Study of Some Zanthoxylum Species by Chemical and DNA Analysis Approaches.

The authentication and traceability of spices is a major concern for industrials and consumers. We focused on species from Zanthoxylum genera which are used for many different applications by local populations and also for trading as spices (dried pericarps or whole fruits). In this case, literature gives contradictory data about botanical names, and commercial labelling is often confusing. We studied commercial fruits pericarps extracts obtained by supercritical CO2 and analyzed them by GC/MS. The very complex volatile and semi volatile fractions composition of each extract is described. The barcoding method including molecular biology and phylogenetic analyses was also developed in order to check the commercial botanical identification of the raw material. This is a robust method to identify species in berries samples. We used one genetic marker to identify two Rutaceae clusters, including several species of Zanthoxylum genus. These results indicate that Fagara and Zanthoxylum groups could be considered as two different genera. Combination of chemical analysis and DNA analysis provides an original approach to increase chemical and botanical Zanthoxylum genus knowledge.

Chemical Composition of the Fruit Oils of Five Fortunella Species Grown in the Same Pedoclimatic Conditions in Corsica (France).

Fruit oil from five species of kumquat (Fortunella japonica, F. margarita, F. crassifolia, F. obovata, and F. hindsii) grown in the same pedoclimatic conditions have been analyzed by a combination of chromatographic and spectroscopic techniques. The compositions of the five fruit oils were strongly dominated by limonene (84.2-96.3%). Other components present with appreciable contents were myrcene (1.3-12.9%) and germacrene D (0.3-2.4%).

Estudo fitoquímico e avaliação in vitro da atividade anti-Trypanosoma cruzi cepa Y de Pilocarpus spicatus St. Hil. (Rutaceae) / Phytochemical study and in vitro evaluation of the anti-Trypanosoma cruzi Y strain activity of Pilocarpus spicatus A. St. Hil.

A investigação química da espécie Pilocarpus spicatus, popularmente conhecida como jaborandi e usada na medicina tradicional para doenças como estomatite, febre, bronquite e psoríase, teve por objetivo o isolamento e/ou identificação de substâncias ativas e a avaliação da atividade antiparasitária dos extratos frente às formas epimastigotas de Trypanosoma cruzi. O estudo resultou na identificação de nove substâncias, tais como: tridecanona, 2-heptadecanona, espatulenol, aromadendreno, β-cariofileno, ácido 3α-hidroxitirucala-7,24-dien-21-óico, (+)-isoangenomalina, episesamina e sesamina. As estr uturas dos compostos foram elucidadas por análises espectroscópicas e comparação com dados da literatura. Os extratos hexânico e metanólico de folhas e raízes foram testados in vitro contra o Trypanosoma cruzi cepa Y e apresentaram atividade tripanomicida.

The chemical investigation of the species Pilocarpus spicatus - popularly known as jaborandi and used in traditional medicine for diseases, such as stomatitis, fever, bronchitis and psoriasis - aimed to isolate and / or identify the active substances and evaluate the antiparasitic activity of the extracts against the Trypanosoma cruzi epimastigote forms. The study resulted in the identification of nine substances, such as tridecanone, 2-heptadecanone, spathulenol, aromadendrene, β-caryophyllene, 3α-hydroxytirucalla-7,24-dien-21-oic acid, (+)-isoangenomaline, episesamin and sesamin. The structures were elucidated by spectroscopic analysis and comparison with literature data. The hexane and methanol extracts from leaves and roots were tested in vitro against Trypanosoma cruzi Y strain and showed trypanocidal activity.

Estudo farmacognóstico de folhas e raízes da Spiranthera odoratissima A. St. -Hil. (Rutaceae) / Pharmacognostic study of the leaves and roots of Spiranthera odoratissima A. St. -Hil. (Rutaceae)

