Chemotaxonomic contribution to the Sideritis species dilemma on the Balkans

Forty-two samples of Sideritis species (Sideritis scardica, Sideritis raeseri, Sideritis syriaca, Sideritis taurica and Sideritis lanata) from the Balkan Peninsula were evaluated for their polyphenolic profiles in order to establish a correlation between the taxonomy, geographical location and nature and content of phenolic compounds.Eight compounds were detected in all analyzed Sideritis samples: 5-caffeoylquinic acid, lavandulifolioside, verbascoside, isoscutellarein 7-O-allosyl(1→2)glucoside, hypolaetin 7-O-[6‴-O-acetyl]-allosyl(1→2)glucoside, isoscutellarein 7-O-[6‴-O-acetyl]-allosyl(1→2)glucoside, 3′-O-methylhypolaetin 7-O-[6‴-O-acetyl]-allosyl(1→2)glucoside and 4′-O-methylhypolaetin 7-O-[6‴-O-acetyl]-allosyl-(1→2)-[6″-O-acetyl]-glucoside). They present from 50 to 80% of total phenolic content in S. scardica, S. raeseri, S. syriaca and S. taurica and up to 90% in S. lanata and the similarity of their polyphenolic profiles implies that they are systematically very closely related.Based on their polyphenolic patterns, very good differentiation between the samples of S. lanata (sect. Hesiodia) and S. scardica, S. syriaca and S. raeseri (sect. Empedoclia) was observed, that is mainly due to the very high content of 5-cafeoylquinic acid and very low amount of phenylethanoid glycosides and flavonoid glycosides.The obtained results demonstrate considerable degree of similarity between S. scardica, S. raeseri and Bulgarian S. syriaca that give contribution to the dilemma that Bulgarian S. syriaca is very similar to Turkish S. taurica and suggest further verification of its taxonomic status.     

Chemotaxonomic significance of sesquiterpenes and amide derivatives from Chloranthus angustifolius Oliv.

Phytochemical investigation of the aerial parts of Chloranthus angustifolius Oliv. (Chloranthaceae) resulted in the isolation and characterization of seven sesquiterpenes (1–7) and six amide derivatives (8–13). All structures were established based on analysis of their spectroscopic data. This is the first report of compounds 2 and 8–13 from the family Chloranthaceae, and the first report of compounds 3–5 from C. angustifolius. Moreover, the chemotaxonomic significance of these compounds was summarized.     

Chemotaxonomic studies on rhizome extract compositions of twenty Curcuma species from South India

The chemical composition of volatile methanolic rhizome extracts of twenty Curcuma species was studied and the components were identified using gas chromatography–mass spectrometry (GC-MS) method. The major components identified in the majority of the species were beta-caryophyllene epoxide, camphor, retinal and alloaromadendrene oxide. Based on the presence of major chemical components, cluster analysis was performed for all the Curcuma species studied. All the twenty species were grouped based on the presence or absence of a particular compound and a dendrogram was constructed, which grouped the 20 species into eight clusters. By conventional morphological methods, the identification of Curcuma up to species level is difficult; hence the chemical composition of the rhizome methanolic extracts can be used as an important tool for species identification and chemotaxonomic study.     

Chemotaxonomic significance of limonoids and triterpenoids from Dictamnus angustifolius G. Don ex Sweet

Phytochemical investigation of the root bark of Dictamnus angustifolius G. Don ex Sweet (Rutaceae) resulted in the isolation and characterization of three degraded limonoids (1–3), five limonoids (4–8) and four triterpenoids (9–12). All structures were elucidated on the basis of spectral analysis. Among them, compounds 4, 6, 8, 9 and 12 were isolated from the genus Dictamnus for the first time. Compounds 10 and 11 were obtained from D. angustifolius for the first time. Moreover, the chemotaxonomic significance of these compounds was summarized.     

