Benzophenone C- and O-Glucosides from Cyclopia genistoides (Honeybush) Inhibit Mammalian α-Glucosidase

Beelders, Theresa; Brand, D. Jacobus; Beer, Dalene de; Malherbe, Christiaan J.; Mazibuko, Sithandiwe E.; Muller, Christo J. F.; Joubert, Elizabeth

doi:10.1021/np5007247

Cited by 51 publications

(29 citation statements)

References 25 publications

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“…Authentic reference standards (purity > 95 %) were sourced from Extrasynthese (eriocitrin, narirutin), Sigma-Aldrich (mangiferin, hesperidin, iriflophenone-3-C-glucoside, scolymoside), Chemos GmbH (isomangiferin), and Phytolab (vicenin-2). Maclurin-3-Cglucoside (95 % purity by LC-MS) and iriflophenone-3-C-glucoside-4-O-glucoside (99 % purity by LC-MS) were previously isolated from C. genistoides [45], while phloretin-3′,5′-di-C-glucoside (94 % purity by LC-MS) was isolated from C. subternata. When no authentic reference standard was available, the compound was quantified in terms of equivalents of the most similar available standard.…”

Section: Phenolic Standards and Solventsmentioning

confidence: 99%

Cyclopia Extracts Enhance Th1-, Th2-, and Th17-type T Cell Responses and Induce Foxp3+ Cells in Murine Cell Culture

et al. 2017

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, one of the traditional South African medicinal plants, and other species of the same genus offer noteworthy phenolic profiles, in particular high levels of the anti-allergic xanthone mangiferin. Hot water and 40% ethanol-water (v/v) extracts, prepared from , and were tested for immune-regulating activity using murine splenocytes and mesenteric lymph node cells. The 40% ethanol-water extracts of significantly enhanced production of several types of cytokines, including IL-4, IL-17, and IFN-, by antigen-stimulated splenocytes. A concentration-dependent response was observed, noticeably for IFN- production. The activity of the extracts did not correlate with the content of any of the major phenolic compounds, indicative that other extract constituents also play a role in immunomodulation. Additionally, the increased ratio of CD4CD25Foxp3 Treg cells to total CD4 cells indicated induction of Foxp3 cells when mesenteric lymph node cells were cultured in the presence of these two extracts. This study is the first reporting immunostimulatory activity for , which are widely consumed as the herbal tea known as honeybush, underpinning further investigations into the potential use of its extracts as adjuvants for mucosal immunotherapy.

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Section: Phenolic Standards and Solventsmentioning

confidence: 99%

Cyclopia Extracts Enhance Th1-, Th2-, and Th17-type T Cell Responses and Induce Foxp3+ Cells in Murine Cell Culture

et al. 2017

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“…Food ingredient extracts from C. subternata exhibit antidiabetic and anti‐obesity properties . In vivo studies demonstrated the glucose‐lowering effect of its major xanthone, mangiferin, while several other phenolic compounds in C. subternata are postulated to contribute towards its antidiabetic and anti‐obesity properties . Cyclopia subternata extract is therefore an excellent functional ingredient to include in a reduced‐sugar beverage.…”

Section: Introductionmentioning

confidence: 99%

Phenolic and physicochemical stability of a functional beverage powder mixture during storage: effect of the microencapsulant inulin and food ingredients

et al. 2018

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“…subternata , unpublished results), eriocitrin (Extrasynthese), hesperidin (Sigma-Aldrich), vicenin-2 (Phytolab, Germany), isorhoifolin (Extrasynthese), scolymoside (isolated from C . subternata , unpublished results), and iriflophenone-3- C -β-D-glucoside-4- O -β-D-glucoside (isolated from Cyclopia genistoides [ 49 ]).…”

Section: Methodsmentioning

confidence: 99%

Divide and Conquer May Not Be the Optimal Approach to Retain the Desirable Estrogenic Attributes of the Cyclopia Nutraceutical Extract, SM6Met

et al. 2015

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The genus Cyclopia, an indigenous South African fynbos plant used to prepare honeybush tea, contains phytoestrogenic compounds. An extract from C. subternata, SM6Met, displays three desirable estrogenic attributes for future development of a phytoestrogenic nutraceutical, namely, ERα antagonism, ERβ agonism, and also antagonism of E2-induced breast cancer cell proliferation. Activity-guided fractionation of SM6Met was used in an attempt to isolate and identify compounds conferring the desirable estrogenic profile to SM6Met. Initial liquid-liquid fractionation of SM6Met yielded a polar fraction (PF) and a non-polar fraction (NPF), with the desirable estrogenic attributes retained in the NPF. Subsequent high performance counter-current chromatography (HPCCC) fractionation of the NPF yielded three fractions (F1-F3). Interestingly, the fractions revealed separation of the previously demonstrated positive estrogenic attributes of the NPF into separate fractions, with F1 and F2 acting as ERα antagonists, only F2 inducing antagonism of E2-induced breast cancer cell proliferation and only F3 retaining robust ERβ agonist activity. In terms of major polyphenols, quantitative HPLC and liquid chromatography tandem mass spectrometry (LC-MS/MS) indicated that HPCCC fractionation resulted in a divergence of polyphenolic classes, with F1 emerging as the dihydrochalcone-rich fraction and F2 as the flavanone- and benzophenone-rich fraction, while the xanthones, flavones and phenolic acids were retained in F3. F3 was re-engineered into F3R by reassembling the major polyphenols identified in the fraction. F3R could, however, not replicate the effect of F3. In conclusion, although activity-guided fractionation results suggest that retention of all the desirable estrogenic attributes of the original SM6Met in one fraction is not an attainable goal, fractionation is a useful tool to enhance specific desirable estrogenic attributes.

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Benzophenone C- and O-Glucosides from Cyclopia genistoides (Honeybush) Inhibit Mammalian α-Glucosidase

Cited by 51 publications

References 25 publications

Cyclopia Extracts Enhance Th1-, Th2-, and Th17-type T Cell Responses and Induce Foxp3+ Cells in Murine Cell Culture

Cyclopia Extracts Enhance Th1-, Th2-, and Th17-type T Cell Responses and Induce Foxp3+ Cells in Murine Cell Culture

Phenolic and physicochemical stability of a functional beverage powder mixture during storage: effect of the microencapsulant inulin and food ingredients

Divide and Conquer May Not Be the Optimal Approach to Retain the Desirable Estrogenic Attributes of the Cyclopia Nutraceutical Extract, SM6Met

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