Iridoids. An Updated Review. Part I.

Chemical Constituents from Himatanthus articulata

“…The 13 C-NMR (HBBD and DEPT) spectra of 1a showed five signals for δCH and one δCH2 of the sugar unit. Seven δH signals in the 1 H-NMR spectrum have been assigned to the same sugar moiety by the ho-monuclear 1 H, 1 H-COSY and also by comparison with literature data 5,9 . The peaks at m/z 332 (2.0%, 1f) and 33l (20.0%, 1g) observed in the EIMS spectra are compatible with the 2,3,4,6-tetra-O-acetyl-1-O-β-D-glucopyranosyl group.…”

“…Peaks in the EIMS spectrum corresponding to fragments 1b-1e are in agreement with the structure of 1. To establish the β-D-glucopyranosyl moiety at the β-position of the carbon C-l, the δC-1 (93,33 ppm) and δH-1 (5, 10; br) were compared with the models 1β-O-acetyl (2b) 9 and 1β-O-glucopyranosyl (2c) 9 , and with those of the penta-O-acetylplumeride glucoside (2a), previously isolated from H. phageadaenica. 5 The presence of a carboxylic acid group in 1 was confirmed by the signals at δH 3.93(s), δC 51.50(CH3) and 170.50 (C) in the 1 H-and 13 C-NMR spectra of the methyl ester obtained after treatment of la with diazomethane.…”

Iridoids from Vitex cymosa

“…In other studies, derivatives of aucubin and mussaenosidic acid were found in various Vitex species 4,5,6 .…”

“…We now report the isolation and identification, from the leaves of V. cymosa, of a new iridoid, closely related to 3 which was named tarumal (1), as well as the known compounds viteoid II (2) and agnuside (4).…”

Phytochemical profile and analgesic evaluation of Vitex cymosa leaf extracts

“…Their chemical structures were identified by means of one and two dimensional 1 H and 13 C NMR techniques, as well as by mass spectral data, which were in accordance with previously reported data. From the dichloromethane extract, VD, the iridoids tarumal, 21 ) and agnuside, 23 (Boros & Stermitz, 1990); the flavonoids kampferol, 1, 3'-O-methyl-luteolin, 2, luteolin, 3, pachypodol, 4, and apigenin, 5 (Agrawal, 1989); and the triterpenes 2α,3α-hydroxy-oleanolic acid, 15, 2α,3β-hydroxy-oleanolic acid, 16, 2α,3α-hydroxy-ursolic acid, 17, 2α,3β-hydroxy-ursolic acid, 18, 2β,3β,19α-hydroxy-ursolic acid, 19, (Mahato & Kundu, 1994), and 28-O-glucosyl-2α,3α,19α-hydroxy-ursolic acid ester, 20 (Seto et al, 1984), were isolated. From the ethyl acetate extract, VA, orientin, 6, iso-orientin, 7, vitexin, 8, iso-vitexin, 9, 2"-O-caffeoyl-orientin (Leitão & Delle Monache, 1998), 11, 2"-O-p-hydroxybenzoyl-orientin, 10, (Leitão & Delle Monache, 1998) protocatechuic acid, 12, vanilic acid, 13, and p-hydroxybenzoic acid, 14, were isolated.…”