Search

Pharbitidis Semen has worldwide recognition in traditional medicine for the treatment of several illnesses apart from its purgative properties, and it is also reported to show anticancer effect. However, limited pharmacological studies are available on the extract or resin glycosides fraction of Pharbitidis Semen. The purpose of this study was to determine the mechanism of the colon cancer cell cytotoxic effect of a purified resin glycoside fraction from Pharbitidis Semen (RFP). Our results showed that the RFP-induced cell death was mediated by the caspase-independent and autophagy-protective paraptosis, a type of cell death that is characterized by the accumulation of cytoplasmic vacuoles and mitochondria swelling. RFP significantly stimulated endoplasmic reticulum stress, inhibited proteasome-dependent degradation, and activated the MAPK signaling pathway in human colon cancer cell lines. Furthermore, we found that RFP activated chloride intracellular channel-1 (CLIC1) and increased the intracellular Cl− concentration. Blockage of CLIC1 by DIDS (disodium 4,4′-diisothiocyanato-2,2′-stilbenedisulfonate hydrate) attenuated cell death, cytoplasmic vacuolization, and endoplasmic reticulum stress, suggesting that CLIC1 acts as a critical early signal in RFP-induced paraptosis. In conclusion, results obtained indicated that the cytotoxic effect of RFP in colon cancer cells was the outcome of paraptosis mediated by activation of CLIC1.

Six pentasaccharide resin glycosides from Ipomoea cairica, including four new acylated pentasaccharide resin glycosides, namely cairicoside I–IV (1–4) and the two known compounds cairicoside A (5) and cairicoside C (6), were isolated from the aerial parts of Ipomoea cairica. Their structures were established by a combination of spectroscopic, including two dimensional (2D) NMR and chemical methods. The core of the six compounds was simonic acid A, and they were esterfied the same sites, just differing in the substituent groups. The lactonization site of the aglycone was bonded to the second saccharide moiety at C-2 in 1–4, and at C-3 in 5–6. Compounds 1 and 5, 4 and 6 were two pairs of isomers. The absolute configuration of the aglycone in 1–6 which was (11S)-hydroxyhexadecanoic acid (jalapinolic acid) was established by Mosher’s method. Compounds 1–4 have been evaluated for inhibitory activity against α-glucosidase, which all showed inhibitory activities.

Resin glycosides are well known as purgative ingredients, which are characteristic of certain crude drugs such as Mexican Scammony Radix, Orizabae Tuber, and Jalapae Tuber, all of which originate from Convolvulaceae plants. Depending on their solubility in ether, these are roughly classified into two groups—jalapin (soluble) and convolvulin (insoluble). Almost all jalapins hitherto isolated and characterized had common intramolecular macrocyclic ester structures. These are composed of 1 mol of oligoglycoside of hydroxyl fatty acid (glycosidic acid) partially acylated by some organic acids at the sugar moiety, some examples of which are ester-type dimers. On the other hand, convolvulin is regarded as an oligomer of a variety of acylated glycosidic acids. This review describes the isolation and structural elucidation of resin glycosides from some Convolvulaceae plants, including Ipomoea operculata, Pharbitis nil, Quamoclit pennata, Calystegia soldanella, and I. muricata.

High performance liquid chromatography profiling with mass spectrometry detection was applicable to identify known and novel multidrug-resistance glycolipid inhibitors from the complex resin glycosides mixture of Ipomoea alba L., Convolvulaceae, seeds. Albinosides X and XI were purified by recycling liquid chromatography and their structural elucidation was accomplished by nuclear magnetic resonance. Albinoside XI exerted a strong potentiation of vinblastine susceptibility in multidrug-resistant human breast carcinoma cells. Keywords: HPLC–MS profiling, Glycolipid, Resin glycoside

LETTER, Oligosaccharide containing macrolides of resin glycosides were effectively constructed by MeOTf promoted intramolecular glycosylation of dodecyl thioglycosyl donors. Synthesis of a key disaccharide intermediate of tricolorin A and total synthesis of tricolorin F were successfully achieved by this approach.