Bruce A. Bohm

University of British Columbia - Vancouver | UBC · Department of Botany

Umbelliferone and a new monohydroxymonomethoxycoumarin have been isolated from Hydrangea macrophylla Ser. The new coumarin has been shown to be a derivative of daphnetin. It is present largely in a bound form in all parts of the plant and is especially abundant in the roots. Chromatographic characteristics of the compound as well as those of severa...

Flavonoid profiles were determined for 11 species representing five genera of Calyceraceae: Acicarpha, Boöpis, Calycera, Gamocarpha, and Nastanthus. Kaempferol, quercetin, 6-methoxykaempferol, and 6-methoxyquercetin (patuletin) were unequivocally identified. Kaempferol and quercetin occurred as 3-O-mono- and 3-O-diglycosides, whereas the latter two...

Seventy-three taxa of the genus Lupinus in North America have been studied for their flavonoid constituents. In all, 56 compounds were isolated and either partially or totally characterized. Flavonoid types encountered were flavones, C-glycoflavones, isoflavones, flavonols, and, tentatively, flavanones. Further structural modifications seen were O-...

Flavonoid profiles have been determined for all nine species of Lithophragma recognized by R. L. Taylor. Kaempferol, quercetin, isorhamnetin, and myricetin occurred in various combinations of 3-mono-, 3-di-, and 3-tri-glycosides, 3,7-diglycosides, and 7-monoglycosides although not all taxa had all such derivatives. The dihydrochalcone glucoside phl...

Two putative intergeneric hybrids between Tolmiea menziesii and Tellima grandiflora were discovered in Oregon and Washington. These plants are morphologically intermediate in several floral features between the presumed parental taxa. Evidence from flavonoid chemistry and karyology support the contention that these plants are of intergeneric hybrid...

Flavonoid profiles have been determined for 16 species of Mitella and for the two monotypic genera, Bensoniella and Conimitella. With a single exception the profiles are based upon the flavonols kaempferol, quercetin, and myricetin. The flavanone eriodictyol was seen in two Japanese species of Mitella. The flavonols exist as a series of 7-O-mono-,...

Sixty flavonoids were isolated from aerial parts of Heuchera micrantha var. diversifolia and identified. The flavonoid aglycones represented were kaempferol, quercetin, isorhamnetin, myricetin, laricytrin (myricetin-3′-O-methyl ether), syringetin (myricetin-3′,5′-di-O-methyl ether), and luteolin. Flavonol glycosylation patterns included 3-O-monogly...

Thirty-three flavonoids have been isolated from Heuchera cylindrica Dougl. var. glabella (T. & G.) Wheelock and at least partially identified. The flavonols kaempferol, quercetin, isorhamnetin, myricetin, and syringetin and the flavone luteolin were found. The flavonols occur in a variety of glycosylated forms, monoglycosides, diglycosides, triglyc...

The flavonoid constituents of Heuchera villosa var. villosa, H. parviflora var. parviflora, and H. glabra have been studied. The predominant flavonoids present in all three species were mono-, di-, and triglycosides of kaempferol, quercetin, and myricetin. Isorhamnetin, larycitrin, syringetin, and luteolin were also seen in some species. Dihydromyr...

The phenolic compounds in leaf material of 52 taxa of the Caprifoliaceae representing 11 genera have been examined. The cyanogenetic glycoside sambunigrin was found to occur only in certain members of Sambucus. Chlorogenic acid isomers and simple phenolic acids were identified in all taxa examined; coumarins were of more limited distribution. The f...

The total flavonoid complement of leaves of Cladothamnus pyrolaeflorus Bong. (Ericaceae) has been determined. Four mono- and two di-glycosides of kaempferol and two mono- and two di-glycosides of quercetin were isolated and identified. The structures agree with compounds reported to occur in the family.

Twenty-seven flavonols were isolated from entire plants of Tellima grandiflora (Pursh) Dougl. Kaempferol and quercetin occurred as their 3-glucosides, 3-galactosides, 3-arabinosides, 3-rutinosides, and 4′-glucosides. Myricetin occurred as the 3-glucoside and 3-galactoside. Twelve acylated derivatives based upon the 3-glucosides and 3-galactosides o...

