Flavonoids in Parahebe and Veronica: a chemosystematic study

Flavone glycosides are the main flavonoid leaf constituents in the related genera Parahebe and Veronica (Scrophulariaceae), in agreement with former chemical studies of the family. In Parahebe there are groups of species in which there are mainly luteolin glycosides, and groups in which 6-hydroxyluteolin dominates. Small amounts of apigenin occur in many taxa. Glycosylation is usually in the 7-position but 4′- and 5-glycosides were also found. In Veronica a larger variety of flavone aglycones was found: e.g. luteolin, apigenin, chrysoeriol, tricin and three different 6-hydroxyflavones. They are often present in the plants in the form of glucuronides. Glycosylation is in the 7-or-5-position. Most species of both genera have a distinctive pattern of flavonoid glycosides in their leaves which can be used for identification. Populations of P. catarractae are an exception in showing three different patterns, but here the variety in flavone profiles corresponds to the pattern of morphological and geographic variation within this taxon. Anthocyanins are responsible for the blue, mauve and pink colours of the flowers in the two genera. In Veronica they are based on delphinidin, whereas in Parahebe catarractae on both delphinidin and cyanidin.     

Iridoid glucosides of Odontites verna

Five iridoids have been identified in the whole plant of Odontites verna.     

Iridoid glucosides from Pedicularis

Pedicularis palustris contains the iridoid glucosides aucubin and gardoside methyl ester, and five hydroxy derivatives of 8-epi-deoxyloganin, together with boschnaloside and three hydroxy derivatives of boschnaloside. From P. silvatica, plantarenaloside, 8-epiloganin and euphroside have been isolated. Euphroside is also present in P. lapponica, in addition to aucubin and mussaenoside. Chemical evidence for the structure of euphroside is presented. Pedicularioside is shown to be identical with penstemoside, and the former name is thus redundant.     

Iridoid glucosides from Utricularia australis and Pinguicula vulgaris (lentibulariaceae)

Utricularia australis contained 6-deoxycatalpol, a new iridoid glucoside, besides aucubin, gardoside and mussaenosidic acid. From Pinguicula vulgaris was isolated catalpol, globularin and 10-(Z)-cinnamoyl-catalpol, the latter being a new compound. Thus, the iridoids found in Lentibulariaceae belong to structural types which are common in Scrophulariaceae and related families.     

Iridoid glucosides from Melampyrum

Melampyrum arvense and M. cristatum contain, besides aucubin, 8-epiloganin and melampyroside, a new natural iridoid glucoside: gardoside methyl ester. In addition, M. arvense contains mussaenoside and M. cristatum mussaenosidic acid, another novel iridoid glucoside.     

Iridoid glycosides of Rehmannia glutinosa

From the roots of Rehmannia glutinosa var. purpurea and R. glutinosa var. hueichingensis, besides four known iridoid glucosides, catalp     

Iridoid glucosides from Campsis chinensis

Two new iridoid glucosides, 5-hydroxycampenoside and cachineside I, were isolated together with tecomoside from leaves of Campsis chinensis and their structures were elucidated. The absolute stereochemistry of 5-hydroxycampenoside has been established by X-ray analysis, and the structural correlation between 5-hydroxy-campenoside and tecomoside has been determined by spectral and chemical experiments.     

The genus Comus: Non-flavonoid glucosides as taxonomic markers

Previous proposals for subdivision of the genus Cornus are reviewed. Twenty-seven authenticated Cornus species have been studied for their content of non-flavonoid glucosides. Two distinct groups of taxa can be distinguished on this basis: one, containing a hydroxycyclohexadienone glucoside, along with salidroside, its reduced counterpart, and the second, characterized by containing various iridoid glucosides. The two types of glucosides are apparently mutually exclusive.     

Iridoid glucosides in Griselinia, Aralidium and Toricellia

From three of five investigated species of Griselinia a new iridoid glucoside, griselinoside, was isolated. It was found to be present also in foliage of Aralidium pinnatifidum and Toricellia angulata, accompanied in the former by aralidioside another novel iridoid glucoside. The structures and absolute configurations of the two iridoids were elucidated by NMR spectroscopy and chemical conversions. From G. littoralis and T. angulata the glucosides magnolioside and syringoside respectively were isolated. ¹³C NMR spectra are given for thirteen iridoid derivatives.     

A chemosystematic survey of the fern genus Bommeria

A phytochemical survey of the species of Bommeria showed that foliage of the members of this genus contains a variety of flavonol and flavone glycosides. The distributions of chemical and morphological characters in Bommeria correlated to circumscribe infrageneric affinities: B. hispida and B. subpalaecea comprise one evolutionary line, while B. pedata and B. ehrenbergiana form a second. Flavonoid data may also be applied in concert with spore morphology in defining intergeneric species groups within Bommeria and Hemionitis.     

A chemosystematic study of the phenolics of Sonchus

Thirty-three Sonchus, one Embergeria, one Babcockia and five Taeckholmia species were surveyed for their phenolic constituents. The coumarins scopoletin and aesculetin were found as major constituents of Embergeria, Babcockia and Taeckholmia species, and in lesser amount in some Sonchus species. Six flavone glycosides were identified: apigenin 7-glucuronide, apigenin 7-rutinoside, luteolin 7-glucoside, luteolin 7-glucuronide, luteolin 7-rutinoside and luteolin 7-glucosylglucuronide and the systematic significance of their distribution is discussed.     

