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In this study, phenolic acid compositions in fourteen taxa of Boraginaceae were analyzed by HPLC-UV to obtain informative chromatographic data. In general, 9 phenolic acid compounds were identified in different studied taxa. m-coumaric acid (1.80-1962.09 mg/kg), salicylic acid (13.22-867.35 mg/kg), ferulic acid (0.00-661.69 mg/kg), and pcoumaric acid (12.10-392.48 mg/kg) were characterized as the main compounds of the studied taxa. The results indicated that m-coumaric acid was the main phenolic acid in Heterocaryum rigidium, Myosotis sylvatica, and Solenanthus stamineus. Furthermore, salicylic acid was the main phenolic acids of Myosotis sylvatica and Nonnea caspica. Also, the highest amounts of ferulic acid and p-coumaric acid were detected in Myosotis sylvatica and Heliotropium europaeum, respectively. The qualitative and quantitative evaluation of these compounds was used for the characterization of the taxa and for revealing their phytochemical similarity and differentiation. Hierarchical cluster analysis showed that the studied taxa were classified into two main clusters (I and II) based on main phenolic acid compounds. Cluster I included Heterocaryum rigidum, Solenanthu stamineus, and Lappula microcarpaa, and the rest studied taxa grouped in cluster II. The chemotaxonomic significance of the isolated compounds was discussed. [ABSTRACT FROM AUTHOR]

Our previous studies have found that the aerial part of Hyptis rhomboides and the seed of Hyptis suaveolens contain xanthine oxidase (XO) inhibitors, inspiring us to investigate the chemical constituents of H. suaveolens stem. The EtOH extract of H. suaveolens stem was fractionated by liquid‐liquid partitioning, followed by separation over Sephadex LH‐20, silica gel, and reverse‐phase column chromatography, centrifugal partition chromatography, and semi‐preparative RP‐HPLC, to give 17 bioactive isolates. Of these, dimethyl melitrate A (9) is a new natural product, 10 is likely (7″ E)‐9′‐methyl melitrate A, only caffeic acid (2) is the same as those isolated from the seed of the same plant, and only nepetoidins A (14) and B (11) are the same as those from H. rhomboides stem. Nepetoidin B (11) showed the best anti‐XO activity. Rosmarinic acid (3) is the most abundant (>661 ppm; w/w, dried stem), while melitric acid (12) (>277 ppm), caffeic acid (2; >125 ppm), and methyl rosmarinate (4; >81 ppm) are the major ones. This outcome could serve as a good basis for chemotaxonomy of the Hyptis plants and is beneficial for developing H. suaveolens stem as anti‐hyperuricemic nutraceutical. [ABSTRACT FROM AUTHOR]

Widespread worldwide Peucedanum plants (Apiaceae) have been used for centuries as plant medicines. The polymorphism of this genus is consistent with chemotaxonomically and therapeutically significant differences in the composition of secondary metabolites. GC-MS of Peucedanum tauricum M.B. volatiles from the headspace (HS) and hydrodistilled essential oil (HD), both obtained simultaneously from flowers (FL), immature and ripe fruits (IF, MF) and leaves (L1-L3) collected at the time of harvesting of generative organs, show differences in the chemical profiles of HS and HD from the same parts of the plant, and between organs (FL, IF, MF vs. L1-L3). The presented studies on the variability of biometabolites in the phenological period indicated the optimal harvesting time, focused on two molecular chemotaxonomic markers of PT; guaia-1(10),11-diene and guaia-9,11-diene (in generative organs iHD at 25.5–32.1% and 26.8–33.6%; and in their HS at 29.4–41.3% and 25.0–29.4%, respectively). This is the first report on the analysis of fresh aerial parts of Peucedanum sp. in which GC-MS of HS and HD was performed simultaneously during the vegetation period. The importance, with possible limitations, of GC-MS analysis of HS and HD as an evaluation tool useful in the chemotaxonomy of Peucedanum plants was also discussed. [ABSTRACT FROM AUTHOR]

The aim of this paper is to present a comprehensive overview of the main aims and scopes in screening of botanicals, a task of which thin-layer chromatography (TLC) is, on an everyday basis, confronted with and engaged in. Stunning omnipresence of this modest analytical technique (both in its standard format (TLC) and the high-performance one (HPTLC), either hyphenated or not) for many analysts might at a first glance appear chaotic and random, with an auxiliary rather than leading role in research, and not capable of issuing meaningful final statements. Based on these reflections, our purpose is not to present a general review paper on TLC in screening of botanicals, but a blueprint rather (illustrated with a selection of practical examples), which highlights a sovereign and important role of TLC in accomplishing the following analytical tasks: (i) solving puzzles related to chemotaxonomy of plants, (ii) screening a wide spectrum of biological properties of plants, (iii) providing quality control of herbal medicines and alimentary and cosmetic products of biological origin, and (iv) tracing psychoactive plants under forensic surveillance. [ABSTRACT FROM AUTHOR]

