Search

Eugenia L. is the most specious Neotropical genus in the Myrtaceae family, which many species are essential oil producers. Here, we aim to investigate the use of the main compounds of the essential oils of 73 species of Eugenia as chemosystematic markers and understand their evolutionary history within the genus. We designed four matrices of phytochemical data based on literature review of the composition of essential oils of the Eugenia species. Then, the phytochemical matrices were combined with well-known molecular markers for the genus in order to test the best coding strategy for the use of phytochemical data as phylogenetic markers. Statistical analyses of correlation, regression and principal component analysis were also performed. We discovered the addition of phytochemical data increased the support values of the phylogenetic analysis, corroborating and making the infrageneric circumscription proposed for Eugenia more robust (PP > 94). PCA statistical analyses corroborated the phylogenetic hypothesis with the pattern of distribution of Eugenia sections reflected on the infrageneric phylogenetic relationships of these sections. Over evolutionary time, the diversification of species in Eugenia sections was concomitant with the increase in the variety of types of chemical compounds present in the essential oils of their representatives, as indicated by the results of statistical analyzes (r > 0.8; p -value < 0.05). The conclusion of this study is that essential oils can perform the role of chemosystematic markers in Eugenia. [Display omitted] • Chemosystematic analysis using molecular and phytochemical data previously published. • Elucidation of the use of essential oils as chemosystematic markers. • Determining the evolutionary history of essential oils in the genus Eugenia. • Support values and phylogenetic indices corroborate an initial hypothesis. • Eugenia diversification was correlated with increased of compounds in essential oils. [ABSTRACT FROM AUTHOR]

In this article, the first complete phytochemical study of Stachys sylvatica (Lamiaceae) aerial parts, collected in Tuscan-Emilian Apennine, is reported. Twenty-three known compounds were isolated from the chloroform, chloroform-methanol 9:1 and methanol extracts; they were subsequently characterized by means of one- and two-dimensional nuclear magnetic resonance spectroscopy (1D- and 2D-NMR) and mass spectrometry as six simple phenolic derivatives (chlorogenic acid (1), caffeic acid (2), p-coumaric acid methyl ester (3), niduloic acid (4), hydroxytyrosol (5), tyrosol (6)), one glycosylated aliphatic alcohol (ebracteatoside B (7)), six glycosylated phenylpropanoids (decaffeoyl verbascoside (8), lavandulifolioside (9), betanyoside F (10), verbascoside (11), isoacteoside (12), cystanoside D (13)), four flavonoids (stachyspinoside (14), chrysoeriol 7-O-β-D-glucopyranoside (15), naringenin 7-O-(6"-E + Z-p-coumaroyl)-β-D-glucopyranoside (16), apigenin 7-O-(6"-E + Z-p-coumaroyl)-β-D-glucopyranoside (17)), three lignans (syringaresinol 4'-O-β-D-glucopyranoside (18), pinoresinol 4-O-β-D-glucopyranoside (19), 2-episesaminol 2-O-β-D-glucopyranoside (20)) and three ionones (loliolide (21), vomifoliol (22), (3S,5R,6R,7E,9R)-3,5,6,9-tetrahydroxy-7-megastigmene (23)). In addition, a further phenolic derivative (ethyl caffeate (b)) and four carboxylic acids (azelaic acid (a), trihydroxyoctadecadienoic acid (c), trihydroxyoctadecenoic acid (d) and dihydroxydodecadienoic acid (e)) have been tentatively identified by ultra-high performance liquid chromatography coupled to an electrospray ionization source high-resolution Orbitrap mass spectrometer (UHPLC-ESI-HR-Orbitrap/MS). Chemosystematic relationships between S. sylvatica and other related species were highlighted. [ABSTRACT FROM AUTHOR]

Widely distributed in Central America, South Africa and Asia, the Annonaceae family is made up of about 130 genera and 2,300 species. Among the genus of this family stands out the genus Annona, constituted of 118 species where 13 are producers of edible fruits. Plants of this genus have significant importance in the discovery of new drugs and cosmetics. Chemotaxonomy is an area of botany that uses chemical data in solving taxonomic problems. The present study aimed to identify groups of flavonoids of species in the genus Annona. A review of the literature in the Google Academic and Scielo databases on works published between 2000 and 2017, with the keywords - flavonoids, genus Annona, 2,245 articles were retrieved, which by the analysis of the title \ abstract was selected 05 papers. The study allowed to catalog 25 substances, being 24 flavonols, 3 flavanols and 1 flavone. Therefore, flavonols can be considered as one of the chemical markers of the genus Annona.

