A ring-D aromatic withanolide from Salpichroa origanifolia

Veleiro, Adriana S.; Oberti, Juan C.; Burton, Gerardo

doi:10.1016/0031-9422(92)80042-d

Cited by 36 publications

(61 citation statements)

References 10 publications

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“…tristis var. lehmannii ) have supported the molecular proposal . Now, with new knowledge concerning approximately 85% of the Salpichroa species, more accurate conclusions can be made.…”

Section: Resultsmentioning

confidence: 54%

“…The dichloromethane extract of the aerial parts of S . scandens from Argentina ( Sample 1 ) was subjected to chromatographic purification to yield the new compound 1 , and the known salpichrolides A, C, I, and S ( Fig. ).…”

Section: Resultsmentioning

confidence: 99%

“…tristis var. lehmannii ( Dammer ) Keel . Many of these compounds exhibit interesting biological activities such as antifeedant, antiproliferative, and cancer chemopreventive effects …”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Phytochemical Study of the Genus Salpichroa (Solanaceae), Chemotaxonomic Considerations, and Biological Evaluation in Prostate and Breast Cancer Cells

Basso

González

Barboza

et al. 2017

Chemistry & Biodiversity

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Twelve Salpichroa taxa have been phytochemically analyzed. From the aerial parts of S. scandens, four known salpichrolides A, C, I, S, and an unreported withanolide named salpichrolide V (1), were isolated. In S. dependens, S. gayi, S. glandulosa subsp. glandulosa, S. glandulosa subps. weddellii, S. leucantha, S. micrantha, S. microloba, S. proboscidea, S. ramosissima, S. tristis var. tristis, and S. weberbauerii, no withanolides were found. The chemical content of ca. 85% of the Salpichroa taxa is in agreement with molecular studies, which suggest that Salpichroa and Jaborosa, a genus considered morphologically close to Salpichroa, are distant in the systematic of the Solanoideae subfamily. Moreover, the in vitro cytotoxic activity of a set of natural salpichrolides and derivatives was examined against two prostate carcinoma cell lines (PC3 and LNCaP) and two human breast cancer cell lines (MCF-7 and T47D). Several compounds showed moderate activity (IC = 64.91 - 29.97 μm).

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“…tristis var. lehmannii ) have supported the molecular proposal . Now, with new knowledge concerning approximately 85% of the Salpichroa species, more accurate conclusions can be made.…”

Section: Resultsmentioning

confidence: 54%

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Phytochemical Study of the Genus Salpichroa (Solanaceae), Chemotaxonomic Considerations, and Biological Evaluation in Prostate and Breast Cancer Cells

Basso

González

Barboza

et al. 2017

Chemistry & Biodiversity

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“…Withanolides are a group of C‐28 steroidal lactones and lactols isolated from several genera of the Solanaceae family . A small group of these compounds, termed salpichrolides, were isolated from Salpichroa origanifolia and exhibited antiestrogenic effects . Salpichrolides such as Salpichrolide A (Fig.…”

Section: Introductionmentioning

confidence: 99%

Exploring the molecular basis of action of ring D aromatic steroidal antiestrogens

2015

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Salpichrolides are natural plant steroids that contain an unusual six-membered aromatic ring D. We recently reported that some of these compounds, and certain analogs with a simplified side chain, exhibited antagonist effects toward the human estrogen receptor (ER), a nuclear receptor whose endogenous ligand has an aromatic A ring (estradiol). Drugs acting through the inhibition or modulation of ERs are frequently used as a hormonal therapy for ER(+) breast cancer. Previous results suggested that the aromatic D ring was a key structural motif for the observed activity; thus, this modified steroid nucleus may provide a new scaffold for the design of novel antiestrogens. Using molecular dynamics (MD) simulation we have modeled the binding mode of the natural salpichrolide A and a synthetic analog with an aromatic D ring within the ERα. These results taken together with the calculated energetic contributions associated to the different ligand-binding modes are consistent with a preferred inverted orientation of the steroids in the ligand-binding pocket with the aromatic ring D occupying a position similar to that observed for the A ring of estradiol. Major changes in both dynamical behavior and global positioning of H11 caused by the loss of the ligand-His524 interaction might explain, at least in part, the molecular basis of the antagonism exhibited by these compounds. Using steered MD we also found a putative unbinding pathway for the steroidal ligands through a cavity formed by residues in H3, H7, and H11, which requires only minor changes in the overall receptor conformation.

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“…Thell collected in the provinces of Cordoba [1,2], Buenos Aires [3,4] and Salta [5], we have isolated thirteen withanolides (salpichrolides), eleven of which contain an aromatic D ring. The main withanolides salpichrolide A (1), salpichrolide G (2) and salpichrolide C (3), are feedant deterrants for Tribolium castaneum and Musca domestica [6].…”

Section: Introductionmentioning

confidence: 99%