Isoflavones have been widely studied and have attracted extensive attention in fields ranging from chemotaxonomy and plant physiology to human nutrition and medicine. Isoflavones are often divided into three subgroups: simple O-substituted derivatives, prenylated derivatives, and glycosides. Simple O-substituted isoflavones and their glycosides, such as daidzein (daidzin), genistein (genistin), glycitein (glycitin), biochanin A (astroside), and formononetin (ononin), are the most common ingredients in legumes and are considered as phytoestrogens for daily dietary hormone replacement therapy due to their structural similarity to 17-β-estradiol. On the basis of the known estrogen-like potency, these above isoflavones possess multiple pharmacological activities such as antioxidant, anti-inflammatory, anticancer, anti-angiogenetic, hepatoprotective, antidiabetic, antilipidemic, anti-osteoporotic, and neuroprotective activities. However, there are very few review studies on the protective effects of these novel isoflavones and their related compounds in cerebral ischemia reperfusion. This review primarily focuses on the biosynthesis, metabolism, and neuroprotective mechanism of these aforementioned novel isoflavones in cerebral ischemia reperfusion. From these published works in in vitro and in vivo studies, simple O-substituted isoflavones could serve as promising therapeutic compounds for the prevention and treatment of cerebral ischemia reperfusion via their estrogenic receptor properties and neuron-modulatory, antioxidant, anti-inflammatory, and anti-apoptotic effects. The detailed mechanism of the protective effects of simple O-substituted isoflavones against cerebral ischemia reperfusion might be related to the PI3K/AKT/ERK/mTOR or GSK-3β pathway, eNOS/Keap1/Nrf-2/HO-1 pathway, TLRs/TIRAP/MyD88/NFκ-B pathway, and Bcl-2-regulated anti-apoptotic pathway. However, clinical trials are needed to verify their potential on cerebral ischemia reperfusion because past studies were conducted with rodents and prophylactic administration. [ABSTRACT FROM AUTHOR]

The paper is a continuation of the author’s studies on the genus Achillea L. in Silesia. The present analysis for azulene content (Stahl’s EP reagent) included more than 9600 milfoil plants collected by the author in 2001-2002 in 420 Czech localities and more than 980 plants from 121 localities, from collections of Czech botanists (J. Danihelka, K. Karlova, S. Špinarová). Azulene-containing milfoils were found to occur in the eastern part of the Czech Republic: this is an extension of the distribution area of such milfoils in eastern Silesia. The Silesian azulene-containing forms are probably a result of dispersal from the south. [ABSTRACT FROM AUTHOR]

Toonamicrocarpavarin (1), a new tirucallane-type triterpenoid, along with eight known ones, piscidinol A (2), toonaciliatavarin E (3), toonayunnanin A (4), 7-acetyneotrichilenone (5), hispidol A (6), odoratone (7), phellochin (8), toonaciliatavarin D (9), were isolated from T. ciliata. Their structures were identified on the basis of ESIMS, HREIMS and 1 D/2D NMR analysis. The cytotoxic activity of the new compound was also evaluated. All compounds were obtained from T. ciliata for the first time, which plays an important role in chemotaxonomy of the plant T. ciliata. [ABSTRACT FROM AUTHOR]

Cannabis (Cannabis sativa L.) is a complex, polymorphic plant species, which produces a vast array of bioactive metabolites, the two major chemical groups being cannabinoids and terpenoids. Nonetheless, the psychoactive cannabinoid tetrahydrocannabinol (Δ 9 -THC) and the non-psychoactive cannabidiol (CBD), are the two major cannabinoids that have monopolized the research interest. Currently, more than 600 Cannabis varieties are commercially available, providing access to a multitude of potent extracts with complex compositions, whose genetics are largely inconclusive. Recently introduced legislation on Cannabis cultivation in many countries represents a great opportunity, but at the same time, a great challenge for Cannabis research and development (R&D) toward applications in the pharmaceutical, food, cosmetics, and agrochemical industries. Based on its versatility and unique capabilities in the deconvolution of the metabolite composition of complex matrices, metabolomics represents an ideal bioanalytical tool that could greatly assist and accelerate Cannabis R&D. Among others, Cannabis metabolomics or cannabinomics can be applied in the taxonomy of Cannabis varieties in chemovars, the research on the discovery and assessment of new Cannabis -based sources of bioactivity in medicine, the development of new food products, and the optimization of its cultivation, aiming for improvements in yield and potency. Although Cannabis research is still in its infancy, it is highly foreseen that the employment of advanced metabolomics will provide insights that could assist the sector to face the aforementioned challenges. Within this context, here, the current state-of-the-art and conceptual aspects of cannabinomics are presented. [ABSTRACT FROM AUTHOR]

A survey was conducted in the Maritimes region of eastern Canada to measure the phytochemical diversity of prenylchalcone, soft resins (alpha & beta acids), and flavonol constituents from 30 unique wild-growing populations of hops (Humulus lupulus L.). Based on cone chemometrics, the majority of accessions (63.3%) are native Humulus lupulus ssp. lupoloides , with cones containing both xanthogalenol and 4'- O -methyl xanthohumol as chemotaxonomic indicator molecules. Interestingly, the leaves of all verified Humulus lupulus ssp. lupulus accessions accumulated high proportions (>0.20 total flavonols) of two acylated flavonol derivatives (kaempferol-3- O -(6"- O -malonyl)-β-D-glucopyranoside; quercetin-3- O -(6"- O -malonyl)-β-D-glucopyranoside), both previously unreported from hops leaves. The native lupuloides accessions examined possess only trace amounts of this compound in their leaves (<0.10 total flavonols), suggesting its potential utility as a novel, leaf-derived chemotaxonomic marker for subspecies identification purposes. A leaf-derived taxonomic marker is useful for identifying wild-growing accessions, as leaves are present throughout the entire growing season, whereas cones are only produced late in summer. Additionally, the collection of cones from 10-meter tall wild plants in overgrown riparian habitats is often difficult. The total levels of alpha acids, beta acids, and prenylchalcones in wild-collected Maritimes lupuloides cones are markedly higher than those previously reported for lupuloides individuals in the westernmost extent of its native range and show potentially valuable traits for future cultivar development, while some may be worthy of immediate commercial release. The accessions will be maintained as a core germplasm resource for future cultivar development. [ABSTRACT FROM AUTHOR]

