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At least 19 recordsLinked to original sources
PubMed1999

Phylogenetic relationships of Rutaceae: a cladistic analysis of the subfamilies using evidence from RBC and ATP sequence variation.

Sequence data for plastid rbcL and atpB from members of Anacardiaceae, Burseraceae, Cneoraceae, Meliaceae, Ptaeroxylaceae, Rutaceae, and Simaroubaceae were analyzed cladistically to evaluate the familial and subfamilial circumscriptions of Rutaceae. Taxa representing all subfamilies and tribes were sampled. The analysis shows that Rutaceae are paraphyletic, with Spathelia and Dictyoloma (Rutaceae), Harrisonia (Simaroubaceae), Cneorum (Cneoraceae), and Ptaeroxylon (Ptaeroxylaceae) forming a clade sister to all other Rutaceae. Circumscription of Rutaceae to include all of these taxa is recommended. This analysis indicates that Simaroubaceae and Meliaceae are the outgroups closest to Rutaceae. Correlation of the molecular phylogenies with biochemical data indicates that chemotaxonomic information is more reliable than fruit type as an indicator of familial and subfamilial circumscriptions. The subfamilial classification needs revision; none of the subfamilies of more than one genus is monophyletic.

Journal Article↗
PubMedDate not supplied

Isoflavonoids in the Rutaceae family: 1. Fortunella obovata, Murraya paniculata and four Citrus species.

Several types of compounds with immunoreactivity similar to isoflavonoids were detected in water: ethanol extracts of leaves of Fortunella obovata Hort. ex Tanaka, Murraya paniculata Jack. and four Citrus species, namely C. aurantium L, C. grandis Osbeck, C. limonia Osbeck., and C. sinensis Osbeck (Rutaceae). The chromatographic mobilities of the immunoreactive substances were compared with those of authentic standards, revealing a spectrum of isoflavonoid metabolites in all plants studied. Aglycones as well as glycosides were recognized, namely daidzin, genistin, daidzein, genistein, formononetin, biochanin A, prunetin, and several incompletely characterized isoflavonoids. A subsequent HPLC-MS study verified the identities of the main immunoreactive isoflavonoids and established the identities of several others, viz. glycitein, glycitin, ononin and sissotrin, including the malonylated and acetylated isoflavonoid glucosides. The estimated content of the individual immunoreactive entities ranged from a few microg to about 2 mg/kg (dry weight). It is concluded that the isoflavonoid metabolic pathway is present throughout the Rutaceae family.

Chromatography, High Pressure Liquid↗
PubMed2004

Hydroxybenzoic acid derivatives in a nonhost rutaceous plant, Orixajaponica, deter both oviposition and larval feeding in a rutaceae-feeding swallowtail butterfly, Papilio xuthus L.

A Rutaceae-feeding swallowtail butterfly. Papilio xuthus L., feeds on various rutaceous plants but always rejects Orixa japonica Thunb. (Rutaceae). Females were strongly deterred from laying eggs by a methanolic extract of O. japonica leaves. Larvae also rejected a diet leaf medium impregnated with O. japonica leaf extracts. Several components in the water-soluble fraction of the leaf extract were found to deter both oviposition and feeding responses. Two major deterrent compounds were characterized as 5-[[2-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl]oxy]-2-hydroxybenzoic acid and adisyringoyl aldaric acid. These compounds induced potent deterrence of both oviposition and larval feeding by P. xuthus, which suggests a congruent chemosensory mechanism of allomonal chemicals acting on both female tarsal chemoreceptors and larval maxillary taste receptors.

Animals↗
PubMed2004

Anxiolytic-like actions of leaves of Casimiroa edulis (Rutaceae) in male Wistar rats.

