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Satureja kitaibelii Wierzb. ex Heuff. is endemic species of central Balkan that lives along the Balkan mountains range. The aim of this research was to study the variability of n-alkane profiles of four S. kitaibelii populations growing wild in Serbia in regards to biogeography and chemotaxonomy. Using GC/MS and GC/FID, seventeen n-alkane homologues (C19–C35) were identified. n-Hentriacontane (C31) was dominant in all populations, except in population Djerdap and Rtanj were it was co-dominant with n-nonacosane (C29). Population Temsica and Poganovo also had high percentages of n-nonacosane and n-tritriacontane (C33). However, these two compounds had similar quantities in population Poganovo. Statistical analyses showed differences between studied populations based on n-alkane profiles. Moreover, geographically closer populations had a similar profile.

Twenty-two known compounds were isolated from the 95% alcohol extract of the fruits of Illicium simonsii Maxim, including seven sesquiterpenoids (16–22) and fifteen lignans (1–15). In the present research, compounds 3 ((7S,8R,8′S)-3,3′-dimethoxy-4,4′,9-trihydroxy-7,9′-epoxylignan-7′-one), 4 ((−)-(7′S,8S,8′R)-4,4′-dihydroxy-3,3′,5,5′-tetramethoxy-7′,9-epoxylignan-9′-ol-7-one), 5 ((+)-8-hydroxypinoresinol), 6 ((+)-8-hydroxymedioresinol), 8 ((2R,3R)-2β-(4″-hydroxy-3″-methoxybenzyl)-3α-(4′-hydroxy-3′-methoxybenzyl)-γ-butyrolactone 2-O-(β-D-glucopyranoside), 12 ((+)-8-methoxyisolariciresinol), 13 (α-conidendrin), 14 (boehmenan) and 15 (7R,8R,7′E-7′,8′-didehydro-4,7,9,9′- tetrahydroxy-3-methoxy-8-O-4′-neolignan) were reported from the Illicium genus for the first time, and compounds 1 (simulanol), 7 ((+)-secoisolariciresinol monoglucoside), 10 ((+)-9-O-β-D-glucopyranosyl lyoniresinol), 11 ((+)-isolariciresinol), 18 (neoanisatin), 19 (veranisatin A), 20 (4,5-d2-8′-oxo-dihydrophaseic acid) and 22 (Oligandrumin A) were firstly isolated from the plant. Their structures were elucidated on the basis of NMR spectroscopic and mass spectrometric data. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.

The present study reports about the phytochemical analysis of a sample of Daphne oleoides Schreb. subsp. oleoides (family Thymelaeaceae) collected from the Majella National Park. Twenty components, belonging to different classes of natural products, have been identified by means of spectroscopic and spectrometric techniques: [monomeric (4), bis- (5, 7–10, 20) and trimeric coumarins (11), including aglycones and glycosides, coumarinolignoid (6); flavonoids (16–19); glycosidic furolignans (14, 15), glucosidic phenylpropanoids (12, 13), cyclic tetrapyrrole derivatives (2, 3), unsaturated triglyceride (1)]. Besides the chemosystematic markers of the genus (4–10, 12, 14–18, 20) several other components were identified for the first time in the species (17, 20) and/or in the Daphne genus (1–3, 13, 19). The observed composition was discussed from the chemotaxonomic standpoint and compared with those recognized from a Sardinian accession. It was observed a pronounced difference in the two metabolites patterns, most probably attributable to geographic isolation of the studied populations and, in some extent, also by the different environmental conditions, evidencing a possible tendency of D. oleoides to the infraspecific chemovariability. Considering the wide traditional uses of Daphne spp. in ethnomedicine of several countries, also the pharmacologic potential of the identified secondary metabolites is discussed.

Twenty compounds, including three flavonoids (1–3), two coumarins (4 and 5), three stilbenoids (6–8), two diterpenoids (9 and 10), two phenolic acids (11 and 12), two phenolic glycosides (13 and 14), two lignanoids (15 and 16) and four triterpenoids (17–20), were firstly isolated by chromatographic methods from the stem barks of Acanthopanax leucorrhizus Harms. Their structures were elucidated by spectroscopic methods and comparison with previously reported spectral data. Among them, compounds 6 and 7 are new, and compound 8 is reported for the first time from the genus Acanthopanax. This paper deals with the isolation, structural elucidation and chemotaxonomic significance of the metabolites from A. leucorrhizus.

