Gas chromatographic determination of the laxative 1,8-dihydroxyanthraquinone in urine and faeces

Baars, A.J.; Vermeulen, Roel; Breimer, D. D.

doi:10.1016/s0021-9673(01)99018-1

Cited by 10 publications

(4 citation statements)

References 2 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…When it comes to the tricyclic anthraquinone derivatives which comprise a huge part of our research, anthraquinone aglycones, their glycosides, and their dimers have been examined for their therapeutic potential to date. The well-known characteristic of 1,8-dihydroxyanthraquinone derivatives is their laxative properties [ 34 ]. Besides, their biological influences (with a special emphasis on cancer) of aloe-emodin [ 35 ], aloin [ 36 ], chrysophanol [ 37 , 38 ], emodin [ 39 , 40 ], physcion [ 41 ], rhein [ 42 ], sennoside A, and sennoside B [ 43 , 44 ] were revealed.…”

Section: Introductionmentioning

confidence: 99%

Structure-activity relationship of anticancer drug candidate quinones

ÖZENVER,

SÖNMEZ,

BARAN

et al. 2024

Turkish Journal of Chemistry

View full text Add to dashboard Cite

Breast cancer is one of the most prevalent cancer types worldwide. Chemotherapy is a substantial approach in the management of breast cancer despite the occurrence of chemotherapy-associated side effects and the development of multidrug resistance in cancer cells. At this point, a variety of quinone derivatives may represent potential as possible anticancer drug candidates due to possessing structural similarity towards clinically used anticancer drugs like doxorubicin. Therefore, we investigated the cytotoxic effects of various quinone derivatives with structural diversity towards a variety of breast cancer cells. We further determined their toxicity in healthy cells to evaluate their drug capability potential. Eighteen quinone derivatives (arbutin, hydroquinone, alkannin, lapachol, lawsone, juglone, aloe-emodin, aloin, cascaroside A (8-O- β -D-glucoside of 10-C -β -D-glucosyl aloe-emodin anthrone), chrysophanol, chrysophanol-8-O- β -D-glucoside, emodin, emodin-8-O- β -D-glucoside, frangulin A (emodin-6-O- a -L-rhamnoside), physcion, rhein, sennoside A, sennoside B (sennoside A and sennoside B are stereoisomers and rhein-dianthrone diglycosides in which β -D-glucose units are bound to the OH groups of rhein anthrones at their 8 th positions) were tested on MCF-7, SK-BR-3, MDA-MB-468, and MDA-MB-231 breast cancer cells and on H9c2 healthy rat cardiac myoblast cells in terms of their cytotoxicity and toxicity, respectively. The resazurin reduction assay was used to determine the cytotoxicity. Among the tested compounds, two naphthoquinone derivatives alkannin and juglone exhibited remarkable cytotoxicity on breast cancer cells and exhibited alleviated toxicity profiles on healthy cells deserving further investigation as possible drug candidates against breast cancer. Structure-activity relationships of these compounds were also evaluated and discussed. Alkannin and juglone, which are naphthoquinone derivatives isolated from natural sources, may be promising agents in the development of drug-candidate molecules with increased efficacy and safety for breast cancer.

show abstract

Section: Introductionmentioning

confidence: 99%

Structure-activity relationship of anticancer drug candidate quinones

ÖZENVER,

SÖNMEZ,

BARAN

et al. 2024

Turkish Journal of Chemistry

View full text Add to dashboard Cite

show abstract

“…Danthron, Figure 1, is a naturally occurring anthraquinone derivative which has been widely used as a laxative since the beginning of last century. 7 Moreover, danthron and its derivatives have also been found to exhibit antifungal 8 and anticancer ability. 9−12 However, due to its danger as a possible human carcinogen, 13−16 the U.S. Food and Drug Administration (FDA) ordered the withdrawal of danthron-containing products from the U.S. market for use as laxative 17 and it is restricted to patients who have already been diagnosed as having terminal cancer in U.K. 18 Danthron has five previously reported polymorphs in the Cambridge Structural Database (CSD), refcode: DHANQU.…”

Section: ■ Introductionmentioning

confidence: 99%

“…In particular 1,8-dihydroxyanthraquinone (danthron) and its derivatives, such as emodin, aloe-emodin, chrysophanol, physcion, and rhein are the most studied compounds for their known pharmacological activity. Danthron, Figure , is a naturally occurring anthraquinone derivative which has been widely used as a laxative since the beginning of last century . Moreover, danthron and its derivatives have also been found to exhibit antifungal and anticancer ability. − However, due to its danger as a possible human carcinogen, − the U.S. Food and Drug Administration (FDA) ordered the withdrawal of danthron-containing products from the U.S. market for use as laxative and it is restricted to patients who have already been diagnosed as having terminal cancer in U.K …”

Section: Introductionmentioning

confidence: 99%

Solid Forms, Crystal Habits, and Solubility of Danthron

et al. 2015

View full text Add to dashboard Cite

The polymorphism, crystal habits, and solubility of 1,8-dihydroxyanthraquinone (danthron) were investigated in acetic acid, acetone, acetonitrile, nbutanol, and toluene. The solubility was determined for the commercially available form (FI) from 293.15 K to 318.15 K by the gravimetric method. The influence of solvents on crystal habit and polymorphic form has been investigated. Three different crystal habits of danthron were obtained from slow evaporation and cooling experiments. By evaporation, thin squares of FI were obtained from nbutanol and toluene solutions while both FI and fine needles of FII were obtained from acetone and acetonitrile solutions. In addition, needle-shaped solvate crystals were obtained from acetic acid solutions and the structure of the solvate was solved by single crystal X-ray diffraction. From cooling crystallization experiments, mixtures of FI and FII were often obtained from various solvents, but FI and FII possess distinct habits which can be easily distinguished by visual comparison. Slurry conversion experiments have established that FI is the thermodynamically stable polymorph of danthron at ambient conditions. Differntial scanning calorimetry (DSC) and high-temperature powder X-ray diffraction (PXRD) have shown that both FI and FII will transform into a high-temperature form (FIV) around 435 K to 439 K before this form melts at 468.5 K. FI, FII, and FIV have been characterized by transmission and high-temperature PXRD, scanning electron microscopy, infrared spectrometry, Raman spectrometry, thermogravimetric analysis, and DSC. The solubility of danthron FI in the pure organic solvents of the present work and in the temperature range investigated is below 4.3 % by weight and decreases in the order toluene, acetone, acetonitrile, and n-butanol.

show abstract

“…C. senna L.) Caesalpinaceae are used as laxatives. Sennoside A (1) and sennoside B (2), the stereoisomers of rhein dianthrone with two glucose molecules, are the major compounds (Lemmens, 1977), gas-liquid chromatography (Baars et al, 1976), radioimmunoassay (Atzorn et al, 1981) and high-performance liquid chromatography (HPLC) (Erni and Frei, 1978; Gorler * Author to whom correspondence should be addressed.…”

Section: Introductionmentioning

confidence: 99%