The Geography of Phytochemical Races

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188 4 Intercontinental Disjunctions Western Australia, as one might have expected. This observation was in agreement with conclusions drawn on the basis of morphological differences (Ornduff, 1974). 4.2.4 Icacinaceae One of the most serious contributors to chemical ecology-chemical geography has been the Brazilian natural product chemist Otto Gottlieb (see Gottlieb and Kubitzki, 1983; Gottlieb, 1986, 1990). It has been his goal to examine chemical profi les of target taxa, not just from the point of view of presence or absence of a suite of compounds, but rather to investigate the levels of complexity involved in the processes by which the compounds are elaborated. Among other things, his work has involved searches for regular changes in oxidation level of a set of compounds, or for situations where there has been a switch between different biochemical pathways (e.g., shikimate to acetate/malonate), or differences in the way plants protect component compounds from degradation. Following these analyses is not always easy, with point scores being tallied for certain structural aspects within each class of compounds and the calculation of various indices of evolutionary advancement. Detailed consideration is given to the steps involved in forming end products, with recognition given not only to compounds that are specialized or “advanced” because they have had substituents added to the base structure, but also to those that have been modifi ed in ways that make them appear simpler then the base structure, that is, the loss of a functional group originally present. An example of this is seen below, where loss of a carbon atom through oxidation leads to a derived (advanced) molecule. The example to be described, admittedly one whose chemistry is diffi cult, is, nonetheless, typical of the approach. In the case of Icacinaceae, Kaplan et al. (1991) studied the increase in complexity of terpenoid compounds of selected members of the family as a function of where, in the geographic range of the family, the various genera occur. Although the work was set in a taxonomic context—using chemical features to assess the proper placement of the family—our interest lies in the chemical changes that appear to be associated with geography. Icacinaceae are a moderate-sized, primarily tropical family consisting of 52 genera, many of which are monotypic, and 300 species. Additional background on taxonomic problems surrounding the family can be found in the 1991 paper by Kaplan et al. Chemical data have been used by Dahlgren (1980) to assess these relationships with related families, but the application involved simple presence or absence data (iridoids) and did not touch upon the dynamic nature of the pathways involved. The genera and relevant chemistry of Icacinaceae involved in this example are given in Fig. 4.8, using the format of Kaplan et al. (1991) wherein the four sets of genera, grouped according to chemical similarity, are listed according to geographic areas. The geographic areas represented range from eastern Australia (Queensland) westward through Melanesia, southeastern Asia, India, and Africa to South America.
4.2 Across the Indian Ocean (Primarily) 189 Fig. 4.8 Compounds 324–331, terpenoids and alkaloids from some Icacinaceae Group 1 consists of Apodytes from Queensland, the monotypic Cantleya, native to Borneo, Malaysia, and Sumatra, and Lasianthera from New Caledonia. The terpenoid chemistry of this group is comparatively simple with cantleyoside [324], an ester of loganin and secologanic acid, and cantleyine [325], an artifact obtained from the former, having been isolated from all three genera. Group 2 genera, for which appropriate data are available, are Merriliodendron, a monotypic genus, from Malaysia, Melanesia, and Micronesia, Nothapodytes and the “distantly related” Cassinopsis from India. The compounds from Group 2 are more complex, having
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The Geography of Phytochemical Race
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Dr. Bruce A. Bohm 3685 West 15th Av
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Acknowledgments I thank many worker
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x Abstract which biosynthetic step
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xii Zusammenfassung Leider wurden n
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xiv Contents 2.3.11 Thymus (Lamiace
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xvi Contents 4 Intercontinental Dis
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xviii Contents 6.8 Kerguelen Island
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2 1 Introduction It is useful to me
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4 2 Examples Within Continents Fig.
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Chapter 3 After the Ice According t
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3.1 North America 127 Fig. 3.1 Comp
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3.1 North America 129 7-O-glucoside
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3.1 North America 131 been found to
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3.1 North America 133 structural ty
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3.1 North America 135 Two species c
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246 6 Oceanic Islands Fig. 6.1 Loca
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248 6 Oceanic Islands Fig. 6.2 Comp
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250 6 Oceanic Islands levels of spe
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254 6 Oceanic Islands Compound Chem
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256 6 Oceanic Islands been cytogene
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264 6 Oceanic Islands Fig. 6.8 Map
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266 6 Oceanic Islands (formerly the
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272 6 Oceanic Islands A single popu
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286 7 Polar Disjunctions and variet
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288 7 Polar Disjunctions Fig. 7.2 C
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290 7 Polar Disjunctions Fig. 7.3 C
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292 7 Polar Disjunctions (1978), an
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294 7 Polar Disjunctions Table 7.1
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296 7 Polar Disjunctions occurs thr
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Chapter 8 Conclusions Some years ag
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302 Bibliography Amico, V., Caccame
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304 Bibliography Bennett, K. D. 199
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306 Bibliography Caccamese, S., R.
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308 Bibliography ———, Hussain
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310 Bibliography Del Pero Martinez,
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312 Bibliography ——— 1987. A
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314 Bibliography ———. 1878. F
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316 Bibliography Herz, W. and Kumar
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318 Bibliography Jutila, H. M. 1996
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320 Bibliography Levin, D. A. 1976.
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322 Bibliography Masuda, M., Abe, T
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324 Bibliography ———. 1966. A
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326 Bibliography Prus-Glowacki, W.
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328 Bibliography Sanders, R. W. 197
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330 Bibliography ———, Morgan,
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332 Bibliography Takhajan, A. 1969.
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334 Bibliography von Rudloff, E. 19
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336 Bibliography ———, Koenig,
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Plant Family Index Algae Codiaceae,
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Plant Genus Index Algae Chondrococc
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Plant Genus Index 343 Bryophytes (l
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346 Subject Index Cyanogenesis, gen
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348 Subject Index Romania, 36 Rooib
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The Geography of Phytochemical Races

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