Glycosides senna

Anthraquinone glycosides found in senna (Cassia fistulosa) and Aloe spp. have been included in some commercial cathartics. Vicine is a glycoside in fava beans (Vida faba), and causes hemolytic anemia in people who have a genetic deficiency of glucose-6-phosphate dehydrogenase activity in their red blood cells. Fava beans are grown as a protein supplement for livestock. 

The most important anthraquinone glycosides are sennosides, found in the senna leaves and fruits (Cassia senna or Cassia angustifolia). These are, in fact, dimeric anthraquinone glycosides. However, monomeric anthraquinone glycosides are also present in this plant. 

N.A. Cassia senna L. Anthraquinone, beta-sitosterol, rhein, dianthrone glucosides, sennosides A, sennosides B, naphthalene glycosides, aloe-emodine, mucilage.99 100 Laxative, stimulant, cathartic, anticancer, cathartic. 

The active constituents in both senna leaf and fruit are dianthrone glycosides, principally sennosides A and B (Figure 3.33). These compounds are both di-O-glucosides of rhein... 

Sandnes D, Johansen T, Teien G, Ulsaker G. Mutagenicity of crude senna and seima glycosides in Salmonella typhi-murium. Pharmacol Toxicol 1992 71(3 Pt l) 165-72. 

Sandnes, D., Johansen, T., Teien, G. and Ulsaker, G. (1992) Mutagenicity of crude senna and senna glycosides in Salmonella typhimurium. Pharmacol. Toxicol. 71, 165-172. 

The first comprehensive 2D system was developed in the late 1970s by Erni and Frei, who applied IEX x RPC to the analysis of senna glycosides from plant extracts.61 In the subsequent decades, comprehensive MD-HPLC methods have been further developed, mainly for peptides and proteins,62 3 but also for separation of various natural products such as phenolic and flavone antioxidants64 and carotenoids.65 The theoretical aspects of MD-HPLC techniques have also been further developed.66-68... 

Examples of how the composition is listed include Sennae folium, 415-500 mg, corresponding to 12.5 mg of hydroxyanthracene glycosides, calculated as Sennoside B or Valerianae radix 900 mg. 

Other than abdominal cramps, which occur in approx 10% of patients, it does not appear that senna causes any serious adverse gastrointestinal effects (Muller-Lissner, 1993). Products containing crystalline glycosides of senna are more stable, more reliable, and cause less cramping than products made from the crude drug (Curry, 1986). 

Anthrone or its tautomer anthrol or its hydroxy derivatives (i.e., the aglycones) are found to exert purgative effects. However, the anthraquinone glycosides are usually present in several herbal drugs, such as senna, cascara, rhubarb and aloes. 

Mereto, E., M. Ghia, and G. BrambUla. 1996. Evaluation of the potential carcinogenic activity of senna and cascara glycosides for the rat colon. Cancer Lett. 101(l) 79-83. 

Vanderperren, B., M. Rizzo, L. Angenot, et al. 2005. Acute Uver failure with renal impairment related to the abuse of senna anthra-quinone glycosides. Ann. Pharmacother. 39(7-8) 1353-1357. 

Pharmacopeias of Europe, India, and China specify that senna leaf must contain a minimum of 2.5% hydroxy-anthracene glycosides, calculated as sennoside B. Senna fruit typically contains 3-5% sennosides. Pharmacopeias of Europe and India recognize Senna alexandrina as two species, S. angustifolia, which must contain a minimum of 3.4%, and S. acutifolia, which must contain a minimum of 2.2% hydroxyanthracene glycosides, calculated as sennoside B. 

Concomitant use of senna or sickle-pod senna is cautioned with antiarrhythmic drugs, thiazide diuretics, corticosteroids, licorice, and botanicals containing cardiac glycosides, as long-term use of senna or sickle-pod senna as a laxative can cause or exacerbate potassium loss (Brinker 2001 De Smet 1993 ESCOP 2003). 

No induction of aberrant crypt foci (considered putative preneoplastic lesions) or increases in incidence of chemically induced aberrant crypt foci were observed in rats fed diets containing up to 0.2% anthraquinone glycosides from senna for 56 days (Mereto et al. 1996). 

In the Salmonella typhimurium reversion assay, senna glycosides were inactive in all strains, except for a slight but significant increase in mutant frequency in TA102 in the absence and presence of liver microsomes. Extracts of senna fruit and senna leaf demonstrated weak activity in TA97a, TAIOO, and TA102 in the presence of liver microsomes, and... 

Rikans, L., and T. Yamano. 2001. Mechanisms of cadmium-mediated acute hepatotoxicity. J. Biochem.Mol. Toxicol. 14(2) 110-117. Sandnes, D., T. Johansen, G. Teien, and G. Ulsaker. 1992. Mutagenicity of crude senna and senna glycosides in Salmonella typhimurium. Pharmacol. Toxicol. 71(3, Pt. 1) 165-172. Seybold, U., N. Landauer, S. Hillebrand, and ED. Goebel. 2004. Senna-induced hepatitis in a poor metabolizer. Ann. Intern. Med. 141(8) 650-651. 

C16H12O5, Mr 284.27, orange needles, mp. 209-210 °C, uv ,a, 431 nm (C2H5OH). An octaketide that occurs in senna leaves (Cassia senna, Fabaceae), rhubarb roots, in chrysarobinum (see chrysarobin), lichens (Parmelia species), and fungi (Aspergillus and Penicillium species), as well as in glycosidically bound form in Cassia species. It has a weak spasmolytic activity. 

S. A-G occur in the leaves and fruits of Cassia species (C. senna, C. angustifolia, Fabaceae) and in rhubarb roots, sometimes as oxalyl derivatives (senno-sides E, F). S. are mostly formed from the corresponding anthrone glycosides when the senna leaves are dried. Drugs containing S. are used in therapy for acute constipation (see table, p. 581). 

Anthraquinone glycosides have long been used medicinally as cathartics and laxatives. Plant-derived drugs of this type include aloes Aloe species), cascara sagrada (Rhamnus purshiams), frangula (Rhamnus frangula), rhubarb (Rheum officinale), rumex or yellow dock (Rumex crispus) and senna (Cassia spp.). Many of the commercial preparations (patent medicines) based on these plants are readily available. 

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