Mulinolic acid, a diterpenoid from Mulinum crassifolium

Absolute Configuration of Mulinolic Acid

“…Recrystallization de mulinolic acid from ethyl acetate a room temperature yielded white crystals, which were suitable for X-ray diffraction analysis. The spectroscopic data showed resemblance with those similar mulinane structures reported in the literature [4][5][6][7][8][9][10][11] . The relative stereochemistry of mulinolic acid was assigned based on careful analysis of the ROESY experiment 6 , and in this work we have assigned the absolute configuration of this diterpene using X-ray crystal analysis.…”

Crystal structure of methyl 8-hydroxy-3-isopropyl-5a,8-dimethyl-2,3,4,5,5a,6,7,8,10a,10b-decahydrocyclohepta[e]indene-3a(1H)-carboxylate, C21H34O3

“…The fractions were then re-chromatographied by HSCCC using the above stated parameters and n-hexane: EtOAc: acetonitrile 5:3:5 v/v/v as solvent system and several pure diterpenoids were isolated, including mulinenic acid [5], mulinic and isomulinic acids [6] and 17-acetoxymulinic acid [7,8]. From fraction F7, 50 mg of mulinolic acid [9], was obtained after re-chrystalization from n-hexane: …”

“…We are not able to determine the absolute stereochemistry by X-ray methods and the con guration shown here was chosen to be in accord with that reported in previous chemical studies [9]. The structure consists of a mulinic acid skeleton and the isopropyl, methyl groups and methyl ester at C3, C8, C16 and C5 are β-oriented respectively, whereas the hydroxyl groups at C13 is α- 2-x,1/2+y, 3/2-z).…”

Diterpenoids from Azorella compacta (Umbelliferae) active on Trypanosoma cruzi

“…Compound separation was monitored by thin-layer chromatography. The compounds were isolated and purified through column and thin-layer chromatographies, and the derivatives were submitted to crystallization, sublimation and vacuum distillation, as previously described (Loyola et al 1996). The structure of the natural products was determined by spectroscopic techniques in homo-and heteronuclear 2D-NMR experiments (Loyola et al 1996).…”

“…Two plants, yareta (Azorella compacta) and chuquican (Mulinum crassifolium), from the Umbelliferae family are rich sources of diterpenoids, compounds with a variety of biological activities (Esquivel et al 1989, Loyola et al 1996, 1997a. Both plants are extensively used in folk medicine against diabetes, bronchitis, high-altitude sickness, pneumonia, rheumatism, and have also wound healing effects (Gunckel 1967, Wickens 1995.…”