Phytochemistry

Phytochemical data in taxonomy have inherent appeal by offering

a look at relationships of plants via internal characters and at still

another level of structural organization. Secondary metabolites

(e.g., alkaloids and terpenoids) also have major ecological roles

in the relation of plants to their environment. Certain kinds of

phytochemical data, therefore, are likely to be of value in determining

phylogeny, whereas others are of even greater value in understanding

predator-prey and other ecological relationships. Through it all,

phytochemical characters have continued to prove valuable in

helping solve different kinds of taxonomic problems. It is clear

that phytochemistry is here to stay as a source of comparative data

for understanding relationships, but it also must be recognized

that interest in these data has fl agged considerably in the face of

mushrooming DNA data.

History of Phytochemistry in Plant Taxonomy

One might suggest that the history of phytochemistry in plant

classifi cation dates back to the earliest Materia Medica of Dioscorides

(ca. 300 B.C.). Here and into the later age of the herbalists (1470–1670),

plants were grouped in part on their medicinal properties, which

obviously derived from chemical substances (Gibbs 1963). For

serious use of phytochemistry in plant classifi cation, however

one of the earliest studies must be that of Abbott (1886). She

examined the distribution of saponins (triterpenoids or steroids)

in plants and made several useful (although naive by

our standards) general assertions about the role of chemical

data in evolutionary studies. The early work of Reichert (1916,

1919) on starches must be mentioned as also should that on

terpenoids of Eucalyptus by Baker and Smith (1920). Mez and

coworkers (1922) in Konigsberg, Germany, carried out a series

of innovative serological studies on plant relationships, but the

affinities so demonstrated among the angiosperms were so

controversial and criticized by workers that few people took

the results seriously. By modern standards, we view the work

as technically flawed. This actually hindered legitimate serological

efforts in plant taxonomy until more recently. McNair

(1934, 1935, 1945) published a remarkable series of insightful

papers on the taxonomic and ecological roles of alkaloids,

cyanogenetic, and sulphur compounds. Mirov (e.g., 1948)

contributed many papers on terpenes in Pinus and their taxonomic

significance. The early review on taxonomy and chemistry

of plants by Weevers (1943) also should be noted.

Despite these and other early suggestive studies, the direct

and more general application of phytochemical data to taxonomic

problems did not appear until the mid-1950s. Hegnauer

(1954, 1958) from the Netherlands was an early contributor,

and he used the term chemotaxonomy in his writings. Bate-

Smith from England pointed out (1958) the potential of phenolics

in classification. Many genetic and phytochemical studies

were published in the latter part of this decade, but the most

influential with a direct taxonomic focus were those from R.

E. Alston and B. L. Turner of the University of Texas at Austin.

They began with examination of flavonoids in Baptisia (Leguminosae)

especially to help in interpreting complex patterns of

hybridization. This proved a good system to analyze because

the morphological differences among the species were as striking

as the flavonoid markers. The publication in 1963 of their

book, Biochemical Systematics, was an important step in drawing

attention to the field and helping to consolidate it. Establishment

of the Phytochemical Society of North America (preceded

by the Plant Phenolics Group of North America) and

the Phytochemical Section of the Botanical Society of America

were also important steps at this time. In England, Tony Swain

of Cambridge was very active, as demonstrated by his edited

books Chemical Plant Taxonomy (1963) and Comparative Phytochemistry

(1966), as was Jeffrey Harborne of the University of

Reading with his Comparative Biochemistry of the Flavonoids

(1967) and Phytochemical Phylogeny (1970). Serology also

made an early comeback as evidenced by the books of Leone,

Taxonomic Biochemistry and Serology (1964) and Hawkes, Chemotaxonomy

and Serotaxonomy (1968). For good historical

overviews, see Crawford (2000) and Harborne (2000).

From these beginnings has come a wide variety of books

and papers on uses of phytochemistry in plant classification,

all falling under the labels of chemotaxonomy, chemosystematics,

biochemical systematics, or taxonomic biochemistry. Once

again, it is impossible here to review all the literature and

types of compounds potentially useful in solving taxonomic

problems. The in-depth review by Giannasi and Crawford

(1986) is recommended; the overview in this chapter has

drawn heavily from that paper.

General Phytochemical and

Chemotaxonomic Texts and References

A few books and general reviews might be cited here to give

an indication of the resources available on selected topics of

chemotaxonomic interest. General texts include those of Smith

(1976), Ferguson (1980), Gottlieb (1982), and Harborne and

Turner (1984). Symposia volumes of a general chemosystematic

scope include those edited by Swain (1963), Bendz and Santesson

(1974), Averett (1977), Bisby, Vaughan, and Wright (1980),

and Goldstein and Etzler (1983). General literature reviews include

those by Alston, Mabry, and Turner (1963), Alston (1965,

1967), Turner (1967, 1969, 1974, 1977a), Erdtman (1968),

Throckmorton (1968), Fairbrothers et al. (1975), Harborne

(1984a, 2000), Kubitzki (1984), Reynolds (2007), and Waterman

(2008). Phytochemical phylogeny has been addressed directly

in the symposium volumes edited by Harborne (1970)

and Young and Seigler (1981). Ecological aspects of phytochemistry,

especially in plant-animal interactions and coevolution,

have been covered by Chambers (1970), Harborne (1977,

1978), and Rosenthal and Berenbaum (1992). Books dealing

with general surveys of plant secondary metabolites and their

biochemistry include those of Geissman and Crout (1969), Bell

and Charlwood (1980), Robinson (1980), Goodwin and Mercer

(1983), Harborne (1984b), and Wink (1999a). Medicinal plants

have been treated by Frohne and Jensen (1998) and Cseke et al.

(2006), as well as in the earlier work of Tetenyi (1970), which

also dealt with chemistry of infraspecific taxa. Compendia

of what compounds have been reported previously in which

taxa have been compiled by Hegnauer (1962–1996) and Gibbs

(1974). Phytochemical surveys of selected, large, plant families

have been included in symposia on Compositae (Heywood,

Harborne, and Turner 1977; Hind and Beentje 1996) plus an

in-depth survey of the flavonoids in that family (Bohm and

Stuessy 2001), Labiatae (Harley and Reynolds 1992), Leguminosae

(Harborne, Boulter, and Turner 1971), Rutaceae (Waterman

and Grundon 1983), Solanaceae (D’Arcy 1986), and Umbelliferae

(Heywood 1971a). Macro- and micromolecules have

been surveyed for the fungi (Frisvad, Bridge, and Arora 1998).

Biochemical prospecting was reviewed by Seidl, Gottlieb, and

Kaplan (1995). Serological techniques have been discussed by

Leone (1964), Hawkes (1968), and Jensen and Fairbrothers

(1983), and chromatographic methods by Robards, Haddad