Microdetermination of Diosgenin from Fenugreek (<i>Trigonella foenum-graecum</i>) Seeds

Taylor, Wesley G.; Elder, J.L.; Chang, Peter R.; Richards, K. W.

doi:10.1021/jf000467t

Cited by 82 publications

(72 citation statements)

References 17 publications

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“…19). It has been reported that when the diosgenin glycoside, dioscin, was orally administered to rats, diosgenin was very poorly absorbed (0.2%; ref.…”

Section: Discussionmentioning

confidence: 99%

“…1) is an aglycone of the steroidal saponin, dioscin, which is present at relatively high concentrations in the tubers of wild yams (Dioscorea villosa Linn) and the seeds of fenugreek (Trigonella foenum graecum Linn; refs. 19,20). Diosgenin is used for the commercial synthesis of steroid products, such as cortisone, pregnenolone, and progesterone.…”

Section: Introductionmentioning

confidence: 99%

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Chemoprevention of Azoxymethane/Dextran Sodium Sulfate–Induced Mouse Colon Carcinogenesis by Freeze-Dried YamSanyakuand Its Constituent Diosgenin

Miyoshi

Nagasawa

Mabuchi

et al. 2011

Cancer Prevention Research

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The effects of sanyaku, a traditional Chinese medicine [freeze-dried powder of the yam tuber (Dioscorea)], and its major steroidal saponin constituent, diosgenin, on colon carcinogenesis were investigated. Male ICR mice were subjected to a single intraperitoneal injection of azoxymethane (AOM; 10 mg/kg body weight) followed by administration of 1.5% dextran sodium sulfate (DSS) in drinking water for 7 days to establish carcinogenesis. Commercial diosgenin or sanyaku, which contained diosgenin at 63.8 AE 1.2 mg/ kg dry weight, was given in the diet at 20, 100, or 500 mg/kg for 17 weeks. Groups of mice that received diosgenin or sanyaku at all doses yielded significantly less number of colon tumors compared with the AOM/DSS-treated mice. Occurrence of colonic mucosal ulcer and dysplastic crypt induced by AOM/DSS treatment was also significantly decreased by the administration of diosgenin and sanyaku, which was in accordance with the significant reduction of AOM/DSS-mediated increases in expression of inflammatory cytokines such as IL-1b by diosgenin and sanyaku. Furthermore, elevated levels of serum triglyceride in the AOM/DSS-treated mice tended to be reduced in mice given diosgenin and sanyaku. Microarray and realtime reverse transcriptase PCR analyses revealed that diosgenin administration increased 12-fold the expression of lipoprotein lipase, which may contribute to reduced serum triglyceride levels. Other genes altered by diosgenin included those associated with antioxidative stress responses and apoptosis, such as heme oxygenase-1, superoxide dismutase-3, and caspase-6. Our results imply that the Chinese medicine sanyaku and the tubers of various yams containing diosgenin as food could be ingested to prevent colon carcinogenesis in humans. Cancer Prev Res; 4(6); 924-34. Ó2011 AACR.

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“…19). It has been reported that when the diosgenin glycoside, dioscin, was orally administered to rats, diosgenin was very poorly absorbed (0.2%; ref.…”

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Chemoprevention of Azoxymethane/Dextran Sodium Sulfate–Induced Mouse Colon Carcinogenesis by Freeze-Dried YamSanyakuand Its Constituent Diosgenin

Miyoshi

Nagasawa

Mabuchi

et al. 2011

Cancer Prevention Research

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“…The crude products were determined using thin layer chromatography (TLC) with Merck Silica Gel 60F-2504 glass plates. The product was analyzed by 1 …”

Section: General Methods For Dg Preparationmentioning

confidence: 99%

“…and other plants such as Smilax bockii warb and Trigonella foenum graecum. [1,2] DG has exhibited biological effects in the treatment of various diseases such as hypercholesterolemia, climacteric syndromes including diabetic neuropathy and even cancer. [3][4][5][6] It has also been claimed to have an osteogenic property.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological evaluation of arginyl–diosgenin conjugate as a potential bone tissue engineering agent

