Diterpene quinone of Salvia Linn. and their taxonomic significance

Abstract We have analysed diterpene quinone constituents of 79 species (containing variety and form) in the genus Salvia by different chemical methods, and found that 38 species of them contain diterpene quinone on this ground, as well as its morphologic, histological structure of root and geographical distribution, we come to a conclusion as follows: l. According to literatural and our analytical date, so far the diterpene quinone have mainly been found in the Labiatae plants that possess the fertile stamen 2 versatile namely in Salvia Linn., upon which a new subfamily Salvioideae is preliminarily proposed here. 2. Deterpene quinone, as a chemotaxonomic charater, is of phylogenetic significance and can be used for identifying the spicies of the genus. 3. A further rearrangement of some species of some series and sections in attribu-tion is needed.     

The chemotaxonomic significance of the phenyl pyrone aloenin in the genus Aloe

The phenyl pyrone, aloenin was positively identified in 16 species in a greater chemotaxonomic study on 380 species of Aloe. A large number of species have previously been suggested to be related on the basis of their macromorphological characters. The leaf exudate composition of the 16 species are presented together with a summary of the salient morphological characters. The possible taxonomic relationships between aloenin producing species, not previously thought to be associated with one another are discussed and illustrates the need to explore additional characters of taxonomic value in this large genus of ca. 420 species where no natural classification system exists.     

Phylogenetic relationships of Salvia (Lamiaceae) in China: Evidence from DNA sequence datasets

With 84 native species, China is a center of distribution of the genus Salvia (Lamiaceae). These species are mainly distributed in Yunnan and Sichuan provinces (southwestern China), notably the Hengduan Mountain region. Traditionally, the Chinese Salvia has been classified into four subgenera, Salvia, Sclarea, Jungia, and Allagospadonopsis. We tested this classification using molecular phylogenetic analysis of 43 species of Salvia from China, six from Japan, and four introduced species. The nuclear ribosomal internal transcribed spacer region and three chloroplast regions (rbcL, matK, and trnH-psbA) were analyzed by maximum parsimony, maximum likelihood, and Bayesian methods. Our results showed that the Chinese (except Salvia deserta) and Japanese Salvia species formed a well-supported clade; S. deserta from Xinjiang grouped with Salvia officinalis of Europe. In addition, all introduced Salvia species in China were relatively distantly related to the native Chinese Salvia. Our results differed from the subgeneric and section classifications in Flora Reipublicae Popularis Sinicae. We suggested that sections Eusphace and Pleiphace should be united in a new subgenus and that sect. Notiosphace should be removed from subg. Sclarea and form a new subgenus. Our data could not distinguish a boundary between subg. Allagospadonopsis and sect. Drymosphace (subg. Sclarea); the latter should be reduced into the former. Further clarification of the phylogenetic relationships within Salvia and between Salvia and related genera will require broader taxonomic sampling and more molecular markers.     

Capsaicinoid profiles are not good chemotaxonomic indicators for Capsicum species

Capsaicinoids have been suggested as an aid in identifying Capsicum species. The distribution of seven capsaicinoids and their chemotaxonomic significance were examined within nearly 200 accessions of six Capsicum species. The seven capsaicinoids were separated and quantified using high-performance liquid chromatography. The capsaicinoid profiles were not consistent when examined within a species, therefore they have limited use as a chemotaxonomic indicator. In addition, the generalization that capsaicin and dihydrocapsaicin are always the major capsaicinoids was not true, exceptions were found for some of the accessions studied.     

Tocopherol and fatty acid composition of twenty-five species of Onagraceae Juss.

