Antibacterial activity of withanolides, labdane glucosides, flavonoids and other constituents from two populations of Physalis patula.

Two populations of Physalis patula Miller collected in different localities (Querétaro and Teotihuacán) of Central México were analyzed. Eight new compounds including three withanolides, physapatolides A-C (1-3), two labdanes, 12-epi-physacoztomatin (10) and physapatulone (12), besides three 12-O-glucosyl labdanes, patulosides A-C (13-15), were isolated from these collections. A series of known withanolides, flavonoids, labdanes, sucrose esters, and sterols were also isolated.

Lactols from Physalis grisea.

From the extracts of stems and leaves as well as of calyxes of Physalis grisea were isolated four withalactols, the new griselactols A (3) and B (6) and the known physapubescin (1) and peruvianolide E (2). Other four known compounds were also isolated, kaempferol 3-O-β-sophoroside (5) and three sterols. The structures of compounds were elucidated by extensive spectroscopic data analyses, chemical and physical-chemical methods, including electronic circular dichroism (ECD), and by comparison with data described in the literature.

Sucrose esters from the calyxes of Physalis chenopodifolia.

Three new sucrose esters, physachenoses A-C (1-3) and the known withanolide, physachenolide D (4), were isolated from the calyxes of Physalis chenopodifolia Lam. Analysis of the MS, 1D and 2D NMR spectra of the new compounds allowed to determine their structures as 3'-O-dodecanoyl-2,3,4-tri-O-isobutyrylsucrose (1), 3'-O-dodecanoyl-2,4-di-O-isobutyryl-3-O-2-methylbutanoylsucrose (2), and 3'-O-dodecanoyl-2-O-isobutyryl-3-O-2-methylbutanoylsucrose (3).

Labdanes, Withanolides, and Other Constituents from .

Chemical investigation of the aerial parts (except fruits and calixes) of var. led to the isolation of a series of new labdane-type diterpenoids, including the closely related compounds -, the labdane glucosides and , a mixture of the epimeric alcohols and , and one labdanetriol, isolated as its tri--acetyl derivative . In addition, three new withanolides (-) and six known compounds were isolated.

Chemical Composition and Antimicrobial Activity of Ageratina deltoidea.

The chemical study of Ageratina deltoidea afforded grandiflorenic acid (1), ent-kaurenoic acid (2), and eight benzylbenzoates (3 - 10), two of them, 3,5-dimethoxybenzyl 2,3,6-trimethoxybenzoate (5) and 4-(β-d-glucopyranosyloxy)-3-hydroxybenzyl 2,6-dimethoxybenzoate (9), described for the first time. In addition, the new sesquiterpene lactone deltoidin C (13), together with the known 11 and 12, the phenolic compounds: ayanin, 2,6-dimethoxybenzoic acid, methyl 3,4-dihydroxycinnamate, chlorogenic acid, and 3,5-dicaffeoylquinic acid were also isolated. The structures of these compounds were determined by spectroscopic methods and chemical reactions.

Terpenoids from Melampodium perfoliatum.

The phytochemical study of the aerial parts of Melampodium perfoliatum afforded six melampolides (1, 3, 5-8), a eudesmanolide (9), two diterpene lactones (10, 11), and two ent-kaurane derivatives (12, 13), together with the known melampodin (2) and polymatin A (4). The structures of the compounds were elucidated by physical data analysis and chemical reactions. Compounds 2, 4, 5, and 10 exhibited dose-dependent anti-inflammatory activity on the 12-O-tetradecanoylphorbol-13-acetate-induced ear edema model, with ID values of 1.

Cytotoxic 20,24-epoxywithanolides from Physalis angulata.

A new withanolide, physangulide B (1), was isolated from calyxes of Physalis angulata. This compound was also present in the aerial parts along with the known physangulide (4), which was isolated as the acetonide 3, and 24,25-epoxywithanolide D (6). Structures of these compounds were determined by analysis of their spectroscopic data, which indicated the presence of a 20,24-epoxy group in both physangulides.

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.

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.

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.