Forty-six ferns, representing 28 genera and 8 families, were examined for hydroxylated cinnamic acids and benzoic acids. In most plants examined the "basic complement" of cinnamic acids, p-coumaric, caffeic, and ferulic, was present. In these plants p-hydroxybenzoic acid, protocatechuic acid, and vanillic acid were generally also present. Of much m...

The phenolic acid pattern of 17 species of Impatiens is presented. The presence of naphthoquinone derivatives in four new species is reported. A discussion of some prominent unidentified phenolic compounds on two-directional chromatograms is presented which includes discussion of possible forms in which naphthoquinones may exist in the living plant...

This book provides an overview of geographic patterns in the distribution of plant secondary metabolites in natural populations. Examples include most common natural product classes: acetylenic derivatives; alkaloids; carotenoids; cyanogenic glycosides; flavonoids; terpenes of various sizes; as well as other structural types less easily categorized...

th birthday. Our laboratory's study of Lasthenia (Asteraceae) began with an examination of flavonoid profiles of all species of the genus. The finding of two distinct flavonoid races within the L. californica complex led us to investigate environmental factors that might have been responsible for selection of these particular forms. Data were gathe...

Investigation of lipophilic exudates from the aerial parts of Balsamorhiza sagittata and B. macrophylla afforded three new highly oxygenated guaianolides (1-3), in addition to known guaianolides, germacranolide and eudesmane acids. Their chemical structures were elucidated by spectroscopic methods and the data for the compounds are reported in Tabl...

The total flavonoid complements of Erythroxylum rufum and E. ulei have been determined. Erythroxylum rufum contains kaempferol and quercetin-3-O-mono- and diglycosides and ombuin-3-O-rhamnosylglucoside. Ombuin is quercetin-7,4′-dimethyl ether and has been found in other Erythroxylum species. Erythroxylum ulei makes kaempferol, quercetin, and myrice...

Leaf glands of Ceanothus species excrete a lipophilic material that contains a variety of flavonoids. Most of these are aglycones, but some glycosides were also observed. Seven out of eight species exhibit flavonols, whereas flavones are excreted by only one species. Four species produce flavanones and dihydroflavonols; one excretes a remarkable qu...

Lasthenia californica sensu Ornduff consists of two races that differ in their flavonoid pigments and edaphic tolerances. Recent phylogenetic studies of Lasthenia have revealed that members of L. californica sensu Ornduff belong to two phylogenetic species. The relationship of the edaphic races to these new species and to each other is the focus of...

Two edaphic races of Lasthenia californica sensu Ornduff (races A and C) grow in parapatry on a serpentine outcrop at Jasper Ridge Biological Preserve, California. The races occupy distinct edaphic habitats that have different water-holding capacities. We predict that the two races will show differentiation in reproductive strategies related to the...

Summary • Sodium, potassium, calcium, and magnesium ion uptake physiology and tolerance to sodium and magnesium were characterized in two edaphic races (A and C) of two closely related species in the Lasthenia californica complex. • Uptake rates of race A plants were 20-fold higher for Na+, and 2-fold higher for Ca2+ and Mg2+ than those of race C p...

Individual plants of Glehnia littoralis (Apiaceae) collected at four coastal sites in western North America (California, Oregon, Washington and British Columbia) were surveyed for their furanocoumarin and polyacetylene patterns and compared with those from plants collected in Japan. The rhizomes accumulated considerable amounts of two polyacetylene...

This study explored the soils and vegetation of four of the five known ultramafic sites in Sri Lanka. Soil chemical and physical features were typical of ultramafic substrates. A preliminary taxonomic survey identified 45 species of angiosperms, none of which is endemic to the island or restricted to ultramafic soils. However, populations of severa...

Norlindh (1977) reckoned that Calenduleae are composed of only eight genera. With some taxonomic adjustment the tribe is still thought to comprise eight genera (Nordenstam, 1994, 1996). Within Bremer’s (1994) treatment of the family, Calenduleae are one of the smallest tribes with about 110 species. Flavonoid data are available for a single species...

Although Karis and Ryding (1994a) treat genera representing Tageteae as subtribe Pectidinae of resurrected tribe Helenieae (here treated within Heliantheae s.l., Chapter 11), we prefer to list it in this book as a distinct tribe following Strother (1977). Robinson (1981) elected to include these closely related genera as subtribe Pectidinae of trib...

