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The Geography of Phytochemical Races

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118 2 Examples Within Continents<br />

Table 2.21 Distribution <strong>of</strong> kaempferol and quercetin glycosides in Cnidoscolus spinosus (after<br />

Kolterman et al., 1970)<br />

Population No. b Kaempferol glycosides Q-Glysa GAL GLC RHM RGR RUT RHM RUT<br />

Northwestern 3 0c 0 3 3 3 1 0<br />

Central 3 2 2 1 2 2 1 1<br />

Southeastern 2 0 0 0 2 0 1 2<br />

a Q = quercetin; Glys = glycosides; GAL = galactoside; GLC = glucoside; RHM = rhamnoside;<br />

RGR = 3-O-rhamnosylgalactoside; RUT = rutinoside.<br />

b Number <strong>of</strong> populations sampled.<br />

c Number <strong>of</strong> populations exhibiting the compound.<br />

in the middle <strong>of</strong> the range possessed all <strong>of</strong> the compounds observed in the species,<br />

with reduction in numbers in both the southeastern and northwestern populations.<br />

<strong>The</strong> authors suggested that range expansion in both directions from ancestral populations<br />

in the middle <strong>of</strong> the present distribution could account for the observed pr<strong>of</strong>i les.<br />

Sample size is a problem in this study, as noted by the authors.<br />

2.7.22 Cupressus (Cupressaceae)<br />

Zavarin et al. (1967b) described the occurrence <strong>of</strong> tropolone derivatives, sevenmembered<br />

ring compounds, in species representing both the Old World and New<br />

World members <strong>of</strong> Cupressus, the true cypresses. Owing to the diffi culty <strong>of</strong> acquiring<br />

samples <strong>of</strong> these heartwood constituents, coupled with diffi culties in purifi cation<br />

and analysis, sampling was very limited. Nonetheless, suffi cient differences<br />

between populations were noted to suggest that a wider sampling using more conservative<br />

sampling methods, allied with more sensitive analytical techniques, might<br />

provide useful insights into relationships within the genus. Two examples serve<br />

to illustrate the variety <strong>of</strong> structures involved, and hence biosynthetic step differences<br />

between populations. Cupressus sargentii Jepson occurs from Santa Barbara<br />

County in the south to Mendocino County in the north (Fig. 2.74) and is felt by<br />

some workers to exist in two forms, one coastal and one from inland. <strong>The</strong> inland<br />

form was shown to accumulate four compounds, nootkatin [237] as a major component<br />

(see Fig. 2.75 for structures 237–241), β-thujaplicin [238] and β-thujaplicinol<br />

[239] as lesser components, and β-dolabrin [240] as a trace component. <strong>The</strong> coastal<br />

form exhibited the simpler pr<strong>of</strong>i le, in that it lacks β-thujaplicinol and β-dolabrin.<br />

<strong>The</strong> two forms share the capacity to make both the basic terpene-derived tropolones,<br />

as well as the sesquiterpene-derived tropolone nootkatin, but differ in the oxidation<br />

level <strong>of</strong> the tropolone ring.<br />

Two collections <strong>of</strong> C. arizonica Greene also exhibited differences involving the<br />

same set <strong>of</strong> compounds: a sample from Mexico afforded β-thujaplicin as a minor<br />

component and nootkatin, whereas a specimen from the Chiricahua Mountains in

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