Chemical composition and biological activity of Laennecia schiedeana.

The chemical study of Laennecia schiedeana afforded three sterols, five diterpenes, five flavonoids, three caffeoyl derivatives of quinic acid, and two triterpenes. Evaluation of the cytotoxic activity of the extracts and isolated metabolites showed that 15-methoxy-16-oxo-15,16H-strictic acid was the most active compound [(15.05 +/- 2.

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.

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.

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.

Chemical constituents of Roldana lineolata.

The new eremophilanolide 1, the known eremophilane derivatives 2 and 3, already described as part of mixtures, the known compounds hyperin, 2''-acetylhyperin and two calenduladiol esters were isolated from Roldana lineolata. Their structures were determined by spectroscopic methods. Compounds 1 and 2 as well as their acetylated and oxidized derivatives were tested against several fungi strains.

Cacalol derivatives from Roldana angulifolia.

Four new modified eremophilanes, angulifolide (1) and angulifolins A-C (2-4), and two new triacetylglucosides (7 and 8) were isolated from Roldana angulifolia, together with several known compounds. The structures of the new compounds were elucidated by spectroscopic analysis and chemical reactions. The absolute configuration of compounds 2 and 3 was established by Mosher ester methodology.

Sucrose esters from the fruits of Physalis nicandroides var. attenuata.

Three 2,3,1',3'-tetraacyl- and two 2,3,3'-triacylsucroses, nicandroses A-E (1-5), were isolated from the fruits of Physalis nicandroides var. attenuata. The acyl groups in these new compounds were identified as decanoyl, isobutyryl, 2-methylbutanoyl, and acetyl.

Eremophilanes from Senecio mairetianus and some reaction products.

Eight new eremophilanolides (1, 2, 4-7, 9, and 10), a new eremophilane (13), and several known compounds were isolated from the roots and aerial parts of Senecio mairetianus. The chemical structures were proposed taking into consideration spectroscopic analyses and chemical transformations. X-ray diffraction analysis of 2, 4, and 9 confirmed their structures.

Labdanes and withanolides from Physalis coztomatl.

Aerial parts of Physalis coztomatl afforded a new labdane diterpene, physacoztomatin (1), and five new withanolides, physacoztolides A-E (5-9). Six known compounds were also isolated. The structures of the new compounds were established after analyses of their spectroscopic data and by means of chemical transformations.

Eremophilane esters of Robinsonecio gerberifolius and their rearranged products. Study of the coupling constants (2)J(H, H), (3)J(H, H) and (4)J(H, H).

In the course of the basic hydrolysis of four eremophilane esters isolated from Robinsonecio gerberifolius, some rearrangements, eliminations, and additions occurred. Five compounds were obtained, three of them not previously described. Additionally, a new sesquiterpene was produced by autooxidation of compound 1.

Androstane and withanolides from Physalis cinerascens.

Two new withanolides, cinerolide and 24,25-dihydrowithanolide S, together with the new androstane, cinedione, and the known withanolides, visconolide, physalactone, withanolide S and 4beta-hydroxywithanolide E were isolated from the EtOAc extract of leaves, flowers and stems of Physalis cinerascens. The structures of these compounds were established by spectroscopic methods and that of cinerolide was confirmed by X-ray diffraction analysis.

Insect growth inhibition by tocotrienols and hydroquinones from Roldana barba-johannis.

The methanol extract from the aerial parts of Roldana barba-johannis (Asteraceae) afforded sargachromenol, sargahydroquinoic acid, and sargaquinoic acid. These natural products and their corresponding acetylated and methylated derivatives showed insecticidal and insect growth regulatory activities against the Fall Armyworm [Spodoptera frugiperda J.E.

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.

18-Acetoxywithanolides from Physalis chenopodifolia1.

Five new withasteroids, physachenolides A - E were isolated from the acetone and methanol extracts of leaves, flowers and stems of Physalis chenopodifolia Lam. The structural assignments of these compounds were based on spectral evidence. The absolute configuration of physachenolide A was established by X-ray analysis.