Chemotaxonomic significance of the essential oils of 18 Ferula species (Apiaceae) from Iran

To evaluate the chemotaxonomic significance of the essential oils of 23 populations of 18 Iranian Ferula species, the chemical composition of the oils was investigated by GC/FID and GC/MS. Altogether, 84 constituents, representing 81.3-99.7% of the total composition of the oils, have been identified. The composition of six species of the genus, i.e., F. oopoda, F. foetida, F. behboudiana, F. diversivittata, F. galbaniflua, and F. hezarlalehzarica, has been reported for the first time. The main constituents identified were α-terpinyl acetate (73.3%), 2,3,4-trimethylthiophene (2; 49.0%), sabinene (75.3%), verbenone (5; 69.4%), β-pinene (59.0-66.3%), and (Z)-β-ocimene (41.7%). Cluster analysis (CA) of the percentage content of the essential oil components of the Ferula species resulted in the characterization of four groups, i.e., taxa containing either i) monoterpene hydrocarbons, ii) oxygenated monoterpenes, iii) organosulfur compounds, or iv) monoterpene, sesquiterpene, and aliphatic hydrocarbons as the principal classes of compounds. Based on the results obtained, the chemical independence of F. hirtella from F. szowitsiana and of F. galbaniflua from F. gummosa at the specific level was concluded and their positions as distinct species were confirmed. The chemotaxonomic relationships among the representatives of the genus Ferula have been discussed in detail.     

Sesquiterpenoids and flavonoids from Pteris multifida Poir.

Phytochemical research of Pteris multifida Poir. led to the isolation of fifteen compounds, including six flavonoids (1–6) and nine sesquiterpenoids (7–15). Their structures were characterized by NMR, MS, ORD and CD data. Compounds kaempferol 3-O-α-L-rhamnoside-7-O-β-D-glucoside (1), myricetin 3-O-β-D-glucoside (2), kaempferol 3-O-β-D-glucoside (4), luteolin-7-O-β-D-rutinoside (5), quercetin-3-O-α-L-rhamnopyranoside (6), (2S,3S)-12-hydroxypterosin Q (7), (2S,3S)-pterosin Q (8), 2-hydroxypterosin C (9) and (2S)-12-hydroxypterosin A (10) were first isolated from P. multifida, and compounds 1–2 and 10 were first isolated from the family Pteridaceae. Furthermore, the chemotaxonomic significance of the isolates was discussed.     

壮丽含笑中的倍半萜成分及其化学分类学意义

壮丽含笑 (ＭｉｃｈｅｌｉａｌａｃｅｉＷ Ｗ Ｓｍｉｔｈ)为木兰科含笑属植物 ,常绿乔木 ,分布于我国云南西南部 ,生于海拔 15 0 0ｍ的林中。枝粗壮 ,花梗具佛焰苞状苞片约 5枚 ,心皮狭卵圆形具 3～ 4ｍｍ的花柱等特征 ,形态分类学上认为该种是含笑属中较原始而特殊的种类 (刘玉壶等 ,1996)。通过初步药理筛选实验 ,表明其嫩枝的脂溶性提取物在浓度为 1 5 μｇ/ｍＬ时对两种人肿瘤细胞株ＨＣＴ - 8及ＳＩＨａ的抑制率分别为5 7 0 %及 2 1 3% ,对ＧＬＣ - 82细胞株的抑制率尤其明显 ,为 84 6% ;对ＣｏｎＡ刺激的小鼠脾淋巴细胞增殖反应在浓…     

Flavones and anthocyanins from the leaves and flowers of Japanese Ajuga species (Lamiaceae)

Flavones and anthocyanins were isolated from the leaves and flowers of 14 Ajuga taxa (Lamiaceae), which are all native or naturalized in Japan. Of 13 flavones obtained from the leaves, 11 were characterized as apigenin, luteolin, 6-hydroxyluteolin and acacetin glycosides. Ten flavones were isolated from the flowers. Ten anthocyanins were isolated from the flowers. Six of these anthocyanins were identified as acylated delphinidin glycosides and four were shown to be acylated cyanidin glycosides. Japanese Ajuga taxa were chemotaxonomically discussed by their distribution patterns, especially foliar flavonoids.     

