A New Monoterpenoid Glucoindole Alkaloid From Dipsacus asper

Abstract

The monoterpenoid glucoindole alkaloids comprise a large class of structurally complex natural products that have attracted widespread attention owing to their biological activities and structural diversity. In the present study, we investigated the constituents of a methanol extract of Dipsacus asper roots and obtained a new monoterpenoid glucoindole alkaloid, (3 R,5 S)-5-carboxyvincosidic acid 22-loganin ester (1), together with the known alkaloid (3 S,5 S)-5-carboxystrictosidic acid 22-loganin ester (dipsaperine) (2). We herein report our structural elucidation of 1 by spectroscopic analysis and its anti-inflammatory activity as revealed by its inhibition of nitric oxide production in lipopolysaccharide-activated RAW264.7 cells.

Dipsacus and Scabiosa Species—The Source of Specialized Metabolites with High Biological Relevance: A Review

“…Some representatives of Dipsacus and Scabiosa biosynthesize chemical compounds of various classes, mainly triterpenoid derivatives (Table 2) [5][6][7]12,21,22,27,40,48,49,51,65,66,81,82,[88][89][90][91][92][93][94][95][96], which possess a variety of bioactivities. In addition, iridoids [6,7,13,22,27,33,34,65,66,75,78,84,89,[92][93][94][95][96][97][98][99][100] (Table 3), phenolic acids [6,24,27,29,…”

“…In addition, iridoids [6,7,13,22,27,33,34,65,66,75,78,84,89,[92][93][94][95][96][97][98][99][100] (Table 3), phenolic acids [6,24,27,29,33,34,43,46,53,65,66,[73][74][75][76]81,89,[92][93][94][95]97,99,101] (Table 4), and flavonoids [7,33,34,42,43,46,…”

“…maritima [7,84] (Table 3). Dipsanosides A-N, dipsasperoside A and B, lisianthioside, triplostoside A, and cocculoside were characteristic only for roots of D. asper [6,13,22,89,92,93,96,[98][99][100]. Sweroside and sylvestrosides III-IV were found in two Dipsacus species: D. asper roots and D. fullonum leaves and roots [6,22,27,33,34,65,66,92,93,96,99].…”