A chemosystematic study of some geraniaceae

The flavonoids of five Geranium, fourteen Erodium and four Monsonia species were studied. Quercetin was the most common aglycone with lesse     

Terpenoid chemosystematic studies of Abies grandis

Cortial essential oil from 395 typical Abies grandis and Abies grandis-Abies concolor intermediate trees collected in 48 locations was analyzed for composition of its monoterpenoids. The monoterpenoids were composed primarily of α-pinene, camphene, β-pinene, β-phellandrene and bornyl acetate, with tricyclene, 3-carene, myrcene and limonene in secondary quantities. Camphene, present in larger amounts in A. grandis and in smaller amounts in A. concolor var. lowiana, was used as a marker for studying intergradation of the two species in western and northwestern United States. A. grandis from northern Montana, Idaho and Washington, from British Columbia and Oregon and from Washington coastal areas could be classified as typical while the rest of the populations showed various degrees of intermediacy. The variability patterns agreed with the hypothesis that introgressive hybridization was the main reason for the intermediacy. Compared with morphological evaluations, the intermediate populations were chemically significantly more A. concolor-like. Typical A. grandis exhibited little population-to-population variability, in spite of its large geographic range. The results are correlated with and explained on the basis of existing paleobotanical records.     

The genus Juniperus in Mexico and Guatemala: Numerical and chemosystematic analysis

The variation leaf constituents (mostly terpenoids) was analyzed from each of the taxa of Juniperus in Mexico and Guatemala by numerical taxonomic methods. These results were compared with those of a previous study utilizing morphological characters. In general, the two agree on the major groups. Differences between more closely related species were more apparent with the chemical data, whereas more distantly related taxa sometimes appeared to be more closely related chemically due to the presence of a single component such as α-pinene in high concentration in each of the oils. Four large groups are apparent; the deppeanan; flaccidan; monticolan; and the oneseeded (pinchotii) complex. Some taxa (J. durangensis, J. standleyi, J.jaliscana) are still of uncertain affinities. This study confirms the morphological data indicating that J. patoniana Martínez should be reduced to a variety of J. deppeana (J. deppeana var. patoniana (Martínez) Zanoni, comb. et stat. nov). No samplestypical of J. monosperma were found in Mexico and J. monosperma var. gracilis (sensu Martinez) was found to not be closely allied with J. monosperma from the USA but has some uncertain affinities with species of the one-seeded complex. These relationships need to be examined in more detail. J. blancoi appears to be closely related to J. scopulorum. This information on the junipers of Mexico and Guatemala should prove invaluable to future studies on the evolution of the Juniperus in North America.     

Iridoid and other constituents of Canthium subcordatum

The main constituent of the stem bark of Canthium subcordatum was found to be shanzhiside methyl ester, an iridoid recently described for two Mussaenda species; it is accompanied by the new iridoid shanzhisin methyl ester gentiobioside. No alkaloids were detected.     

A comparative study of the flavonoids of Medicago radiata with other Medicago and related Trigonella species

The flavonoid glycosides of Medicago radiata as well as M. arabica, M. polymorpha, M. sativa, Trigonella coerulescens, T. foenum-graecum and T. spicata were studied in detail. Major glycosides identified were the 7-glucuronides of apigenin, luteolin, chrysoeriol and tricin, as well as lesser amounts of di- and triglucuronides of chrysoeriol and tricin. Also identified were the 3-robinobioside and 3,7-diglucoside of kaempferol, along with lesser amounts of quercetin-3,7-diglucoside, 4′,7-dihydroxyflavone, 3′,4′,7-trihydroxyflavone, formononetin and daidzein. Twelve other Medicago and Trigonella species were also studied for their flavonoid aglycones. The systematic position of M. radiata is discussed.     

Flavonoid glycosides and the chemosystematics of Eucalyptus camaldulensisis

Leaf flavonoid glycosides of Eucalyptus camaldulensis were identified as kaempferol 3-glucoside and 3-glucuronide; quercetin 3-glucoside, 3-glucuronide, 3-rhamnoside, 3-rutinoside and 7-glucoside, apigenin 7-glucuronide and luteolin 7-glucoside and 7-glucuronide. Two chemical races were observed based on the flavonoid glycosides. These races correspond to the northern and southern populations of species growing in Australia. The Middle Eastern species examined were found to belong to the southern Australian chemical race. The major glycosides of E. occidentalis proved to be quercetin and myricetin 3-glucuronide.     

A chemotaxonomic study of Brassica oleracea with particular reference to its relationship to Brassica alboglabra

A chemotaxonomic study has been made of Brassica oleracea L., its horticultural varieties and Brassica alboglabra Bailey with reference to seed proteins, certain isoenzymes and isothcioyanates. The results of the investigation do not support separate species status in respect of B. alboglabra.     

Effects of precursors on serially propagated Digitalis lanata leaf and root cultures

Serially propagated Digitalis lanata leaf and root cultures established from germinated seeds were studied for digoxin production. Leaf cultures were grown and maintained in a medium containing benzyl adenine, and root cultures in the same medium with indoleacetic acid. A consistently high digoxin content, as determined by radio-immunoassay, is present in the leaf culture (9.0 mg % dry wt) and in root culture (1.9 mg % dry wt) as compared to unorganized cells (0.06 mg % dry wt). Leaf liquid cultures grew very rapidly as compared to the root cultures and the unorganized cell suspension cultures. The concentration of digoxin increased in both leaf and root cultures by adding to the medium either sodium glycocholate, cholesteryl acetate, or progesterone. Smilageninacetate increased the digoxin content of root cultures but not that of leaf cultures. Lanosterol and 5β-androstan-3,17-dione did not significantly increase the concentration of digoxin. Deoxycholic acid was toxic to the tissues studied.