Anthraquinone Derivatives in Vegetable Laxatives

Os, F. H. L. van

doi:10.1159/000136682

Cited by 22 publications

(9 citation statements)

References 7 publications

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“…Plants such as Frangulae cortex ( Rhamnus frangula ), Cascara sagrada ( Rhamnus purshiana ) and also rhubarb ( Rheum palmatum ) contain other anthranoids such as frangula, aloe‐emodin, chrysophanol and rhein 2 , . 3 …”

Section: Natural Sourcesmentioning

confidence: 99%

“…The basic structure for all anthranoid laxatives is an anthracene ring ( Figure 1), to which a hydroxyl or carbonyl function is substituted at C‐9 and hydroxygroups at C‐8 for the laxative function 3 . Based on the group present at C‐10, anthranoids can be divided into three groups: anthrones, anthraquinones and dianthrones (Table 1).…”

Section: Chemical Structurementioning

confidence: 99%

See 1 more Smart Citation

Review article: anthranoid laxatives and their potential carcinogenic effects

Gorkom¹,

Vries

Karrenbeld

et al. 1999

Aliment Pharmacol Ther

157

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Anthranoid laxatives are widely used laxatives of natural origin. Because of their chemical structure they are carried unabsorbed to the large bowel, where metabolism to the active aglycones takes place. These aglycones exert their laxative effect by damaging epithelial cells, which leads directly and indirectly to changes in absorption, secretion and motility. Damaged epithelial cells can be found as apoptotic bodies in the pigmented colonic mucosa, characteristic for pseudomelanosis coli. Pseudomelanosis coli is a condition caused by chronic (ab)use of anthranoid laxatives and has recently been associated with an increased risk of colorectal carcinoma. In vitro and animal studies have shown a potential role of anthranoid laxatives in both the initiation and promotion of tumorigenesis. Studies in humans have also suggested tumour promoting activities for these laxatives. Although the short-term use of these substances is generally safe, long-term use cannot be recommended.

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Section: Natural Sourcesmentioning

confidence: 99%

Section: Chemical Structurementioning

confidence: 99%

Review article: anthranoid laxatives and their potential carcinogenic effects

Gorkom¹,

Vries

Karrenbeld

et al. 1999

Aliment Pharmacol Ther

157

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“…The main anthraquinone compounds in the bark extract from cascara sagrada are aloe -emodin, chrysophanol, and rhein, and the chemical structures of these anthraquinone compounds are displayed in Figure 54.3 . 2 During the drying process, the free anthrones and their corresponding O -glycosides are oxidized to dianthrone -and anthraquinone -O -glycosides to diminish the emetic properties of the bark extract. In plants, these anthranoid moieties (aglycon) are usually linked with a sugar (e.g., glucose, rhamnose) to a carbon at C10 (C -glycoside) or to a hydroxyl group at C1 or C8 ( O -glycoside).…”

Section: Chemical Compositionmentioning

confidence: 99%

Cascara ( Frangula purshiana Cooper)

Barceloux

2008

Medical Toxicology of Natural Substances

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“…In the fresh bark the latter compounds are present as anthrone O-glycosides (glucofrangulin A anthrone, see fig. 1), which, supposedly, are responsible for serious side effects seen in the stomach after oral administration [ 1 ]. Therefore, the bark should not be used before at least 1 year to allow oxi dation of the anthrones to take place.…”

Section: Anthraquinone O-glycosides: Glucofrangulin Rhein Monoglucosidementioning

confidence: 99%

“…Their chemistry is complex ( fig. 1): besides featur ing two characteristic hydroxyl groups and different other substituents, the anthranoid skeleton consists of an anthraquinone, an an- throne or a dianthrone, depending on the oxi dation state of carbon-10 [ 1 ]. Therefore, it can be argued that the term anthraquinone laxa tives, often used to characterize this class of laxatives, merely describes a fraction of the anthranoid structures and should be avoided.…”

Section: Introductionmentioning

confidence: 99%

Metabolism and Pharmacokinetics of Anthranoids

Witte¹

1993

Pharmacology

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Anthranoid derivatives are used all over the world as a treatment for constipation. These compounds are present in several drugs of plant origin, especially as O- or C-glycosides. Besides featuring different substituents, the aglycone might consist of an anthraquinone, an anthrone or a dianthrone. So far, detailed information concerning their metabolism and pharmacokinetic characteristics is available only in a few cases. The best characterized compounds are sennoside, a dianthrone O-glycoside present in senna leaves and senna pods, and its aglycone (rhein anthrone). After oral administration, sennoside is degraded only in the lower parts of the gastrointestinal tract, releasing its active metabolite rhein anthrone. Nowadays, this process is understood at the molecular level. A study with ¹⁴C-labelled rhein anthrone administered intracecally to rats, revealed that the compound is scarcely absorbed. Since on the contrary its anthraquinone equivalent is absorbed to a much larger extent, it is inferred that dianthrone- or anthrone-glycosides exhibit a lower systemic availability than anthraquinone O-glycosides.

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Anthraquinone Derivatives in Vegetable Laxatives

Cited by 22 publications

References 7 publications

Review article: anthranoid laxatives and their potential carcinogenic effects

Review article: anthranoid laxatives and their potential carcinogenic effects

Cascara ( Frangula purshiana Cooper)

Metabolism and Pharmacokinetics of Anthranoids

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