Phytochemistry represents a large interdisciplinary research area which apply the chemical knowledge in plant biology, biochemistry and physiology. Since centuries, the technology related to the isolation and characterization of phytochemicals (plant secondary metabolites) developed gradually towards a holistic approach of omics' technology, as part of the "systems biology" concept. This review underlines the scientific progress during the last eight decades, from "classical" phytochemistry to metabolomics, applied on plants and food and reflects not only the role of phytochemicals as key-molecules with essential roles in plants and with great benefits on animal and human health, but also their involvement in plant chemotaxonomy, food technology and authenticity. First, a selection of the major groups of phytochemicals and their main bioresources. The metabolomic technology is presented, as a high-throughput analytical platform to identify, by untargeted or targeted techniques, the fingerprint or key metabolites of a specific pathway in plants or for authentication of a food matrix. Updated literature data are presented, including a summary of eight decades of achievements of the research group related to Chemistry and Biochemistry of Natural Products at the University of Agricultural Sciences and Veterinary Medicine Cluj-Napoca, celebrating now 150 years of existence. [ABSTRACT FROM AUTHOR]

This study concerns to evaluate the morphological and flavonoid variations, and chemotaxonomy among seven Scutellaria species. The limits of Scutellaria species were disturbed by different factors including hybridization and polymorphism. For this purpose, 39 Scutellaria accessions were collected from different natural habitats of Zagros region, Iran. A total of 15 quantitative and 20 qualitative morphological characters were studied. Leaf flavonoids were extracted using MeOH solution. The flavonoid classes were investigated using thin layer chromatography, column chromatography, UV-spect and LC-MS/MS (liquid chromatography mass spectrometry). To detect the taxonomic status of Scutellaria species, statistical analyses such as cluster, dissimilarity tree, and ordination methods were applied. The results of this research showed five flavonoid classes in different Scutellaria species including isoflavone, flavone, flavanone, flavonol and chalcone. Based on the cluster analysis of flavonoid and morphological data, the members of Scutellaria section Scutellaria were accurately separated from those of Scutellaria section Lupulinaria. Our study revealed a relationship between Scutellaria patonii and Scutellaria multicaulis. Moreover, the trichomes such as strigose, lanate, tomentose, pannous in leaf and stem, petiole, calyx, the form of leaf apex, and inflorescence length were found as diagnostic characters. Based on our results, the flavonoid and morphological markers display the taxonomic status of inter and intra-specific levels in Scutellaria. [ABSTRACT FROM AUTHOR]

Abstract Seven germacranolides – balsamin, izospiciformin, stizolin, 9α-hydroxyparthenolide, 8α- E- (4′-hydroxy)-senecioyloxy-9α-hydroxyparthenolide, stizolicin and 11βH,13-dihydrostizolicin, as well as one undescribed phenol glycoside 3-(3,4-dihydroxyphenyl) propyl senecioate 3- O -β-glucopyranoside were isolated from the leaves of Stizolophus balsamita growing in Iran. Three coumarins, scoparone, scopoletin, umbelliferone and two guaianolides, cynaropicrin and desacylcynaropicrin 8α-(Z)-(4′-hydroxy-2′-methyl)butenoate (= cebellin F) were isolated from the leaves of Psephellus sibiricus. Phytochemical profile of Stizolophus balsamita growing in Iran differs from that of Stizolophus balsamita growing in Kazakhstan. Therefore, the taxonomic separation of Stizolophus balsamita from Iran is suggested. The results also suggest that isolated coumarins may be a chemotaxonomic marker of the Psephellus species. Moreover, the presence of germacranolides in Centaureinae species with stout apical spine ended bracts of flower (S. balsamita) and guaianolides in other species with appendages of the bracts without apical spine (P. sibiricus) suggests a possible connection between the chemical structure of the sesquiterpene lactones and morphology of flowers in the species of the Centaureinae subtribe. In addition, we propose a new 1H NMR approach for the detection of hydroxyl groups in sesquiterpene lactones. Graphical abstract Image 1 Highlights • Phytochemical profiles of Stizolophus balsamita and Psephellus sibiricus are described. • An undescribed phenol glucoside has been isolated from S. balsamita. • Correlation of chemical and morphological structure of plants of Centaureinae. • Suggested taxonomic separation of Stizolophus balsamita from Iran. • New approach of detection of OH group in sesquiterpene lactones. [ABSTRACT FROM AUTHOR]

The first phytochemical investigation of the bark of Styrax suberifolius Hook. Et Arn. (Styracaceae) successfully isolated and identified seventeen phenylpropanoids, including ten benzofuran derivatives ( 1–10 ), two ditetrahydrofurans ( 11 and 12 ), two neolignans ( 13 and 14 ) and three phenyl alkanols ( 15–17 ). Compounds 2-(3-hydroxy-4-methoxyphenyl)-7-methoxy-5-benzofuranpropa- nol ( 5 ), (+)-cedrusin ( 6 ), (−)-(7R,8 S )-dihydrodehydrodiconiferyl alcohol 4- O -β- d - glucopyranoside ( 8 ), (−)-(7 S ,8R)-dihydrodehydrodiconiferyl alcohol 4- O -β- d - glucopyranoside ( 9 ), (+)-(7 S ,8R)-dihydrodehydrodiconiferyl alcohol ( 10 ), (+)-(7 S ,8R) -erythro-4,7,9,9′-tetrahydroxy-3,3′-dimethoxy-8- O -4′-neolignan ( 13 ), (−)-symplocos- neolignan A ( 14 ), (−)-7- O -ethylguaiacylglycerol ( 15 ), 2-[4-(3-hydroxypropyl)-2- methoxyphenoxy]-1,3-propanediol ( 16 ) and dihydroconiferyl alcohol ( 17 ) have not been recorded in Styrax Linn. previously. The chemotaxonomic significance of isolated compounds is discussed. [ABSTRACT FROM AUTHOR]