Chemotaxonomic relationships in Onagraceae have been investigated at the level of leaf and flower compounds but not for seed traits. The objective of this study was to characterize a set of 26 accessions (25 species, 7 genera) of this family for seed oil content, fatty acid composition, tocopherol content and composition, and to evaluate the chemotaxonomic implications of the results. The accessions showed a large variation for all the traits. Gamma-linolenic acid was exclusively found in Oenothera spp. where two groups, showing different concentrations of gamma-linolenic acid and alpha-tocopherol, were observed. The species of Clarkia Pursh were markedly different to the rest of species, showing low alpha-linolenic acid and low gamma-tocopherol concentration. Circaea lutetiana L. had a characteristic tocopherol profile, with high levels (13%) of beta-tocopherol. Variation for fatty acid and tocopherol composition in Epilobium spp. suggested some phylogenetic relationships. The annual species E. pankulatum Nutt. showed a characteristic composition very similar to the closely related Boisduvalia densiflora (Lindl.) S. Watson. The accessions of the phylogenetically related E. fleischeri Hochst. and E. dodonaei Vill., also showed similar fatty acid and tocopherol composition. The results of this study suggest a potential chemotaxonomic value of seed fatty acids and tocopherols in Onagraceae.     

Weitere hirsutinolide aus Vernonia-arten

The investigation of two Bolivian Vernonia species afforded, in addition to known compounds, five further enollactones of the hirsutinolide type and a new hydroxyzaluzanine. The structures were elucidated by intensive ¹H NMR studies and some chemical transformations. The results show again that the hirsutinolides are probably of chemotaxonomic importance in the large genus Vernonia.     

Neue chalkon-derivate aus südafrikanischen Helichrysum-arten

The investigation of two South African Helichrysum species afforded in addition to known compounds two new chalcone derivatives, four related dihydrochalcones,5,7,8-trimethoxyflavone and 5-methoxy-7,8-methylenedioxyflavone. The structures are elucidated by spectroscopic methods and some chemical transformations. The chemotaxonomic situation in the large genus Helichrysum is discussed, in the light of these results.     

Polyphenolics of Salvia--a review.

Salvia is an important genus widely cultivated and used in flavouring and folk medicines. The genus has attracted great interest so much so that it has been the subject of numerous chemical studies. It is a rich source of polyphenols, with an excess of 160 polyphenols having been identified, some of which are unique to the genus. A large number of these polyphenolic compounds are apparently constructed from the caffeic acid building block via a variety of condensation reactions. The nature of these polyphenols which have been reported is compiled in this report together with some bioactivity data in an effort to show the rapid development in the phytochemistry and the therapeutic applications of the Salvia species.     

Salvia (Lamiaceae) is not monophyletic: implications for the systematics, radiation, and ecological specializations of Salvia and tribe Mentheae

Salvia, with over 900 species from both the Old and New World, is the largest genus in the Lamiaceae. Unlike most members of the subfamily Nepetoideae to which it belongs, only two stamens are expressed in Salvia. Although the structure of these stamens is remarkably variable across the genus, generally each stamen has an elongate connective and divergent anther thecae, which form a lever mechanism important in pollination. In a preliminary investigation of infrageneric relationships within Salvia, the monophyly of the genus and its relationship to other members of the tribe Mentheae were investigated using the chloroplast DNA regions rbcL and trnL-F. Significant conclusions drawn from the data include: Salvia is not monophyletic, Rosmarinus and Perovskia together are sister to an Old World clade of Salvia, the section Audibertia is sister to subgenus Calosphace or the monotypic Asian genus Dorystaechas, and the New World members of section Heterosphace are sister to section Salviastrum. Owing to the non-monophyly of Salvia, relationships at the next clearly monophyletic level, tribe Mentheae, were investigated.     

782. SALVIA INVOLUCRATA

Salvia involucrata Cav., the Rose‐leaf sage, is a species endemic to east Mexico which has been in cultivation since at least the late 18th century. It is little‐known as a native species but is widely cultivated and various cultivars and cultivated hybrids are also known. Salvia puberula Fern. is treated as belonging to S. involucrata but has been subject to different interpretations over the years.     