• A new flavonol triglycoside, a new lignanamide and seven knowns were isolated from Atriplex semibaccata. • Compounds 7 , 8 and 9 exhibited cytotoxic activity against CCRF-CEM cells. • Chemotaxonomic significance study of A. semibaccata depending upon the isolated compounds was summarized. The chemical characterization of the 70% hydromethanolic extract of Atriplex semibaccata (family: Chenopodiaceae) afforded a new methoxylated flavonol triglycoside, atrisemibaccatoside A (1), and a new lignanamide, (N -[(E)-m-hydroxycinnamoyl]tyramine (7), as well as, five known flavonols (2–6) and two lignanamides (8–9). The structures of the isolated compounds were established depending upon LR&HR-FAB-MS, 1D and 2D NMR spectroscopic analyses. The cytotoxic activity of the isolated compounds (1–4, and 7–9) was investigated. Compounds 7, 8 and 9 weakly inhibited the proliferation of leukemia CCRF-CEM cells with IC 50 values of 78.5, 46.3, and 71.2 μg/ml, respectively, and exhibited no cytotoxicity against Hela and HSC-2 cancer cells. A chemosystematic significance study was evaluated depending upon the chemical constituents of A. semibaccata comparing with those of other Atriplex species. [ABSTRACT FROM AUTHOR]

Four sesquiterpene lactones (SLs), including three undescribed proline-SL conjugates, the guaianolides calophyllamine A and 8-epiixerisamine A, and the eudesmanolide calophyllamine B, were isolated from the methanol extract of Hieracium calophyllum R. Uechtr. (Compositae) flowering heads. Another known guaianolide, crepiside E, was detected in Hieracium L. species for the first time. Their structures were elucidated using extensive 1D and 2D NMR spectroscopy in combination with HRMS. The isolated SLs were used as external standards for qualitative and quantitative LC-MS analysis of the dry methanol extracts of the flowering aerial parts of 28 Hieracium species from the Balkan Peninsula. Guaianolides were the dominant SLs in 27 species studied. The chemosystematic significance of detected SLs was evaluated using multivariate statistics (PCA, nMDS and UPGMA). Differentiation between the main groups was well supported. All four compounds significantly and equally contributed to the differences between the species. In addition, the eudesmanolide calophyllamine B could be a significant chemosystematic marker for H. sect. Villosa (Griseb.) Gremli s.l. and Glauciformia (Freyn) Zahn –Italica (Fr.) Av. Touv. [ABSTRACT FROM AUTHOR]

Introduction Hieracium s. str. represents one of the largest and most complex genera of flowering plants. As molecular genetics seems unlikely to disentangle intricate relationships within this reticulate species complex, analysis of flavonoids and phenolic acids, known as good chemosystematic markers, promise to be more reliable. Data about pharmacological activity of Hieracium species are scarce. Objective Evaluation of the chemosystematic significance of flavonoids and phenolic acids of methanol extracts of aerial flowering parts of 28 Hieracium species from the Balkans. Additionally, investigation of antioxidant potentials of the extracts. Methods Comparative qualitative and quantitative analysis of flavonoids and phenolic acids was performed by LC-MS. Multivariate statistical data analysis included non-metric multidimensional scaling (nMDS), unweighted pair-group arithmetic averages (UPGMA) and principal component analysis (PCA). Antioxidant activity was evaluated using three colorimetric tests. Results Dominant phenolics in almost all species were luteolin type flavonoids, followed by phenolic acids. Although the investigated Hieracium species share many compounds, the current classification of the genus was supported by nMDS and UPGMA analyses with a good resolution to the group level. Hieracium naegelianum was clearly separated from the other investigated species. Spatial and ecological distances of the samples were likely to influence unexpected differentiation of some groups within H. sect. Pannosa. The vast majority of dominant compounds significantly contributed to differences between taxa. The antioxidant potential of the extracts was satisfactory and in accordance with their phenolics composition. Conclusions Comparative LC-MS analysis demonstrated that flavonoids and phenolic acids are good indicators of chemosystematic relationships within Hieracium, particularly between non-hybrid species and groups from the same location. Copyright © 2017 John Wiley & Sons, Ltd. [ABSTRACT FROM AUTHOR]