Anxiolytic-like actions of an aqueous extract of the leaves of Casimiroa edulis (Ce) La Llave ex Lex. (Rutaceae) were studied in male Wistar rats in the elevated plus-maze test, whether effect on locomotion were studied in the open-field task, and its possible antidepressant-like actions in the forced swimming task. In the elevated plus-maze test, diazepam (Dz) (1.30 mg/kg; P < 0.05) and Casimiroa edulis (25.0 mg/kg, P < 0.05; 35.0 mg/kg, P < 0.05) increased open arms exploration (i.e., anxiolytic-like action). Doses of 45.0 mg/kg (P < 0.05) and 55.0 mg/kg (P < 0.05) of Casimiroa edulis reduced locomotion in the elevated plus-maze test and in the open-field test. In the forced swimming task, desipramine (dmi) (32.0 mg/kg; P < 0.05) reduced immobility (i.e., antidepressant-like action). Conversely, as compared to control rats, neither diazepam (Dz) (1.30 mg/kg) nor Casimiroa edulis (25.0 mg/kg) modified immobility in the forced swimming task. However, diazepam (P < 0.05) or Casimiroa edulis (P < 0.05), when co-administered, canceled the antiimmobility actions of desipramine. In conclusion, the leaves of Casimiroa edulis (Rutaceae) produced anxiolytic-like actions in male Wistar rats, with several side actions, namely, reduced locomotion and neutralization of the antidepressant-like actions of desipramine.

Animals↗
PubMed1999

Screening for biological activity and chemical composition of Euodia borbonica var. borbonica (Rutaceae), a medicinal plant in Reunion Island.

Three simple coumarins; scoparone, limettin and psoralen have been isolated as major components from the leaves of Euodia borbonica var. borbonica (Rutaceae) together with xanthoxylin, a common phenolic compound in Rutaceae family. Their structures were elucidated through GC/MS and NMR studies. A minor furocoumarin, bergapten, was also detected in the extracts. Preliminary biological tests on ethanolic leaf extracts did not show any activity.

Cell Culture Techniques↗
PubMed2002

Screening of eight alkaloids and ten flavonoids isolated from four species of the genus Boronia (Rutaceae) for antimicrobial activities against seventeen clinical microbial strains.

Eight alkaloids and ten flavonoids isolated from four species of Boronia of the Rutaceae were screened against 17 clinical microbial strains. Of the test compounds, three acridone and one quinolone alkaloids and eight flavonoids were reported as novel natural products. Screening was carried out by the standard disc diffusion method. Of the tested compounds, six alkaloids and seven flavonoids including the novel products were active against six clinical strains. The active compounds showed mild to moderate activities against Bacillus subtilis, Staphylococcus aureus, Sarcina lutea, exterotoxigenic Escherichia coli, Salmonella typhi and Klebsiella sp. Of the active flavonoids, some exhibited fairly significant activity towards Staphylococcus aureus, Sarcina lutea, Salmonella typhi and Klebsiella sp. The flavonoids were observed to have higher spectrum and magnitude of activity than those of the alkaloids. A standard ampicillin disc was used to compare the results.

Alkaloids↗
PubMed2006

Karyotypic analysis of Skimmia japonica (Rutaceae) and related species.

A karyotypic analysis of three species of Skimmia (Rutaceae) in East Asia was performed that examined 88 individuals from 53 localities. Chromosome numbers of S. japonica, S. reevesiana and S. arisanensis were 2n=30, 31, 32 (=30+0-2B), 2n=60 and 2n=60, respectively. The chromosome number of S. arisanensis was reported for the first time. All species had a large chromosome pair or quartet (the first pair or quartet) with a median-submedian centromere in the karyotype. In S. japonica the arm ratio of this first pair was considerably variable and showed a geographical pattern. In the northern half of the distribution range, Sakhalin, Hokkaido, Honshu, Shikoku and part of Kyushu, the arm ratio was 1-1.2, while in the southern half, part of Kyushu, Ryukyu and Taiwan, the arm ratio was very variable and ranged from 1.2 to 2.4. In S. japonica the first pair was sometimes rather heteromorphic; however, the heteromorphism was not related to sex of the plant.

Chromosomes, Plant↗
PubMed2005

Starter substrate specificities of wild-type and mutant polyketide synthases from Rutaceae.