The chemotaxonomic value of the diglucoside anthrone homonataloside B in the genus Aloe

The chemotaxonomic value of the only known diglucoside anthrone from Aloe, homonataloside B, is discussed. This compound has been detected in only 14 species in a chemotaxonomic survey of 380 Aloe species. The homonataloside B-accumulating species are only found in Africa with none of the Malagasy endemics producing this compound. A summary of the morphological variation is presented together with the taxonomic distribution of this unique anthrone. The representatives of this distinct chemotype occupy disparate positions in the largely artificial hierarchy of the present classification system. Species included in this chemotype provide chemical evidence of hybridisation in Aloe.     

An untargeted metabolomic approach in the chemotaxonomic assessment of two Salvia species as a potential source of α-bisabolol

α-Bisabolol is a commercially important aroma chemical currently obtained from the Candeia tree (Vanillosmopsis erythropappa). Continuous unsustainable harvesting of the Candeia tree has prompted the urgent need to identify alternative crops as a source of this commercially important sesquiterpene alcohol. A chemotaxonomic assessment of two Salvia species indigenous to South Africa is presented and recommended as a potential source of α-bisabolol. The essential oil obtained by hydrodistillation of the aerial parts was analysed by gas chromatography coupled to mass spectrometry (GC–MS) and mid-infrared spectroscopy (MIRS). Orthogonal projections to latent structures–discriminant analysis (OPLS–DA) were used for multivariate classification of the oils based on GC–MS and MIRS data. Partial least squares (PLS) calibration models were developed on the MIRS data for the quantification of α-bisabolol using GC–MS as the reference method. A clear distinction between Salvia stenophylla and Salvia runcinata oils was observed using OPLS–DA on both GC–MS and MIRS data. The MIR calibration model showed high coefficient of determination (R² = 0.999) and low error of prediction (RMSEP = 0.540%) for α-bisabolol content.     

Histolocalization of chemotaxonomic markers in Brazilian Vernonieae (Asteraceae)

Vernonieae are well represented in South America by subtribe Lychnophorinae, with 104 Brazilian species, some of them rare and endangered. Lychnophorinae are well known for producing metabolites of high pharmaceutical and chemotaxonomic value. Despite the importance of secondary metabolites in Lychnophorinae, there is still little evidence regarding the secretory structures responsible for producing these compounds. Therefore, in this study we investigated 15 species representative of the main lineages of Lychnophorinae, with the following objectives: to identify where the chemotaxonomic markers of Lychnophorinae are secreted and stored and in which developmental stage of the organ these metabolites are found. Samples of stems and leaves were processed according to the usual techniques in plant anatomy. It was found that the main sites of secondary metabolite biosynthesis are glandular trichomes, epidermal cells and parenchyma tissues. Metabolites from glandular trichomes, especially sesquiterpene lactones (STL), are prevalent in the early developmental stages of organs. The metabolite compounds stored in parenchyma tissues are mainly terpenoids, flavonoids and other phenolic compounds; young and expanded leaves are equally rich in metabolites. Thus, the information obtained in this study is essential for conducting chemotaxonomic studies in this group, helping to promote selective collection and conservation of species.     

Diterpenoid alkaloids with chemotaxonomic significance from Aconitum spathulatum

Diterpenoid alkaloids have been acknowledged as of chemotaxonomic significance in plants from the genus Aconitum (Ranunculaceae). Phytochemical investigation on the Aconitum spathulatum W. T. Wang, an endemic Aconitum species in China, has led to the isolation of twelve C₁₉-diterpenoid alkaloids. The chemotaxonomic significance of these compounds are summarized.     

The occurrence and taxonomic distribution of the anthrones aloin, aloinoside and microdontin in Aloe

A chemotaxonomic survey of 380 species of Aloe indicated the presence of the anthrone isomers aloin A and B together with the aloinoside isomers and microdontin A and B in 36 (10%) species of Aloe. This group, referred to as the microdontin chemotype, is thus characterised by a combination of exudate compounds and not merely a single phytochemical marker, implying taxonomic significance of leaf exudate compounds. The 36 representatives of the group occupy disparate taxonomic positions in the largely artificial hierarchy of the present classification system. Although many of the species have previously been considered as related (based on macromorphology only), a large number of species have not been associated with one another before. The chemical profiles and leaf exudate compositions of the species are presented, followed by a brief summary of the morphological diversity. Whilst conceding the possibility of convergent evolution, the geographical distribution of the species and thoughts on possible relationships between the taxa are discussed.     