A Spiranthera odoratissima A. St.-Hil. (manacá) é um arbusto cujas raízes são utilizadas popularmente contra dores musculares, de estômago e de cabeça, disfunções hepáticas, reumatismo, e como estimulante do apetite. As folhas são empregadas como depurativo do sangue, nas afecções renais e hepáticas. O objetivo deste trabalho foi realizar o estudo morfo-anatômico de S. odoratissima, bem como a triagem fitoquímica, a determinação dos teores de água, cinzas totais e insolúveis em ácido. O material vegetal foi coletado em Leopoldo de Bulhões/ Goiás e os estudos morfo-anatômicos e a triagem fitoquímica foram realizados utilizando as técnicas convencionais. Verificou-se que a folha é hipoestomática, com estômatos anomocíticos e a epiderme apresenta papilas na face abaxial. O mesofilo é dorsiventral e a nervura principal possui drusas de oxalato de cálcio e cavidades secretoras. O pecíolo apresenta sistema vascular em forma circular. Na raiz, em crescimento primário, observou-se cilindro vascular com organização diarca. Na prospecção fitoquímica detectaram-se fenóis, taninos, cumarinas, flavonoides, triterpernos/esteróis, antraquinonas e antocianinas nas folhas e alcaloides, cumarinas, amido e saponinas nas raízes. Esses resultados são parâmetros importantes para o controle de qualidade dessa matéria-prima vegetal.

Spiranthera odoratissima A. St.-Hil. (manacá) is a shrub whose roots are popularly used against stomach pains, headache, muscle pain, liver disorders, rheumatism and as an appetite stimulant. The leaves are used as a blood depurative and for liver and kidney disease. The purpose of this work was to perform the morphological and anatomical study, the phytochemical screening and determine the water content and the levels of total and acid of S. odoratissima. The plant material was collected in Leopoldo de Bulhões/ Goiás and the morpho-anatomical studies and the phytochemical screening were performed using conventional techniques. It was verified that the leaf is hypostomatic, with anomocytic stomata and the epidermis has papillae on the abaxial surface. The mesophyll is dorsiventral and the midrib presents druses of calcium oxalate and secretory cavities. The petiole has a circular vascular system. The root in primary growth presents vascular cylinder with diarchic organization. Phenols, tannins, coumarins, flavonoids, triterpenes/sterols, anthraquinones and anthocyanins were detected in the phytochemical screening of the leaves, and alkaloids, coumarins, saponins and starch were detected in the roots. These results are important parameters for the quality control of the vegetal raw material.

Comparison of the volatile oil composition of three Atalantia species.

The members of the genus Atalantia belonging to the family Rutaceae have many uses in traditional medicine. The aim of the present study was to investigate and compare the chemical composition of essential oils of three species of Atalantia namely Atalantia monophylla (Roxb.) DC., Atalantia racemosa Wight. and Atalantia wightii Tanaka. The extract percentage of the obtained essential oil was found to be 0.2, 0.17 and 0.31% in A. monophylla, A. racemosa and A. wightii respectively. The major compounds identified were alpha-Asarone (28.82%), Sabinene (13.19%), Eugenol methyl ether (12.71%), 1,2-Dimethoxy-4-(2-methoxyethenyl)benzene (11.63%) and beta-Pinene (5.3%) in the essential oil of A. monophylla. In A. racemosa, T-Cadinol (11.08%), Caryophyllene oxide (9.78%), beta-Caryophyllene (9.20%), Spathulenol (7.21%), beta-Phellandrene (5.67%) and Decanal (4.01%) and in A. wightii beta-Caryophyllene (16.37%), D-Limnonene (12.15%), Decanal (10.49%), beta-Myrcene (7.67%), Tetradecanal (6.99%), Caryophyllene oxide (6.29%) and Hexadecylene oxide (5.87%) were the main constituents. Sesquiterpenes were the major class of compounds in A. racemosa and A. wightii, while in A. monophylla the essential oil was predominated by ether compounds. The results showed that GC/MS analysis of essential oils is a significant step in the bio-chemical profiling and bio-prospecting of Atalantia species.

Composição química do óleo essencial e avaliação da atividade antimicrobiana do óleo essencial, extrato etanólico bruto e frações das folhas de Spiranthera odoratissima A. St.-Hil / Chemical composition of the essential oil and evaluation of the antimicrobial activity of essential oil, crude ethanol extract and fractions of Spiranthera odoratissima A. St.-Hil. leaves

