Phytochemistry, structural diversity, biological activities and pharmacokinetics of iridoids isolated from various genera of the family Scrophulariaceae Juss.

Iridoid‐glycoside isolation and purification from Premna fulva leaves

“…Compound 4 , obtained as a white powder, $$[ \alpha ]_D^{22} - 98.2^\circ (c = 0.09,\;{\rm{C}}{{\rm{H}}_3}{\rm{OH}})$$, exhibited an HR‐ESI‐MS deprotonated molecular‐ion peak at m/z 1019.2628 [M+HCOO] − , indicating the molecular formula C 47 H 58 O 22 . The IR absorption bands were consistent with those of hydroxyl (3365 cm −1 ), ester carbonyl (1708 cm −1 ), and an olefinic double bond (1633 cm −1 ) [30]. Signals attributed to four trans olefinic protons at δ H 6.51 and 7.63 (d, J = 16.0 Hz), and at δ H 5.87 and 6.95 (d, J = 12.8 Hz), four pairs of ortho‐coupled aromatic protons at δ H 7.79 (d, J = 8.8 Hz, H‐2″″, 6″″), 6.98 (d, J = 8.8 Hz, H‐3″″, 5″″), 7.72 (d, J = 9.0 Hz, H‐2″″′, 6″″′), and 6.93 (d, J = 9.0 Hz, H‐3″″′, 5″″′), and two peaks attributed to the aromatic methoxy group at δ H 3.79 (3H, s) and 3.80 (3H, s) in the 1 H NMR spectrum of 4 indicated that it contained two trans ‐ p ‐methoxycinnamoyl units.…”

“…The molecular formula of compound 3 , obtained as an amorphous powder, $$[ \alpha ]_{\rm{D}}^{22} - 69.9^\circ (c = 0.07,\;{\rm{C}}{{\rm{H}}_3}{\rm{OH}})$$, was determined to be C 31 H 40 O 16 (668.2316) by HR‐ESI‐MS (a molecular‐ion peak appeared at m/z 713.2317 [M+HCOO] − ), and NMR ( 1 H and 13 C) analyses. The IR spectra absorption bands of 3 were typical of hydroxyl (3321 cm −1 ), ester carbonyl (1712 cm −1 ), and an olefinic double bond (1633 cm −1 ) [30]. A comparison of the 1 H and 13 C NMR, 1 H‐ 1 H COSY, and HMBC spectral data of 3 (Figure S5) with those of 6‐ O ‐( α ‐ L ‐rhamnopyranosyl)‐catalpol [31] indicated very similar signal patterns (see Table 1 and Supporting Information), except for the signals corresponding to the acyl moiety.…”

“…Compound 5 , obtained in the form of an amorphous powder, $$[ \alpha ]_D^{22} - 116.9^\circ (c = 0.06,\;{\rm{C}}{{\rm{H}}_3}{\rm{OH}})$$, showed an LC‐ESI‐MS molecular‐ion peak at m/z 828.2841 [M+HCOO] − , indicating the formula C 41 H 48 O 18 . The IR spectrum of 5 showed absorption bands for hydroxyl (3341 cm −1 ), ester carbonyl (1705 cm −1 ), and an olefinic double bond (1633 cm −1 ) [30]. The 13 C NMR spectra of 5 and 3 were similar, with six typical signals for β ‐glucopyranose and six signals for α ‐ L ‐rhamnopyranose.…”

“…The molecular formula for 6 was C 31 H 40 O 16 , determined based on HR‐ESI‐MS (showing a molecular‐ion peak at m/z 668.2316 [M+HCOO] − ) and NMR ( 1 H and 13 C) analyses. The IR spectrum of 6 displayed absorption bands for hydroxyl (3266 cm −1 ), ester carbonyl (1699 cm −1 ), and an olefinic double bond (1633 cm −1 ) [30]. 1 H NMR peaks attributed to aglycone protons were similar for 6 (Table 1) and 3 .…”

GC/MS profiling of essential oils from Bontia daphnoides L., chemometric discrimination, isolation of dehydroepingaione and evaluation of antiviral activity

“…Scrophulariaceae Juss. is a family of annual and perennial herbs that consists of approximately 74 genera and 1533 species broadly dispersed around the world 7 – 9 . The present concept of Scrophulariaceae includes at least eight major tribes: Aptosimeae, Buddlejeae, Hemimerideae, Leucophylleae, Limoselleae, Myoporeae, Scrophularieae, and Teedieae 10 , 11 .…”