Chemical classification of the essential oils of the Iranian Salvia species in comparison with their botanical taxonomy

The essential oils of eight Salvia species collected from different localities in Iran were analyzed by gas chromatography/mass spectrometry (GC/MS). The analytical results were compared with those previously published for related Iranian sage species in order to identify chemical markers for these species. Salvia eremophila, S. hypoleuca, and S. reuteriana are endemic, while S. atropatana, S. chloroleuca, S. santolinifolia, S. aegyptiaca, and S. macrosiphon also grow wild in neighboring countries. We categorized the Iranian Salvia species into four main chemotypes according to their essential-oil constituents: those which are dominated by 1) monoterpenes, 2) mono- and sesquiterpenes, or 3) sesquiterpenes as the major constituents, and 4) those containing low-molecular-weight acids, aldehydes, and esters, and green-leaf volatiles (GLVs). Likely due to the chemical diversity of different Salvia chemotypes, this categorization was supported by principal component analysis (PCA) for the group sampled here, but not for the values reported in the literature. We identified the following chemical markers: α-pinene, β-pinene, 1,8-cineol, linalool, and borneol in monoterpene-rich species, or β-caryophyllene, germacrene D, bicyclogermacrene, spathulenol, and caryophyllene oxide in sesquiterpene-rich species. Among these, α-pinene, β-caryophyllene, and germacrene D are the most common and abundant in the Salvia species investigated. In accordance with their close biological taxonomy, the chemical similarity of the essential oils of S. santolinifolia and S. eremophila is so high that we may consider them chemically identical.     

Chemotaxonomic relationships within the order charadriiformes

The uropygial gland secretions of Charadriiformes species (Thinocorus rumicivorus, Gallinago gallinago, Scolopax rusticola) were analysed and the quantitative compositions compared with those of other Charadriiformes and Lariformes species. The results are discussed from a chemotaxonomic viewpoint and evidence for a close relationship between Thinocorus and other Charadriiformes is given.     

Chemical taxonomy of the hinge-ligament proteins of bivalves according to their amino acid compositions.

The proteins in the hinge ligaments of molluscan bivalves were subjected to chemotaxonomic studies according to their amino acid compositions. The hinge-ligament protein is a new class of structure proteins, and this is the first attempt to introduce chemical taxonomy into the systematics of bivalves. The hinge-ligament proteins from morphologically close species, namely mactra (superfamily Mactracea) or scallop (family Pectinidae) species, showed high intraspecific homology in their compositions. On the other hand, inconsistent results were obtained with two types of ligament proteins in pearl oyster species (genus Pinctada). The results of our chemotaxonomic analyses were sometimes in good agreement with the morphological classifications and sometimes inconsistent, implying a complicated phylogenetic relationship among the species.     

Diterpenes from Baccharis species

The investigation of ten Baccharis species afforded in addition to known compounds eight new diterpenes, four ent-labdanes, three kaurenes and a clerodane derivative. Furthermore, two new p-hydroxyacetophenones, a flavone, 3′-methoxyxanthomicrol and two matricaria ester derivatives were isolated. The structures were elucidated by spectroscopic methods and a few chemical transformations. The chemotaxonomic situation of the large genus is discussed briefly.     

New labdane derivatives and further constituents of Brickellia species

The investigation of several Brickellia species and two further related species afford besides known compounds four new labdane derivatives, a new acetylenic carbinol and a new dihydrobenzofuran derivative. The structures have been elucidated by spectroscopic methods. The chemotaxonomic aspects are discussed briefly.