Anti-HIV and NO production inhibition activities of epi-aleuritolic acid derivatives

Fifteen epi-aleuritolic acid derivatives were synthesized and evaluated for anti-HIV activity in 293 T cells and NO production inhibition activity. Of the derivatives, 1, 2, 3, 4, 11, and 13 showed relatively potent anti-HIV activity with EC50 values ranging from 5.80 to 13.30 μM. The most potent compound, 3α-2′,2′-dimethylsuccinic acyl epi-aleuritolic acid (11), displayed significant anti-HIV activity with an EC50 value of 5.80 μM. Compounds 1, 3, 4, and 11 showed NO inhibition activity, with IC50 values ranging from 3.40 to 7.10 μM and compound 1 inhibited NO production with an IC50 value of 3.40 μM.

[1]  Li Huang,et al.  Anti-AIDS agents. 78. Design, synthesis, metabolic stability assessment, and antiviral evaluation of novel betulinic acid derivatives as potent anti-human immunodeficiency virus (HIV) agents. , 2009, Journal of medicinal chemistry.

[2]  De-Quan Yu,et al.  Triterpenoids from the stems of Myricaria paniculata , 2005, Journal of Asian natural products research.

[3]  Atta-ur-rahman,et al.  Isotamarixen - a new antioxidant and prolyl endopeptidase-inhibiting triterpenoid from Tamarix hispida. , 2004, Planta medica.

[4]  E. Moilanen,et al.  Dexamethasone inhibits inducible nitric-oxide synthase expression and nitric oxide production by destabilizing mRNA in lipopolysaccharide-treated macrophages. , 2002, Molecular pharmacology.

[5]  K. Lee,et al.  Synthesis and anti-HIV activity of oleanolic acid derivatives. , 2001, Bioorganic & medicinal chemistry letters.

[6]  K. Lee,et al.  Anti-AIDS agents 38. Anti-HIV activity of 3-O-acyl ursolic acid derivatives. , 2000, Journal of natural products.

[7]  K. Lee,et al.  Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids. , 1998, Journal of natural products.

[8]  K. Lee,et al.  Anti-AIDS agents--XXVII. Synthesis and anti-HIV activity of betulinic acid and dihydrobetulinic acid derivatives. , 1997, Bioorganic & medicinal chemistry.

[9]  S. K. Chaudhuri,et al.  Isolation and structural elucidation of pentacyclic triterpenoids from Maprounea africana. , 1995, Journal of natural products.

[10]  J. Pezzuto,et al.  Pentacyclic triterpenes derived from Maprounea africana are potent inhibitors of HIV-1 reverse transcriptase. , 1994, Journal of natural products.

[11]  T. K. Razdan,et al.  Phytolaccanol and epiacetylaleuritolic acid, two triterpenoids from Phytolacca acinosa , 1982 .

[12]  R. C. Carpenter,et al.  13C NMR studies of some lupane and taraxerane triterpenes , 1980 .