The order Brassicales, sensu APG III, belongs to Eurosids, and comprises 17 families and 398 genera. The present work discusses the chemical features of Brassicales through the micromolecular chemical data of its taxa and selected taxonomic markers to assess pertinent affinities between its families by correlating their chemosystematic parameters. Although the chemical data of all families were obtained, the data of Brassicaceae, Capparaceae, and Cleomaceae were the most studied. The chemistry of the Brassicales species is diverse, but it reveals the chemical affinity of its families due to occurrence of flavonoids (35%) and glucosinolates (25%), which were characterized as good chemical markers. The flavonoids consist primarily of flavones and flavonols, presenting a low flavone/flavonol ratio. These micromolecules commonly contain unprotected hydroxyls, which are mainly protected by glucosilation, revealing the basal features of its taxa. In Brassicales, the predominantly allyl glucosinolates are usually found in Brassicaceae, Capparaceae, and Cleomaceae families. In the present study, the results of the chemosystematic analysis confirmed the affinity among the Brassicaceae, Capparaceae, and Cleomaceae families, and supported the concept of their monophyly in the Brassicales order. However, more chemical data of the other families is required to improve the chemosystematic conclusions. [ABSTRACT FROM AUTHOR]

The purpose of this study was to determine the chemosystematic of 14 strains of bacteria in blood cultures from Semarang using 1 reference strain S. typhi NCTC 786, based on the total protein profi les with the similarity relationship analysis based on Simple Matching Coeffi cient (SSM) analysis and algorithm methodof unweighted pair group with averages (UPGMA) presented in a dendrogram. The results showed that thechemosystematic based on the total protein profi les using SDS-PAGE method can classify the member ofbacterial strains of each species. The Clusters respectively consist of 4 strains of S. typhi (similarity: 89.7%),2 strains of Ser. marcescens (similarity: 89.7%), two strains of E. coli, and one strain of Salmonella ssp, S. typhi NCTC 786 (similarity: 100%). Those three incorporated clusters had the similarity value of 75.3%. Those four strains of Ent. cloacae composed in one cluster (similarity: 100%) are incorporated in a cluster consisting of one strain of Kleb. pneumoniae (similarity: 92.9%). Both clusters were incorporated in a cluster consisting of S. typhi NCTC 786 (similarity: 67.9%). Key words: Enterobacteriaceae, chemosystematic, blood cultures, protein profile

Marine animals contain various carotenoids that show structural diversity. These marine animals accumulate carotenoids from foods such as algae and other animals and modify them through metabolic reactions. Many of the carotenoids present in marine animals are metabolites of β-carotene, fucoxanthin, peridinin, diatoxanthin, alloxanthin, and astaxanthin, etc. Carotenoids found in these animals provide the food chain as well as metabolic pathways. In the present review, I will describe marine animal carotenoids from natural product chemistry, metabolism, food chain, and chemosystematic viewpoints, and also describe new structural carotenoids isolated from marine animals over the last decade.