There are numerous chemotaxonomic studies on arthropods, but such are largely missing for millipedes. This appears curious since particularly in millipedes, the major taxa are clearly distinctive by different exocrine products, such as alkaloids (Glomerida), terpenoids (Polyzoniida), phenolics and cyanogens (Polydesmida), and benzoquinones (Juliformia). However, there is low within-taxon variation of the chemicals mentioned which - in almost invariable blends - characterize the particular taxa. The Julida, for instance, one of the three orders of Juliformia, typically produce uniformly composed benzoquinonic secretion profiles across most species, not showing enough heterogeneity for chemotaxonomy. Recently, however, a new class of julid exocrine products, namely complex bends of alkyl esters has been reported. We here tested the chemotaxonomic potential of these compounds by performing a comprehensive study on alkyl esters across the julid tribe Cylindroiulini. Exocrine secretions of 20 species from all five cylindroiuline genera (Allajulus, Cylindroiulus, Enantiulus, Kryphioiulus, Styrioiulus) were analyzed by gas chromatography – mass spectrometry. Apart from typical benzoquinones, 33 alkyl esters and 1 alkenyl ester belonging to hexyl-, octyl-, octenyl- and nonyl-esters with saturated and mono-unsaturated acid moieties ranging from C13 - C18 were detected. Only two species (Cylindroiulus caeruleocinctus and C. luridus) exhibited no esters at all. Ester profiles appeared to be specific, indicating five major chemical groups in cylindroiulines, characterized by specific ester arrangements. We here provide evidence for i) the widespread occurrence of alkyl esters in the Julidae, ii) their high specificity, iii) their intra-species stability, iv) along with sufficient inter-species variability, rendering them promising novel tools for millipede chemotaxonomy.

The study aimed to investigate the chemical composition of Paliavana tenuiflora Mansf., an endemic Brazilian species that belongs to Gesneriaceae family. By chromatographic, spectroscopic and cheminformatics techniques it was possible to isolate and elucidate eleven compounds: a new naphthoquinone named as tenuiflorone (1), besides known compounds 7-metoxy-8-hydroxy-α-dunnione (2), tectoquinone (3), 2-(p-hydroxyphenyl) ethyl hexacosanoate (4), 2-(3′,4′-dihydroxyphenyl) ethyl hexacosanoate (5), caffeic acid (6), presilphiperfolan-9-ol (7), β-sitosterol (8), stigmasterol (9), β-sitosterol-3-O- d -glucopyranoside (10) and stigmasterol-3-O- d -glucopyranoside (11). This is the first time that secondary metabolites were isolated from species belonging to Paliavana genus, with the isolation of a new naphthoquinone named as tenuiflorone. The results obtained contribute to the chemotaxonomy of the Gesneriaceae family.

Phytochemical investigation on the aerial parts of Trachelospermum dunnii led to the isolation and identification of 16 compounds, including nine dibenzylbutyrolactone lignans ( 1 – 9 ), two furanoid lignans ( 10 – 11 ), one dihydrobenzofuran lignan ( 12 ), one aryltetralin lignan ( 13 ), two flavonoids ( 14 – 15 ), and one phenolic compound ( 16 ). The structure of compound 1 was elucidated by means of spectroscopic analyses, including HRESIMS, and 1D and 2D NMR experiments. Compounds 1–16 are reported from title plant for the first time, while compounds 1 – 2 , 10 – 12 , and 14 – 16 have not been recorded previously in genus Trachelospermum . The dibenzylbutyrolactone lignans may serve as chemotaxonomic markers of T. dunnii .

The phytochemical investigation on Bidens bipinnata Linn. (Asteraceae) led to the isolation and identification of 38 compounds, including nine ceramides ( 1 – 9 ), thirteen flavonoids ( 10 – 22 ), five phenylpropanoids ( 23 – 27 ), four aliphatics ( 28 , 35–37 ), one pyrimidine ( 29 ), four steroids ( 30 – 33 ), one triterpenoid ( 34 ) and one polyacetylene ( 38 ). All chemical structures were established on the basis of MS and NMR spectroscopic data. In addition to five newly reported compounds (2S, 3S, 4R, 8E)-2-(2′(R), 3′(R)-dihydroxytriocosanoylamino]-8-octadecene-1, 3, 4-triol ( 1 ), (2S, 3S, 4R, 8E)-2-[(2′R)-2′-hydroxytetracosanoylamino]-10-octadecene-1, 3, 4-triol/(2S, 3S, 4R, 8E)-2-[(2′R)-2′-hydroxytriocosanoylamino]-10-octadecene-1, 3, 4-triol ( 2 / 3 ) and (2R) isookanin-4′-methoxy-7- O -β- d -glucopyranoside/(2S) isookanin-4′-methoxy-7- O -β- d -glucopyranoside ( 10 / 11 ), nine compounds ( 4 – 9 , 25 , 26 , 38 ) were isolated from the Bidens genus for the first time. Meanwhile, the compounds 12 , 13 , 16–21 , 30 – 34 were reported firstly from Bidens bipinnata Linn. On the basis of chemical research, the chemotaxonomic significance of the isolated compounds has been summarized.