Flavonoids from the leaves and twigs of Knema elegans

Knema elegans, a tropical evergreen plant, belongs to Myristicaceae family. Phytochemical investigation on the leaves and twigs of K. elegans led to the isolation and identification of two new flavonoids knemavones A and B (1 and 2), along with fifteen known analogues (3–17). These compounds belong to four subtypes of flavonoids, including chalcones, flavanes, flavones, and isoflavones. The structures of 1 and 2 were elucidated by means of spectroscopic techniques, including HRESIMS, 1D, and 2D NMR experiments. Compounds 3–17 are isolated from the title plant for the first time. Moreover, the new chalcones 1 and 2 could serve as chemotaxonomic markers of K. elegans.     

Flavonoids from the Turkish endemic plant Rhaponticoides mykalea (Hub.-Mor.) M.V.Agab. & Greuter (Asteraceae)

The genus Rhaponticoides, recently segregated from the genus Centaurea, belongs to the family Asteraceae (tribe Cardueae). Rhaponticoides mykalea (Hub.-Mor.) M.V.Agab. & Greuter is an endemic species narrowly distributed in the Aegean part of Turkey. Owing to the existing anthropogenic impacts (such as urbanization and road construction) throughout its distribution range, the species has been the subject of several conservation studies. Phytochemical research on the aerial parts of R. mykalea led to the isolation of a new flavonoid, namely patuletin 7-O-(6″-E-sinapyl)-β-glucopyranoside, together with four known flavonoids from n-butanol extract. The structures of all isolated compounds were elucidated by spectroscopic analysis (1D and 2D NMR, HR-ESI-MS), as well as by comparison with the relevant literature data. All of the compounds have been isolated from the genus Rhaponticoides for the first time.     

红花桑寄生枝叶总黄酮提取工艺

以Al(NO3)3显色法于510nm测定红花桑寄生枝叶提取液的吸光度,聚酰胺提纯,以芦丁为标准计算含量,正交实验方法探讨以乙醇为溶剂提取该类化合物的最佳工艺条件,结果表明,桑寄生叶最佳提取条件是溶剂为70％乙醇、料液比1：35、80℃条件下提取3h;桑寄生枝的最佳提取条件是溶剂为50％乙醇、料液比1：15、80℃条件下提取3h,在对应条件下桑寄生总黄酮平均得率叶为9.47%,枝为5.25%。     

Flavonoids in the leaves of Hillebrandia and Begonia species (Begoniaceae)

The fresh leaves of Hillebrandia sandwicensis and 126 Begonia taxa were chemotaxonomically surveyed for flavonoids. Of their taxa, H. sandwicensis and 119 species, one variety and three hybrids were analyzed for flavonoids for the first time. Ten flavonols and eleven C-glycosylflavones were isolated and characterized as quercetin 3-O-rutinoside (1), kaempferol 3-O-rutinoside (2), isorhamnetin 3-O-rutinoside (3), quercetin 3-O-glucoside (4), quercetin 3-methyl ether 7-O-rhamnosylglucoside (5), quercetin 3,3'-dimethyl ether 7-O-rhamnosylglucoside (6), quercetin glycoside (13), quercetin glycoside (acylated) (14), kaempferol glycoside (17) and quercetin 3-O-rhamnoside (18) as flavonols, and isovitexin (7), vitexin (8), isoorientin (9), orientin (10), luteolin 6-C-pentoside (11), luteolin 8-C-pentoside (12), schaftoside (15), isoschaftoside (16), chrysoeriol 6,8-di-C-pentoside (19), apigenin 6,8-di-C-arabinoside (20) and isovitexin 2''-O-glucoside (21) as C-glycosylflavones. Quercetin 3-O-rutinoside (1) alone was isolated from H. sandwicensis endemic to Hawaii. Major flavonoids of almost Begonia species was also 1. Begonia species were divided into two chemotypes, i.e. flavonol containing type and C-glycosylflavone containing type. Of 14 section of the Begonia, almost species of many section, i.e. sect. Augustia, Coelocentrum, Doratometra, Leprosae, Loasibegonia, Monopteron and Ruizoperonia, were flavonol types. On the other hand, C-glycosyflavone type was comparatively most in sect. Platycentrum.     

