6'''-Feruloylspinosin

J Agric Food Chem. 2011 Jun 22;59(12):6594-604.

Distribution of free amino acids, flavonoids, total phenolics, and antioxidative activities of Jujube (Ziziphus jujuba) fruits and seeds harvested from plants grown in Korea.[Pubmed: 21574660]

Fruit pulp and seeds from the jujube plant possess nutritional and medicinal properties. The bioactive components have been shown to vary both with cultivar and with growing conditions. Most studies report the components of varieties from China.
METHODS AND RESULTS:
We measured free amino acid, individual phenolic, and total phenolic content, and antioxidative activities in three jujube fruit pulp extracts from Boeun-deachu, Mechu, and Sanzoin cultivars and two seed extracts (Mechu and Sanzoin) from plants grown in Korea. In g/100 g dry weight, total free amino acid content measured by ion-exchange chromatography ranged from 5.2 to 9.8 in the pulp and from 4.0 to 5.3 in the seed. Total phenolic content measured by Folin-Ciocalteu ranged from 1.1 to 2.4 in the pulp and from 3.6 to 4.6 in the seed. Flavonoids were measured by HPLC and ranged from 0.7 to 1.8 in the pulp and from 3.2 to 4.0 in the seed. Flavonoids were identified by HPLC elution position and UV/vis and mass spectra. Fruits contained the following flavonoids: procyanidin B2, epicatechin, quercetin-3-O-rutinoside (Q-3-R), quercetin-3-O-galactoside (Q-3-G), kaempferol-glucosyl-rhamnoside (K-G-R), and two unidentified compounds. Seeds contained the following flavonoids: saponarin, spinosin, vitexin, swertish, 6'''-hydroxybenzoylspinosin (6'''-HBS), 6'''-Feruloylspinosin (6'''-FS), and one unidentified substance. Dimensions and weights of the fresh fruit samples affected phenolic content. The distribution of the individual flavonoids among the different samples varied widely. Data determined by the FRAP antioxidative assay were well correlated with total phenolic content. In a departure from other studies, data from the DPPH free radical assay were not correlated with FRAP or with any of the measured compositional parameters.
CONCLUSIONS:
Because individual jujube flavonoids are reported to exhibit different health-promoting effects, knowledge of the composition and concentration of bioactive compounds of jujube products can benefit consumers.

Phytomedicine. 2016 Mar 15;23(3):293-306.

Evaluating ancient Egyptian prescriptions today: Anti-inflammatory activity of Ziziphus spina-christi.[Pubmed: 26969383]

To determine the active ingredients of Z. spina-christi, we fractionated the extracts for bioassays and identified the active compounds.
METHODS AND RESULTS:
Epigallocatechin, gallocatechin, spinosin, 6'''-Feruloylspinosin and 6''' sinapoylspinosin and crude extracts of seed, leaf, root or stem were analyzed for their effect on NF-κB DNA binding by electromobility shift assay (EMSA) and nuclear translocation of NF-κB-p65 by Western blot analysis. The binding mode of the compounds to NF-κB pathway proteins was compared with the known inhibitor, MG-132, by in silico molecular docking calculations. Log10IC50 values of gallocatechin and epigallocatechin as two main compounds of the plant were correlated to the microarray-based mRNA expression of 79 inflammation-related genes in cell lines of the National Cancer Institute (NCI, USA) as determined. The expression of 17 genes significantly correlated to the log10IC50 values for gallocatechin or epigallocatechin. Nuclear p65 protein level decreased upon treatment with each extract and compound. Root and seed extracts inhibited NF-κB-DNA binding as shown by EMSA. The compounds showed comparable binding energies and similar docking poses as MG-132 on the target proteins.
CONCLUSIONS:
Z. spina-christi might possess anti-inflammatory activity as assumed by ancient Egyptian prescriptions. Five compounds contributed to this bioactivity, i.e. epigallocatechin, gallocatechin, spinosin, 6'''-Feruloylspinosin and 6''' sinapoylspinosin as shown in vitro and in silico.

J Asian Nat Prod Res. 2011 Dec;13(12):1151-7.

A novel spinosin derivative from Semen Ziziphi Spinosae.[Pubmed: 22115038]

METHODS AND RESULTS:
A novel spinosin derivative, 6‴-(4‴'-O-β-D-glucopyranosyl)-vanilloyl spinosin (1) was isolated from the methanol extract of Semen Ziziphi Spinosae, together with five known flavonoids, swertish, spinosin, 6'''-Feruloylspinosin , isospinosin and kaempferol 3-O-α-L-rhamnopyranosyl-(1 → 2)-O-[O-α-L-rhamnopyranosyl-(1 → 6)]-β-D-glucopyranoside, and two alkanoids, zizyphusine and 6-(2',3'-dihydroxyl-4'-hydroxymethyl-tetrahydro-furan-1'-yl)-cyclopentene[c]pyrrole-1,3-diol.
CONCLUSIONS:
The structure of compound 1 was elucidated by spectroscopic methods including UV, IR, ESI-TOF-MS, 1D, and 2D NMR techniques.