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Background of the Study: Tropical plants of the Ficus genus (Moraceae) are among the earliest fruit trees that humans have cultivated. Since ancient times, many folk medicines have used species of this genus to treat a variety of ailments. Evidence from earlier investigations has shown these plants contain abundant secondary metabolites with a variety of structural properties and biological functions. Place and Duration of Study: The research was carried out at the University of Nairobi (Faculty of Science and Technology, Department of Chemistry) from January to June 2022. Aim: The study focuses on isolating and identifying secondary metabolites from the stem bark of Ficus thonningii Blume found in Kenya and their chemotaxonomic significance. Methodology: Dried powdered stem bark of Ficus thonningii was extracted by maceration at room temperature using CH2Cl2/CH3OH (1:1) to yield a crude extract which was fractionated in a chromatographic column (CC) using silica gel (60 – 120 mesh) as an adsorbent eluting with EtOAc/n-hexane followed by CH3OH/EtOAc. The fractions were purified using silica gel (70 – 230, 230 – 400 mesh) CC and chromatotron eluting with solvents of different polarity, as well as a crystallization technique. Structures of the isolated compounds were elucidated and identified using the spectroscopic method (NMR (1D and 2D)) and by comparison with reported literature data. Results: Phytochemical investigation of the stem bark of Ficus thonningii afforded seven compounds, including yukovanol (1), 5,7,4?-trihydroxy-3?-(2-hydroxy-3-methyl-3-butenyl)isoflavone (2), cajanin (3), taxifolin (4), protocatechuic acid (5), saccharose (6), and stigmasterol (7). Compounds 1 - 3, 5 and 7 were not reported from F. thonningii until now. Further, compound 6 is being isolated from the genus Ficus for the first time. Conclusion: The chemotaxonomic significance of the isolated phytochemicals demonstrates the taxonomic position of F. thonningii in the genus Ficus and explains its multiple ethnomedicinal applications.
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Salvia officinalis is a well-studied and popular medicinal plant containing toxic thujones, rather limitedphytochemical and pharmacological studies have been performed on other Salvia spp. The aim of the studywas to perform phytochemical and chemotaxonomic studies of Salvia genus species (n = 16) from Ukraineto identify the most promising species for the pharmaceutical industry. The content of essential oils from theleaves of 16 Salvia spp. has been studied by gas chromatography/mass spectrometry (MS) and polyphenols byhigh performance liquid chromatography/MS, and a chemotaxonomic study has been performed by calculationof coefficients of occurrence, originality, and pair affinity. The Salvia spp. is characterized by the presence ofmonoterpenoids, hydroxycinnamic acids – derivatives of caffeic acid, and flavonoids – derivatives of luteolinand apigenin. The highest content of essential oil is observed in the leaves of S. officinalis, S. grandiflora, andS. scabiosifolia (1.41%–1.85%). The highest amount of hydroxycinnamic acids is in the leaves of S. pratensis,S. illuminata, S. austriaca, and S. verticillata; the highest content of flavonoids and phenolic compounds isfound in the leaves of S. grandiflora, S. pratensis, S. illuminata, S. nemorosa, S. pendula, S. sylvestris, S.nutans, S. verticillata, and S. cernua. The chemical profile of the genus has been determined; it is characterizedby terpenoids such as α- and β-pinene, camphane derivatives (camphene, camphor, and borneol), p-cymene,1,8-cineol, limonene, phenolic compounds (caffeic and rosmarinic acids), and flavonoids (cynaroside,cosmosiin, hispidulin, and cirsimaritin). A rather high concentration of toxic _- and _-thujone is typical onlyin the essential oil of S. officinalis (33.6% and 6.5%, respectively). The most promising species for use in thepharmaceutical industry are S. grandiflora, S. cernua, S.pratensis, S. nemorosa, and S. verticillata.