Draba borealis DC. is a perennial wild plant from the Arctic regions of Canada and USA. The seed and a whole plant of D. borealis were extracted and analysed by LC-MS for intact glucosinolates (GLs). Several identifications were confirmed by isolation. The identification of eleven compounds is reported in the seed and in the whole plant, including 3-methylsulfinylpropyl- ( 1 ), 4-methylsulfinylbutyl- ( 2 ), 5-methylsulfinylpentyl- ( 3 ), 3-methylsulfanylpropyl- ( 5 ), 6-methylsulfinylhexyl- ( 6 ), 5-methylsulfanylpentyl- ( 7 ), 6-methylsulfanylhexyl- ( 8 ), 4-methylsulfanylbutyl- ( 9 ), 8-methylsulfinyloctyl- ( 10 ), 9-methylsulfinylnonyl- ( 11 ), and 7-methylsulfanylheptyl- ( 12 ). Two additional GLs, 1-methylpropyl- ( 4 ) and 7-methylsulfinylheptyl- ( 13 ) GLs, were also proposed. This is the first report of occurrence of GLs 1 – 3 , 5 – 9 and 12–13 from the genus Draba . Finally, the taxonomic perspective of the GL side chains in Draba genus was also discussed. [ABSTRACT FROM AUTHOR]

In the present research, we report the isolation of five 30-noroleanane triterpenoid saponins ( 1–5 ), nine oleanane triterpenoid saponins ( 6–14 ), and twenty-one other compounds ( 15–35 ) from the whole plants of Salicornia europaea Linn. Compound 1 , 3- O - β -glucopyranosyl-(1 → 2)-[ β -xylopyranosyl-(l→3)]- β -glucuronopyranosyl 30-noroleanolic acid 28- O - β -glucopyranosyl ester, is a previously undescribed nortriterpenoid saponin. The chemical structures were established by detailed analysis of the MS and NMR spectroscopic data or comparison with literature data. Furthermore, the chemotaxonomic significance of 30-noroleanane triterpenoids was discussed in the family Chenopodiaceae and Amaranthaceae. [ABSTRACT FROM AUTHOR]

Phytochemical studies on several parts of Dalbergia tonkinensis Prain led to the isolation and determination of one alkaloid 1 , thirty flavonoids and flavonoid glycosides 2-31 , one sesquiterpene 32 and one phenol 33 . The chemical structures of the isolated constituents were determined by analysis of their NMR data and comparison to those of reference compounds. Among the isolated compounds, 3-(1 H -indol-3-yl)-2-methoxypropanamide ( 1 ) is a new compound in literature and it is the only indole derivative isolated from the genus Dalbergia . In addition, new compound 1 and buteaspermanol ( 14 ) demonstrate the close relationship among the species of the subfamily Faboideae. Carboxyethylflavanones 18-21 and neroplomacrol ( 32 ) could be seen as biochemical markers for the family Fabaceae, whereas naringin ( 17 ) and 4-formyl phenol ( 33 ) are considerably regarded as chemotaxonomic indicators for the genus Dalbergia . The chemotaxonomic aspects of these metabolites are discussed in detail. [ABSTRACT FROM AUTHOR]

Phytochemical study of the ethanol extract of the leaves of Pseuderanthemum tunicatum afforded eleven known compounds including madagascin ( 1 ), harunganol B ( 2 ), eicosanoic acid ( 3 ), dotriacontanoic acid ( 4 ), friedelin ( 5 ), lupeol ( 6 ), β-sitosterol ( 7 ), stigmasterol ( 8 ), β-sitosterol 3- O -β- d -glucopyranoside ( 9 ), stigmasterol 3- O -β- d -glucopyranoside ( 10 ) and apigenin 7- O -β- d -glucopyranoside ( 11 ). Acetylation of compound 1 afforded madagascin diacetate ( 1a ), described here for the first time. The structures were established by interpretation of their spectral data, including IR, UV, MS, 1D- and 2D- NMR ( 1 H, 13 C, DEPT 135, 1 H– 1 H COSY, HMQC, HMBC and NOESY), as well as by comparison with literature data. In the present study all the compounds are isolated for the first time from the species P. tunicatum . Compounds 1 and 2 have never been reported from the Acanthaceae family. Compounds 4 and 6–11 have been previously isolated from the genus Pseuderanthemum , and compounds 3 and 5 from the family Acanthaceae. The chemotaxonomic significance of the isolated compounds is discussed. [ABSTRACT FROM AUTHOR]

Objective: Diterpene alkaloids are secondary plant metabolites and chemotaxonomical markers with a strong biological activity. These compounds are characteristic for the Ranunculaceae family, while their occurrence in other taxa is rare. Several species of the Spiraea genus (Rosaceae) are examples of this rarity. Screening Spiraea species for alkaloid content is a chemotaxonomical approach to clarify the classification and phylogeny of the genus. Novel pharmacological findings make further investigations of Spiraea diterpene alkaloids promising. Results: Seven Spiraea species were screened for diterpene alkaloids. Phytochemical and pharmacological investigations were performed on Spiraea chamaedryfolia, the species found to contain diterpene alkaloids. Its alkaloid-rich fractions were found to exert a remarkable xanthine-oxidase inhibitory activity and a moderate antibacterial activity. The alkaloid distribution within the root was clarified by microscopic techniques. [ABSTRACT FROM AUTHOR]