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.

Phytochemical investigations on the immature buds of Cinnamomum cassia (cassia buds) led to the isolation of fifteen compounds, including two phenylmethanol glycosides (1 and 2), two phenylethyl glycosides (3–5), two butanol glycosides (6 and 7), a megastigmane sesquiterpenoid (8), a pair of isomeric monoterpenoids (9) and their glycosides (10), a monoterpenoid glycoside (11), a geraniol type monoterpenoid (12), two phenolic glycosides (13 and 14), and cinnamic acid (15). Their structures were identified by spectroscopic analyses and comparison with literature data. Compounds 1, 2, and 4–13 were isolated from Cinnamomum cassia for the first time, and compounds 1, 2, 4–7, and 9–11 were reported in the Lauraceae family for the first time. The chemotaxonomic significance of these compounds was discussed.

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.

Seventeen compounds were isolated from the aerial parts of Sheareria nana S. Moore. Their structures were elucidated by spectroscopic methods and by comparison of the reported spectral data. They consisted of two sterols (1 and 12), five triterpenoids (2–6), two lignanoids (7 and 16), two diterpenoids (8 and 9), two phenylpropanoids (10 and 11), three flavonoids (13, 15 and 17) and one quinone (14). The taxonomic influence of these compounds in the position of this species within the Compositae family was discussed. As the result, the neo-clerodane diterpenes (soulidiol and soulidiol 18-O-β-D-glucoside), sterol (α-spinasterol-3-O-β-D-glucoside) and triterpenoids (urs-12-ene and olean-12-ene) might depict the taxonomic position for S. nana in Compositae and demonstrate the relationships between S. nana and some species of Astereae and Inuleae.

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 (1H, 13C, DEPT 135, 1H–1H 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.

Phytochemical investigation of the aerial parts of Berchemiella wilsonii (Schneid.) Nakai (Rhamnaceae) led to the isolation of four flavonoids (1–4), three phenolic acids (5–7), two megastigmane derivatives (8–9) and one triterpene (10). The structures of these compounds were elucidated as taxifolin (1), (−)-epicatechin (2), quercetin 3-O-a- l -arabinopyranoside (3), vitexin (4), methyl p-hydroxycinnamat (5), 3,4-dihydroxybenzoic acid (6), 2-hydroxy-4-methoxy-3,6-dimethyl benzoic acid (7), (3S,5R,6R,7E,9S)-3,5,6,9-tetrahydroxy-7-en-megastigmane (8), (6S,9R)-roseoside (9) and lupeol (10) on the basis of NMR spectral data and comparison with literature values. These results are the first chemical constituent data of the genus Berchemiella, and the chemotaxonomic significance of these compounds is discussed.

Seven flavonoids such as luteolin (1), luteolin 7-O-β-glucopyranoside (2), luteolin 3'-O-β-glucopyranoside (3), chryseriol (4), apigenin (5), apigenin 7-O-β-glucopyranoside (6) and astragalin (7) and one coumarin, scopoletin (8) were isolated from the aerial parts of Impatiens hypophylla Makino var. hypophylla (Family: Balsaminaceae). Structures of these compounds were elucidated on the basis of spectroscopic methods. All these compounds were isolated for the first time from I. hypophylla var. hypophylla.

The chemical investigation of whole plants Piper boehmeriifolium (Miq.) Wall. ex C. DC. led to the isolation of 22 compounds, including two lignans ( 1 – 2 ), sixteen amide alkaloids ( 3 – 18 ), one diterpene ( 19 ), two monoterpenes ( 20 – 21 ), and one phenylpropanoid ( 22 ). Their structures were elucidated by extensive spectroscopic analyses including NMR, MS, and by comparison with the literature. Compounds 1 – 2 , 6 – 7 , 11 – 12 , 14 , and 17 – 22 were firstly isolated from P. boehmeriifolium , while compounds 2 , and 19 – 20 were isolated from Piper genus for the first time. The chemotaxonomic significance of these isolated compounds is discussed.