Trattinnickia burserifolia has yielded the known ursanes, alpha-amyrenone, alpha-amyrin, 3-epi-alpha-amyrin, 3alpha,16beta-dihydroxyurs-12-ene, the oleananes beta-amyrenone, beta-amyrin, 3-epi-beta-amyrin, 3alpha,16beta-dihydroxyolean-12-ene, the tirucallane acids 3alpha-hydroxytirucall-8,24-dien-21-oic, 3alpha-hydroxytirucall-7,24-dien-21-oic and 3-oxotirucall-8,24-dien-21-oic, the dammaranes dammarenediol-II and 3alpha,20(S)-dihydroxydammar-24-ene. Besides it was isolated the new monoterpene 2(S*)-phenylacetoxy-4(R*)-p-mentha-1(7),5-diene and, the new triterpenes 3beta-phenylacetoxyurs-12-ene, 3beta-phenylacetoxyolean-12-ene and 3beta,16beta,11alpha-trihydroxyurs-12-ene. The triterpenes from T. burserifolia, T. rhoifolia and Dacryodes were analyzed in mixture. Their 13C NMR spectra showed that the major triterpenes were in T. burserifolia alpha-amyrin and beta-amyrin; in T. rhoifolia alpha-amyrin, beta-amyrin, 3-epi-alpha-amyrin, 3-epi-beta-amyrin, and lupenone; in T. rhoifolia alpha-amyrin, beta-amyrin, 3-epi-alpha-amyrin, 3-epi-beta-amyrin, 3alpha-hydroxytirucall-8,24-dien-21-oic acid and 3alpha-hydroxytirucall-7,24-dien-21-oic acid; in D. hopkinsii alpha-amyrin, beta-amyrin, lupeol, tirucallol, sitosterol and stigmasterol. Aspects of chemosystematic of the tribe Protieae are discussed.

Our taxonomic interest in the Neoraputia stimulated an investigation of N. paraensis searching for alkaloids. Fractions were monitored by ¹H NMR and ESI-MS/MS and only those which showed features of anthranilate alkaloids and flavonoids absent in the previous investigations were examined. Stems afforded the alkaloids flindersine, skimmianine, 8-methoxyflindersine and dictamnine; leaves yielded 3',4',7,8-tetramethoxy-5,6-(2",2"-dimethylpyrano)-flavone, 3',4',5,7,8-pentamethoxyflavone, 5-hydroxy-3',4',6,7-tetramethoxyflavone, 3',4'-methylenedioxy-5,6,7-trimethoxyflavone and 5-hydroxy-3',4'-methylenedioxy-6,7-dimethoxyflavone. The alkaloids have remained undiscovered for 10 years. A number of flavonoids isolated from N. paraensis, N. magnifica, Murraya paniculata, Citrus sinensis graft (Rutaceae), Lonchocarpus montanus (Leguminosae) were evaluated for their ability to inhibit the enzymatic activity of the protein glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma cruzi. Highly oxygenated flavones and isoflavone were the most actives.

Iridoids represent a large group of monoterpenoid compounds that apparently seem to be formed in plants by an alternative cyclization of geranyl diphosphate. The structures of these compounds are based on a cyclopentan-[C]-pyran skeleton, carbocyclic iridoids, and oxidative cleavage at the 7,8-bond of the cyclopentane moiety affords the so called secoiridoids. On biogenetic grounds the iridoid formation may be considered to start from iridodial cation and follow diversification through 27 different routes. Iridoids have been used as chemical markers for the Corniflorae, Gentianiflorae, Loasiflorae and Lamiiflorae superorders. The number and nature of the iridoids occurring in plants are a measure of the complexity of the routes involved in their biosynthesis. In chemosystematics, the value of iridoid character shows important significance in plant classification, phylogeny and evolution

Marine animals contain various carotenoids that show structural diversity. These marine animals accumulate carotenoids from foods such as algae and other animals and modify them through metabolic reactions. Many of the carotenoids present in marine animals are metabolites of β-carotene, fucoxanthin, peridinin, diatoxanthin, alloxanthin, and astaxanthin, etc. Carotenoids found in these animals provide the food chain as well as metabolic pathways. In the present review, I will describe marine animal carotenoids from natural product chemistry, metabolism, food chain, and chemosystematic viewpoints, and also describe new structural carotenoids isolated from marine animals over the last decade. [ABSTRACT FROM AUTHOR]

