Chemotaxonomic Value Research Articles

Chemotaxonomic analysis of Astragalus caprinus (Fabaceae) based on the flavonic patterns

In previous work, 14 flavonol glycosides were characterised in the leaves of Astragalus caprinus, an endemic Fabaceae, widely distributed in North West Africa. These compounds included quercetin and kaempferol derivatives, glycosylated by two, three or four sugars with an aliphatic or aromatic acyl moiety. In this paper, we describe the flavonoid patterns of 404 individual plants investigated by HPLC and subjecting the resulting data to cluster analysis. This analysis highlighted four chemotypes associated with a high accumulation of a kaempferol triglycoside, a kaempferol tetraglycoside with its acylated derivatives, two quercetin tetraglycoside derivatives and methylated diglycoside derivatives, respectively. A discriminant analysis validated the chemotaxonomic value of the four chemical polymorphisms. These chemotypes were more or less abundant according to geographical sites which corresponded to different climatic conditions.

The Chemistry of Exploding Ants, Camponotus SPP. (Cylindricus COMPLEX)

A detailed comparative analysis of the exocrine chemistry of nine Bruneian Camponotus species in the cylindricus complex is reported. Workers of these species are known to have hypertrophied mandibular glands and release their glandular contents suicidally from the head by rupturing the intersegmental membrane of the gaster. All of the species produce mixtures of polyacetate-derived aromatics, including hydroxyacetophenones, which display pH-dependent color changes, and aliphatic hydrocarbons and alcohols. In addition, three species contained (6R)-2,6-dimethyl-(2E)-octen-1,8-dioic acid (9) or (3S)-8-hydroxycitro-nellic acid (10a), previously unreported from insects. These compounds were characterized from their spectral data, and confirmed by comparison with synthetic samples. The allomonal role of these compounds is based on numerous field observations, and their chemotaxonomic value is presented.

Fatty acid and tocochromanol patterns of some Turkish Boraginaceae—a chemotaxonomic approach

The plant family Boraginaceae is known to produce a set of unusual fatty acids in the seed oils. In this study, the fatty acid, tocopherol, tocotrienol and plasto‐chromanol‐8 contents of some Onosma species (Onosma sericeum, O. armeniacum and O. polioxanthum) all belonging to sect. Onosma, Anchusa leptophylla subsp. leptophylla, Alkanna froedini and Paracaryum stenophyllum were determined. Some of the studied species are endemic for Turkey. While oleic, linoleic and alpha linolenic acid are the highest as usual fatty acids, gamma linolenic and stearidonic acids are more variable unusual fatty acids in studied genera patterns and the relative concentrations some of these fatty acids and partly also the tocochromanols in Boraginaceae seed oils are suggested to have chemotaxonomic value in this family. In particular, the presence or absence of chain elongation to erucic acid (22:1) and the presence or absence of Δ6‐methylene‐interrupted polyenoic acids such as γ‐linolenic and stearidonic acid are determined and marked as indicators of taxonomic relationship.

Bioactive Polymethoxyflavones and Flavanone Glycosides from the Peels of Citrus Deliciosa

Six biologically active flavonoids were isolated from the fruit peels of Citrus deliciosa. Analysis off their spectral data (UV, MS, 1H, 13C and 2D NMR experiments) confirmed their structures as four polymethoxyflavones (5-0-demethylnobiletin 1; tangeritin 2; nobiletin 3 and 5,7,8,3’,4’-pentamethoxyflavone 4) as well as two flavanone glycosides (hesperetin-7-0-glucoside 5 and hesperidin 6). The IH NMR assignment of3 and the isolation of 5 from Rutaceae is reported for the first time. The isolated flavonoids displayed antibacterial activities against a series of G +ve and G –ve bacteria. The chemotaxonomic value of the present findings has been verified, and some of the isolated flavonoids may provide good markers for chemotaxonomical studies of Citrus species.