A phytochemical study on whole Leathesia nana plants led to isolation of 22 compounds, including 12 bromophenols ( 1 – 12 ), 1 megastigmane sesquiterpene ( 13 ), 4 monoindole alkaloids ( 14 – 17 ), and 5 other small molecules ( 18 – 22 ). Their structures were elucidated by 1 H and 13 C NMR spectroscopy, HRESIMS data, and by comparison with closely related compounds published previously. Compounds 8 – 11 , 13 , 14 , and 17 – 22 were first reported from Leathesia nana , while 1 – 7 , 12 , 15 , and 16 had been previously isolated, which could be considered chemotaxonomic markers. In addition, the biological activities of all of the compounds were evaluated with protein tyrosine phosphatase 1b (PTP1B). Compounds 1 – 3 and 5 – 7 exhibited potent inhibitory effects on PTP1B with IC 50 values of 9.40, 4.30, 7.94, 14.64, 16.40, and 10.95 μ M, respectively, while the other compounds showed no obvious activities (IC 50 values > 20 μ M).

From the dichlormethane and methanol extracts of the aerial parts of Stachys tetragona Boiss. & Heldr. ex Boiss. sixteen secondary metabolites were isolated, namely one triterpenic acid and two sterols from the nonpolar extract, as well as three flavonoids, one phenolic acid, six phenylethanoid glycosides, one neolignan and two iridoids from the polar extract. Structural elucidation was mainly based on 1D & 2D NMR spectra. Comparing the flavonoid pattern of S. tetragona with previously investigated Stachys taxa growing wild in Greece, it can be seen that S. tetragona is similar to S. ionica, as both produce isoscutellarein derivatives, while from the rest of the taxa only chrysoeriol derivatives have been isolated. To the best of our knowledge, kaempferol, lamiophloside A and (7S,8R)-urolignoside are isolated for the first time from the genus Stachys L.

In the present work, we report the isolation of five alkaloids from the seeds of Erythrina rubrinervia. Four of the isolated alkaloids are erythrinoid type alkaloids which were identified as erysodine (1), erysovine (2), erythraline (3) and erysotrine (4), plus an indolic alkaloid which was identified as hypaphorine (5). The analysis of spectroscopic data for the alkaloid l- hypaphorine shows that the published structure (5a) must be revised, and the correct structure is that depicted as the structure 5c. The chemical structures were elucidated by full spectroscopic analysis. The chemotaxonomic significance of those findings in the genus Erythrina is also discussed.

The taxonomic usefulness of selected marker compounds was investigated by analyzing the chemotaxonomy of 25 taxa in the Korean Campanulaceae. Our data permit discrimination of the source plants of crude drugs listed in the Korean Pharmacopoeia and the Korean Herbal Pharmacopoeia. Chemotaxonomic analysis methods were validated, and quantitative measurements of six marker compounds were made using HPLC. Marker compound similarities among taxa were identified through multivariate statistical analyses (principal component analysis and hierarchical cluster analysis). The chemical analysis method was validated with regard to linearity, lower limit of detection, lower limit of quantitation, precision, accuracy, and recovery. The analysis revealed differences in the marker compound composition of each genus. Eight genera comprising Adenophora, Codonopsis, Asyneuma, Campanula, Hanabusaya, Platycodon, Wahlenbergia, and Peracarpa clustered according to the chemical classification. The results indicated that the six marker compounds used in this analysis were useful in identifying Korean Campanulaceae. These marker compound data were able to successfully discriminate among the three species that are sold as the crude drug Adenophorae Radix.

We examined the foliar flavonoids of Chrysanthemum arcticum subsp. arcticum and yezoense, and related Chrysanthemum species. Five flavonoid glycosides (luteolin 7-O-glucoside and 7-O-glucuronides of luteolin, apigenin, eriodictyol and naringenin) were isolated from these taxa. Luteolin 7-O-xylosylglucoside, luteolin, apigenin and quercetin 3-methyl ether were found in subsp. yezoense as very minor compounds that were not recognised by high-performance liquid chromatography/photodiode array (HPLC/PDA). The related species C. yezoense contained acacetin 7-O-rutinoside and some methoxylated flavone aglycones as major compounds. Thus, C. arcticum was distinguished from C. yezoense according to their flavonoid profiles.

