Norcyperone, a Novel Skeleton Norsesquiterpene from Cyperus rotundus L.

Abstract

A novel norsesquiterpene, named norcyperone (1), and three known compounds: (-)-clovane-2,9-diol (2), rosenonolactone (3), and 5α,8α-epidioxy-(20S,22E,24R)-ergosta-6,22-dien-3β-ol (4) were isolated from the rhizomes of Cyperus rotundus L. The structure of 1 was elucidated as 8,11,11-trimethylbicyclo[5.3.1]undecane-5α, 8α-epoxy-3-one on the basis of extensive spectroscopic analyses, including 1D- and 2D-NMR, MS experiments, and single-crystal X-ray diffraction. This is the first report of a 8,11,11-trimethyl- bicyclo[5.3.1]undecane-3-one type norsesquiterpene with a tetrahydrofuran ring at C-5 and C-8.

Iridoids and other constituents from Cyperus rotundus L. rhizomes

“…2 Furthermore, the plant possesses different biological activities such as antioxidant, [3][4][5] cytotoxic, 3,5 anti-allergic, 6,7 antipyretic, anti-inflammatory, antiemetic, hypotensive, 8 anticonvulsant, 9 anti-malarial, antimicrobial, 10,11 anti-diarrhoeal, 12 anti-diabetic, 5,13,14 hepatoprotective, 14,15 and insecticide. 16,17 The previous phytochemical studies of C. rotundus L. led to the isolation of sesquiterpenes, 13,[18][19][20][21][22][23] flavonoids, 3,5,8,24,25 phenylpropanoids, 5,26,27 phenolic acids, 5,26 alkaloids, 28 and saponins. 29 In 2013 Zhou and Zhang reported the isolation of iridoid glycosides from C. rotundus rhizomes.…”

Complete assignments of 1H and 13C NMR data for two new sesquiterpenes from Cyperus rotundus L.

“…[6] Sesquiterpenes have been considered as its characteristic secondary metabolites and should be responsible for those activities. Previous phytochemical investigations have described the presence of sesquiterpenes with diverse skeletons such as patchoulane, rotundane, eudesmane, guaiane, cadinane, and caryophyllene types in C. rotundus L. [7,8] As a part of our research program that involves studying naturally occurring sesquiterpenes, [9,10] two guaiane type sesquiterpenes (1, 2) and four patchoulane type sesquiterpenes (3)(4)(5)(6) were isolated from the rhizomes of C. rotundus L., of which 1 and 3 were new compounds. This paper describes the structural determination and the complete assignments of 1 H and 13 C NMR data of those sesquiterpenes.…”

L’étude interdisciplinaire des parfums anciens au prisme de l’archéologie, la chimie et la botanique : l’exemple de contenus de vases en verre sur noyau d'argile (Sardaigne, vie-ive siècle av. J.-C.)

“…Le clovanediol a été retrouvé dans quelques espèces exotiques non pertinentes au regard de la provenance et de la période. Il a été détecté, parmi les sources possibles, dans des souchets, Cyperus rotundus L. (rhizome, Xu et al , 2008) et C. longus L. (plante entière, Xu et al , 2004, 569), bien attestés par ailleurs en archéobotanique en Égypte (Vartavan et Asensi Amorós, 1997, 94-101) et dont certaines espèces étaient utilisées comme alimentaire, pour aromatiser la bière, en médicinal, dans les parfums et comme oléagineux. Le composé est également attesté dans une sauge, malheureusement avec une origine géographique, les Canaries, peu vraisemblable pour la période (Gonzales et al , 1975, p. 705).…”