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Aims: To evaluate the antibacterial, antioxidant and phytochemical composition of Combretum tanaense extracts. Study Design: Laboratory-experimental design was used in this study. Place and Duration of Study: Fresh roots of Combretum tanaense were obtained from Mount Kenya University botanical garden in Thika (Kiambu County-Kenya). The study was carried out between November 2017 and February 2018 at Mount Kenya University Biochemistry and Pharmacognosy laboratories. Methodology: Duplicate voucher specimens were prepared and deposited at the East Africa herbarium housed at the National Museums of Kenya and Mount Kenya University herbarium. Extraction of total extracts of C. tanaense roots was conducted according to standard procedures. Agar well diffusion and 2-2-diphenyl picryl hydrazyl (DPPH) assay methods were used to evaluate antibacterial and free radical scavenging activities of the extracts. All assays were performed in triplicate. Antibacterial data was presented as a mean zone of inhibition ± SEM while free radical scavenging activities were expressed regarding IC50. Phytochemical screening was carried out using standard procedures to ascertain the presence or absence of various phytochemical groups in the test plant. Results: The current study indicated that Combretum tanaense root extracts had antibacterial activities against the selected gram-positive and gram-negative bacterial strains. The highest activity was recorded against gram-negative bacteria (Haemophilus influenza) by exhibiting inhibition zones of 13.32±0.15 mm and 12.82±0.36 mm for methanol and water extracts respectively. Antioxidant activities for both methanol and water extracts were ten times higher compared to that of standard (L-ascorbic acid). The extracts were found to have saponins, phenols including tannins and glycosides. Conclusion: Extracts of Combretum tanaense have compounds that exhibit antibacterial and antioxidant activities. From the results obtained, the ability of the extracts to inhibit bacterial growth and scavenge for free radicals was due to the presence of phenolic compounds and will be attributed to the healing properties of this plant. This study recommends further studies including toxicity and isolation of active compounds for the development of products with pharmaceutical value.
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ABSTRACT Phytochemical investigation of the methanol extract of the aerial parts of Peucedanum chryseum (Boiss. & Heldr.) D.F.Chamb., Apiaceae, led to the isolation of a dihydrofuranochromone, cimifugin (1); a phloroacetophenone glucoside, myrciaphenone A (2); and a flavonoid glycoside, afzelin (3) along with two phenylacylated-flavonoid glycosides: rugosaflavonoid C (4), and isoquercitrin 6"-O-p-hydroxybenzoate (5). The structures of compounds 1-5 were elucidated by extensive 1D- and 2D-NMR spectroscopic analysis in combination with MS experiments and comparison with the relevant literature. All compounds are reported for the first time from this species and compounds 2, 4, and 5 from the genus Peucedanum and from Apiaceae.
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ABSTRACT In this study, a comprehensive phytochemical characterization of two morphologically related species from the genus Espeletia Mutis ex Bonpl., namely, Espeletia grandiflora Humb. & Bonpl. and Espeletia killipii Cuatrec., Asteraceae, has been performed by gas chromatography coupled to flame ionization detection, gas chromatography coupled to mass spectrometry and ultra-high performance liquid chromatography coupled to ultraviolet and high-resolution mass spectrometry. Analysis of ethanol extracts (70%, v/v) from leaves and concomitant compound dereplication allowed the identification of major peaks, most of them new reports for the genus Espeletia or the subtribe Espeletiinae. Chemical characterization of resins essential oils indicated several similarities and differences between both species and from other members of the subtribe. Chemometric analysis (hierarchical clustering analysis and orthogonal partial least-squares discriminant analysis) applied to the essential oil composition of 31 species from Espeletiinae furthermore allowed the identification of three primary clusters correlated with the taxonomy. Hence, this study underscored qualitative and semiquantitative differences between the chemical composition of leaves and resins of E. grandiflora and E. killipii, provided information on chemotaxonomy and described the presence of different trends in the essential oil composition from species of Espeletiinae.
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ABSTRACT Plants from the Momordica genus, Curcubitaceae, are used for several purposes, especially for their nutritional and medicinal properties. Commonly known as bitter gourds, melon and cucumber, these plants are characterized by a bitter taste owing to the large content of cucurbitacin compounds. However, several reports have shown an undisputed correlation between the therapeutic activities and polyphenolic flavonoid content. Using ultra-high performance liquid chromatography quadrupole time of flight mass spectrometry in combination with multivariate data models such as principal component analysis and hierarchical cluster analysis, three Momordica species (M. foetida Schumach., M. charantia L. and M. balsamina L.) were chemo-taxonomically grouped based on their flavonoid content. Using a conventional mass spectrometric-based approach, thirteen flavonoids were tentatively identified and the three species were found to contain different isomers of the quercetin-, kaempferol- and isorhamnetin-O-glycosides. Our results indicate that Momordica species are overall very rich sources of flavonoids but do contain different forms thereof. Furthermore, to the best of our knowledge, this is a first report on the flavonoid content of M. balsamina L.