The First Report on the Occurrence of Furofuranoid Lignan Glucosides in Acanthaceae

A new furofuranoid lignan glucoside ((+)-epipinoresinol-4?-ß-D-glucoside) and the known lignan glucoside phillyrin ((+)-epipinoresinolmethyl ether-4?-ß-D-glucoside), were isolated from the aerial parts of Anisacanthus virgularis Nees, along with some known steroids, a terpenoid and flavonoids. Their structures were elucidated on the basis of spectral analysis, chemical derivatization and/or direct comparison with authentic samples. Furofuranoid lignans are reported in the family Acanthaceae for the first time. Their potential biological activity and chemotaxonomic value are discussed.

Chemotaxonomic Features Associated with Flavonoids of Cannabinoid-Free Cannabis (Cannabis sativa subsp. sativa L.) in Relation to hops (Humulus Lupulus L.)

The major flavonoids present in the leaves and flowers of the cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) cultivars Felina and Futura are orientin (1), vitexin (2), luteolin-7-O-g-D-glucuronide (3), and apigenin-7-O-g-D-glucuronide (4), while prenylated flavonoids, to which the potent estrogenicity of hops (Humilus lupulus L.) is associated, are absent. The different composition of flavonoids has chemotaxonomic value.

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

Abstract 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 .

Phytoecdysteroid profiles in seeds of Sida spp. (Malvaceae).

Procedures are presented for the assessment of the phytoecdysteroid profiles in small plant samples (ca. 25 mg), using seeds of Sida spp. as an example. The procedures are suitable for the analysis of minute or valuable samples and provide copious information for chemotaxonomic purposes. Methanolic extracts of the plant material, after partitioning against hexane, were separated by reversed-phase gradient HPLC monitored by PAD, RIA and bioassay. Aliquots of the fractions were also treated with Helix pomatia hydrolases, followed by RIA and bioassay, in order to assess the presence of hydrolysable ecdysteroid conjugates. Further information could also be obtained by separation of samples using normal-phase gradient HPLC. Among 11 species of Sida examined, seed extracts of S. acuta (= S. carpinifolia) and S. rhombifolia were found to contain significant amounts of ecdysteroids, seed extracts of S. filicaulis contained only moderate levels, whilst the remaining species showed no detectable levels of ecdysteroids. The ecdysteroid profiles of the extracts of the three positive species were significantly different, demonstrating that phytoecdysteroids have chemotaxonomic value in this genus.

Comparative studies on Orobanche cernua L. and O. cumana Wallr. (Orobanchaceae) in the Iberian Peninsula

The systematic treatment of Orobanche cumana Wallr. and O. cernua L. is controversial. Whereas some authors consider O. cumana as an infraspecific taxon of O. cernua, others treat it as a separate species. Furthermore, the nomenclature of the sunflower broomrape is unclear, and both names are found without qualification in the literature. The objective of the present study has been to evaluate the distribution, morphology, and ecology of O. cernua and O. cumana in the Iberian Peninsula, as well as their seed oil fatty acid profile, which is a trait of great chemotaxonomic value. O. cernua was found parasitizing wild Compositae, mainly Artemisia sppwhereas O. cumana was exclusively found on cultivated sunflower. Both species clearly differ in morphological traits, especially plant height and build, length and structure of the inflorescence, corolla length and colour. Both species are characterized by contrasting seed oil fatty acid profiles, with high oleic acid concentration in O. cernua and high linoleic acid concentration in O. cumana. The evaluation of both taxa in the Iberian Peninsula gives additional support to those authors that treat them as separate species.

Comparative studies on Orobanche cernua L. and O. cumana Wallr. (Orobanchaceae) in the Iberian Peninsula

The systematic treatment of Orobanche cumana Wallr. and O. cernua L. is controversial. Whereas some authors consider O. cumana as an infraspecific taxon of O. cernua , others treat it as a separate species. Furthermore, the nomenclature of the sunflower broomrape is unclear, and both names are found without qualification in the literature. The objective of the present study has been to evaluate the distribution, morphology, and ecology of O. cernua and O. cumana in the Iberian Peninsula, as well as their seed oil fatty acid profile, which is a trait of great chemotaxonomic value. O. cernua was found parasitizing wild Compositae, mainly Artemisia sppwhereas O. cumana was exclusively found on cultivated sunflower. Both species clearly differ in morphological traits, especially plant height and build, length and structure of the inflorescence, corolla length and colour. Both species are characterized by contrasting seed oil fatty acid profiles, with high oleic acid concentration in O. cernua and high linoleic acid concentration in O. cumana . The evaluation of both taxa in the Iberian Peninsula gives additional support to those authors that treat them as separate species.