Two new triterpenes ( 1 – 2 ) and seven steroids ( 3 – 9 ) were isolated from the fruiting bodies of Ganoderma duripora . Structure elucidation of these compounds was generated by a combination of spectroscopic means (HRTOFMS, 1 H and 13 C NMR). There are significant differences between the compounds isolated from Ganoderma duripora and from the other Ganoderma species, suggesting that we need to reconsider the classification of G. duripora according to the taxonomy of chemistry.

A chemical investigation of Dioscorea collettii led to the isolation of twenty-nine compounds, including six steroid saponins ( 1 – 6 ), thirteen monocyclic phenols ( 7 – 19 ), two flavonoids ( 20 – 21 ), three sterols ( 22 – 24 ), and five cyclodipeptides ( 25 – 29 ). The chemical structures of these compounds were elucidated using spectroscopic methods and by comparing their data to that reported in the literature. This study is the first report of compounds 2 – 4 , 7 , 14 – 17 , 21 , and 23 – 24 in D. collettii , while compounds 8 – 13 , 18–20 , and 25 – 29 were first isolated from the genus Dioscorea and the family Dioscoreaceae. The chemotaxonomic significance of the isolated compounds is discussed.

Phytochemical study on the Philippine endemic Annonaceae plant Uvaria valderramensis afforded a new highly oxygenated seco -cyclohexene derivative, valderepoxide ( 1 ), along with the six known compounds uvamalols D ( 2 ) and G ( 3 ), grandiuvarone ( 4 ), 2′-hydroxy-3′,4′,6′-trimethoxychalcone ( 5 ), valderramenol B ( 6 ) and benzoic acid. The structure of 1 was determined through extensive spectroscopic analyses including 1D, 2D NMR and HRESIMS. Its relative stereochemistry was established using 2D-NOESY. This is the first report on the isolation of polyoxygenated compounds 1 – 3 and chalcone 5 from U. valderramensis .

Phytochemical investigation of the ethanolic extract from the leaves of Cinnamomum parthenoxylon (Jack) Meisn. led to the isolation of (3R, 4R, 3′R, 4′R)-6,6′-dimethoxy-3, 4, 3′, 4′-tetrahydro-2H, 2′H-[3, 3′]bichromenyl-4, 4′-diol (1), 4-hydroxybenzaldehyde (2), 1,2,4-trihydroxybenzene (3), kaempferol-3-O-α-l-rhamnoside (4), herbacetin (5), quercetin-3-O-α-l-rhamnoside (6), daucosterol (7), and β-sitosterol (8). The structures were established by extensive analysis of their MS and NMR spectroscopic data and comparison with literature data. In the present research, all of the isolated compounds 1–8 are reported for the first time in the species C. parthenoxylon. Compounds 1–6 were firstly isolated from genus Cinnamomum. Compounds 1, 3, 5 and 6 have not been reported from any species in Lauraceae family. The chemotaxonomic significance of the isolated compounds is discussed.

Chemical study of the aerial parts of Anthospermum emirnense led to the isolation of one original iridoid glycoside (1) along with six known iridoids (2–7), three lignans (8–10), two flavonoids (11–12), one coumarin (13), two anthraquinones (14–15), two benzoic acids (16–17) and three triterpenoids (18–20). These results are the first chemical data on non-volatile constituents of this genus. The chemotaxonomic significance of these compounds is discussed.

Forty-seven secondary metabolites were isolated from Ajania salicifolia (Mattf.) Poljak, including eight sesquiterpenoids, two diterpenoids, three triterpenoids, four steroids, three flavonoids, five coumarins, five lignans, nine phenylpropanoids, five other phenolic compounds, and three acetylenes. Their chemotaxonomic significance within the genus Ajania (the tribe Anthemideae) of the family Asteraceae is discussed. (C) 2016 Elsevier Ltd. All rights reserved.

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.

In this study, 7 compounds were isolated from a hydroalcoholic extract of Polygala altomontana: aurapten (1), α-spinasterol (2) dihydrostyryl-2-pyrone (3) and styryl-2-pyrones (4–7). The styryl-2-pyrone (5) is new in the literature and although the others are known compounds this is the first time they have been isolated from the species P. altomontana. This is the second species of the genus Polygala to present the accumulation of dihydrostyryl-2-pyrones and styryl-2-pyrones. The chemotaxonomic significance of this data for the Polygala genus was summarized.

