Chlorinated Plant Steroids and their Biological Activities

Abstract

A b s t r a c t A r t i c l e I n f oThe present review describes the biological activities of natural plant chlorinated steroids. About forty biologically active chlorinated steroids have shown confirmed cytostatic, antineoplastic, anti-eczematic, antidiabetic, antibacterial, and other activities. The structures and reported and predicted activities of chlorinated steroids are available. With the computer programme PASS and based on structure-activity relationships (SAR), some additional activities are also predicted, which point towards new possible applications of these lipids. This review emphasizes the role of chlorinated steroids as an important source and potential leads for drug discovery and they are of great interest to chemists, physicians, biologists, pharmacologists and the pharmaceutical industry.

Biological Activity and Structural Diversity of Steroids Containing Aromatic Rings, Phosphate Groups, or Halogen Atoms

“…The distribution of biological activity percentages for aragusterol C is depicted in Figure 33. Another compound, aragusteroketal C (157), which is a steroid with a dimethylketal structure, was also isolated from the same sponge. This chlorinated steroid displayed cytotoxic activity against the KB tumor cell line, with an IC 50 value of 4 ng/mL [191].…”

Production and Structural Diversification of Withanolides by Aeroponic Cultivation of Plants of Solanaceae: Cytotoxic and Other Withanolides from Aeroponically Grown Physalis coztomatl

“…A small number of chlorinated withanolides have previously been encountered in plants of Solanaceae as minor metabolites and many of these occur as 5,6-chlorohydrins containing 5α-chloro-6β-hydroxy substituents [25,[44][45][46][47][48]. It has been suggested that the chlorine atom present in these 5,6-chlorohydrins may originate from NaCl present in the plant [2].…”

Newly discovered naturally occurring organohalogens

“…The Madagascan sponge Amphimedon sp. contains amphimedonoic acid (66) and psammaplysene E (67), along with the known 3,5-dibromo-4-methoxybenzoic acid. 29 Neither compound is active against human epidermoid carcinoma KB cells (IC 50 > 10 µg/mL).…”

“…An excellent review of chlorinated plant steroids and their biological activities has appeared. 66 A series of steroidal withanolides, including eleven new examples and two known chlorine-containing ones, were isolated from the plant Physalis peruviana L. (Solanaceae), and were evaluated for their cytotoxicity against prostate and renal cancer cells. 67 The two known chlorinated examples (not shown) physalolactone and 4-deoxyphysalolactone 2 are inactive.…”