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On the phytochemical investigation of a 70% ethanol extract of the fruits of Opuntia ficus-indica, (Cacataceae), we could result in the isolation of thirteen phenolic compounds including seven flavonoids (1 - 9) and four simple phenolic glycosides (10 - 13) by column chromatographic methods. Among the isolated compounds, picein (11), androsin (12), and 1-O-feruloyl-β-D-glucopyranoside (13) were isolated for the first time from O. ficus-indica; additionally, this is the first report benzyl-O-β-D-glucopyranoside (10) from the genus Opuntia. The structures of the compounds were determined by spectral data analysis which included 1D, 2D NMR spectrum and ESIMS.
Subject(s)
Ethanol , Flavonoids , Fruit , Glycosides , Opuntia , Phenol , Statistics as TopicABSTRACT
Cimicifugeae is one of the rich sources for various active components and the health promoting and therapeutic values of the components have been corroborated by long-term use in folk medicine and traditional Chinese medicine. Increasing interest in Cimicifugeae pharmaceutical resources has led to the further discoveries of triterpenoid saponins, phenolic compounds, chromones, and many other compounds in various species of Cimicifugeae, and to the investigations on their chemotaxonomy, molecular phylogeny, and bioactivities. Based on our pharmacophylogenetic studies, the progress in phytochemistry, chemotaxonomy, molecular biology, and phylogeny of Cimicifugeae had been summarized since 2007, especially Cimicifuga L. ex Wernisch. and Actaea L., and their relevance to therapeutic efficacy. An exhaustive literature survey is used to characterize the global scientific effort in the phytochemical and biological studies of Cimicifugeae. More triterpenoid saponins have been found in various species, among which the cimigenol type (type A) is predominant. The versatile bioactivities of saponins and extracts, as well as those of phenolics and other ingredients, were summarized and discussed. The morphology-based five-genus classification of Cimicifugeae is not supported by molecular phylogeny. Molecular phylogeny based on nuclear and chloroplast DNA sequences tends to merge Cimicifuga Wernisch., Souliea Franch., and Actaea L. into a single genus. It is indispensable to integrate the emerging technologies into Cimicifugeae research for both the sustainable utilization of Cimicifugeae pharmaceutical resources and finding novel compounds with potential clinical utility and less adverse effects. Systems biology and omics technologies would play an increasingly important role in booming pharmaceutical research involving bioactive compounds of Cimicifugeae. © 2013 Tianjin Press of Chinese Herbal Medicines.
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Objective: To study the chemical constituents from the leaves of Oplopanax horridus. Methods: The chemical constituents were isolated and purified by column chromatography on silica gel and Sephadex LH-20 gel columns, 1H-NMR and 13C-NMR were applied for the identification of chemical structure. Results: Ten compounds were isolated and identified as dammara-20,24-dien-3β-ol acetate (1), phytol (2), 16Z,19Z-pentacosadienoic acid (3), β-sitosterol (4), (3. S,8. S-falcarindiol (5), maltol (6), acankoreagenin (7), daucosterol (8), stigmasterol-3-. O-β-. D-glucopyranoside (9), and acankoreoside A (10). Conclusion: Compounds 1-3, 6, and 10 are isolated from this plant for the first time. Compounds 1-3 and 6 are isolated from the plants in genus Oplopanax Miq. for the first time. Moreover, Compounds 1, 3, and 6 are isolated from the plants in the family of Araliaceae for the first time.
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Some phytochemical investigations were carried on the roots of Ouratea turnarea. This work led to the isolation of menisdaurin, epicatechin, β-sitosterol-3-O-β-D-glucopyranoside and astragenol-3-O-β-D-xylopyranoside, the last compound is reported for the first time from the Ochnaceae family. Their structures were established by direct interpretation of their spectral data, mainly HRESI-MS, 1D and 2D NMR, and by comparison with literature.