Chalcone synthases (CHSs) and acridone synthases (ACSs) belong to the superfamily of type III polyketide synthases (PKSs) and condense the starter substrate 4-coumaroyl-CoA or N-methylanthraniloyl-CoA with three malonyl-CoAs to produce flavonoids and acridone alkaloids, respectively. ACSs which have been cloned exclusively from Ruta graveolens share about 75-85% polypeptide sequence homology with CHSs from other plant families, while 90% similarity was observed with CHSs from Rutaceae, i.e., R. graveolens, Citrus sinensis and Dictamnus albus. CHSs cloned from many plants do not accept N-methylanthraniloyl-CoA as a starter substrate, whereas ACSs were shown to possess some side activity with 4-coumaroyl-CoA. The transformation of an ACS to a functional CHS with 10% residual ACS activity was accomplished previously by substitution of three amino acids through the corresponding residues from Ruta-CHS1 (Ser132Thr, Ala133Ser and Val265Phe). Therefore, the reverse triple mutation of Ruta-CHS1 (mutant R2) was generated, which affected only insignificantly the CHS activity and did not confer ACS activity. However, competitive inhibition of CHS activity by N-methylanthraniloyl-CoA was observed for the mutant in contrast to wild-type CHSs. Homology modeling of ACS2 with docking of 1,3-dihydroxy-N-methylacridone suggested that the starter substrates for CHS or ACS reaction are placed in different topographies in the active site pocket. Additional site specific substitutions (Asp205Pro/Thr206Asp/His207Ala or Arg60Thr and Val100Ala/Gly218Ala, respectively) diminished the CHS activity to 75-50% of the wild-type CHS1 without promoting ACS activity. The results suggest that conformational changes in the periphery beyond the active site cavity volumes determine the product formation by ACSs vs. CHSs in R. graveolens. It is likely that ACS has evolved from CHS, but the sole enlargement of the active site pocket as in CHS1 mutant R2 is insufficient to explain this process.

Acyltransferases↗
PubMed2005

Alkaloids from Oriciopsis glaberrima Engl. (Rutaceae).

Two alkaloid derivatives, oriciacridone A and B, were isolated from the stem bark of Oriciopsis glaberrima (Rutaceae). The structures were elucidated by a detailed spectroscopic analysis. The extract exhibited in vitro significant antimicrobial activity against a range of micro-organisms.

Acridines↗
PubMed2006

Acridone and furoquinoline alkaloids from Teclea gerrardii (Rutaceae: Toddalioideae) of southern Africa.

The combined hexane/CH(2)Cl(2) extract of the stem bark of Teclea gerrardii (Rutaceae: Toddalioideae) has yielded two acridone alkaloids, 3-hydroxy-1-methoxy-N-methylacridone (tegerrardin A) (1) and 3-hydroxy-N-methyl-1-(gamma,gamma-dimethylallyloxy)acridone (tegerrardin B) (2), three known acridones (3-5), two known furoquinolines (6,7), and the acridone precursor tecleanone (8). Arborinine (3) and evoxine (6) displayed moderate antiplasmodial activity against the CQS D10 strain of Plasmodium falciparum, with IC(50) values of 12.3 and 24.5 microM, respectively.

Acridines↗
PubMed2004

Photo-activated DNA binding and antimicrobial activities of furoquinoline and pyranoquinolone alkaloids from rutaceae.

To find novel photo-active compounds of potential use in photochemotherapy from higher plants, photo-activated antimicrobial and DNA binding activities of the furoquinolines, skimmianine, kokusaginine, and haplopine, and a pyranoquinolone, flindersine, from two species of Rutaceae plants were investigated. TLC overlay assays against a methichillin-resistant strain of Staphylococcus aureus and Candida albicans were employed to test antimicrobial properties. All of the tested compounds showed photo-activated antimicrobial activity against S. aureus in the order of kokusaginine > haplopine, flindersine > skimmianine. Weaker activity was found for C. albicans. Photo-activated DNA binding activity of these compounds was investigated by a method using restriction enzymes and a specially designed 1.5 kb DNA fragment. Kokusaginine showed inhibition against all of the 16 restriction enzymes. Haplopine showed a similar inhibition pattern but the binding activity against Asc I and Sma I with restriction sequences consisting only of G and C was very weak. Skimmianine showed binding activity against Xba I, BciV I, Sal I, Pst I, Sph I and Hind III, but very weak or no activity was found for the other restriction enzymes. A pyranoquinolone, flindersine, showed no activity against any of the restriction enzymes. Photo-activated DNA binding activity of furoquinolines was therefore in the order of kokusaginine > haplopine > skimmianine, which was the same order as their photo-activated antimicrobial activity against S. aureus. Therefore, it was concluded that DNA is one of the cellular targets for the furoquinolines to exert their biological activities, similar to psoralens. However, because flindersine showed photo-activated antimicrobial activity against S. aureus but did not show photo-activated DNA binding activity, it is clear that there are other cellular target components for this compound to exert photo-toxic activity.