Plant chemotypes or chemical polymorphisms are defined by discrete variation in secondary metabolites within a species. This variation can have consequences for ecological interactions or the human use of plants. Understanding the molecular basis of chemotypic variation can help to explain how variation of plant secondary metabolites is controlled. We explored the transcriptomes of the 3 cardinal terpene chemotypes of Melaleuca alternifolia in young leaves, mature leaves, and stem and compared transcript abundance to variation in the constitutive profile of terpenes. Leaves from chemotype 1 plants (dominated by terpinen-4-ol) show a similar pattern of gene expression when compared to chemotype 5 plants (dominated by 1,8-cineole). Only terpene synthases in young leaves were differentially expressed between these chemotypes, supporting the idea that terpenes are mainly synthetized in young tissue. Chemotype 2 plants (dominated by terpinolene) show a greater degree of differential gene expression compared to the other chemotypes, which might be related to the isolation of plant populations that exhibit this chemotype and the possibility that the terpinolene synthase gene in M. alternifolia was derived by introgression from a closely related species, Melaleuca trichostachya. By using multivariate analyses, we were able to associate terpenes with candidate terpene synthases. [ABSTRACT FROM AUTHOR]

This work describes the isolation and characterization of twenty-nine compounds from the fruits of Rhus typhina L., including eleven flavonoids ( 1–11 ), eleven phenols ( 12–22 ), two pentacyclic triterpenes ( 23–24 ), two organic acids ( 25–26 ), one lumichrome ( 27 ), one courmarin ( 28 ) and one pyrimidine ( 29 ) on the basis of their spectroscopic data. Compounds apigenin ( 1 ), daidzein ( 4 ), orobol ( 5 ), 3′, 5, 5′, 7-tetrahydroxyflavanone ( 6 ), naringenin ( 7 ), butein ( 8 ), (-)-catechin ( 9 ), quercetin-3- O - α - L -(3″- O -galloyl)-rhamnoside ( 11 ), 2-hydroxybenzoic acid ( 13 ), 4-hydroxybenzaldehyde ( 14 ), vanillin ( 15 ), methyl 3,4-dihydroxybenzoate ( 16 ), 3,5-dihydroxybenzamide ( 18 ), tyrosol ( 19 ), caffeic acid ( 20 ), 3-(2,4,6-trihydroxyphenyl)-1-(4-hydroxyphenyl)-propan-1-one ( 21 ), phlorizin ( 22 ), friedelin ( 23 ), oleanolic acid ( 24 ), 4,4-dimethyl-heptanedioic acid ( 25 ), anthranilic acid ( 26 ), lumichrome ( 27 ), scoparone ( 28 ) and uracil ( 29 ) have not been recorded before in this plant. This is the first report on the occurrence of compounds 4–7 , 9 , 11 , 13–14 , 16 , 18–21 , 25–29 from the genus Rhus . Moreover, the chemotaxonomic significance of these isolated compounds was also summarized. [ABSTRACT FROM AUTHOR]

Five flavonoid glycosides, three chlorogenic and one benzoic acid were isolated from leaves of seven species belonging to the genera Notopleura , Palicourea and Psychotria. In most species, common flavonol glycosides based upon quercetin and kaempferol were recorded, which corresponds well to literature data on other species of the Psychotria alliance. From Notopleura polyphlebia , however, the new dihydroflavonol glycoside ( 2R,3R )-7,4′- O -dimethyl-aromadendrin 5- O -β- d -apiofuranosyl-(1→6)-β- d -glucopyranoside ( 1 ) was isolated, which is remarkable in terms of both the structure of the aglycone as well as the rarity of apiose as sugar moiety. In addition to flavonoids, benzoic and chlorogenic acids are a common and frequently neglected feature in the alliance, but all appear to be of limited chemosystematic significance when compared to tryptamine-iridoid alkaloids prominently known from this group. [ABSTRACT FROM AUTHOR]

A phytochemical investigation of Lagotis brevituba led to the isolation of 16 compounds, including five phenylpropanoids ( 1 – 5 ), eight flavonoids ( 6 – 13 ), one iridoid ( 14 ), one phenolic compound ( 15 ) and one triterpene ( 16 ). The structures of these compounds were identified by spectroscopic methods and a comparison of their data with those reported in the literature. This is the first report of compounds 1 , 2 , 7 – 13 and 15 from the genus Lagotis . The chemotaxonomic significance of these compounds has also been summarized. [ABSTRACT FROM AUTHOR]

Eight Hypericum species native to Southern Turkey from Drosanthe and Olympia sections were investigated for the presence of several bioactive compounds, namely, hypericin, pseudohypericin, hyperforin, adhyperforin, the chlorogenic, neochlorogenic, caffeic and 2,4-dihydroxybenzoic acids, hyperoside, isoquercitrin, quercitrin, quercetin, avicularin, rutin, (+)-catechin, (−)-epicatechin, mangiferin, I3, II8-biapigenin, and amentoflavone for the first time. Plants were harvested at flowering, dried at room temperature, dissected into different tissues, and assayed for chemical contents. HPLC analysis of methanolic fractions displayed similar chemical profile and significant quantitative differences among the investigated taxa. The present results support the taxonomic value of hypericins, rutin, and mangiferin at the sectional level and make an important contribution to our current knowledge about Hypericum chemistry. Such kind of data could also be beneficial for explanation of the chemotaxonomic utility of the corresponding compounds as well as phytochemical evaluation of the species tested. [ABSTRACT FROM AUTHOR]

Lathraea squamaria L. (Orobanchaceae) is a non-chlorophyllous root parasitic plant; the phytochemistry of this plant has received little previous attention. In this study, we report the isolation and identification of two isomeric phenylethanoid glycosides, acteoside ( 1 ) and isoacteoside ( 2 ) that have not been previously described in this plant. Furthermore, unsubstituted benzoic acid ( 3 ) has been detected in the plant for the first time, and the presence of iridoid glycoside aucubin ( 4 ) was confirmed in all investigated plant parts. The chemotaxonomic significance of the determined compounds is discussed. [ABSTRACT FROM AUTHOR]