Eight phenolic compounds, including two catechins (1 and 2), two proanthocyanidins (3 and 4), three lignans (5–7), and one phenol (8), were isolated from roots of Vaccinium dunalianum Wight (Ericaceae), together with two triterpenes (9 and 10). All of them were isolated from the title plant for the first time. Their chemical structures were established based on the extensive MS and NMR spectroscopic analysis. Compounds 6–10 acquired initially from the genus Vaccinium, showed some significances in chemotaxonomy.

Phytochemical investigation of Cajanus scarabaeoides (L.) Thouars (Fabaceae) led to the isolation of six compounds. The chemical structures of all compounds were determined by spectroscopic methods. All isolates were reported from this species for the first time. The presence of these compounds is consistent with the chemical classes reported from other members of the genus Cajanus. In summary, this study reported six compounds isolated from Cajanus scarabaeoides and discussed the plant chemotaxonomy of Cajanus genus.

A new glycoside of polymethoxylated flavonol, citrusunshitin A (1), together with five known analogues (2–6) were isolated from peels of Citrus reticulata Blanco. The structure of 1 was elucidated by NMR and MS data, and further confirmed by single-crystal X-ray diffraction. Compounds 1–5 were isolated from C. reticulata Blanco. for the first time, and 1–6 were considered as the chemotaxonomic markers for the species C. reticulata Blanco.

Myricaria laxiflora is an endangered evergreen shrub that is the only species in the genus Myricaria narrowly distributed in the Three Gorges region in China, which has a highly tolerant to waterlogging. The chemical investigation of M. laxiflora led to the isolation and the structural elucidation of nine compounds ( 1 – 9 ), including one new oleanane type triterpenoid, (5 R , 8 R , 9 R , 10 R , 13 S , 17 S , 18 S ) 25, 28-dihydroxy- D -friedoolean-14-en-3-one ( 2 ). Their chemical structures were unambiguously elucidated by analysis of NMR and high resolution ESI mass spectroscopic data as well as by comparison with literature data, with the structure of 1 supported by X-ray crystallography. All these compounds were reported for the first time in M. laxiflora. Besides, compounds 1 and 6 were not previously known in the genus Myricaria. Finally, compounds 1 – 9 were assumed to contribute to the survival of M. laxiflora under waterlogging stress by eliminating the reactive oxygen species (ROS).

Marine pleustonic species such as the hydrozoans Velella velella and Physalia physalis , are known to drift in the world's oceans driven by winds, currents and tides. Here we present the first chemotaxonomic characterization, based on the fatty acid (FA) profile, of these two charismatic oceanic species that thrive in the interface layer between air and the water column in adult stages. Moreover, we compared their FA profiles with those from other representative cnidarian orders (Rhizostomeae, Anthomedusae, Siphonophorae, Alcyonacea, Scleractinia, Helioporacea and Pennatulacea). Velella velella and P. physalis mainly differed in the presence of symbiotic dinoflagellates markers (18:3 n -6, 18:4 n -3 and 20:5 n -3 polyunsaturated FAs), present in higher percentage in the former, and bacterial markers (odd-numbered, branched and 18:1 n -7 FAs), which were more representative in the latter. When comparing these species' FA profiles with the ones of other cnidarians orders, the presence/absence of endosymbionts and of specific FAs (tetracosapentaenoic and tetracosahexaenoic acids) as well as the latitudinal habitats were the main drivers for the distinction between groups.

Naphthoquinone patterns found in Drosera hybrids between quinone-heterogenous parent species are reported here for the first time. Quinone patterns are constant in and characteristic for all taxa investigated. Each investigated parent species contains only one quinone isomer (either plumbagin or 7-methyljuglone), whereas all investigated hybrids between quinone-heterogenous parent species contain both isomers at almost equal concentrations, which indicates co-dominant heredity resulting from expression of both parental loci affecting regioselectivity in the biosynthesis of these acetogenic metabolites. This allows predictions on hybridity (and possibly on parentage) in some taxa of the genus.

