A chemosystematic study of Veronica: Iridoid glucosides

Caffeoyl-catalpol, isoferuloyl-catalpol, protocatechuoyl-catalpol, benzoyl-catalpol, p-hydroxybenzoyl catalpol (catalposide), vanilloyl-catalpol and cinnamoyl-aucubin have been isolated from several Veronica species (Scrophulariaceae) in a more or less pure state. The first four compounds have never been recorded in plants before. A PC survey of forty-three species of the genus sensu lato has shown a general presence of aucubin and catalpol. They are accompanied in many of the species by a complex mixture of esters, especially esters of catalpol with aromatic acids. In only one species have aucubin esters been found. Loganin has been identified in five species, this being the first time that this compound has been found in the Scrophulariaceae. Loganin is accompanied by unidentified loganin esters in the same five species. From the systematic point of view the complex mixtures of esters of catalpol in Veronica seem to be noteworthy. Species of Globularia, Erinus, Scrophularia Verbascum, Wulfenia, Catalpa and Plantago investigated either totally lacked ester glucosides in leaves or contained mainly different types of esters. The possible systematic meaning of these results is briefly discussed.     

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.     

Systematic implicationsofflavonoid patterns in Haplopappus segregates

Complex flavonoid patterns are correlated with primitive woody taxa and high base chromosome numbers among Haplopappus segregates. Variability among flavonoid complements supports the polyphyletic interpretation of the genus.     

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.     

Flavonoid variation in Xanthisma texanum: Infrapopulation and interpopulation variation

Fourteen flavonoids were isolated from Xanthisma texanum. Chemosystematic interpretations are made concerning the origin and distribution of the infraspecific taxa of the species.     

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.     

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.     

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     

Flavonoids of the Muhlenbergia montana complex

Specimens from natural populations of Muhlenbergia montana (Nutt.) Hitch. and related species were analysed for their flavonoid content. Twenty-four flavonoids from 14 species were separated and 22 of the compounds identified. Most were glycosylated derivatives of luteolin, apigenin and tricin. Two flavonols, quercetin 3-O-rutinoside and quercetin 3-O-glycoside, and two flavanones were also identified. Flavonoid patterns were distinct for all perennial species and identical for the two annual species examined. Phenetic analysis of the flavonoid characters does not support the inclusion of the annual species M. crispiseta and M. peruviana as part of the M. montana complex.     

Chemosystematics of the hydrophyllaceae: Flavonoids of three species of eriodictyon

Eleven flavonoids, nine aglycones and two glycosides were isolated from Eriodictyon tomentosum, E. angustifolium and E. Californicum. Aglycones included the flavanone homoeriodictyol, the flavones apigenin, luteolin, chrysoeriol, 6-methoxyapigenin, 6-methoxyapigenin 7-methyl ether, 6-methoxyapigenin 4′-methyl ether, 6-methoxyluteolin and 6-methoxyluteolin 3′-methyl ether, glycosides were the 3-O-glucosides of quercetin and kaempferol.     

Flavonoids and the evolution of the angiosperms

Data on the distribution of flavonoids in the angiosperms are summarized and patterns of occurence are shown to be related to plant evolution. Different flavonoid types are regarded as primitive or advanced characters on the basis of biosynthetic complexity and on correlated frequencies of occurrence with morphological and anatomical features. The evolutionary significance of distribution patterns of proanthocyanidins, glycosylflavones, biflavonoids, 6- and 8-hydroxyflavonoids and anthocyanins is discussed in turn. The importance of these various distribution patterns is considered in relation to an ecological function for these flavonoids.     

Flavonoids of artificial interspecific hybrids in Lasthenia

The flavonoids of artificial interspecific hybrids in Lasthenia indicate differences in inheritance patterns among various classes of these compounds. Inheritance of production of anthochlors, kaempferol, and some patuletin glycosides is additive. Inheritance of production of luteolin and quercetin glycosides is not always additive, and in some progenies quercetin glycosides are produced that do not occur in the parents.     