Twenty-four compounds were obtained from the extract of the leaves of I. urceolatus , which were divided into saturated fatty alcohols ( 1 and 2 ), triterpenoids ( 3 – 8 and 14 – 16 ), lignanoids ( 9 , 20 and 22 ), coumarins ( 10 and 19 ), flavonoids ( 11 – 13 , 21 , 23 and 24 ) and others ( 17 and 18 ). Among them, compounds 1 , 2 , 17 and 18 were firstly obtained from the genus Ilex , others were isolated from this species for the first time. The chemotaxonomic relationships between I. urceolatus and other species of genus Ilex were also discussed. As a result, the isolated compounds closely matched the ones obtained in other species of the genus. [ABSTRACT FROM AUTHOR]

The content of glycosides in Kirengeshoma palmata and Jamesia americana (Hydrangeaceae) have been investigated. The former contains loganin and secoiridoids, including the alkaloid demethylalangiside. The latter contains no iridoids, but the known glucosides arbutin, picein and prunasin. In order to futher investigate the chemotaxonomy of the family Hydrangeaceae, the distribution of the iridoid and secoiridoid glucosides as well as the known biosynthetic pathways to these compounds have been reviewed. However, only a few genera of the family has been investigated. Loganin, secologanin, and derivatives of these are common. The genus Deutzia is characteristic in containing more structurally simple iridoids in which C-10 has been lost during biosynthesis. Such compounds have so far only been reported from the genus Mentzelia (Loasaceae). The taxonomic relationships between Hydrangeaceae and the closely related Cornaceae and Loasaceae is discussed and found to agree well with recent DNA sequence results. [ABSTRACT FROM AUTHOR]

Four triterpenoids ( 1 – 4 ), nine steroids and steroid glycosides ( 6 – 11 , 13 – 15 ) and two flavonoids ( 17 – 18 ) were isolated from the roots of Clerodendrum indicum , whereas three triterpenoids ( 1 , 4 and 5 ), six steroids and steroid glycosides ( 9 – 10 , 12 – 14 , 16 ) and one phenylethanoid glycoside ( 19 ) were obtained from the roots of Clerodendrum villosum . This is the first report of chemical constituents of C. villosum , and the first report of compounds 1 , 3 – 4 , 6 – 11 and 13 – 15 from C. indicum . Among the steroids isolated, six of them are the characteristic 24β-ethylsteroids with Δ 25 -unsaturation. Their chemotaxonomic significance within the subfamily Ajugoideae (Teucrioideae) of the family Lamiaceae is discussed. [ABSTRACT FROM AUTHOR]

Five flavonoids, four feruloyl amide derivatives, pinoresinol, lanost-9-en-3β-ol and three steroids from the leaves of Dracaena cochinchinensis (Lour.) S. C. Chen. Of these, compound 4 was identified as a new homoisoflavanone. This publication is the first reported purification of compounds 3 , 4 , 6 – 12 from D. cochinchinensis. We also indicate the chemotaxonomic importance of these metabolites. [ABSTRACT FROM AUTHOR]

Seven compounds, including three labdane diterpenes ( 1 , 4 , 6 ), one bisnorlabdane diterpene ( 2 ), one steroid ( 3 ), one sesquiterpene ( 5 ) and one kawalactone ( 7 ) were isolated from the rhizomes of Amomum uliginosum J.Koenig. Compounds 1 – 4 , 6 and 7 were firstly isolated from the genus Amomum . This work represented the first phytochemical study on this plant. The chemotaxonomic significance of these compounds was summarized. [ABSTRACT FROM AUTHOR]

As part of our ongoing investigation of the stenoendemic plants belonging to the Brassicaceae family, we report on the chemistry of Fibigia triquetra (DC.) Boiss. ex Prantl for the first time. Different plant parts (flower, leaf, stem, and seed) of F. triquetra were characterized and quantified for glucosinolates (GLs) according to the ISO 9167-1 EU official method based on the HPLC analysis of desulfo-GLs. A taxonomic screening showed that F. triquetra contained relatively high levels of C-4 GLs, namely but-3-enyl GL (gluconapin, 1a), 4-methylsulfanylbutyl GL (glucoerucin, 3a), and 4-methylsulfinylbutyl GL (glucoraphanin, 5a). GC-MS analysis of the volatile fractions obtained after enzyme hydrolysis and/or HPLC-ESI-MS of intact GLs confirmed the GL profile. Four minor GLs, namely isopropyl GL (glucoputranjivin, 6a), sec-butyl GL (glucocochlearin, 7a), pent-4-enyl GL (glucobrassicanapin, 2a), and 5-methylsulfanylpentyl GL (glucoberteroin, 4a) were also identified and quantified while 4-methylpentyl GL, 5-methylhexyl GL, and n-heptyl GL, were tentatively identified by GC-MS of their degradation products. Based on the major, as well as the minor GLs, this study shows differences in chemotaxonomy between F. triquetra and the related Degenia velebitica (Degen) Hayek as well as other investigated species of the genus Fibigia. [ABSTRACT FROM AUTHOR]

A new xanthone, 1,5-dihydroxy-2,3-methylenedioxyxanthone ( 1 ), was isolated from four species of Polygala ( Polygala campestris, Polygala densiracemosa, Polygala linoides and Polygala pulchella ). In addition, three other xanthones and one sterol were isolated from extracts of these species: 1,5-dihydroxy-2,3-dimethoxyxanthone ( 2 ), 1,5-dihydroxy-3-methoxyxanthone ( 3 ), 1,5-dihydroxy-6′,6′dimethylpyrano[2′,3':3,2]xanthone ( 4 ) and α-spinasterol ( 5 ). The xanthone 1 is new in the literature and although the others are known compounds this is the first time they have been isolated from these species. The chemotaxonomic significance of these data for the Polygala genus is reported. [ABSTRACT FROM AUTHOR]