Phytochemical investigation of Gentianella turkestanorum (Gentianaceae) afforded nineteen compounds, including six xanthones ( 1–6 ), two triterpenoids ( 7–8 ), eight flavones ( 9–16 ) and three iridoids ( 17–19 ). Here, we firstly reported that 1-hydroxy-3,5-dimethoxyxanthone ( 4 ), 1, 8-dihydroxy-3-methoxyxanthone ( 5 ), apigenin ( 9 ), quercetin ( 10 ), luteolin-7- O -glucoside ( 12 ) and three other compounds (1, 8-dihydroxy-3-methoxyxanthone ( 5 ), apigenin-7- O -gluco (1″ → 3‴) glucoside ( 15 ) and luteolin-7- O -gluco (1″ → 3‴) glucoside ( 16 )) could be isolated from G. turkestanorum . The occurrence of chemical data and the sequence data might be employed as common constituents of the genera Gentianella , Lomatogonium and Swertia .

Chemical investigation of the marine red alga Laurencia pinnata collected from Nanji Island of China resulted in the isolation and identification of three new eudesmane (selinane) sesquiterpenes, 1 beta-bromoselin-11-en-4 alpha-ol (1), 1 beta-bromo-4 alpha,5 alpha-epoxyselinane (2), and 1 beta-bromoselin-3,11-diene (3), and one new 6,8-cycloeudesmane sesquiterpene,1 beta-bromo-6,8-cycloselin-4(15)-ene (4), together with one known eudesmane sesquiterpene, 1 beta-bromoselin-4(15),11-diene (5), two known chamigrane sesquiterpenes, 2,10-dibromo-3-chlorochamigr-7-ene (6) and 2,10-dibromo-3-chlorochamigr-7-en-9-ol (7), one kahukuane diterpene, kahukuene B (8), and one parguerane diterpene, 15-bromoparguer-9(11)-en-16-ol (9). These halogenated isolates were found in L. pinnata for the first time, and they support the taxonomic position of this species under the genus Laurencia. Eudesmane derivatives (1-5) are predominant and rarely reported from this genus, and they may be taken as chemotaxonomic markers for L. pinnata in the future. (C) 2015 Elsevier Ltd. All rights reserved.

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.

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.

Chemical investigation on the whole plants of Stenosolenium saxatile led to the isolation of three naphthoquinones ( 1 ??? 3 ), five pyrrolizidine alkaloids (PAs) ( 4???8 ), and six phenolic acids ( 9???14 ). The structure of the isolated compounds was elucidated by different spectrometric methods ( 1 H NMR, 13 C NMR and ESI-MS). These results are the first chemical data on constituents of this genus. The chemotaxonomic relationships between the genera Stenosolenium , Onosma , Arnebia , Echium and Lithospermum are also discussed.

Phytochemical investigation of the roots of Dianella ensifolia led to the isolation of eleven known compounds, including two aromatics ( 1 , 2 ), two chromones ( 3 , 4 ), and seven flavonoids ( 5 – 11 ). The structures of these compounds were elucidated on the basis of spectral analysis and comparison with data reported in literature. In the present research, all of the isolated compounds 1 – 11 were reported for the first time in the species D. ensifolia . Compounds 1 – 4 and 7 – 11 were firstly isolated from the genus Dianella . Compounds 1 , 2 , 8 , and 9 have not been reported from any species in Liliaceae family. The chemotaxonomic significance of the isolated compounds was summarized.

The volatile secondary metabolites emitted from the buds of 22 different species and two varieties of birch were analyzed using headspace solid-phase microextraction and gas chromatography-mass spectrometry (HS-SPME/GC-MS) methods. The volatile compositions of 21 birch buds are reported for the first time, to our knowledge. Both the mass spectral data and the calculated retention indices were used to identify the compounds. 273 different components were found and the structures of 200 compounds were precisely identified. An additional 46 compounds were classified according to their group. The terpenes were the biggest group of volatile compounds secreted by birch buds, including 13 monoterpenes, 10 C13 norterpenes, 12 norsesquiterpenes and 108 sesquiterpenes. Among the volatiles of the birch buds, 79 aliphatic compounds, 13 aromatics and six furan derivatives were also detected. Based on our chemical analyses, three different groups of birches were separated. Specific features of the first group included the presence of C13 norterpenes and norsesquiterpenes. Meanwhile, buds of the second group of birches were relatively abundant in sesquiterpenes while they did not emit C13 norterpenes or norsesquiterpenes. Buds from the third group of birches were rich in methyl and ethyl salicylates. Some characteristic features were also found for the eight other birch species that were not classified into either of the three groups. The study of the volatile secondary metabolites emitted by birch buds provided information useful for Betula genus chemotaxonomy.