In the earlier days of the 20th Century it was often suggested that plant secondary metabolites, flavonoids included, represented waste materials of plant metabolism. It was also suggested, light-heartedly one assumes, that the major use of these compounds was to challenge the ingenuity of natural product chemists! Even after functions had been ide...

According to Heywood and Humphries (1977), Anthemideae consist of 101 genera with about 1400 species. Bremer and Humphries (1993) see the tribe as comprising 109 genera with 1741 species. Bremer (1994; followed by Arriagada and Miller, 1997) lists 109 genera and 1740 species. We have found flavonoid information for members of 44 genera. By far the...

In this chapter we will present a brief overview of flavonoid biosynthesis, along with comments on genetic control of the various steps. Our goal is to demonstrate that the very considerable amount of information that has ac­cumulated on the formation and control of flavonoids in a variety of plant species applies equally well to the pathway in Ast...

In this chapter we examine flavonoid occurrence patterns at the subtribal level. Two problems plague us in our efforts to find patterns of flavonoids at this level. The first has been with us from the outset, but it appears to manifest itself most acutely in examining subtribes, namely, sampling error. There are vast gaps in our knowledge of flavon...

In this chapter we discuss patterns of flavonoid occurrence at the subspecific and varietal levels. There is no general agreement on how these two ranks should be used (e.g., Hamilton and Reichard, 1992), and we will not comment on this aspect of infraspecific taxonomy. For a detailed discussion see Stuessy (1990). Our sole interest here is to docu...

We concern ourselves in this chapter with a moderately detailed view of the flavonoid chemistry of Asteraceae. Attention will be given to the individual flavonoid types that have been reported, flavones, flavonols, flavanones, chalcones, and the like, and to the diversity of substitution patterns that underlie the richness of the family’s pigment p...

According to Jones (1977), Vernonieae consist of about 70 genera and something in excess of 1450 species. Bremer (1994) circumscribed the tribe to comprise 98 genera owing in part to new genera described by H. Robinson during the period 1987-1992 (See Bremer, 1994, for pertinent references), but his species count is around 1300. Robinson (1996a) in...

The study of natural hybridization using secondary metabolites, particularly flavonoids, attracted a good deal of attention following the pioneering work of Ralph Alston and his colleagues at the University of Texas. Sorting out the complex patterns in populations of hybridizing Baptisia species by morphological means alone was extremely difficult...

According to Cabrera (1977) Mutisieae, a largely South American tribe, comprise 89 genera with ca. 974 species. Bremer (1994) sees the tribe as comprising 76 genera with ca. 970 species, but he excludes the Barnadesiagroup of genera. Mutisieae as presented by Cabrera (1977) were apportioned into four subtribes: Barnadesiinae, Gochnatiinae, Nassauvi...

Grau (1977) considers that Astereae consist of 135 genera with about 2500 species, Bremer (1994) lists about 170 genera and nearly 3000 species, and Nesom (1994a) gives “at least” 189 genera and about 3020 species. The main centers of distribution are the Americas and southern Africa (Grau, 1977). Recent ITS sequence data suggest that the North Ame...

Bremer (1994) recognizes 98 genera and some 1550 species in his view of Lactuceae. Tomb (1977) listed only 70 genera but estimated the tribe as comprising about 2300 species. Our knowledge of the flavonoid chemistry of the tribe is based upon reports for 39 genera. Sampling is again a prob­lem, with many of these genera being represented in our dat...

It is the purpose of the present chapter to look at flavonoid occurrence patterns at the tribal level to see if any characteristic flavonoid feature or collection of features emerges. Since several major reassessments of tribal boundaries have appeared recently, we are presented with opportunities to examine the usefulness of flavonoids in arguing...

There has been ongoing debate over the years concerning tribal boundaries within Asteraceae and what the relationships among the tribes might be. Surprisingly, perhaps, much less attention has been given to the question of subfamilies. Any in-depth study of inter-tribal relationships, however, is bound to result in a grouping of tribes, a logical o...

In this chapter we present examples of the application of flavonoid distri­bution patterns to studying relationships among genera that are, or have been, the topic of debate in the literature. One of the guides used for select­ing examples to discuss in this context has been the taxonomic treatments of the various tribes presented by Bremer and his...

In this chapter we present summaries of the application of flavonoid chemistry to relationships among species within various genera. Some of the situations to be discussed involve extensively studied and well known genera, e.g., Achillea, Artemisia, Bidens, Coreopsis, Dahlia, and Parthenium. Other examples involve much smaller groups of species as...

