Seasonal variation in alkaloid composition and antiproliferative activity of Stylophorum lasiocarpum (Oliv.) Fedde

Abstract

Stylophorum lasiocarpum (Oliv.) Fedde (Papaveraceae) belongs to traditional Chinese medicine herbs but there was minimal information on the content of alkaloids in this plant. Extracts from the aerial part and roots were examined by liquid chromatography with UV and mass spectrometric detection, with nineteen alkaloids identified. Changes in alkaloid content over the entire vegetation period of a one-and two-year old plant were studied. The protoberberine alkaloids, coptisine and stylopine, were found to be the main substances in extracts of the aerial part irrespective of the plant's age and time of harvest. Variable amounts of protopine, sanguinarine, chelerythrine, chelirubine, macarpine, chelilutine and berberine were also recorded in the aerial part. The roots contained significantly larger quantities of all alkaloids than the aerial part with the levels of most alkaloids varying from May to October, peaking in the middle of the vegetation period. Coptisine was the dominant alkaloid in all samples. The antiproliferative activities of the root extract and of seven individual alkaloids were tested on A375 human malignant melanoma cells. The significant dose-dependent toxicity of the root extract was attributed largely to the quaternary benzo[c]phenanthridine alkaloids, macarpine and sanguinarine.

Study of alkaloid berberine and its interaction with the human telomeric i-motif DNA structure

“…Berberine is a plant alkaloid and together with coptisine, jatrorrhizine, columbamine, corysamine, and palmatine belongs to the group of quaternary protoberberine alkaloids [7]. The protoberberines are distributed in such plant families as Papaveraceae, Berberidaceae or Fumariaceae, among others, as well as a few examples in Magnoliaceae and Convolvulaceae [8] [9]. The molecule of berberine is a planar molecule with an extended π-delocalized system having a partial positive charge on N7 [7] (Figure 1c).…”

The capability of minor quaternary benzophenanthridine alkaloids to inhibit TNF-α secretion and cyclooxygenase activity

“…Extracts obtained from these plants, especially M. cordata and S. canadensis, have been used in traditional medicine for their anti-inflammatory effects, particularly against plaque build-up and gingivitis (Šimánek et al 2003). Varying amounts of the major alkaloids sanguinarine and chelerythrine and the minor ones chelirubine, sanguirubine, chelilutine, sanguilutine, and macarpine have been found in these plants (Suchomelova et al 2007;Šimánek et al 2003;Slaninova et al 2014;Sebrlova et al 2015).…”

Introduction of macarpine as a novel cell‐permeant DNA dye for live cell imaging and flow cytometry sorting

“…MA (Figure ) was used experiments in the form of chloride and was isolated from S. lasiocarpum as previously described by Šebrlová et al. (). Briefly, dried ground roots were extracted with methanol.…”

“…Macarpine (MA; Figure ) is a quaternary benzophenanthridine alkaloid (QBA) isolated from plants Macleaya microcarpa or Stylophorum lasiocarpum (Pěnčíková et al., , Šebrlová et al., ). QBAs are a group of interesting natural products that display antiproliferative, antimicrobial, antifungal and anti‐inflammatory activities (reviewed by Slaninová et al., ).…”