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The genus Fritillaria is a botanical source for various pharmaceutically active components, which have been commonly used in traditional Chinese medicine for thousands of years. Increasing interest in Fritillaria medicinal resources has led to additional discoveries of steroidal alkaloids, saponins, terpenoids, glycosides and many other compounds in various Fritillaria species, and to investigations on their chemotaxonomy, molecular phylogeny and pharmacology. In continuation of studies on Fritillaria pharmacophylogeny, the phytochemistry, chemotaxonomy, molecular biology and phylogeny of Fritillaria and their relevance to drug efficacy is reviewed. Literature searching is used to characterize the global scientific effort in the flexible technologies being applied. The interrelationship within Chinese Bei Mu species and between Chinese species, and species distributed outside of China, is clarified by the molecular phylogenetic inferences based on nuclear and chloroplast DNA sequences. The incongruence between chemotaxonomy and molecular phylogeny is revealed and discussed. It is essential to study more species for both the sustainable utilization of Fritillaria medicinal resources and for finding novel compounds with potential clinical utility. Systems biology and omics technologies will play an increasingly important role in future pharmaceutical research involving the bioactive compounds of Fritillaria.
Subject(s)
Animals , Humans , China , Drugs, Chinese Herbal , Chemistry , Pharmacology , Fritillaria , Chemistry , Classification , Molecular Structure , Phylogeny , Plants, Medicinal , Chemistry , ClassificationABSTRACT
Augusta has traditionally been placed in the tribe Rondeletieae, subfamily Cinchonoideae. However, recent molecular phylogenies positioned it near to Wendlandia (Ixoroideae), but locate A. longifolia near to the clade Ixoroidinae II. The study of A. longifolia afforded two coumarins, five flavonoids, three triterpenoids and one benzoic acid derivative. These metabolites reinforce the separation of Augusta as a monospecific genus, and Lindenia as a genus of three species, closely related to Wendlandia.
Augusta tem sido tradicionalmente colocada na tribo Rondeletieae, Cinchonoideae subfamília. No entanto, recentes filogenias moleculares posicionou-a perto de Wendlandia, porém localizando A. longifolia perto do clado Ixoroidinae II. O estudo de A. longifolia resultou em duas cumarinas, cinco flavonoides, três triterpenoides e um derivado do ácido benzóico. Estes metabolitos reforçam a separação da Augusta como um gênero monoespecífico, e Lindenia como um gênero de três espécies, intimamente relacionada com Wendlandia.
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Phytochemical studies on the aerial parts of Prangos uloptera, an endemic Iranian species of the genus Prangos, yielded five coumarins, xanthotoxin (1), prangenin (2), scopoletin (3), deltoin (4) and prangolarin (5). The structures of these coumarins were elucidated by spectroscopic means, and the antioxidant potential of 1-5 was evaluated by the DPPH assay. The chemotaxonomic significance of 1-5 is also discussed.
Os estudos fitoquímicos das partes aéreas de Prangos uloptera, uma espécie do gênero Prangos endêmica do Irã, forneceram cinco cumarinas, xantotoxina (1), prangenina (2), escopoletina (3), deltoína (4) e prangolarina (5). As estruturas destas cumarinas foram elucidas através de métodos espectroscópicos e o potencial antioxidante de 1-5 foi avaliado pelo ensaio de DPPH. O significado quimiotaxonômico de 1-5 também é discutido.
Subject(s)
Antioxidants/pharmacology , Antioxidants/chemistry , Apiaceae , Apiaceae/chemistry , Coumarins , Furocoumarins/pharmacology , Furocoumarins/chemistryABSTRACT
The morphological parameters used to establish close connections among species taxonomically different into the Rubiaceae family is complex, mainly due to the lack of information on habitat and morphoanatomical characters in the lower hierarchic groups, for example, Chimarrhis genus. The micromolecular profile of delimited species into determined taxa can be useful to establish the boundaries among close taxonomic groups, and to indicate evolutionary phylogenetic trends into the taxa. Several indole alkaloids isolated from C. turbinata showed to be a valuable tool to support the taxonomic classification performed by Robbrecht, who established the most recent taxonomy for Rubiaceae, based on morphological characters, and concluded that Chimarrhis belong to Condamineae, and subfamily Cinchonoideae.