According to the systematic review of Inuleae by Merxmüller et al. (1977), we are dealing with about 180 genera with some 2100 species. A quite different view of the tribe is held by Anderberg (1989, 1991a,b,c, 1994, 1996) who sees Inuleae sensu stricto as comprising 38 genera and about 480 species. He places the remaining genera in either Plucheea...

Nordenstam (1977) listed 100 genera in his systematic review of Senecioneae, but Bremer’s (1994) recent synthesis suggests 120. Even more recently, Nordenstam (1996) lists 123. The reason for the generic increase in the tribe stems mainly from segregates being pulled out of Senecio in a fashion similar to what has happened to Vernonia. The most act...

In addition to examination of presence and absence and frequencies of occurrence of flavonoid data in Asteraceae for purposes of testing subfamilial, tribal, and subtribal delimitations (Chapters 18–20), which comprised essentially a phenetic perspective, it is also appropriate to consider the data in a phylogenetic context. Use of flavonoids to in...

This chapter is designed to teach about biology and distribution of Asteraceae (or Compositae*) in a broad sense so that correlations drawn with flavonoid chemistry in other chapters of the book will be more meaningful. This is a difficult task; so much material on the family exists that it is impossible to present successfully (and succinctly!) al...

The tribe Heliantheae is one of the largest and most morphologically variable of Asteraceae. This size and complexity has led to two different subtribal classifications in recent years (Robinson, 1981; Stuessy, 1977), which in turn have stimulated detailed morphological cladistic analyses and discussions of the entire tribe (Karis, 1993b; Karis and...

It is our purpose in this chapter to talk about variation in flavonoid profiles among populations within species. Most workers recognize that chemical variants occur naturally, and that such differences may be grounds for additional studies, which may in time lead to formal recognition of infraspecific taxa. Infraspecific taxa based solely on chemi...

In the preceding chapters we attempted to bring together as much flavonoid occurrence data as possible in order to address the usefulness of the information in dealing with problems of relationships among various groups within Asteraceae. Flavonoid data have been very instructive in certain instances, particularly when dealing with situations at th...

The information in Chapter 1 offered an overview of the general biology of Asteraceae and their distribution. What has not been discussed are changing concepts of tribes and subfamilies, phylogeny, and biogeography of the family. These are the syntheses of information about groups and subgroups in space and evolutionary time. This chapter begins wi...

E. C. Bate-Smith, one of the great pioneers in the application of plant chemicals to taxonomic problems, once described flavonoids as "privileged compounds," (pers. comm) Flavonoids, more than any other secondary metabolite, best meet the requirements for use of chemicals in taxonomic studies: (1) structural diversity; (2) widespread occurrence; (3...

According to Robinson and King (1977) and King and Robinson (1987), Eupatorieae comprise approximately 2000 species arrayed in 180 genera. Bremer et al. (1994) recognize only 170 genera but put the species number nearer 2400. Before we proceed with description of flavonoids of the tribe, it is necessary to attend to some nomenclatural problems. One...

Flavonoids are secondary plant products that have previously been shown to be helpful in determining relationships among plant groups. This work presents comprehensively the occurrence, patterns of variation, and systematic and evolutionary importance of flavonoids in the sunflower family (Asteraceae), the largest family of flowering plants (23,000...

Transectional studies of Lasthenia californica in the Jasper Ridge Biological Preserve (Stanford University) have documented the existence of two races (A and C) based upon flavonoid chemistry, achene morphology, allozymes, and flowering time differences. The two races coexist on a serpentine outcrop and have maintained a sharply defined pattern of...

The 16 endemic Hawaiian species of Lysimachia are a monophyletic lineage that has radiated into a diversity of environments. Genetic diversity in 48 populations of eleven of the thirteen extant species was evaluated using starch gel electrophoresis of eight enzymes encoded by 11 loci. For the genus as a whole (i.e, the mean across all species) ther...

The flavonoid profiles of seven species ofAbrotanella and one species ofIschnea have been shown to be based upon kaempferol 3- and quercetin 3-O-glycosides and a delphinidin glycoside. Glucosides, glucuronides, arabinosides, diglucosides, and rutinosides of the flavonols were identified. The profile ofIschnea consisted solely of quercetin 3-O-gluco...