In the course of a phytochemical and chemotaxonomical investigation for the Castanopsis (Fagaceae) species, fifteen compounds, including two triterpene hexahydroxydiphenoyl esters ( 1 and 2 ), seven gallotannins ( 3 – 9 ), three flavonoids ( 10–12 ), and three other compounds ( 13–15 ) were isolated from the leaves of Castanopsis fargesii Franch. Their structures were elucidated by means of spectroscopic methods and in comparison with published data. All these compounds were obtained from this species for the first time. Moreover, ethyl glucopyranoside ( 15 ) was firstly isolated from the genus Castanopsis . 6- O -Galloyl- β - d -glucose ( 3 ) and 3,4′,5,7-tetrahydroxyflavone ( 11 ) have not been reported from any species in Fagaceae family. The chemotaxonomic significance of these compounds was summarized. [ABSTRACT FROM AUTHOR]

Phytochemical investigation of the leaves of Iris albicans afforded eleven known compounds, including seven isoflavonoids ( 1 – 7 ) and four xanthones ( 8 – 11 ). The structures of these compounds were elucidated on the basis of spectral analysis and literature data. All compounds were reported for the first time from I. albicans . The chemotaxonomic significance of the isolated compounds was summarized. [ABSTRACT FROM AUTHOR]

A phytochemical study on the rhizomes of Smilax riparia led to the isolation of 16 saponin compounds, including nine furostanol steroidal saponins (1–4, 6, 7, 10, 12, 14), six spirostanol steroidal saponins (5, 8, 9, 11, 13, 15) and one 20-carboxylic acid γ-lactone steroidal saponin (16). The structures of these compounds were identified by spectroscopic methods and comparison of their data with those reported in the literature. This is the first report of compounds 1, 4, 5, 8, 9, 11–16 from the genus Smilax . The chemotaxonomic significance of the isolated compounds has also been summarized. [ABSTRACT FROM AUTHOR]

This investigation focused on the qualitative and quantitative composition of essential oil compounds of European Origanum vulgare. Extracts of 502 individual O. vulgare plants from 17 countries and 51 populations were analyzed via GC. Extracts of 49 plants of 5 populations of Israeli Origanum syriacum and 30 plants from 3 populations of Turkish Origanum onites were included to exemplify essential oil characteristics of ‘high-quality’ oregano. The content of essential oil compounds of European O. vulgare ranged between 0.03% and 4.6%. The monoterpenes were primarily made up of sabinene, myrcene, p -cymene, 1,8-cineole, β -ocimene, γ -terpinene, sabinene hydrate, linalool, α -terpineol, carvacrol methyl ether, linalyl acetate, thymol and carvacrol. Among the sesquiterpenes β -caryophyllene, germacrene D, germacrene D-4-ol, spathulenol, caryophyllene oxide and oplopanone were often present in higher amounts. According to the proportions of cymyl-compounds, sabinyl-compounds and the acyclic linalool/linalyl acetate three different main monoterpene chemotypes were defined. The cymyl- and the acyclic pathway were usually active in plants from the Mediterranean climate whereas an active sabinyl-pathway was a characteristic of plants from the Continental climate. [ABSTRACT FROM AUTHOR]

An investigation of Hedyotis corymbosa resulted in the isolation of eighteen compounds, including six iridoids ( 1 – 6 ), six monocyclic phenols ( 7 – 12 ), one triterpene ( 13 ), two sterols ( 14 – 15 ), one anthranquinone ( 16 ), one oxylipin ( 17 ) and one coumarin ( 18 ). The compounds were identified as scandoside methyl ester ( 1 ), deacetyl asperulosidic acid ( 2 ), deacetyl asperulosidic acid methyl ester ( 3 ), daphylloside ( 4 ), 10- O -benzoyl deacetyl asperulosidic acid methyl ester ( 5 ), 10- O -benzoyl scandoside methyl ester ( 6 ), p -hydroxybenzaldehyde ( 7 ), 4-methoxybenzene-1,2-diol ( 8 ), Z - p -hydroxyphenylacetyl ( 9 ), p -hydroxybenzoic acid ( 10 ), E - p -hydroxyphenylacetyl ( 11 ), protocatechuic acid ( 12 ), oleanic acid ( 13 ), daucosterol ( 14 ), β -sitosterol ( 15 ), 1-methoxy-2-hydroxyanthraquinone ( 16 ), (9R*,10S*,7E)-6,9,10-trihydroxyocta- dec-7-enoic acid ( 17 ) and hedyotiscone A ( 18 ). Compounds 4 , 7 – 9 , 11 and 17 were isolated from H . corymbosa for the first time, compound 8 was a new natural product. The chemotaxonomic significance of these compounds was summarized in the paper. The presence of (9R*,10S*,7E)-6,9,10-trihydroxyoctadec-7-enoic acid ( 17 ) in H . corymbosa could be used to differentiate it from Hedyotis diffusa . Compounds with a 10- O -benzoyl structure, such as compounds 5 and 6 , could be used as typical components for quality control. [ABSTRACT FROM AUTHOR]

Eight polyprenylated spirocyclic acylphloroglucinol derivatives (PSAPs), hyperascyrones A–H, were isolated from the aerial parts of Hypericum ascyron Linn., together with six known analogs. Their structures were established by spectroscopic analyses including HRESIMS, 1D and 2D NMR, and their absolute configurations were determined by electronic circular dichroism calculations (ECD, Gaussian 09). Structures of previously reported tomoeones C, D, G, and H were revised. Hyperascyrones A–H were evaluated for their cytotoxic and anti-HIV-1 activities, with hyperascyrones C and G exhibiting significant cytotoxicities against HL-60 cell lines with IC 50 values of 4.22 and 8.36 μM, respectively. In addition, the chemotaxonomic significance of these compounds was also discussed. [ABSTRACT FROM AUTHOR]

