16 Negative ESI–MS m/z 609 [M–H]ˉ, m/z 595 [M–H]−m/z 431 [M–H]− of compounds 3, 4 and 7 confirming their structures as rutin, quercetin-3-O-arabinoglucoside and isoquercetin, respectively, together with their aglycone

peak of quercetin at m/z 301 [quercetin-H]−, which is also of compound 10. 17 Compound 6 was obtained as yellow amorphous powder (18 mg), chromatographic properties: Rf values; 0.38 (S1), 0.44 (S2); dark purple spot under UV-light, turned to yellow fluorescence on exposure to ammonia vapors. It gave deep green color and orange fluorescence with FeCl3 and Naturstoff spray reagents, respectively. It showed λmax (nm) (MeOH): 257, 356; (+NaOMe): 272, 326 (sh), 404; (+NaOAC): 273, 323 (sh), 373; (+AlCl3): 275, 433; (+AlCl3/HCl): 270, 360 (sh), 404. Complete acid hydrolysis PI3K Inhibitor Library in vitro resulted in l-arabinose in aqueous phase and quercetin in organic phase (CoPC). 1H NMR (300 MHz, DMSO-d6): δ ppm 12.54 (1H, s, H-bonded OH-5), 7.50 (1H, dd, J = 8.4, 2.5 Hz, H-6′), 7.48 (1H,

d, J = 2.5 Hz, H-2′), 6.82 (1H, d, J = 8.4 Hz, H-5′), 6.38 (1H, d, J = 2.4 Hz, H-8), 6.16 (1H, d, J = 2.4 Hz, H-6), 5.50 (1H, d, J = 1.3 Hz, H-1″), 4.11 (1H, br s, H-2″). 13C NMR (75 MHz, DMSO-d6): δ ppm 178.11 (C-4), 164.77 (C-7), 161.63 (C-5), 156.88 (C-2/9), 148.95 (C-4′), 145.52 (C-3′), 133.84 (C-3), 122.23 (C-6′), 121.44 (C-1′), 116.10 Volasertib chemical structure (C-5′/2′), 108.34 (C-1″), 104.42 (C-10), 99.26 (C-6), 94.20 (C-8), 86.32 (C-4″), 82.55 (C-2″), mafosfamide 77.43 (C-3″), 61.13 (C-5″). On the basis of its chromatographic properties and UV-spectral data, as the previous explained compounds, compound 6 was expected to be quercetin 3-O-glycoside. The acid hydrolysis of 6 afforded quercetin as an aglycone and the sugar moiety was identified as arabinose by CoPC. Negative ESI-MS spectrum exhibited a molecular ion peak at m/z 433.56 [M–H]−, corresponding to molecular weight 434 and molecular formula C20H18O11 for quercetin pentoside, this was further supported

by the fragment ions at m/z 867.12 [2M–H]−, for the dimeric adduct ion and at 301.30 [quercetin-H]−, for quercetin aglycone. 1H NMR spectrum showed a douplet at δ ppm 5.50 with J = 1.3 Hz was characteristic for the anomeric proton of α-l-arabinofuranoside moiety. 1813C NMR spectrum showed in addition to 15 carbon resonances for 3-O-glycosyl-quercetin, 18 three highly downfield shifted peaks at 108.34, 86.32, 82.55 assignable to C-1″, C-4″, and C-2″ of an arabinofuranoside moiety by compared to data. 17, 19 and 20 Accordingly compound 6 was identified as Quercetin 3-O-α-L-arabinofuranoside, which was isolated before from R. polystachya 3 but first time from this species. Compounds 5 and 9 showed UV spectra of two major absorption bands in methanol at λmax 268 nm (band II) and at λmax 333 nm (band I) indicating its flavonoid nature giving the chromatographic properties of the characteristic apigenin nucleus.