Über die Inhaltsstoffe vonValeriana alliariifolia¹

Abstract

From Valeriana alliariifolia we could isolate six new valepotnathydrines by CC and preparative HPLC. One hydrineand a corresponding valepotriate are esterified with an unsaturated acid (3-methyicrotonic acid). Analysis, isolation and structure eludication are reported.

Acylated Iridoids with Cytotoxicity from Valeriana jatamansi

“…Analysis of the 1 H and 13 C NMR spectroscopic data (Tables and ) indicated signals for a trisubstituted olefinic bond [δ H 6.63 (s, H-3); δ C 145.1 (C-3) and 112.4 (C-4)], a hemiketal methine [δ H 6.60 (d, J = 1.8 Hz, H-1); δ C 89.3 (C-1)], and an oxymethylene [δ H 4.24 and 4.13 (each 1H, J = 12.0, H 2 -10); δ C 67.4 (C-10)]. These data, and the presence of one oxygenated quaternary carbon at δ 69.5 (C-5) and six ester carbonyls at δ C 170.6, 171.2, 169.8, 170.7, 169.9, and 173.2, led to the conclusion that compound 1 is a 5-hydroxy-5,6-dihydrovaltrate hydrin-type iridoid with acyloxy substituents. , In addition, four acyloxy substituents were readily assigned by comparison with the 1 H and 13 C NMR data from the reported valepotriates as an isovaleroxy, an acetoxy, a β-(acetoxy)isovaleroxy, and an α-(isovaleroxy)isovaleroxy group, respectively. ,,,− Analysis of the HSQC and 1 H− 1 H COSY spectra of 1 provided unambiguous assignments of proton and carbon signals in the NMR spectra. The connectivities of the acyloxy substituents to the iridoid nucleus were fully assigned by a HMBC experiment.…”

“…11,12 In addition, four acyloxy substituents were readily assigned by comparison with the 1 H and 13 C NMR data from the reported valepotriates as an isovaleroxy, an acetoxy, a β-(acetoxy)isovaleroxy, and an R-(isovaleroxy)isovaleroxy group, respectively. 10,11,14,[17][18][19][20][21][22][23][24] Analysis of the HSQC and 1 H-1 H COSY spectra of 1 provided unambiguous assignments of proton and carbon signals in the NMR spectra. The connectivities of the acyloxy substituents to the iridoid nucleus were fully assigned by a HMBC experiment.…”

Iridoids from the Rhizomes and Roots of Valeriana jatamansi

“…The petroleum ether extract was separated by a combination of chromatographic procedures to afford five new iridoids ( 1 − 5 ) and 10 known compounds. The structures of the known compounds were identified as valtrate, ,, isovaltrate, ,, homovaltrate, , acevaltrate, ,, dihomovaltrate, , didrovaltrate, ,, 1-homodidrovaltrate, acetylhydroxyldihydrovaltrate, , 10-isovaleroxyvaltrate hydrin, − and 10-isovaleroxydiavaltrate hydrin 12,13 by comparison of their spectral data with those reported in the literature.

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Studies of the structure-antioxidant activity relationships and antioxidant activity mechanism of iridoid valepotriates and their degradation products

“…Heteronuclear multiple bond coherence (HMBC) and heteronuclear multiple quantum coherence (HMQC) studies were conducted to confirm the acyl groups’ chemical shift data ( S1 Fig ). The acyl groups, which connect to different positions on the iridoid rings, showed chemical shift differences of 0.2–0.3 ppm in their 13 C NMR spectra (the γ -effect) [ 6 , 31 , 32 ]. Based on the HMBC data, the chemical shifts of the four ester carbonyls were assigned as δ C 172.6 (C-13), 171.2 (C-16), 171.8 (C-22) and 172.2 (C-2’) for AV and δ C 172.6 (C-13), 172.9 (C-16), 168.9 (C-22) and 172.3 (C-2’) for BAV; these results correspond to the data in the literature [ 32 , 33 ] ( S1 Fig ).…”