Development and Validation of a UHPLC-PDA-MS Method for the Quantitative Analysis of Anthraquinones in Bulbine natalensis Extracts and Dietary Supplements

Abstract A UHPLC-photodiode array-MS method was developed and validated for the quantification of one chromone and six anthraquinone type of compounds from Bulbine natalensis plant samples and dietary supplements. Metabolites 1 –  7 were identified based on their retention times and electrospray ionization-MS spectra compared with a mix of previously isolated compounds. The quantification of 1 –  7 was based on photodiode array detection. The optimized separation was achieved using a CORTECS C18 column with a gradient of water/acetonitrile as the mobile phase. Seven compounds were separated within 15 minutes with detection limits of 50 pg on the column. The analytical method was validated for linearity, repeatability, accuracy, limits of detection, and limits of quantification. The relative standard deviations for intra- and inter-day experiments were less than 5% and the recovery efficiency was 98 – 101%. Nine dietary supplements labeled as containing B. natalensis were examined. Anthraquinone-type compounds were detected in only five out of nine dietary supplements, with the total amount ranging from 11.3 to 90.4 mg per daily dose. The analytical method is simple, economic, rapid, and can be applied for quality assessment of B. natalensis and dietary supplements. Electrospray ionization-MS was used for the identification of these compounds in plant samples and dietary products.

[1]  Serge A. T. Fobofou,et al.  Biological activity and stability analyses of knipholone anthrone, a phenyl anthraquinone derivative isolated from Kniphofia foliosa Hochst. , 2019, Journal of pharmaceutical and biomedical analysis.

[2]  Z. Ali,et al.  Anthraquinone-Based Specialized Metabolites from Rhizomes of Bulbine natalensis. , 2019, Journal of natural products.

[3]  D. Powell,et al.  Identification of Compounds with Efficacy against Malaria Parasites from Common North American Plants. , 2016, Journal of natural products.

[4]  Albert J. Ndakala,et al.  A xanthone and a phenylanthraquinone from the roots of Bulbine frutescens, and the revision of six seco-anthraquinones into xanthones , 2014 .

[5]  S. Mukanganyama,et al.  Antiproliferative Activity of the Isofuranonaphthoquinone Isolated from Bulbine frutescens against Jurkat T Cells , 2014, BioMed research international.

[6]  N. Pather,et al.  Bulbine natalensis and Bulbine frutescens promote cutaneous wound healing. , 2012, Journal of ethnopharmacology.

[7]  B. Odhav,et al.  Antifungal activity of stigmasterol, sitosterol and ergosterol from Bulbine natalensis Baker (Asphodelaceae) , 2012 .

[8]  A. Afolayan,et al.  Antimicrobial activity of the solvent fractions from Bulbine natalensis Tuber. , 2012, African journal of traditional, complementary, and alternative medicines : AJTCAM.

[9]  A. Afolayan,et al.  Anabolic and androgenic activities of Bulbine natalensis stem in male Wistar rats , 2010, Pharmaceutical biology.

[10]  A. Afolayan,et al.  Effect of aqueous extract of Bulbine natalensis (Baker) stem on the sexual behaviour of male rats. , 2009, International journal of andrology.

[11]  S. Habtemariam,et al.  Prooxidant action of knipholone anthrone: copper dependent reactive oxygen species generation and DNA damage. , 2009, Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association.

[12]  M. Heydenreich,et al.  Joziknipholones A and B: the first dimeric phenylanthraquinones, from the roots of Bulbine frutescens. , 2008, Chemistry.

[13]  G. Bringmann,et al.  The absolute axial configurations of knipholone and knipholone anthrone by TDDFT and DFT/MRCI CD calculations: a revision , 2007 .

[14]  S. Habtemariam Antioxidant activity of Knipholone anthrone , 2007 .

[15]  G. Bringmann,et al.  The first 6′-O-sulfated phenylanthraquinones: isolation from Bulbine frutescens, structural elucidation, enantiomeric purity, and partial synthesis , 2005 .

[16]  G. Bringmann,et al.  Gaboroquinones A and B and 4'-O-demethylknipholone-4'-O-beta-D-glucopyranoside, phenylanthraquinones from the roots of Bulbine frutescens. , 2002, Journal of natural products.

[17]  G. Bringmann,et al.  Bulbine-Knipholone, a New, Axially Chiral Phenylanthraquinone from Bulbine abyssinica (Asphodelaceae): Isolation, Structural Elucidation, Synthesis, and Antiplasmodial Activity , 2002 .

[18]  R. Kaminsky,et al.  Antiplasmodial activity of knipholone and related natural phenylanthraquinones. , 1999, Planta medica.

[19]  G. Bringmann,et al.  Elucidation of the absolute configuration of knipholone and knipholone anthrone by quantum chemical CD calculations , 1999 .

[20]  B. Abegaz,et al.  Isofuranonaphthoquinones and phenolic and knipholone derivatives from the roots of Bulbine capitata , 1997 .

[21]  T. Fujioka,et al.  Three chromones of Aloe vera leaves , 1997 .

[22]  A. Yenesew,et al.  Chemotaxonomic significance of anthraquinones in the roots of asphodeloideae (asphodelaceae) , 1995 .

[23]  W. Steglich,et al.  Knipholone: a unique anthraquinone derivative from Kniphofia foliosa , 1984 .