A new compound, 4-caffeoyl quinic acid 5- O-methyl ether ( 2), together with 12 known compounds—identified as (2 R,3 R)-pterosin L 3- O-β- d-glucopyrannoside ( 3), β-sitosterol β- d-glucopyranoside ( 4), apigenin 7- Ο-β- d-glucopyranoside ( 5), luteolin 7- Ο-β- d-glucopyranoside ( 6), sucrose ( 7), caffeic acid ( 8), pterosin C 3- Ο-β- d-glucopyranoside ( 9), pteroside C ( 10), 4,5-dicaffeoyl quinic acid ( 11), pteroside A ( 12), wallichoside ( 13) and (2 S)-5,7,3′,5′-tetrahydroxyflavanone ( 14)—were isolated from Pteris multifida. The structure of the new compound was determined by means of physical, chemical and spectroscopic evidence. Compounds 5 and 6 were the main constituents of the plant, with yields of 0.19% and 0.16%, respectively. The cytotoxic activities of 2, 3, and 9– 13 were evaluated against a human cell line (KB cells). Among the isolated compounds, pterosin C 3- Ο-β- d-glucopyrannoside ( 9) and 4,5-dicaffeoylquinic acid ( 11) showed a significant selective cytotoxicity (IC50 2.35 and 5.38, respectively), while moderate activity was observed for compound 2 (IC50 12.3). The chemosystematics of Pteris species is also discussed. [ABSTRACT FROM AUTHOR]

The gliding bacterium Herpetosiphon giganteus Hp a2 was shown to contain γ-carotene, one monoglucosyloxy and two new diglucosyloxy carotenoids with a x-O-acyl-diglucosyloxy carotenoid as main component. Flexirubin-like pigments could not be detected in this organism. As in the Myxobacterales and Cytophagales (Kleinig et al., 1974) menaquinones (MK-6 and MK-7) were found to be the only isoprenoid quinones present in Herpetosiphon. The chemosystematic implications of these findings are briefly discussed. [ABSTRACT FROM AUTHOR]

Simaroubaceae family belongs to the order Sapindales, which in turn is part of Eurosides II (APG IV). It consists of 23 genera: Ailanthus; Amaroria; Brucea; Castela; Eurycoma; Gymnostemon; Hannoa; Holacantha; Homalolepsis; Iridosma; Laumoniera; Leitneria; Nothospondias; Odyendeya; Perriera; Picrasma; Picrolemma; Pierreodendron; Quassia; Samadera; Simaba; Simarouba; Soulamea. Over the years, the classification of Simaroubaceae has changed and there is still a lot to evolve in this direction since there are still not many studies on some of its genera. In this sense, the present work discusses the chemistry of Simaroubaceae through the micromolecular chemical data, evolutionary indexes and chemometric analysis in order to assess affinities between its genera. The chemistry of this family is diverse and includes quassinoids, alkaloids, triterpenes, flavonoids, simple phenolics, coumarins, lignans and quinones. In addition to presenting specificity, quassinoids and alkaloids are prevalent among the substances already identified in the family and can be considered the chemical markers of it. Quassionoids are degraded triterpenes and can be classified as c25, c22, c20, c 19 and c18; c20 being the most common type in the family. The alkaloids already isolated in Simaroubaceae are predominantly beta-carboline and canthinone, both originating from the amino acid tryptophan. The evolutionary indexes calculated for the chemical markers showed great variation between the genera of Simaroubaceae and showed no correlation among them. The chemometric analysis positioned Simaroubaceae close to Rutaceae within the order Sapindales and, among the genera, alkaloids and quassinoids were very important for their distribution in Simaroubaceae considering the evolutionary proximity, corroborating their selection as chemical markers. • Simaroubaceae belongs to the order Sapindales, part of Eurosides II (APG IV). • Simaroubaceae classification changed over the years and still has a lot to improve. • Quassinoids and alkaloids can be considered chemical markers of Simaroubaceae. • Quassionoids are degraded triterpenes and are very specific to this family. • Chemometric analysis positioned Simaroubaceae close to Rutaceae in Sapindales. [ABSTRACT FROM AUTHOR]