Ambronic acid; 3-Oxoolean-18-en-28-oic acid
3D model (JSmol)
|Molar mass||g·mol−1 454.695|
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Moronic acid (3-oxoolean-18-en-28-oic acid) is a natural triterpene. Moronic acid can be extracted from Rhus javanica, a sumac plant traditionally believed to hold medicinal applications. The molecule has also been extracted from Mistletoe (Phoradendron reichenbachianum).
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. 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.
- “Comparative Toxicogenomics Database: moronic acid”.
- 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.
- 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.
- 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.
- CTD’s Moronic acid page from the Comparative Toxicogenomics Database
- NLM/NIH Medical Subject Heading
- KEGG Terpenoid Synthesis Pathway
- Molecules with silly names