Ana L. Pérez-Castorena

Labdanes and Sucrose Esters from Physalis sordida

Eight new compounds, labdanes 2-4, homoergostane 10, and sucrose esters 12-15, were isolated from aerial parts of Physalis sordida together with several known compounds. Structures of the new compounds were elucidated using spectroscopic evidence and chemical transformations. The structure of 10 was confirmed by X-ray crystallographic analysis of its methyl ester. Anti-inflammatory activity of compounds 1, 2, 4, 5, and 12-15 was evaluated using the TPA-induced mouse ear edema test. Compounds 12 (IC(50) 0.26 mumol/ear) and 15 (IC(50) 0.24 mumol/ear) showed anti-inflammatory activity similar to that of indomethacin (IC(50) 0.24 mumol/ear).

Philadelphicalactones C and D and other cytotoxic compounds from Physalis philadelphica

Two new withanolides, philadelphicalactone C (1) and philadelphicalactone D (4), along with the known withaphysacarpin (3), ixocarpanolide (5), philadelphicalactone A (6), and ixocarpalactone A (7) were isolated from the aerial parts of Physalis philadelphica Lam. Structures of these compounds were determined by spectroscopic analyses and that of philadelphicalactone C (1) was confirmed by X-ray crystallographic analysis. Evaluation of the cytotoxic activity of all isolates and the derivative 2 against a panel of human cancer cell lines indicated a potent activity of compounds 2, 3, 6, and 7.

Virginols A-C, three new withanolides from Physalis virginiana.

Virginols A-C are three new withanolides containing an epoxylactol at the side chain. They were isolated from the aerial parts of Physalis virginiana Miller. Structures of these compounds were determined by analyses of their spectroscopic data, including 1D and 2D NMR. The structure of virginol A was confirmed by X-ray diffraction analysis. The anti-inflammatory activity of virginols was evaluated in the TPA-induced ear mouse edema model.

Seco-eremophiladiolides and Eremophilane Glucosides from Pittocaulon velatum

Two seco-eremophiladiolides, velatumolide and epi-velatumolide, the trihydroxyfuranoeremophilane velatumin, and three eremophilane glucosides were isolated from Pittocaulon velatum, together with several known compounds. The structures of these compounds were elucidated by spectroscopic analysis and chemical reactions. The anti-inflammatory activity of the isolated compounds was investigated using the TPA-induced ear edema model.

Anti-inflammatory constituents of Mortonia greggii Gray.

A new phytochemical study of Mortonia greggii (Celastraceae) afforded four friedelan derivatives (1-4), three lupanes (5-7), retusine (8), two esterified polyhydroxyagarofurans (9-10), mortonin C (11) and photomortonin C (12). The anti-inflammatory activity on carrageenan and 12-O-tetradecanoylphorbol-13-acetate induced models of inflammation, as well as the ability to inhibit the nitric oxide (NO) produced by lipopolysaccharide-stimulated mouse peritoneal macrophages were evaluated for the main metabolites. Our results showed that the friedelan dehydrocanophyllic acid methyl ester (1) exhibits an anti-inflammatory effect which could be related to an inhibition of prostaglandin and NO production. The activity of lupeol (5), 29-hydroxylupeol (6) and 29-hydroxylupenone (7) might be involved with the prostanoid synthesis. The presence of the hydroxy groups in 6 appears to be important for activity. The edema inhibition capacity of retusine (8) could be related to a reduction of the prostaglandin production. The agarofuran derivative 10 is an NO inhibitor whose activity is probably not involved in the synthesis of prostaglandins.

Absolute configuration of labdane diterpenoids from Physalis nicandroides.

A mixture of the new epimeric labdenetriols 1 and 2 was isolated from the aerial parts of Physalis nicandroides. The structures of 1 and 2, including their absolute configurations, were established by analyses of their spectroscopic data, together with the X-ray diffraction analysis of acetonide 3 and chemical correlation with (-)-(13E)-labd-13-ene-8α,15-diol (6), whose absolute configuration was also confirmed by X-ray analysis of its dibromo derivative 7. The epimeric labdenediols 8 and 9, the known labdanes 6 and 11, and the acylsucroses 12 and 13 were also isolated. Labdanes 6 and 11 showed moderate anti-inflammatory activities in the induced ear edema model.

A dirhamnopyranoside from Psacalium megaphyllum

Abstract A chemical study of Psacalium megaphyllum afforded some known compounds and the new, kaempferol-3- O -α- l -(3- O -acetyl)rhamnopyranoside-7- O -α- l -rhamnopyranoside. The structure of the flavonol was determined by spectroscopic methods.

Sesquiterpenoids from Pittocaulon filare

The phytochemical study of Pittocaulon filare afforded three oplopanes (1-3), a eudesmane (6), and three oplopane glucosides (7-9), one of them reported as its acetyl derivative (7a), together with several known compounds. The structures of the compounds were elucidated by spectroscopic analysis and chemical reactions. The anti-inflammatory activity of compounds 1-5 was determined using the 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear edema model, and the effect of compounds 1-4 on the recruitment of neutrophils was evaluated using the myeloperoxidase test. Compounds 1 and 2 were the more active anti-inflammatory agents, with lower ID50 values (0.17 and 0.18 μmol/ear, respectively) than indomethacin (0.24 μmol/ear), but they had a lesser effect on the inhibition of neutrophil infiltration than both indomethacin and compound 3, indicating that the tested compounds do not have the same ability to inhibit edema and to prevent cell infiltration.

Modified eremophilanes and anti-inflammatory activity of Psacalium cirsiifolium

Four new modified eremophilanes, together with ten known cacalol derivatives, two caryophyllenes, one aromadendrene and one flavonoid were isolated from Psacalium cirsiifolium. The structures of these compounds were elucidated by spectroscopic analysis. The anti-inflammatory activity of extracts and of seven of the isolated compounds was evaluated on 12-O-tetradecanoylphorbol-13-acetate (TPA) model of induced acute inflammation. The new compound 2α -hydroxyadenostin B (4) showed a dose dependent activity (IC50 0.41 µmol per ear) and a neutrophil inhibition effect as measured by the myeloperoxidase (MPO) assay similar to that of indomethacin at 0.31 and 1.0 µmol per ear.

Diterpenes of Bahia glandulosa

Abstract Ten new diterpenes were isolated along with some known compounds. Eight of the new diterpenes are esters of capric, lauric, myristic and palmitic acids.