomy -induced bone loss Prevents by regula ting RANKL -mediated NF -kB and MAPK signaling pathways. In: Journal of bone and mineral research: the official journal of the American Society for Bone and Mineral Research Volume 26, Number 3, March 2011, pp. 644-656, ISSN 1523-4681. doi: 10.1002/jbmr.242. PMID 20,814,972th
  • C. Li, Z. Yang, C. Zhai, W. Qiu, D. Li, Z. Yi, L. Wang, among other things: maslinic acid potentiates the anti- tumor activity of tumor necrosis factor alpha by inhibiting NF -kappaB signaling pathway. In: Molecular Cancer Volume 9, 2010, pp. 73, ISSN 1476-4598. doi: 10.1186/1476-4598-9-73. PMID 20,367,887th PMC 2.90773 million ( 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, ISSN 1612-1880. doi: 10.1002/cbdv.200900193. PMID 20,491,082th
  • 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, ISSN 1464-3405. doi: 10.1016/j.bmcl.2009.10.017. PMID 19,846,303th
  • 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, ISSN 1439-0221. doi: 10.1055/s-0029-1185481. PMID 19,291,614th
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