Prasinoxanthin—a chemosystematic marker for algae

A new coccoid marine alga (clone Ω 48-23) contained chlorophylls a and b and carotenoids consisting of β,β-carotene (3% of total), β,ε-carotene (1%), zeaxanthin (2%), neoxanthin (21%), two minor unknowns (2 + 2%) and prasinoxanthin (69%). Prasinoxanthin is identical with xanthophyll K, previously considered characteristic of prasinophytes. From spectroscopic and chemical evidence prasinoxanthin is assigned the structure (3′R,-6′R)-3,6,3′ trihydroxy-7,8-dihydro-γ,ε-caroten-8-one, with tentative 3R,6R chirality from biogenetic considerations, thus representing the first algal carotenoid with a γ-end group. The structural relationship between prasinoxanthin and siphonaxanthin (ex Prasinophyceae and Siphonales) is discussed in chemosystematic terms.     

Phytoalexin induction and its chemosystematic significance in the genus Trigonella

Using the drop-diffusate technique, a number of isoflavonoid phytoalexins have been obtained from the excised, fungus-inoculated leaflets of 41 species belonging to the legume genus Trigonella. Leaf diffusates variously contained pterocarpan (medicarpin and maackiain) and isoflavan (vestitol and sativan) derivatives previously associated with genera closely allied to Trigonella. In diffusates from T. calliceras, medicarpin was accompanied by a phytoalexin (designated TC-1) provisionally identified as a new hydroxylated pterocarpan. Most of the Trigonella species were also examined for their ability to release coumarin upon tissue maceration. The combined phytoalexin/coumarin data suggest that three major intrageneric chemical divisions occur in Trigonella; two of these apparently link the genus to Medicado/Factorovskya and Melilotus respectively, whilst the third provides some evidence for a connection with Trifolium. The taxonomic aspects of these findings are discussed in the light of earlier morphological studies which provided evidence for a distinct floral dichotomy amongst Trigonella species.     

Unusual iridoid glycosides in Veronica sects. Hebe and Labiatoides

In a chemosystematic investigation of three Southern hemisphere species of Veronica, namely the Australian Veronica derwentiana Andrews and Veronica perfoliata R.Br. (formerly Derwentia species), and the New Zealand Veronica catarractae G. Forster (formerly a species of Parahebe), the water-soluble constituents were isolated and identified by spectroscopic methods. Apart from other iridoid glucosides common to the genus, three unusual substituted benzoyl esters of aucubin (derwentiosides A–C) were obtained from V. derwentiana and a chlorinated iridoid glycoside (catarractoside) from V. catarractae in addition to other iridoids common to the genus. The chemical profile of V. perfoliata is similar to that of Northern hemisphere species of Veronica because of the presence of characteristic 6-O-catalpol esters. The profile of V. derwentiana is unique, since 6-O-esters of aucubin rather than of catalpol dominate, however, the acyl groups are the same as those present in catalpol esters found in some other Veronica sections. V. catarractae also contains one of the catalpol esters characteristic of Veronica, but in addition three 6-O-rhamnopyranosyl substituted iridoid glycosides, one of which is 6-O-rhamnopyranosylcatalpol. Esters of the latter compound are previously only known from the more derived species in recent phylogenetic trees of sect. Hebe to which V. catarractae now also belongs, but as a more basal member.     

A cyclohexadienone and a cyclohexenone from halleria lucida

Two new compounds, a cyclohexadienone, hallerone and a cyclohexenone, halleridone, were isolated from Halleria lucida. Their structures were established on the basis of spectroscopic data and by chemical behaviour. Hallerone was converted into halleridone.     

Flavonoids from Elaeodendron balae root bark

The root bark of Elaeodendron balae afforded ourateacatechin, ouratea-proanthocyanidin A and a new leucoanthocyanidin derivative elaeocyanidin.     

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.