A Spiranthera odoratissima A. St.-Hil (manacá) é utilizada popularmente como depurativo do sangue, nas afecções renais e hepáticas (chá das folhas) para dores musculares, de estômago, de cabeça, e disfunções hepáticas (chá das raízes). O objetivo desse trabalho foi avaliar a composição química do óleo essencial e a atividade antimicrobiana do óleo essencial, do extrato etanólico bruto e frações obtidos das folhas de S. odoratissima contra bactérias Gram positivas e negativas, e Candida albicans. O extrato bruto das folhas foi obtido por maceração seguido de concentração em rotaevaporador e as frações por partição em coluna filtrante. O pó das folhas foi submetido à hidrodestilação em aparelho de Clevenger e o óleo essencial obtido foi analisado por CG/EM. A atividade antimicrobiana foi avaliada pelo método da diluição em ágar para determinar a concentração inibitória mínima (CIM). Os constituintes majoritários do óleo essencial foram ß-cariofileno (20,64%), γ-muuroleno (17,70%), biciclogermacreno (14,73%), e δ-cadineno (13,40%). No estudo da atividade antimicrobiana de S. odoratissima, os principais resultados foram obtidos contra Staphylococus epidermidis (extrato etanólico bruto, CIM de 0,098 mg/mL), C. albicans (fração hexano, CIM de 0,049 mg/mL), Bacillus cereus (diclorometano, CIM de 0,098 mg/mL), Micrococcus roseus (fração acetato de etila, CIM 0,049 mg/mL), e M. roseus, Micrococus luteus, B. cereus e C. albicans (fração metanol, CIM de 0,391 mg/mL).

Spiranthera odoratissima ("manacá") has been popularly used as a blood cleanser, for liver and kidney diseases (tea from the leaves), as well as for muscle and stomach pains, headache and liver disorders (tea from the roots). The aim of this study was to evaluate the chemical composition of the essential oil and the antimicrobial activity of essential oil, crude ethanol extract and fractions of S. odoratissima leaves against Gram-positive and negative bacteria and Candida albicans. The crude extract of the leaves was obtained by maceration and was concentrated in a rotavapor, while the fractions were obtained by partition on column filter. The powdered leaves underwent hydrodistillation in a Clevenger apparatus and the obtained essential oil was analyzed by GC/MS. The antimicrobial activity was evaluated by using the agar dilution method for determining the minimum inhibitory concentration (MIC). The major constituents of the essential oil were ß-caryophyllene (20.64%), γ-muurolene (17.70%), bicyclogermacrene (14.73%) and δ-cadinene (13.40%). The main results for S. odoratissima antimicrobial activity were found against Staphylococcus epidermidis (crude ethanol extract, MIC of 0.098 mg/mL), C. albicans (hexane fraction, MIC of 0.049 mg/mL), Bacillus cereus (dichloromethane fraction, MIC of 0.098 mg/mL), Micrococcus roseus (ethyl acetate fraction, MIC of 0.049 mg/mL) and M. roseus, Micrococcus luteus, B. cereus and C. albicans (methanol fraction, MIC of 0.391 mg/mL).

Cyclopropane- and spirolimonoids and related compounds from Hortia oreadica.

The dichloromethane extract from taproots of Hortia oreadica afforded six limonoids, these are 9,11-dehydro-12α-acetoxyhortiolide A, hortiolide C, 11α-acetoxy-15-deoxy-6-hydroxyhortiolide C, hortiolide D, hortiolide E, 12ß-hydroxyhortiolide E, in addition to the known limonoid, guyanin. The dichloromethane extract from stems of H. oreadica also afforded two limonoids 9,11-dehydro-12α-hydroxyhortiolide A and 6-hydroxyhortiolide C. As a result of this study and literature data, Hortia has been shown to produce highly specialized limonoids that are similar to those from the Flindersia (Flindersioideae). The taxonomy of Hortia has been debatable, with most authors placing it in the Toddalioideae. Considering the complexity of the isolated limonoids, Hortia does not show any close affinity to the genera of Toddalioideae. That is, the limonoids appear to be of little value in resolving the taxonomic situation of Hortia.

'Buchu' -Agathosma betulina and Agathosma crenulata (Rutaceae): a review.

South Africa has offered the world two indigenous aromatic plants from which commercially important natural products have been developed: Pelargonium graveolens (and its hybrids) the source of geranium oil and Agathosma betulina, from which 'Buchu' oil is produced. Despite the historical use of 'Buchu' and the commercial interest developed around this coveted indigenous resource the (limited) research has not been coherently assembled. This overview aims to unite aspects on the botany, traditional and modern day uses, chemistry and pharmacological data on 'Buchu' which is undeniably one of South Africa's most renowned botanical assets.

Pollen morphology of the genus Skimmia (Rutaceae) and its taxonomic implications.