Liao

Jung

et al. 2017

Chem Biol Drug Des

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Water-soluble arginyl-diosgenin (Arg-DG) conjugate was designed, synthesized, and evaluated for a biological activity. The Arg-DG conjugate was characterized using FT-IR, 1 H NMR, 13 C NMR, and HPLC-MS analyses, followed by a biological activity evaluation. Compared with DG, the Arg-DG conjugate showed a decreased cytotoxicity against L929 cells and an increased antiproliferative activity against hepatocellular cells. The safety of the Arg-DG conjugate was confirmed using the highly sensitive Alamar Blue assay, which indicated that it increased the cellular metabolic activity at suitable concentrations. The Arg-DG conjugate promoted an endothelial tube formation as well. Furthermore, the Arg-DG conjugate improved the bone morphogenetic protein 2 (BMP2)-induced osteoblastic differentiation with synergistic effects on alkaline phosphatase (ALP) activity and mineralization. These results suggest that the Arg-DG conjugate developed in this study has great potentials for biomedical applications such as bone tissue engineering. K E Y W O R D SALP assay, arginyl-diosgenin conjugate, bone tissue engineering, cytotoxicity, tube formation assay | INTRODUCTIONDiosgenin [(25R)-spirost-5-en-3ß-ol] (DG) is a major naturally occurring steroid saponin, which is abundantly distributed in the rootstock of yams (Dioscorea sp.) and other plants such as Smilax bockii warb and Trigonella foenum graecum. [1,2] DG has exhibited biological effects in the treatment of various diseases such as hypercholesterolemia, climacteric syndromes including diabetic neuropathy and even cancer. [3][4][5][6] It has also been claimed to have an osteogenic property. DG was reported to inhibit osteoclastogenesis and enhance osteoblastic cell differentiation and the synthesis of cellular bone matrix protein. [7,8] It has been hypothesized that DG could be a potential activator of bone formation and potential therapeutic agent for bone-related diseases including osteoporosis.[8]However, the medical application of DG is considerably limited because of its solubility problem and associated toxicity. The aqueous solubility of DG was determined to be 0.7 ng/ml (1.69 nm).[9] It was also revealed that the low solubility of DG led to poor bioavailability and gastrointestinal mucosal toxicity. [10] As poor solubility has been recognized as a frequently encountered challenge in the field of pharmaceutics, different approaches have been employed to improve the solubility and bioavailability of poorly watersoluble compounds including DG. [11] For instance, an inclusion of complexation of DG and β-cyclodextrin was formed. [12] Iron oxide nanoparticles loaded with DG were prepared. [13] Improving the solubility of DG and decreasing its intrinsic cytotoxicity or at least avoiding any additional toxicity against normal cells are the major challenges to its biomedical application. Numerous efforts have been made to chemically modify this compound to improve its applicable biological activities. Diosgenyl saponin, dioscin analogues were designed to improve its anticancer a...

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“…1,2) Several in vivo studies have shown that diosgenin is effective in treating various diseases such as hyperglycemia and hyperlipidemia and has been established as a starting material for the production of several steroidal hormones by the pharmaceutical industry. [3][4][5] Diosgenin has also been used in hormone replacement therapy for menopausal women.…”

mentioning

confidence: 99%

Effect of β-Cyclodextrin Derivatives on the Diosgenin Absorption in Caco-2 Cell Monolayer and Rats

Okawara

Tokudome

Todo

et al. 2014

Biological & Pharmaceutical Bulletin

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Orally administrated diosgenin, a steroidal saponin found in the roots of Dioscorea villosa, improves reduced skin thickness in ovariectomized mice, and plays an important role in the treatment of hyperlipidemia. Diosgenin has been noticed as an active element in cosmeceutical and dietary supplements. We have already elucidated that the absolute oral bioavailability of diosgenin is very low; however, a high skin distribution of diosgenin was also observed. The aim of the present study was to examine and compare the effects of β-cyclodextrin (β-CD) and 3 kinds of its derivatives such as hydroxypropyl β-CD on the diosgenin permeability using a Caco-2 model and rat jejunal perfusion. These derivatives of β-CD greatly improved the low solubility of diosgenin. No significant increase was observed in the lactate dehydrogenase leakage from Caco-2 cell, while a slight decrease was found on the transepithelial electrical resistance by diosgenin and β-CD derivatives. However, β-CD derivatives, especially hydroxyethyl β-CD and hydroxypropyl β-CD, markedly enhanced diosgenin permeability across the Caco-2 monolayer and rat jejunum. The bioavailability of diosgenin in the presence of β-CD derivatives were about 4 to 11 fold higher than diosgenin suspension. The mechanisms of these enhancement effects may be due to improvements in solubility and tight junction opening.

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Microdetermination of Diosgenin from Fenugreek (Trigonella foenum-graecum) Seeds

Cited by 82 publications

References 17 publications

Chemoprevention of Azoxymethane/Dextran Sodium Sulfate–Induced Mouse Colon Carcinogenesis by Freeze-Dried YamSanyakuand Its Constituent Diosgenin

Chemoprevention of Azoxymethane/Dextran Sodium Sulfate–Induced Mouse Colon Carcinogenesis by Freeze-Dried YamSanyakuand Its Constituent Diosgenin

Synthesis and biological evaluation of arginyl–diosgenin conjugate as a potential bone tissue engineering agent

Effect of β-Cyclodextrin Derivatives on the Diosgenin Absorption in Caco-2 Cell Monolayer and Rats

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