Application of High‐speed Countercurrent Chromatography–Evaporative Light Scattering Detection for the Separation of Seven Steroidal Saponins from <i>Dioscorea villosa</i>

Yoon, Kee Dong; Chin, Young‐Won; Yang, Min; Choi, Janggyoo; Kim, Jinwoong

doi:10.1002/pca.2342

Cited by 22 publications

(20 citation statements)

References 15 publications

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“…However, these saponins are equally well known for their poor bioavailability, which results from low intestinal permeability and leads to a significant gap in explaining their alleged therapeutic potential [24]. For example, dioscin [1], an important steroid saponin from wild yam, has been shown to exhibit only very low oral bioavailability (0.2%) after high oral dosing (90 mg/Kg) in rats [25,26]. More generally, poor bioavailability has been demonstrated for analogous steroid saponins [24,27–29].…”

Section: Resultsmentioning

confidence: 99%

“…These plants are well known for containing steroidal saponins, mainly belonging to the spirostanol and furostanol classes, and these have been used as chemical marker compounds for quality control of the botanical products [1]. Wild yam, the rhizomes and roots of Dioscorea villosa L., is an important source of diosgenin [2], a phytoestrogen that has been investigated thoroughly from both chemical and biological perspectives [3–5].…”

Section: Introductionmentioning

confidence: 99%

“…Wild yam, the rhizomes and roots of Dioscorea villosa L., is an important source of diosgenin [2], a phytoestrogen that has been investigated thoroughly from both chemical and biological perspectives [3–5]. The methods aimed at targeted isolation and purification of the major steroid saponins in D. villosa were developed by exploring various chromatographic techniques, such as high-speed countercurrent and centrifugal partition chromatographs as well as HPLC [1,6,7]. To date, based on a comprehensive literature survey, twelve steroidal saponins and two flavan-3-ol glycosides have previously been isolated as major secondary metabolites of wild yam [1,2,6–8].…”

Section: Introductionmentioning

confidence: 99%

“…The methods aimed at targeted isolation and purification of the major steroid saponins in D. villosa were developed by exploring various chromatographic techniques, such as high-speed countercurrent and centrifugal partition chromatographs as well as HPLC [1,6,7]. To date, based on a comprehensive literature survey, twelve steroidal saponins and two flavan-3-ol glycosides have previously been isolated as major secondary metabolites of wild yam [1,2,6–8]. Our group recently reported 14 diarylheptanoids [9].…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Lipidated steroid saponins from Dioscorea villosa (wild yam)

Dong¹,

Cai²,

Napolitano³

et al. 2013

Fitoterapia

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Two groups of lipidated steroid saponins including seven new compounds (2, 3, 5, and 7–10) were isolated from the widely used botanical, wild yam (Dioscorea villosa), employing a fractionation protocol of metabolomic mining. This methodology has very recently led to the isolation of 14 diarylheptanoids from the same plant. Together with these lipidated steroid saponins, they establish additional new markers for Dioscorea villosa. The lipidation of steroids with analogue long-chain fatty acids containing different degrees of unsaturation generates entire series of compounds which are difficult to purify and analyze. The structures of the two series of lipidated steroid saponins (series A and B) were demonstrated by a combination of 1D and 2D NMR as well as GC-MS after chemical modification. Series A was determined to be a mixture of lipidated spirostanol glycosides (1–5), while series B (6–10) proved to be a mixture of five lipidated clionasterol glucosides. The latter group represents the first derivatives of clionasterol to be found in D. villosa. The discovery of this specific structural type of aliphatic esters of steroid saponins expands the characterization of the secondary metabolome of D. villosa. It also may inspire biological studies which take into account the lipophilic character and significantly altered physiochemical characteristics of these otherwise relatively polar phytoconstituents.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Lipidated steroid saponins from Dioscorea villosa (wild yam)

Dong¹,

Cai²,

Napolitano³

et al. 2013

Fitoterapia

View full text Add to dashboard Cite

show abstract

“…These plants are well known for containing steroidal saponins, which have been used as marker compounds for quality control of the botanical products. 1 The roots and rhizomes of Dioscorea villosa L. are known as “wild yam”. This species, native to North America, is a twining tuberous vine.…”

mentioning

confidence: 99%

Diarylheptanoids from Dioscorea villosa (Wild Yam)

et al. 2012

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A fractionation methodology aimed at the metabolomic mining of new phytoconstituents for the widely used botanical, wild yam (Dioscorea villosa), makes use of 1D qHNMR and 2D NMR profiles along the preparative fractionation pathway. This quantifiable and structural guidance led to the isolation of 14 diarylheptanoids (1–14), including five new compounds (1–5) with a tetrahydropyrano core skeleton. The structures, including the absolute configurations of both new and previously known diarylheptanoids, were assigned by a combination of HRESIMS, 1D and 2D NMR, 1H iterative full spin analysis (HiFSA), and the Mosher’s ester method. The isolation yields were consistent with yields predicted by qHNMR, which confirms the (semi-)quantifiable capabilities of NMR-based preparative metabolomic mining. The qHNMR-aided approach enabled the identification of new and potentially significant chemical entities from a small fraction of the plant extract and, thereby, facilitated the characterization of the residual complexity of the D. villosa secondary metabolome. LC-MS profiling of different D. villosa accessions further confirmed that the diarylheptanoids represent genuine secondary metabolites, which can serve as a new class of markers for botanical integrity analysis of D. villosa.

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Chemical fingerprint analysis and quantitative determination of steroidal compounds from Dioscorea villosa, Dioscorea species and dietary supplements using UHPLC‐ELSD

Avula

Wang

Ali

et al. 2013

Biomedical Chromatography

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Ultra high-performance liquid chromatography (UHPLC) with evaporative light scattering (ELS) detection was used for the quantification of steroidal saponins and diosgenin from the rhizomes or tubers of various Dioscorea species and dietary supplements that were purported to contain Dioscorea. The analysis was performed on an Acquity UPLC™ system with an UPLC™ BEH Shield RP18 column using a gradient elution with water and acetonitrile. Due to their low UV absorption, the steroidal saponins were observed by evaporative light scattering detection. The twelve compounds could be separated within 15 minutes using the developed UHPLC method with detection limits of 5–12 μg/mL with 2μL injection volume. The analytical method was validated for linearity, repeatability, accuracy, limits of detection (LOD) and limits of quantification (LOQ). The Relative Standard Deviations (RSD) for intra- and inter-day experiments were less than 3.1 %, and the recovery efficiency was 97–101 %. The total content of standard compounds was found to be in the range from 0.01–14.5% and 0.9–28.6 mg daily intake for dry plant materials and solid commercial preparations, respectively. UHPLC-mass spectrometry with a quadrupole mass analyzer and ESI source was used only for confirmation of the identity of the various saponins. The developed method is simple, rapid and especially suitable for quality control analysis of commercial products.

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Application of High‐speed Countercurrent Chromatography–Evaporative Light Scattering Detection for the Separation of Seven Steroidal Saponins from Dioscorea villosa

Cited by 22 publications

References 15 publications

Lipidated steroid saponins from Dioscorea villosa (wild yam)

Lipidated steroid saponins from Dioscorea villosa (wild yam)

Diarylheptanoids from Dioscorea villosa (Wild Yam)

Chemical fingerprint analysis and quantitative determination of steroidal compounds from Dioscorea villosa, Dioscorea species and dietary supplements using UHPLC‐ELSD

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