Acylated preatroxigenin glycosides from Atroxima congolana

Six new acylated bisdesmosidic preatroxigenin saponins named atroximasaponins E-1, E-2 (1, 2), F-1, F-2 (3, 4), and G(1), G(2) (5, 6) were isolated as three inseparable mixtures of the trans- and cis-p-methoxycinnamoyl derivatives, from the roots of Atroxima congolana. Their structures were established through extensive NMR spectroscopic analysis as 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin E-1, 1), and its cis-isomer, atroximasaponin E-2 (2), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-xylopyranosyl-(1-->4)-alpha-L-rhamnopyranosyl-(1-->2)-[6-O-acetyl-beta-D-glucopyranosyl-(1-->3)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin F-1, 3), and its cis-isomer, atroximasaponin F-2 (4), 3-O-beta-D-glucopyranosylpreatroxigenin-28-O-beta-D-apiofuranosyl-(1-->3)-[alpha-L-rhamnopyranosyl-(1-->2)]-[4-O-trans-p-methoxycinnamoyl]-beta-D-fucopyranoside (atroximasaponin G(1), 5), and its cis-isomer, atroximasaponin G(2) (6), respectively

Biotechnological Production of Volatile and Non-Volatile Antioxidant Compounds From Fermented Soy Bean Meal with Trichoderma sp

ABSTRACT Three strains of Trichoderma sp. were screened for β-glucosidase activity and their potential for the breakdown of isoflavone glucosides to the biologically active aglycones in defatted soy bean meal. The main flavonoid products of fermentation process were evaluated by qualitative and quantitative HPLC analysis. Also, the production of volatile compounds in both the crude soy meal (CSM) and defatted soy meal (DSM) cultured by Trichoderma harzianam F.555 were determined by GC-MS. Isoflavones in defatted soy meal fermented by Trichoderma viride, F-516 or T. harzianam F-555 or T. reesei F-417 at 37 °C for 48 h were determined. Daidzein and genistein aglycones concentrations were significantly increased after fermentation to 162% and 362.4 % for T. reesei; 151.3% and 944 % for T. harzianam and up to 80.6% and 711 % for T. viride, respectively. Results showed that fermented defatted soy meal by T. harzianam F-555 T. viride F-516 and T. reesei F-417 increased levels of bioactive genistein (10.44, 8.11 and 4.62 folds, respectively). Moreover, defatted soy meals were fermented separately by T. reesew, T. harzianam F-555 and T. viride F-516 showed highly significant increase of daidzein (2.64, 2.51 and 1.82 folds, respectively) in comparison to unfermented defatted soy meal (DSM). The levels of aglycones increased, while the corresponding levels of glucosides decreased. Furthermore, in fermented defatted soy meal (FDSM) with T. harzianam, compounds such as Butylated Hydroxytoluene (38.19 %), 1,4-Di-anhydro-mannitol (14.25 %) and 2-Dimethyl (isopropyl) silyloxy methyl tetra -hydrofurane (9.62 %) were present at high concentrations as dominant volatiles. While, the major volatile compounds in fermented crude soy meal (FCSM) were 9,12-Octadecadienoicacid (Z,Z), methyl ester (28.08 %), 2,2-Bis[4-(4,6-dichloro-1,3,5-triazin-2-yl)oxy]phenyl]1,1,1,3,3,3hexafluoropropane (10.61 %), Oleic Acid (10.61 %), and 9-Octadecenoic acid-3-[(1-oxohexadecyl)oxy]-2-[(1-oxooctadecyl)-oxy] propyl ester (9.08 %). Total phenolic content and in vitro antioxidant activity of ethanolic extract of (FDSM) with T. harzianam were higher than that in (CSM), (FCSM) and (DSM). Moreover, the major volatile antioxidant-active compound was butylated hydroxytoluene. The current findings indicate that fermentation process carried out in (DSM) inoculated with different microorganisms produced significant changes in flavonoids and volatile contents. Therefore, both volatile and non volatile products of (FDSM) are considered as prospective bioactive and functional by-products of soybean oil production. These data suggest that microbial fermentation of (DSM) might be valuable sources of antioxidant that can be applied in food and pharmaceutical industry

Novel acylated triterpene glycosides from Muraltia heisteria

Four new acylated triterpene glycosides (1-4) have been isolated as two inseparable mixtures of the trans- and cis-3,4,5-trimethoxycinnamoyl derivatives (1,2 and 3,4) from the roots of Muraltia heisteria. The structures of these compounds were elucidated by various 1D and 2D NMR techniques, including H-1 and C-13, COSY, NOESY, HSQC, TOCSY, and HMBC experiments and FABMS. Compounds 3 and 4 were shown to be cytotoxic in a human colon cancer cell line but did not show any ability to potentiate in vitro cisplatin cytotoxicity