Chromones and anthrones from Aloe marlothii and Aloe rupestris

A phytochemical investigation of the leaf exudate of Aloe marlothii has resulted in the isolation of a new chromone (7- O-methylaloeresin A) and a new anthrone (5-hydroxyaloin A 6′- O-acetate). Furthermore 7- O-methylaloesin was isolated as a natural product for the first time from the leaf exudate of Aloe rupestris. The structure elucidation of these compounds was based on spectral data including 2D NMR. The chemotaxonomic value of 7- O-methylaloesin in Aloe series Asperifoliae and section Pachydendron is discussed.

Chemotaxonomic value of the essential oil compounds in species of Teucrium pumilum aggregate

Volatile compounds from the aerial parts of Teucrium lepicephalum Pau and Teucrium carolipaui C. Vicioso ex Pau, both belonging to the Teucrium pumilum aggregate, were analysed by capillary GC and GC–MS. From the common and specific compounds (mono- and sesquiterpenes) of the two taxa, chemical characterization was carried out and taxonomic relationships were assessed. Application of the cluster and k-means discriminant analysis shows a differential chemical relationship between T. lepicephalum and Teucrium carolipaui.

Tocopherol, plastochromanol and fatty acid patterns in the genusLinum

The fatty acid composition of the seed oil has been used as a criterion in searching for a rational infrageneric classification ofLinum L.. The objective of the present study was to evaluate the taxonomic potential of other seed traits such as tocopherols and plastochromanol-8 in this genus. The results revealed that, in addition to fatty acids, tocopherols and plastochromanol-8 possess an important chemotaxonomic value for the genusLinum. Sect.Linum and sect.Syllinum Griseb. clearly differed from each other for the three types of compounds. Sect.Linum was characterized by the presence of plastochromanol-8, a high concentration of linolenic acid, and an intermediate or low concentration of alpha-tocopherol. Contrarily, sect.Syllinum lacked plastochromanol-8 and contained a low concentration of linolenic acid and a high concentration of alpha-tocopherol. The three species evaluated of the sectionLinastrum (Planch.) Bentham showed no common pattern, questioning their classification within the same section.

The chemotaxonomic value of two cinnamoyl chromones, aloeresin E and F, in Aloe (Aloaceae)

SummaryViljoen, A. M. & Van Wyk, B.‐E.: The chemotaxonomic value of two cinnamoyl chromones, aloeresins E and F, in Aloe (Aloaceae). ‐‐ Taxon 48: 747‐754. 1999. – ISSN 0040‐0262.A chemotaxonomic study of the genus Aloe indicates a remarkable quantitative and qualitative similarity in leaf exudate composition between 12 species. The diagnostic leaf exudate profile found in all representatives of this group – a combination of homonataloin A and B with either or both of two recently described cinnamoyl chromones, aloeresin E and F, together with various coumaroyl chromones – may serve as a “fingerprint”. Taxonomic assessment and cladistic analysis of both morphological and chemical data support the transfer of A. pearsonii, previously misplaced in A. ser. Macrifoliae, to A. ser. Mitriformes, and are consistent with the broadening of the circumscription of the latter to include 5 anomalous species: A. angelica, A. yavellana, A. peglerae, A. melanacantha, and A. erinacea.

Chemotaxonomic significance of fatty acids and tocopherols in Boraginaceae

A collection of 45 accessions (36 species, 20 genera) of the family Boraginaceae was evaluated for oil content, fatty acid composition, tocopherol content and composition. All the accessions contained γ-linolenic acid, the lowest content (0.7%) being found in Cerinthe major L. and the highest (24.4%) in Borago officinalis L. Three tocopherol profiles were characterized by the extremes of more than 90% of α-, δ- and γ-tocopherol, respectively. Fatty acids and tocopherols were suggested to have potential chemotaxonomic value in this family.

