Cytotoxic and other withanolides from aeroponically grown Physalis philadelphica

Abstract

Eleven withanolides including six previously undescribed compounds, 16β-hydroxyixocarpanolide, 24,25-dihydroexodeconolide C, 16,17-dehydro-24-epi-dioscorolide A, 17-epi-philadelphicalactone A, 16-deoxyphiladelphicalactone C, and 4-deoxyixocarpalactone A were isolated from aeroponically grown Physalis philadelphica. Structures of these withanolides were elucidated by the analysis of their spectroscopic (HRMS, 1D and 2D NMR, ECD) data and comparison with published data for related withanolides. Cytotoxic activity of all isolated compounds was evaluated against a panel of five human tumor cell lines (LNCaP, ACHN, UO-31, M14 and SK-MEL-28), and normal (HFF) cells. Of these, 17-epi-philadelphicalactone A, withaphysacarpin, philadelphicalactone C, and ixocarpalactone A exhibited cytotoxicity against ACHN, UO-31, M14 and SK-MEL-28, but showed no toxicity to HFF cells.

Withasomniferol D, a New Anti-Adipogenic Withanolide from the Roots of Ashwagandha (Withania somnifera)

“…The translinkage for the A/B ring was further verified by the negative Cotton effect around 340 nm in the ECD measurement of 1 [25], and the configurations at C-5, C-6, and C-7 were assigned accordingly, as depicted in Figure 1. The stereochemistry of H-22 (J = 13.5 and 3.5 Hz) was determined to be α-form on the basis of the typical coupling constants of H-22 reported in a previous study, where the 1 H NMR data of H-22α demonstrated a doublet of doublets with two different coupling constants (J = 9.0-13.8 and 0.5-4.0 Hz) [25,27], while the 1 H NMR data of H-22β showed two similar coupling constants (J = 2.5-7.0, 2.0-5.0 Hz) [28]. The α-orientation of H-22 was also verified by the ROESY correlations of H-16α/H-22 and H-17/H-22 (Figure 3).…”

“…The absolute configuration of 1 was determined by examining the correlations obtained from the ROESY experiment, vicinal proton coupling constants in the 1 H NMR data, and ECD data. The α-position of the epoxy group between C-6 and C-7 was confirmed by the ROESY correlations of H-7/H-8, H-6/H-7, H-6/ H3-19, and H3-19/H-8 and the characteristic coupling constant of 4.0 Hz between H-6 and H-7 (Figure 3), which also suggested a trans-linkage in the conformation of the A/B ring in 1, based on the smaller coupling constant of 0-2 Hz for H-6, which is typical in cis-linkages [25,27,28]. The translinkage for the A/B ring was further verified by the negative Cotton effect around 340 nm in the ECD measurement of 1 [25], and the configurations at C-5, C-6, and C-7 were assigned accordingly, as depicted in Figure 1.…”

Yield and Fruit Properties of Husk Tomato (Physalis phyladelphica) Cultivars Grown in the Open Field in the South of West Siberia

“…Recently, husk tomato has been enjoying increasing attention in many countries, including Russia, due to new information on its chemical composition [4][5][6], health benefits, etc. [7][8][9][10][11]. Over the last few decades in Russia, the crop has been grown only by small farmers and individual gardeners; however, the last century saw quite a lot of attention paid to husk tomato.…”

Phytochemical composition and biological activity of Physalis spp.: A mini-review

“…Crushed leaves are applied over snakebites (Khan et al 2016). The medicinal benefits of P. philadelphica and P. ixocarpa are related to the presence of various bioactive phytochemicals, such as sucrose esters (Choi et al 2006;Xu et al 2018), and antiinflammatory .…”