A utilização de parâmetros apenas morfológicos para posicionar taxonomicamente diversas espécies em sub-famílias e tribos na família Rubiaceae é bastante problemática devido à falta de informações sobre a distribuição geográfica e de características morfoanatômicas nos níveis hierárquicos mais baixos, como por exemplo, o gênero Chimarrhis. O perfil micromolecular de diferentes espécies pode auxiliar na delimitação de tribos indicando tendências filogenéticas mais completas entre as tribos das sub-famílias, já que os metabólitos secundários são expressões de adaptação, regulação e evolução de um determinado táxon. Nesse contexto, os alcalóides indólicos monoterpênicos isolados de Chimarrhis turbinata foram bastante úteis para embasar a classificação taxonômica feita por Robbrecht, em que posiciona Chimarrhis como um gênero da tribo Condamineae e subfamília Cinchonoideae.
Subject(s)
Indole Alkaloids/isolation & purification , Indole Alkaloids/chemistry , Classification , Monoterpenes/isolation & purification , Monoterpenes/chemistry , Rubiaceae/chemistryABSTRACT
El género Clusia L. (Clusiaceae) comprende unas 300 especies que ocurren desde México y el sur de EEUU hasta Bolivia y el sur de Brasil. Entre ellas se incluyen árboles y arbustos, hemiepifitas, epifitas y lianas. El análisis taxonómico del género se dificulta por la pobre preservación de las flores al ser secadas. Este trabajo explora la composición de ceras epicuticulares para caracterizar especies mediante marcadores químicos. Se analizó la composición del extracto obtenido de seis especies mediante lavado de la superficie foliar con hexano. Las especies pudieron separarse en base a la proporción de alcanos, >90% del total en Clusia rosea, C. orthoneura y C. minor, a la presencia de los triterpenos a-amirina y lupeol en C. multiflora, y de friedelina y taraxerol, conjuntamente con C33 y C35 en C. grandiflora y C. schomburgkiana. Los resultados sugieren que la proporción de alcanos y triterpenoides de ceras epicuticulares tiene importancia taxonómica y puede ser utilizada para separar especies o secciones infragenéricas.
The genus Clusia L. (Clusiaceae) encompasses ca. 300 species and occurs from southern USA and Mexico, to southern Brazil and Bolivia. It includes free-standing trees and shrubs, hemiepiphytes, epiphytes, and lianas. Taxonomic analysis of this genus is difficult because of the poor preservation of floral material after drying. This work explores the composition of epicuticular waxes in order to allow characterization, at the species level, using chemical markers. The six species analyzed could be separated using the relative quantity of hexane-soluble compounds extractable from the leaf surface, which amount to >90% in Clusia rosea, C. orthoneura, and C. minor, the presence of the triterpenes a-amyrin and lupeol in C. multiflora, and of friedelin and taraxerol, together with C33 and C35, in C. grandiflora and C. schomburgkiana. The results suggest that the relative proportions of alkanes and triterpenoids in epicuticular waxes may have taxonomic significance for separating species or infrageneric sections.
O gênero Clusia L. (Clusiaceae) compreende umas 300 espécies que ocorrem desde México e o sul dos EE.UU. até Bolívia e o sul do Brasil. Entre elas se incluem árvores e arbustos, hemiepífitas, epífitas e lianas. A análise taxonômica do gênero se dificulta pela pobre preservação das flores ao ser secadas. Este trabalho explora a composição de ceras epicuticulares para caracterizar espécies mediante marcadores químicos. Se analisou a composição do extrato obtido de seis espécies mediante lavado da superfície foliar com hexano. As espécies puderam separar-se em base à proporção de alcanos, >90% do total em Clusia rosea, C. orthoneura e C. minor, à presença dos triterpenos a-amirina e lupeol em C. multiflora, e de friedelina e taraxerol, conjuntamente com C33 e C35 em C. grandiflora e C. schomburgkiana. Os resultados sugerem que a proporção de alcanos e triterpenóides de ceras epicuticulares tem importância taxonômica e pode ser utilizada para separar espécies ou seções infragenéricas.