The flavonoid profiles of the two species of Pterostemon are identical and consist of C-glucosylflavones and 3-O-glycosides of quercetin. The C-glucosylflavone pattern resembles very closely that observed in Itea. The presence of C-glucosylflavones in these two genera provides additional support for the closeness of their relationship, which had be...

The flavonoid profiles of the two species of Pterostemon are identical and consist of C-glucosylflavones and 3-O-glycosides of quercetin. The C-glucosylflavone pattern resembles very closely that observed in Itea. The presence of C-glucosylflavones in these two genera provides additional support for the closeness of their relationship, which had be...

Flavonoids of 12 of the 13 extant species of Lysimachia (Primulaceae) endemic to the Hawaiian Islands were isolated and identified. Whenever possible, at least two populations were sampled. The flavonoid profiles consisted of various combinations of kaempferol, quercetin and isorhamnetin 3-O-mono-, di- and triglycosides, vitexin and isovitexin, and...

A taxonomic revision of the endemic Lysimachia of the Hawaiian Islands was undertaken with the goal of clarifying species boundaries, especially within the L. hillebrandii/L. remyi complex of the previous taxonomic treatment. The endemic species appear to be monophyletic with Malesian affinities. The revision presented here is based upon observatio...

A subcellular enzyme fraction (Mr>20 × 106) from immature sainfoin leaves catalysed the two-step NADPH-dependent reduction of ( + )-dihydromyricetin to ( + )-gallocatechin. No enzyme-mediated (−)-epigallocatechin was formed under the conditions employed, and only traces of 2R,3S-trans-3S,4S-cis-leucodelphinidin were observed. The two-step reductase...

When applied in a mixed inoculum with tomato ringspot nepovirus (TomRSV), flavonoids and related compounds inhibited infectivity in Chenopodium quinoa. Compounds that showed strong anti-viral activity were: quercetin, quercetin 3-methyl ether, quercetin 7-methyl ether, quercetin 3,7,3′4′-tetramethyl ether, galangin 3-methyl ether, morin, robinin, q...

Vacuolar flavonoids were investigated in Acer glabrum and compared to published data. The profile consists of two unidentified flavanones, two kaempferol 3-O-monoglycosides, two quercetin 3-O-monoglycosides, rutin and isorhamnetin. The presence of flavanones sheds new light on the relationship between A. glabrum and its supposed closest relatives....

The flavonoid profiles of some species of the following genera of the Barnadesioideae (Asteraceae) consist of mono- and diglycosides of kaempferol and quercetin: Arnaldoa, Barnadesia, Chuquiraga, Dasyphyllum, Doniophyton, Fulcaldea, and Schlechtendalia. These South American genera previously comprised part of the subtribe Barnadesiinae of Mutisieae...

This study examined variation in morphology and isozymes for 36 populations of Lasthenia californica representing the entire range of the species. These and previous results suggest the formation of two geographical races based on pappus shape, isozymes, and flavonoid chemistry. The races appear to coexist in a population examined in more detail (J...

The vacuolar flavonoid profile of Umbellularia californica consists of 3-O-mono-, di- and triglycosides of kaempferol, quercetin and isorhamnetin together with eriodictyol 7-O-glucoside. The leaf exudate contained no flavonoids but did exhibit a small amount of scopoletin. The two growth forms of this species, a shrubby form from dry habitats and a...

The exudate and vacuolar flavonoid profiles of four species (five taxa) of New Zealand Cassinia were established. The exudate chemistry consists of chalcones, dihydrochalcones and flavanones, several of which lack B-ring oxygenation, and quercetin 3-O- and 7-O-methyl ethers. Vacuolar flavonoids include galangin, eriodictyol-7-O-methyl ether, and a...

Starch gel electrophoresis was used to examine genetic variation in the two subspecies of Menziesia ferruginea from western North America and M. pilosa from the Appalachians. Genetic variation within and among populations of both species was less than expected for widespread long-lived woody perennials but was comparable to levels reported for outc...

The flavonoids and condensed tannins of Hawaiian Vaccinium reticulatum Smith and V. calycinum Smith have been isolated and their structures determined. Flavonoids present in both species were quercetin, quercetin-3- 0-glucoside, quercetin-3-0-galactoside, quercetin-3-0-methyl ether, isorhamnetin, and (-)-epicatechin. The condensed tannin contained...