Moronic acid

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Moronic acid
Moronic acid structure.png
Identifiers
CAS number 6713-27-5 N
PubChem 489941
ChemSpider 429156 YesY
ChEBI CHEBI:30815 YesY
ChEMBL CHEMBL472646 YesY
Jmol-3D images Image 1
Properties
Molecular formula C30H46O3
Molar mass 454.68 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N (verify) (what is: YesY/N?)
Infobox references

Moronic acid (3-oxoolean-18-en-28-oic acid) is a natural triterpene.[1][2] Moronic acid can be extracted from Rhus javanica, a sumac plant traditionally believed to hold medicinal applications.[2] The molecule has also been extracted from Mistletoe (Phoradendron reichenbachianum).[3]

Bevirimat, a derivative of the related triterpenoid betulinic acid, is under development as an anti-HIV drug; however, moronic acid has shown better antiviral profiles in vitro than bevirimat.[4] A particular moronic acid derivative showed potent anti-HIV activity with EC50 values of 0.0085 μM against NL4-3, 0.021 μM against PI-R (a multiple protease inhibitor resistant strain), and 0.13 μM against FHR-2 (an HIV strain resistant to (bevirimat). This derivative has become a new lead for clinical trials and is also active against herpes simplex virus 1.[4]

References[edit]

  1. ^ "Comparative Toxicogenomics Database: moronic acid". 
  2. ^ a b Kurokawa, Masahiko; Basnet, Purusotam; Ohsugi, Mizue; Hozumi, Toyoharu; Kadota, Shigetoshi; Namba, Tsuneo; Kawana, Takashi; Shiraki, Kimiyasu (1999). "Anti-Herpes Simplex Virus Activity of Moronic Acid Purified from Rhus javanica In Vitro and In Vivo". The Journal of Pharmacology and Experimental Therapeutics 289 (1): 72–8. PMID 10086989. 
  3. ^ Rios, María Yolanda; Salinas, David; Villarreal, María Luisa (2001). "Cytotoxic Activity of Moronic Acid and Identification of the New Triterpene 3,4-seco-Olean-18-ene-3,28-dioic Acid from Phoradendron reichenbachianum". Planta Medica 67 (5): 443–6. doi:10.1055/s-2001-15823. PMID 11488459. 
  4. ^ a b Yu, Donglei; Sakurai, Yojiro; Chen, Chin-Ho; Chang, Fang-Rong; Huang, Li; Kashiwada, Yoshiki; Lee, Kuo-Hsiung (2006). "Anti-AIDS Agents 69. Moronic Acid and Other Triterpene Derivatives as Novel Potent Anti-HIV Agents". Journal of Medicinal Chemistry 49 (18): 5462–9. doi:10.1021/jm0601912. PMC 2512972. PMID 16942019. 

External links[edit]