Studies On The Chemical Constituents From Semen Cassiae And The Influence Of Processing

Semen Cassiae, the ripe seed of Cassia obtusifolia L. and Cassia tora L., is a member of the genus Cassia (Leguminosae). In the theory of Traditional Chinese Medicine, the seed is sweet, bitter and salty in flavor, slightly cold in nature and attributive to the liver and large intestine meridians. It has the effects of clearing away liver-fire to improve eyesight and moistening the intestines to relax the bowels, and can be mainly used for the following symptoms, such as liver-heat syndrome with redness, swelling and pain of the eyes, and tears running, headache and dizziness, blurred vision, and constipation due to dryness of the intestine. Semen Cassiae was initially recorded in "Shen Nong Ben Cao Jing’’(《神农本草经》),and it was listed as the top-grade medicine. Semen Cassiae, which has been recorded in Materia Medica of previous dynasties and medical works, is a traditional Chinese herb with high frequency of using, potent effects and rich resource. After the establishment of the People’s Republic of China, each edition of our national pharmacopeia has contained it. In2002, Semen Cassiae was listed as one of the items which can be used for both food and drug by the Ministry of health, which underlines the importance of Semen Cassiae in the aspect of medical care.There are two kinds of clinical usage of semen Cassiae, the raw material and the processed material. The common method of processing is simple parching (parching into yellowish, which means the seeds are stir-baked into yellow surface or till they bulge while there is no change in their interior). The raw semen Cassiae is good at clearing away liver-heat and moistening the intestines and it is usually indicated for redness, swelling and pain of the eyes and constipation. However, since processing reduces the coldness and improves the production of decocting, the processed semen Cassiae has the power of tranquilizing liver and nourishing kidney and it is mainly used for are headache and dizziness, and glaucoma cataract. As a result, the original efficacy was changed by processing, ranging from clearing away liver-heat of the raw material to tranquilizing liver and nourishing kidney of the processed material, thus making it necessary to change the usage of the raw material and the processed material. The change of original effect, which is external manifestation caused by the transformation of internal material basis, is eventually due to the change of chemical composition. Then, how did the chemical constituents change after it was processed? What’s the relationship between chemical constituents change and effect? Although a lot of research on Semen Cassiae has been conducted in recent years, these problems still have not been studied deeply and the mechanism of processing has not been explained well. In this paper, to study the mechanism of processing semen Cassiae, chemical constituents of semen Cassiae were studied intensively, and the impact of processing on the chemical constituents was further examined, laying the foundation for revealing the mechanism of processing.This paper is mainly divided into three parts.First, a comprehensive review was completed from four aspects of resource, chemical constituents, bioactivities and impact of processing on the chemical constituents. The resource research included the origin of semen Cassiae, historical development and appraisal of the similar species. In the aspect of chemical constituents, an overall summary of classification on its main effective constituents (anthraquinones and naphthopyrones) was conducted. Bioactivities mainly included the effects of purging, protecting liver and antioxidating. The impact of processing on the chemical constituents contained historical literature research, the Pharmacopoeia processing method and modern research.Second,20compounds have been isolated from Semen Cassiae by silica gel, polyamide and ODS methods. All of them were elucidated by spectrum analysis (UV, IR, EI-MS,’H-NMR,13C-NMR,2D-NMR) and there were five new compounds among them. Then we tested the new compounds’inhibitory activity of a-glucosidase.20compounds included6,8-dihydroxy-1,2,7-trimethoxy-3-methyl- anthraquinone (1),2-0-β-D-glucopyranosyl-oxy-1,7,8-trimethoxyl-3-methylanthra-quinone (2),2-O-β-D-glucopyranosyloxy-8hydroxy-1,7-dimethoxyl-3-methylanthra-quinone (3),6-O-β-D-glucopyranosyloxy-8-hydroxy-1,2,7-trimethoxyl-3-methyl-anthraquinone (4),6-0-β-D-glucopyranosyloxy-1-hydroxy-2,8-dimethoxyl-3-methylanthraquinone (5), chryso-obtusin (6), emodin (7), chrysophanol (8), aurantio-obtusin (9), chryso-obtusin-2-O-β-D-glucoside (10), aurantio-obtusin-6-O-β-D-glucopyranoside (11), gluco-obtusifolin (12),1-[(β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl)oxy]-8-hydroxyl-3-methyl-9,10-anthraquinone (13), physcion-8-β-gentiobioside(14), Alaternin2-O-β-D-glucopyranoside (15), Cassiaside (16), rubrofusarin-6-β-gentiobioside (17), cassiaside C (18), rubrofusarin triglucoside (19), Physcion-8-O-p-D-glucopyranoside (20).Third, based on the chemical constituents’research, six main effective compounds were selected as markers to explore the change of them in the course of processing, finally in order to examine the impact of processing on the chemical constituents, including three glycosides (we choice rubrofusarin-6-β-gentiobioside, Cassiaside, cassiaside C) and three aglycones (aurantio-obtusin, chryso-obtusin and obtusifolin). As a result, after processing, the glycosides had the trend of reducing overall while some of the aglycones improved and others reduced.