Pollen morphology of the genus Skimmia was studied. Of six species of the genus, five species were investigated by light microscopy and scanning electron microscopy. Pollen grains of Skimmia had striate to striate-reticulate sculpture and variable aperture number (3-7), and these characters differed from even the phylogenetically closest relatives such as Dictamnus and Casimiroa which have 3-colporate pollen grains with reticulate exine. In Skimmia laureola, pollen dimorphism is suggested in the aperture number in accordance with the floral system. Pollen grains of Skimmia japonica, a morphologically very variable species, were extensively surveyed covering its whole distribution area. The grains were also striate to striate-reticulate, and the exine sculpture was not different between varieties. However, the aperture number of S. japonica showed a geographical variation ranging from 4 to 6; in Sakhalin, Hokkaido, most part of Honshu and Taiwan, grains with 4-5 apertures were dominant, while in the southern part of Japan, including the Ryukyu Islands and the Izu Islands, those with 5-6 apertures were common.

[The HPLC fingerprint analysis of Fructus citri].

OBJECTIVE: To study and establish the fingerprint of raw Fructus Citri by phased high performance liquid chromatography. METHOD: The chromatographic conditions were as follows: a Kromasil C18 column was used; the mobile phase was composed of methanol and acetic-water(3.1:100, v/v) with gradient elution; the flow rate was 1.0 ml/min and the UV absorbance detection was set at 284 nm. RESULT: Under the selected chromatographic conditions, good HPLC fingerprints of Fructus Citri were obtained. CONCLUSION: Quality of raw Fructus Citri can be controlled effectively by HPLC fingerprint.

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.

Alkaloids from Dictyoloma vandellianum: their chemosystematic significance.

The dichloromethane extract from leaves of Dictyoloma vandellianum afforded five alkaloids 2-(14'-hydroxy-14',15'-dimethylhexadecanyl)-4-quinolone, 2-(12'-hydroxy-12'-methyltridecanyl)-3-methoxy-4-quinolone, 2-(12'-hydroxy-12'-methyltridecanyl)-4-quinolone, 2-(14'-hydroxy-14',15'-dimethylhexadecanyl)-3-methoxy-4-quinolone, 6-methoxydictyolomide A, besides the known alkaloid 8-methoxyflindersine and beta-sitosterol. The presence of 2-alkyl-4(1H)-quinolones in D. vandellianum shows strong similarities with the Zanthoxyleae, which contains several 2-alkyl-4-quinolones. Thus, the Dictyolomatoideae apparently occupies a position between the proto-Rutaceae genera and the Spathelioideae, but close to the Zanthoxyleae.

Isolation and structure elucidation of a new prenylcoumarin from Murraya paniculata var. omphalocarpa (Rutaceae).

A new C-8 prenylated 5,7-dimethoxycoumarin named omphamurrayin was isolated from the leaves of Murraya paniculata var. omphalocarpa, and its structure was established as 5,7-dimethoxy-8-(1-oxo-2-senecioyl-3-methyl-3-butenyl)-2H-1-benzopyran-2-one on the basis of the spectroscopic evidence. The taxonomic status of M. paniculata var. omphalocarpa is briefly discussed, along with its synonymity to M. paniculata from the chemosystematic viewpoint.

[Direct identification of Retinervus Citri Reticulatae from its confused species by FTIR].

In this paper, direct and accurate identification of Retinervus Citri Reticulatae and its confused species has studied. The IR of Retinervus Citri Reticulatae and its confused species were obtained by Fourier Transform Infrared Spectrum directly. Obvious characteristics for its identification in FTIR were revealed, which can be used to identify Retinervus Citri Reticulatae and its confused Reticulatae and its confused species were directly, fastly and accurately identificated by FTIR.

[Studies on Chinese drugs zhiqiao and zhishi origin investigation and merchandise identification].

OBJECTIVE: To sort out the main original plants of Chinese drugs Zhiqiao and Zhishi. METHOD: Investigating the medicinal plant resources in the growing area and conducting morphological identification of more than 40 pieces of these two commercial drugs. RESULT: A taxonomic table, a distribution table and a commercial drug identification table are given. CONVLUSION: The Chinese medicinal plants Zhiqiao and Zhishi originated from Citrus aurantium and its varieties C. aurantium "Xiucheng", C. aurantium "Xiangcheng" and Poncirus trifoliata x C. aurantium, some other plants from Citrus genus and Poncirus trifoliata are taken as the origin of Zhiqiao and Zhishi only in a few areas.