Mahinda Martínez

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.

New sucrose esters from the fruits of Physalis solanaceus

Three new sucrose esters (1-3) along with several known compounds were isolated from the fruits of Physalis solanaceus. The structural elucidation of the isolates was based on their spectroscopic characteristics mainly those of MS and NMR.

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.

Physalis and physaloids: A recent and complex evolutionary history

The complex evolutionary history of the subtribe Physalinae is reflected in the poor resolution of the relationships of Physalis and the physaloid genera. We hypothesize that this low resolution is caused by recent evolutionary history in a complex geographic setting. The aims of this study were twofold: (1) To determine the phylogenetic relationships of the current genera recognized in Physalinae in order to identify monophyletic groups and resolve the physaloid grade; and (2) to determine the probable causes of the recent divergence in Physalinae. We conducted phylogenetic analyses with maximum likelihood (ML) and Bayesian inference with 50 Physalinae species and 19 others as outgroups, using morphological and molecular data from five plastid and two nuclear regions. A relaxed molecular clock was obtained from the ML topology and ancestral area reconstruction was conducted using the DEC model. The genera Chamaesaracha, Leucophysalis, and Physalis subgenus Rydbergis were recovered as monophyletic. Three clades, Alkekengi-Calliphysalis, Schraderanthus-Tzeltalia, and Witheringia-Brachistus, also received good support. However, even with morphological data and that of the DNA of seven regions, the tree was not completely resolved and many clades remained unsupported. Physalinae diverged at the end of the Miocene (∼9.22Mya) with one trend indicating that the greatest diversification within the subtribe occurred during the last 5My. The Neotropical region presented the highest probability (45%) of being the ancestral area of Physalinae followed by the Mexican Transition Zone (35%). During the Pliocene and Pleistocene, the geographical areas where species were found experienced significant geological and climatic changes, giving rise to rapid and relatively recent diversification events in Physalinae. Thus, recent origin, high diversification, and morphological complexity have contributed, at least with the currently available methods, to the inability to completely disentangle the phylogenetic relationships of Physalinae.

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.

Physalis (Solanaceae) and allied genera: Tzeltalia, a new genus from the highlands of southern Mexico and northwestern Guatemala

A morphological analysis ofPhysalis and several closely related genera, with emphasis on a group of species known as “atypicalPhysalis,” showed that two of the atypical species are better treated as a distinct genus.Tzeltalia is described and two new combinations are made:T. amphitricha andT. calidaria. Restricted to the highlands of Chiapas, Mexico, and adjacent Guatemala,Tzeltalia is distinguished fromPhysalis by a combination of characters including shrubby habit; fasciculate flowers; lobed corolla; scabrate pollen; and non-invaginated, partially open, coriaceous, and reticulate-veined fruiting calyx.ResumenEl análisis de un grupo de especies atípicas dePhysalis y otros géneros relacionados demostró que dos especies deben considerarse como otro género. Se describeTzeltalia, un género restringido a los altos de Chiapas, México, y Guatemala y se hacen dos nuevas combinaciones,T. amphitricha yT. calidaria.Tzeltalia se distingue dePhysalis por una combinación de caracteres que incluyen un habito arbustivo, flores fasciculadas, corola lobulada, polen escabroso, cáliz del fruto no invaginado, parcialmente abierto, coriáceo y con venación reticulada.

Lupane triterpenes with a δ-lactone at ring E, from Lippia mexicana.

Three new lupane-type triterpenes, lippiolide (1), lippiolidolic acid (2), and lippiolic acid (3), were isolated from aerial parts of Lippia mexicana. Compounds 1 and 2 exhibited a δ-lactone at ring E. The known cycloartane triterpene 5 was also isolated. The structures of these compounds were established on the basis of spectroscopic data and chemical reactions, and the structure of compound 1 was confirmed by X-ray diffraction analysis. Anti-inflammatory activity of compounds 1, 3, and 5 was evaluated in the TPA-induced ear mouse edema model. Lupanes 1 and 3 were more active than cycloartane 5.

Two new species of Physalis (Solanaceae) endemic to Jalisco, Mexico

Two new species ofPhysalis, both endemic to Jalisco, Mexico, are described and illustrated:P. longiloba andP. tamayoi.ResumenSe describen e ilustran dos nuevas especies dePhysalis endémicas de Jalisco, México:P. longiloba y.P. tamayoi.

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. The structures of compounds 1 and 6 were confirmed by X-ray analysis of their corresponding acetyl derivatives 2 and 7. The structure of physangulide was originally described as the 22S withanolide 5, now its structure and configuration are revised to 4. Evaluation of the cytotoxic activity of compounds 1-3 against two human cancer cell lines indicated a potent activity of compound 1 and its derivative 2.