orientin and flavone

Plant medicine/herbal extracts are typically complex, encompassing a wide range of flavonoid diversity and biological benefits. Combined with a lack of standards; species authentication profiling is a challenge. A non-targeted screening strategy using two-dimensional (2D) separation and specificity of ultra-high-performance liquid chromatography ion mobility collision-induced dissociation mass spectrometry (UHPLC-IM-CID-MS) has been investigated, to identify the 6-C and 8-C-glycosylflavone isomer orientin/isoorientin and vitexin/isovitexin pairs in Passiflora species. Utilising available standards and "known-unknowns" a reference CCS (collision cross-section) speciation finger print for Passiflora extracts could be generated to illustrate species profiling.. SPE was performed to extract flavonoids of interest from powdered and ground Passiflora leaf. Chromatographic separation was achieved via UHPLC and analysis performed using positive/negative ion electrospray coupled with linear T-wave IM-MS (calibrated to perform accurate mass and CCS measurements).. Comparative phytochemical screening of Passiflora alata, P. edulis, P. incarnata and P. caerulea leaf extracts has generated CCS, CID IM product ion spectra, 2D separation with UHPLC-IM-MS, enabling the unequivocal identification of flavone C-glycosides in complex extracts. A phytochemical reference CCS library was generated comprised of "knowns" and "known-unknowns". Isomers have been differentiated using a CCS metric enabling novel CCS specific isomeric quantitation of co-eluting isomers.. The screening approach illustrated has the potential to play an important role in the profiling of medicinal plants to determine phytochemical make-up and improve consumer safety through generation of highly specific speciation profiles.

Topics: Apigenin; Chromatography, High Pressure Liquid; Flavones; Flavonoids; Glucosides; Glycosides; Isomerism; Luteolin; Mass Spectrometry; Passiflora; Phytochemicals; Plant Extracts; Plants, Medicinal

Flavone C-glycosides are difficult to be deglycosylated using traditional chemical methods due to their solid carbon-carbon bond between sugar moieties and aglycones; however, some bacteria may easily cleave this bond because they generate various specific enzymes.. A bacterial strain, named W12-1, capable of deglycosylating orientin, vitexin, and isovitexin to their aglycones, was isolated from human intestinal bacteria in this study and identified as Enterococcus faecalis based on morphological examination, physiological and biochemical identification, and 16S rDNA sequencing. The strain was shown to preferentially deglycosylate the flavone C-glycosides on condition that the culture medium was short of carbon nutrition sources such as glucose and starch, and its deglycosylation efficiency was negatively correlated with the content of the latter two substances.. This study provided a new bacterial resource for the cleavage of C-glycosidic bond of flavone C-glycosides and reported the carbon nutrition sources reduction induced deglycosylation for the first time.

Topics: Adult; Apigenin; Carbon; Enterococcus faecalis; Feces; Flavones; Flavonoids; Gastrointestinal Microbiome; Glucosides; Glycosides; Humans; Intestines; Male; RNA, Ribosomal, 16S; Sequence Analysis, RNA

Orientin, a C-glycosyl dietary flavone profusely found in rooibos tea and passion fruit have gained much attention owing to their multiple pharmacological potentials. The present study intends to investigate the anti-proliferative and anti-inflammatory efficacy of Orientin in 1,2-dimethyl hydrazine (DMH) induced colorectal cancer (CRC) in rats. Animals were arbitrarily segmented into six groups and fed with high-fat diet. Group 1 served as control. Group 2 received weekly subcutaneous injections of DMH (20 mg/kg b.w.), for first 15 weeks. Group 3 administered with Orientin (10 mg/kg b.w., i.p.) whereas Groups 4-6 treated with Orientin in three phases, namely initiation (along with DMH), post-initiation (post-DMH injection) and entire period. Orientin ameliorates tumor marker levels significantly (p < 0.05) and reinstates the histological changes induced by DMH. The proliferative markers (PCNA and Ki67) were observed to be suppressed significantly (p < 0.05) in Orientin treated rats. Orientin abrogates (p < 0.05) the inflammatory mast cells and diminishes the expression of pro-inflammatory NF-κB and cytokines (TNF-α and IL-6). It also down-regulates over expression of inflammatory inducible enzymes (iNOS and COX-2) significantly (p < 0.05) and further substantiated by GLIDE XP and QPLD studies. Overall results promptly elucidate the anti-proliferative and anti-inflammatory efficacy of Orientin against CRC. Orientin can be developed as a promising chemotherapeutic agent, on further validation of other molecular mechanisms.

Topics: 1,2-Dimethylhydrazine; Animals; Anti-Inflammatory Agents; Antineoplastic Agents; Biomarkers, Tumor; Carcinogenesis; Cell Proliferation; Colon; Colorectal Neoplasms; Cytokines; Flavones; Flavonoids; Glucosides; Inflammation; Male; NF-kappa B; Rats; Rats, Wistar

Exploration for inhibitors against expression of IgE receptor (Fc epsilonRI) on human mast cell, a significant trigger to acute and chronic allergic symptoms, disclosed epigallocatechin gallate (EGCG), epicatechin gallate, and gallocatechin gallate as active principles. Additionally, the anthocyanidin, delphinidin, and the flavone, tricetinidin, possessing a pyrogallol function were also revealed to suppress expression of Fc epsilonRI. Structure-activity relationship analysis among catechins, anthocyanidins, and flavones revealed the pyrogallol moiety to be crucial for biological potency. Furthermore, EGCG was clarified to reduce generation of gamma-chain subunit to suppress expression of Fc epsilonRI on human mast cells.

Topics: Anthocyanins; Anti-Allergic Agents; Catechin; Cell Line; Flavones; Flavonoids; Gene Expression; Humans; Hypersensitivity; Mast Cells; Receptors, IgE

Topics: Flavones; Flavonoids; Glucosides; Glycosides