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 inOenotheraspp. where two groups, showing different concentrations of gamma-linolenic acid and alpha-tocopherol, were observed. The species ofClarkiaPursh were markedly different to the rest of species, showing low alpha-linolenic acid and low gamma-tocopherol concentration.Circaea lutetianaL. had a characteristic tocopherol profile, with high levels (13%) of beta-tocopherol. Variation for fatty acid and tocopherol composition inEpilobiumspp. suggested some phylogenetic relationships. The annual speciesE. paniculatumNutt. showed a characteristic composition very similar to the closely relatedBoisduvalia densiflora(Lindl.) S. Watson. The accessions of the phylogenetically relatedE. fleischeriHochst. andE. dodonaeiVillalso 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.

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.

Correlation of glutathione and ascorbate and their dependence on age and season in human lymphocytes: [formula omitted] H. Therriault, A.M. Cantin, T. F,l^p, H. Payette and J.R. Wagner IUGS (d'Youville), 1036 Belvedere Sud, Sherbrooke QuÈbec Canada J1H 4C4

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 inOenotheraspp. where two groups, showing different concentrations of gamma-linolenic acid and alpha-tocopherol, were observed. The species ofClarkiaPursh were markedly different to the rest of species, showing low alpha-linolenic acid and low gamma-tocopherol concentration.Circaea lutetianaL. had a characteristic tocopherol profile, with high levels (13%) of beta-tocopherol. Variation for fatty acid and tocopherol composition inEpilobiumspp. suggested some phylogenetic relationships. The annual speciesE. paniculatumNutt. showed a characteristic composition very similar to the closely relatedBoisduvalia densiflora(Lindl.) S. Watson. The accessions of the phylogenetically relatedE. fleischeriHochst. andE. dodonaeiVillalso 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.

Xanthones from hypericum japonicum and H. henryi

From the aerial part of Hypericum japonicum, one new xanthone glycoside, 1,5-dihydroxyxanthone-6- O- β- d-glucoside, one novel dimer xanthone, bijaponicaxanthone, and the first natural prenylated xanthone, 1,3,5,6-tetrahydroxy-4-prenylxanthone, were isolated together with the four known xanthones, 1,5,6-trihydroxyxanthone, isojacereubin, 6-deoxyisojacareubin and 4′,5′-dihydro-1,5,6-trihydroxy-4′,4′,5′-trimethylfurano (2′,3′:4,5) xanthone. Five previously known xanthones, kielcorin, cadensin, 1,7,-dihydroxyxanthone, 1,5-dihydroxy-4-methoxyxanthone and 1,2,5-trihydroxyxanthone were also found in the dichoromethane extract of the stems and leaves of H. henryi. Their structures were elucidated by spectroscopic and chemical methods. Some of the compounds from H. japonicum were found to exert an interesting coagulant activity in an in vitro test. The chemotaxonomic value of xanthones is discussed briefly.

3-Hexyl-5-Methylindolizidine Isomers from Thief Ants, Solenopsis (Diplorhoptrum) Species

The venom alkaloids from the workers of nine collections of Solenopsis (Diplorhoptrum) from California contain either (5E,9E)-3-hexyl-5-methylindolizidine (1c) or (5Z,9E)-3-hexyl-5-methylindolizidine (1d) along with cis-2-methyl-6-nonylpiperidine. The structures of these compounds were determined from their mass spectra and by comparison of their GC-FTIR spectra with those of a synthetic mixture. In view of the facts that a third diastereomer of 3-hexyl-5-methylindolizidine had been reported in previous collections of Solenopsis (Diplorhoptrum) queens from Puerto Rico, and that indolizidines along with other ant venom alkaloids are sequestered by amphibians, the determination of species in this difficult group of ants is significant. In particular, the chemotaxonomic value of the stereochemistry of these venom alkaloids is discussed.