The first phytochemical investigation on the vine stems of Millettia dorwardi Coll. et Hemsl led to the isolation of ten flavonoids (isoafrormosin 1 , formononetin 2 , afrormosin 3 , padmakastein 4 , liquiritigenin 5 , 4 H -1-Benzopyran-4-one,7-hydroxy-5,8-dimethoxy-3-(4-methoxyphenyl)-isoflavone 6 , 4 H -1-Benzopyran-4-one,7-hydroxy-3-(3-hydroxy-5-methoxyphenyl)-6-methoxy 8 , 4 H -1-Benzopyran-4-one,6-methoxy-3-(4-methoxyphenyl)-6,4′-dimethoxyisoflavone 9 , irisolidone 10 , prunetin 11 ), one heterocycle (5-5′-dibuthoxy-2-2′-bifuran 7 ) and one new isoflavone glycoside (4 H -1-Benzopyran-4-one,5-hydroxymethyl-3-(4-methoxyphenyl)-6-β- d -glucopyranoside-isoflavone 12 ). Their structures were determined by extensive analysis of their spectroscopic data. Among them, compounds 4 , 6 – 10, 12 were for the first time isolated from this genus. The chemotaxonomic importance of these compounds was also summarized. [ABSTRACT FROM AUTHOR]

A phytochemical investigation of four species of Dryobalanops resulted in the isolation of 26 compounds. This study, reports the existence of several types of oligostilbenoids such as ampelopsin F ( 9 ), isoampelopsin F ( 10 ), stenophyllol A ( 15 ), upunaphenol D ( 17 ) and vaticanol C ( 20 ) that have not been reported from the tribe Shoreae. The data support previous studies using morphological characters that placed Dryobalanops in the tribe Dipterocarpeae. In addition, this is the first report of compounds with the skeletons of flexuosol A ( 16 ) and nepalensinol E ( 17 ) from Dipterocarpaceae. [ABSTRACT FROM AUTHOR]

Nine withanolides were isolated from the aerial parts of Deprea bitteriana , D eprea cuyacensis , and D eprea zamorae . D . bitteriana yielded two withaphysalins, D. cuyacensis gave two 13,14-seco withaphysalins, while D. zamorae yielded five physangulidines. The compounds were fully characterized by a combination of spectroscopic methods (1D and 2D NMR and MS). All compounds isolated from D . bitteriana and D. cuyacensis were obtained as epimeric mixtures at C-18. The structure of physangulidine D was confirmed by X-ray diffraction analysis. The skeletons found in this research support the chemotaxonomical position of the genus Deprea in the tribe Physalideae. [ABSTRACT FROM AUTHOR]

The detection and early identification of natural products (NPs) for dereplication purposes require efficient, high-resolution methods for the profiling of crude natural extracts. This task is difficult because of the high number of NPs in these complex biological matrices and because of their very high chemical diversity. Metabolite profiling using ultra-high pressure liquid chromatography coupled to high-resolution mass spectrometry (UHPLC–HR-MS) is very efficient for the separation of complex mixtures and provides molecular formula information as a first step in dereplication. This structural information alone or even combined with chemotaxonomic information is often not sufficient for unambiguous metabolite identification. In this study, a representative set of 260 NPs containing C, H, and O atoms only was analysed in generic UHPLC–HR-MS profiling conditions. Two easy to use quantitative structure retention relationship (QSRR) models were built based on the measured retention time and on eight simple physicochemical parameters calculated from the structures. First, an original approach using several partial least square (PLS) regressions according to the phytochemical classes provided satisfactory results with an easy calculation. Secondly, a unique artificial neural network (ANN) model provided similar results on the whole set of NPs but required dedicated software. The retention prediction methods described in this study were found to improve the level of confidence of the identification of given analytes among putative isomeric structures. Its applicability was verified for the dereplication of NPs in model plant extracts. [ABSTRACT FROM AUTHOR]

The phytochemical investigation of Grazielia multifida aerial parts yielded eight compounds, including four ent -kaurenic acid diterpenes derivatives, 15-tiglinoyloxy-ent-kaur-16-en-19-oic acid ( 1 ), 15-hydroxy-ent-kaur-16-en-19-oic acid ( 2 ), 17-hydroxy-ent-kaur-15-en-19-oic acid ( 3 ) and 15-isovaleroyloxy-ent-kaur-16-en-19-oic acid ( 4 ), one amino acid, tryptophan ( 5 ), and three flavonoids, eupafolin ( 6 ), guaijaverin ( 7 ) and quercitrin ( 8 ). The structures of the isolated compounds were established based on analysis of their spectroscopic data and comparison with literature. All the compounds were isolated from this species for the first time. The chemotaxonomic significance of the absence of sesquiterpene lactones in G. multifida has also been summarized. [ABSTRACT FROM AUTHOR]

During a survey of plant-associated bacteria in northeast Mexico, a group of 13 bacteria was isolated from agave, maize and sorghum plants rhizosphere. This group of strains was related to Cupriavidus respiraculi (99.4 %), but a polyphasic investigation based on DNA-DNA hybridization analysis, other genotypic studies and phenotypic features showed that this group of strains actually belongs to a new Cupriavidus species. Consequently, taking all the results together, the description of Cupriavidus plantarum sp. nov. is proposed. [ABSTRACT FROM AUTHOR]

In Japan, seven species and eight varieties of wild grapes were identified, among which the main species are Vitis coignetiae Pulliat, V. flexuosa Thunb., and V. ficifolia Bunge var. lobata (Regel) Nakai (syn. V. thunbergii Sieb. et Zucc.). This paper summarizes the identification and classification of wild grapes native to Japan based on the past reports. Their distributions in Japan and physiological and ecological traits are also reviewed for effective practical use for grape breeding in the future. [ABSTRACT FROM AUTHOR]