Iridoids from the Roots of Valeriana jatamansi

Abstract

Three new iridoids, jatamanins N–P (1–3), along with the seven known iridiods 4–10, were isolated from the roots of Valeriana jatamansi. Compound 1 is an unusual iridoid bearing two epoxy bridges between C(3) and C(6) and between C(1) and C(10), forming a unique cage‐like rigid skeleton. The structures of the new compounds were assigned on the basis of spectroscopic methods.

Valeriana jatamansi: An herbaceous plant with multiple medicinal uses

“…Thirteen new iridoids Jatamanins A–M ( 41–53 ) were also extracted from whole plants (Lin et al, ). Likewise, three new iridoids, jatamanins N ( 54 ), O ( 55 ), and P ( 56 ), were isolated from the roots of this herb (Li, Wu, Li, Li, & Li, ). Xu et al () has isolated three new natural iridoids including valeriandoids D–F ( 57 – 59 ).…”

“…In addition, a valepotriate known as valeriotetrate A ( 125 ) was also detected and quantified from the roots of this herb (Yu et al, ). Two valepotriates, namely, volvatrate A ( 126 ) (Wang et al, ; Li et al, ) and jatamandoid A ( 127 ) (Xu et al, ) were isolated from the roots of V. jatamansi whereas patriscabrol ( 128 ) from the whole plant of this species (Lin et al, ). Several valepotriate compounds and their analogues, namely, acetovaltrate ( 129 ), 8, 11‐desoidodidrovaltrate ( 130 ), desoxidodidrovaltrate ( 131 ), isovaltrate isovaleroyloxyhydrin ( 132 ), 1,5‐dihydroxy‐3,8‐epoxyvalechlorine ( 133 ), rupesin E ( 134 ), didrovaltrate acetoxy hydrin ( 135 ), 10‐acetoxyvaltrathydrin ( 136 ), isovaleroxyhydroxy‐didrovaltrate (IVHD‐valtrate) ( 137 ), 5‐hydroxydidrovaltrate ( 138 ), (3S,4R,5S,7S,8S,9S)‐3,8‐epoxyoctahydro‐4,8‐dimethylcyclopenta[ c ]pyran‐7‐ol ( 139 ), (3S,4S,5S,7S,8S,9S)‐3,8‐epoxy‐7‐hydroxy‐4,8‐dimethylperhydrocyclopenta[ c ]‐pyran ( 140 ), 4,7‐dimethyloctahydrocyclopenta[ c ]pyran ( 141 ), hexahydro‐6‐hydroxy‐7‐(hydroxymethyl)‐4‐methylenecyclopenta[ c ]pyran‐1(3 H )‐one ( 142 ), (4β,8β)‐8‐methoxy‐3‐methoxy‐10‐methylene‐2,9‐dioxatricyclo[4.3.1.0 3,7 ]decan‐4‐ol ( 143 ), isovalerate isovaleroxyhydrin ( 144 ), and homoisovaltrate ( 145 ) were also studied.…”

“…The molecular mechanisms of IVHD‐valtrate ( 137 ) showed that it modulate the expression of numerous molecules by enhancing (p53, Rb, p21, and p27) and reducing (Mdm2, E2F1, Cyclin B1, Cdc25C, and Cdc2) their level. It was also observed to down‐regulate the proportion of Bcl‐2/Bax and Bcl‐2/Bad and enhance the cleavage of PARP and caspases, which indicated its potential as a therapeutic agent for ovarian cancer and for development of novel chemotherapeutic compounds (Li et al, ). Recently, three new minor valepotriate isomers, jatamanvaltrates Z1 ( 70 ), Z2 ( 71 ), and Z3 ( 72 ) extracted from V. jatamansi , displayed moderate cytotoxicity against the lung adenocarcinoma (A549), metastatic prostate cancer (PC‐3M), colon cancer (HCT‐8), and hepatoma (Bel7402) cell lines with IC 50 values of 2.8–8.3 μM (Lin et al, ).…”

“…More recently, five new iridoids, named as chlorovaltrate P-T (102-106), along with six known analogues, (4β,8β)-8-methoxy-3-methoxy-10-methylene-2,9- (125) was also detected and quantified from the roots of this herb (Yu et al, 2006). Two valepotriates, namely, volvatrate A (126) Li et al, 2013) and jatamandoid A (127) (145) were also studied.…”

Three new iridoids from leaves ofCornus officinalis

“…From these resonances, a p-hydroxycinnamic acid group could be identified readily, which was further supported by 1 H -1 H COSY and HMBC correlations ( Figure 2). The rest signals established patterns of an iridoid with a basic backbone related to jatamanin P [8].…”