Since Myrtaceae is considered a complex family concerning the taxonomic classification due to the elevated number of components, difficult morphologic differentiation, and relatively low amount of studies in area, this article describes the potentiality of classification using chemometrics applied to UPLC-qToF/MS-MS dataset for chemotaxonomy investigation of leaves of fifteen species from the genus Psidium, Plinia, Myrciaria, and Eugenia into the Myrtaceae family. The use of a multivariate tool was indispensable to detect marker compounds since an elevated number of information on chromatograms did not provide conclusive data. The results offered an adequate classification among genus and species, principally based on ellagic acid, catechin, epicatechin, isoquercitrin, quercitrin, reynoutrin, madecassic acid, asiatic acid, and morin, used as marker compounds. Therefore, the method was useful and permitted the satisfactory chemotaxonomic distinction among the genus.

The phytochemical investigation of the ethyl acetate fraction of Polygala longicaulis Kunth resulted in the isolation and identification of two dihydrostyryl-2-pyrones (1–2). This is the third species of the Polygala L. genus, along with Polygala altomontana Ludtke, Boldrini & Miotto and Polygala sabulosa A.W. Benn., to present the accumulation of dihydrostyryl-2-pyrones. The data reported herein make an important contribution to the chemotaxonomy of this genus. This is the first report of dihydrostyryl-2-pyrone (1) and dihydrometisticin (2) in P. longicaulis and the first report of dihydrometisticin in the genus Polygala. Furthermore, this is the first grouping of non-xanthone-producing Polygala species.

A new sesquiterpenoid, 1α,4β,8β,9β-eudesmane-tetrol-1-O-β-D-glucopyranoside (1), together with nine known compounds (2–10), were isolated from Merremia yunnanensis. The structures of these compounds were elucidated by spectroscopic methods and compared to data in the literature. All these compounds (1–10) were firstly isolated from this plant, and compounds 3, 5, 7, and 10 were reported from the Merremia genus for the first time. The significance of the chemotaxonomy for these compounds is described herein.

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.

Thirty-four reported compounds were obtained from Anemone vitifolia Buch.-Ham., and were identified as triterpenoid saponins (1–28), flavonoid glycosides (29–32) and steroidal saponins (33–34). The structure of these compounds was determined by physicochemical constants and spectral analyses (NMR, MS, IR). Twelve compounds (7, 8, 10, 14, 20, 21, 23, 26–28, 30 and 32) were firstly identified in genus Anemone. Compounds 2, 4 and 14 can be considered as characteristic components of A. vitifolia. Finally, the chemotaxonomic significance of these compounds is discussed.

From the leaves of Aphananthe aspera (Thunb.) Planch. (Family: Cannabaceae), six flavonol glycosides, such as quercetin 3-O-β-glucopyranoside (1), kaempferol 3-O-β-glucopyranoside (2), quercetin 3-O-rutinoside (3), kaempferol 3-O-rutinoside (4), quercetin 3-O-neohesperidoside (5) and kaempferol 3-O-neohesperidoside (6) were isolated and identified. Structure elucidation of these compounds was performed on the basis of NMR spectral data. All these compounds were isolated for the first time from the genus Aphananthe. Chemotaxonomic significance and distribution of these flavonoid derivatives among the genera of Cannabaceae are explained in detail.

A new flavanone, epoxynymphaeol C ( 1 ), was isolated from the acetone extract of the leaves of Macaranga tanarius , together with two known compounds, nymphaeols B ( 2 ) and C ( 3 ). The structure of the new compound was determined by NMR and mass spectral data. Chemotaxonomic significance for the presence of the flavanone derivatives in M. tanarius is discussed.

The order Ericales, sensu APG III, belongs to the Asterids. It comprises around 25 families and 347 genera distributed in 4 clades: Balsaminoids, Polemonioids, Primuloids and Ericoids. Their species are widely distributed in arctic, temperate and tropical regions. A comparison between phylogenetic and chemical data for Ericales demonstrated a low correlation, except for Primuloid families. Flavonoids and triterpenes were characterized as good taxonomic markers for the order, due to their general occurrence and molecular diversity. Nevertheless, saponins are markers only for Primulaceae and lignans are the exclusive markers for Styracaceae. Analyses of correlation among chemical parameters based on flavonoidal, morphological and chemo-morphological indexes, showed low phylogenetic affinity for certain groups, positioning Primuloids and Balsaminoids as the highest and the lowest evolutionary advanced taxa, respectively. Flavonoids produced are mainly flavonols rather than flavones. Hydroxyl protection occurs mainly by glycosylation and to a lesser extent by methylation. These data confirmed the primitive status for the order.