Alkaloids↗
PubMed2006

Phebaclavin I, a novel 3-prenylated coumarin, and trichoclin acetate, a new natural furocoumarin, from the aerial parts of Phebalium aff. tuberculosum (Rutaceae).

Phebaclavin I, a novel 3-prenylated coumarin, was isolated from the aerial parts of Phebalium aff. tuberculosum (Rutaceae) together with five known related compounds, Phebaclavin A, B, D, G, H. The structure of phebaclavin I was established by spectroscopic methods. Several other known coumarins were obtained, including trichoclin acetate, a furocoumarin isolated for the first time from a natural source, but previously described from acetylation of trichoclin.

Acetylation↗
PubMed2004

Laboratory evaluation of methanolic extract of Atlantia monophylla (Family: Rutaceae) against immature stages of mosquitoes and non-target organisms.

Methanolic extracts of the leaves of Atlantia monophylla (Rutaceae) were evaluated for mosquitocidal activity against immature stages of three mosquito species, Culex quinquefasciatus, Anopheles stephensi, and Aedes aegypti in the laboratory. Larvae of Cx. quinquefasciatus and pupae of An. stephensi were found more susceptible, with LC50 values of 0.14 mg/l and 0.05 mg/l, respectively. Insect growth regulating activity of this extract was more pronounced against Ae. aegypti, with EI50 value 0.002 mg/l. The extract was found safe to aquatic mosquito predators Gambusia affinis, Poecilia reticulata, and Diplonychus indicus, with the respective LC50 values of 23.4, 21.3, and 5.7 mg/l. The results indicate that the mosquitocidal effects of the extract of this plant were comparable to neem extract and certain synthetic chemical larvicides like fenthion, methoprene, etc.

Aedes↗
PubMed2004

Trypanocidal activity of Meliaceae and Rutaceae plant extracts.

The in vitro trypanocidal activity of 22 extracts and 43 fractions of plants belonging to the families Meliaceae and Rutaceae was evaluated. The extracts from leaves of Conchocarphus heterophyllus and branches of Trichilia ramalhoi were the most active. The trypanocidal activity seems to be increased by fractionation of the extracts. Fractions from C. heterophyllus and Galipea carinata were the most active and a 100% lysis of the parasites was observed for five fractions. From one of them were isolated two flavonoids: flavone and 7-methoxyflavone, which showed weak trypanocidal activity. The results obtained from the extracts and fractions revealed that the order Rutales is a promising source for the search of new drugs for Chagas disease. Phytochemical studies with the other active fractions are underway in order to isolate compounds, which could be associated with observed activities.

Animals↗
PubMed1999

[Bullous phototoxic contact dermatitis caused by Ruta graveolens L. (garden rue), Rutaceae. Case report and review of literature].

A patient developed severe bullous phototoxic contact dermatitis caused by Ruta graveolens L. (garden rue) which belongs to the Rutaceae family. To date only a few cases of phototoxic reactions to the garden rue have been reported. The phototoxic components of Ruta graveolens L. are the fouranocoumarins 5-methoxypsoralen (bergapten) and 8-methoxypsoralen (xanthotoxine), and the furanoquinoline dictamnine whose phototoxic properties were recently discovered. Since the garden rue is frequently cultivated, it should be considered in the differential diagnosis of phototoxic phytodermatitis.

5-Methoxypsoralen↗
PubMed2000

In vitro activity of Rutaceae species against the trypomastigote form of Trypanosoma cruzi.

The activity of crude plant extracts of nine species of Rutaceae against the trypomastigote form of Trypanosoma cruzi was evaluated at 4 mg/ml. Thirty-two crude extracts were tested and eight of them showed significant activity (>80%). The most active extract was obtained from the stems of Pilocarpus spicatus (97.3%). Fractionation of the active crude extracts provided 25 fractions which were tested against the trypomastigote form of T. cruzi at 2 mg/ml. Of these six showed significant activity (>80%). The most active fractions (100%) were obtained from the leaves of Almeidea coerulea (butanol fraction) and Conchocarpus inopinatus (dichloromethane fraction).

Animals↗