New Quinoline Alkaloids from Ruta chalepensis

Abstract

The roots of Ruta chalepensis, collected from the northern Saudi desert, yielded two new quinoline alkaloids, namely, 2-¿6'-(2H-benzo[d]1' ',3' '-dioxolen-5' '-yl)hexyl¿-hydroquinolin-4-one (1) and 2-¿6'-(2H-benzo[d]1' ',3' '-dioxolen-5' '-yl)hexyl¿-4-methoxy-quinoline (2). Nine previously reported alkaloids, dictamnine, pteleine, skimmianine, rutacridone, isogravacridonechlorine, maculosidine, graveoline, graveolinine, and 4-methoxy-1-methyl-2(1H)-quinolinone, and coumarins, chalepensin, and umbelliferone were also isolated. Structure elucidations were based primarily on 1D and 2D NMR analyses and chemical transformations. Antimicrobial activity of these compounds is discussed.

Platelet Aggregation Inhibitors from Aerial Parts of Ruta Chalepensis Grown in Jordan

“…Pharmacological studies carried out with different extracts of Ruta species reported the antiinfl ammatory properties (Atta and Al-Kofahi, 1998), antipyretic (Al-Said et al 1990), antifertility activity (Ulubelen et al 1994), antifungal (Ali-Shtayeh et al 1999) and antibacterial effect (El Sayed et al 2000). Contact dermatitis and photoxicity characterized by erythema, itching and burning of the skin is a common toxic effect, which is usually associated with all Ruta species (Gijon et al 1995;Heskel et al 1983).…”

“…Phytochemical investigations of R. chalepensis reported isolation of furanocoumarins, acridone and quinoline alkaloids, terpenoids, saponins and tannins (El Sayed et al 2000;El Tawil et al 1980;Gray and Watermann, 1978;Husain and Devy, 1998;Ulubelen et al 1988). However, published literature did not report anti-platelet activity of R. chalepensis herb or its constituents.…”

A New Coumarin and Carbazole Alkaloid from Clausena vestita D. D. Tao

“…Analysis of the 1 H-and 13 C-NMR spectra, including HSQC, coupled with biogenetic considerations, suggested the presence of a C 10 terpenoid side chain with two trisubstituted oxirane rings in the molecule. The 1 H-NMR chemical shifts of the 3-H singlet (MeÀC(3')) and the CH double doublet (HÀC(2')) coupled with 13 Cchemical shifts of C(2') and a fully substituted C-atom C(3'), and the 1 H-chemical shifts of two 3 H-singlets (Me 2 ÀC(7')) and the CH double doublet (HÀC(6')) coupled with 13 C-chemical shifts of C(6') and a fully substituted C-atom C(7') suggested the presence of two trisubstituted oxirane rings, respectively. The connectivity of these signals was elucidated by HMBCs of HÀC(2') with C(3') and MeÀC(3'), of HÀC(6') with Me a ÀC(7'), Me b ÀC(7'), and C(7').…”

In Vitro and In Vivo Activity of Selected Plant Extracts against Papaya Carica papaya L.) Anthracnose (Colletotrichum gloeosporioides)

“…The findings of this study are in agreement with previous reports on the antifungal activity of Echinops sp., Ruta chalepensis, Thymus serrulatus and Artemisia genus [13,14,16,23]. Previous phytochemical investigation of Ruta chalepensis resulted in isolation of a number of alkaloids and coumarins and the active ingredients of this plant have antifungal properties that could prove beneficial to agriculture [12,24].…”

“…There is a need for continued research efforts to developing effective and economical alternative methods for the management of papaya anthracnose. Most plant specious used in this experiment had medicinal value and are known to contain a number of secondary substances with antimicrobial properties and are toxic to phytopathogens [6,[12][13][14][15][16][17].…”