Chemotaxonomic significance of flavonoids and phenolic acids in the Hieracium rohacsense group (Hieracium sect. Alpina; Lactuceae, Compositae)

Five apomictic taxa from the Hieracium rohacsense group were studied for their phenolic constituent composition. The following substances represent dominant compounds in the leaves: chlorogenic acid, 3,5-dicaffeoylquinic acid, luteolin 7-O-β- -glucopyranoside, luteolin 4′-O-β- -glucuronopyranoside and apigenin 4′-O-β- -glucuronopyranoside. Within the group only quantitative differences were found, luteolin 7-O-glucoside being the most important chemotaxonomic marker. Each taxon has its own specific quantitative pattern, invariable within the taxon. Based on these characteristic profiles, H. rohacsense can be distinguished from a closely related and still undescribed taxon from Mt. Pip Ivan. The proportion of luteolin 7-O-glucoside to apigenin 4′-O-glucuronoside also clearly separates the individuals of two morphologically close species—H. ratezaticum and H. pseudocaesium, which corresponds to a few slight but recognisable morphological and phenological characteristics. The ontogenetic stage of leaf development and seasonal variation are also important factors, which must be taken into consideration, as the quantity of the substances changes during leaf ontogeny and with season.     

Erythrinoid and indol alkaloids isolated from the seeds of Erythrina rubrinervia Kunth: Chemotaxonomic significance

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.     

Sesquiterpene lactones from the leaves of Magnolia sirindhorniae

Five sesquiterpene lactones, costunolide (1), santamarine (2), reynosin (3), parthenolide (4), and lipiferolide (5), were isolated from the leaves of Magnolia sirindhorniae. Their structures were identified by analysis of spectroscopic data and comparison with those reported in the literature. Compound 5 was isolated from the Magnolia for the first time, and this is the first report of the isolation of the sesquiterpene lactones from M. sirindhorniae.     

Alkaloids from the leaves of Isatis indigotica fortune and their chemotaxonomic significance

From the leaves of Isatis indigotica Fortune, one new alkaloid, namely (2E)-N-(2-hydroxyphenyl)-2-(1-hydroxy-3-oxoindolin-2-ylidene) acetamide (1), together with four known ones, such as phaitanthrin D (2), methyl quindoline-11-carboxylate (3), cephalandole B (4) and 2,2-di (3-indolyl)-3-indolone (5) were isolated and identified. The structure of compound 1 was elucidated by means of spectroscopic analysis, including HRESIMS together with 1D and 2D NMR experiments. Compounds 1, 2 and 5 were obtained from this genus for the first time. Chemotaxonomic significance of these compounds is described herein.     

唐古特白刺叶黄酮类及酚酸类成分的分离鉴定

从蒺藜科植物唐古特白刺（ＮｉｔｒａｒｉａｔａｎｇｕｔｏｒｕｍＢｏｒ．）叶中分得８个黄酮类及酚酸类化合物,经理化常数测定和波谱学方法确定了它们的化学结构,分别为：３甲氧基４羟基反式桂皮酸（１）、对羟基反式肉桂酸（２）、３羟基４甲氧基苯甲酸（３）、邻羟基苯甲酸（４）、３,５二甲醚山柰黄素７ＯβＤ葡萄糖甙（５）、３甲醚山柰黄素７ＯβＤ葡萄糖甙（６）、异鼠李素７ＯβＤ葡萄糖甙（７）、异鼠李素３ＯβＤ芸香糖甙（８）。以上化合物均为首次从该植物中得到,可以作为白刺属化学分类学的特征性化合物。     

Chemical evidence from the flavonoids relevant to the classification of Mains species

The phenolic compounds of the leaf and bark of Malus species have been examined. The dihydrochalcone phloridzin and a range of flavonoids occur in all barks, but eight compounds were found in only a limited number of species and their distribution shows a relationship with the taxonomy of Malus , providing useful additional characters. The various proposed classifications of Malus species are discussed in the light of this evidence and that of Rehder is found to be in best agreement except for his placing of M'. florentina which, by its chemistry, is clearly related to the section Docyniopsis. The geographical distribution of the distinctive phenolics suggests a wide spreading of early Malus probably from south-east Asia as far as North America and a later diversification confined almost entirely to Eurasia. The different phenolic patterns are discussed and related to proposed phytogenies of Malus.