Brittonia, 37(2), 1985, pp. 169-178. © 1985,by the New York BotanicalGarden, Bronx, NY 10458 CHEMOSYSTEMATIC STUDIES IN THE CHRYSOBALANACEAE. I. F L A V O N O I D S I N P A R I N A R I LIDIO CORADIN, DAVID E. GIANNASI, 1 AND GHILLEAN T. PRANCE Coradin, Lidio (Seq~o do Bot~nica, Centro Nacional de Recursos Gen6ticos, CENARGEN-EMBRAPA, Ave. W5 Norte (Parque Rural), Caixa Postal 102372, 70000-Brasilia-D.F., Brazil), David E. Giannasi (Department of Botany, University of Georgia, Athens, GA 30602), and GhiUean T. Prance (New York Botanical Garden, Bronx, NY 10458-9980). Chemosystematic studies in the Chrysobalanaceae. I. Flavonoids in Parinari. Brittonia 37: 169-178. 1985.--A survey of flavonoids in 31 Asian, African and Neotropical species of Parinari showed a predominance of flavonol glycosides based on myricetin, quercetin, and kaempferol. The African taxa split into two groups based on the presence or absence of myricetin glycosides. The Neotropical taxa, a complex of closely related species, are chemically very similar to each other and lack myricetin, as does one group of African species. The Asian taxa are similar to the Neotropical ones in their flavonoid patterns and lack of myricetin glycosides. The presence of myricetin, considered a primitive flavonoid character, suggests that the African species producing this flavonol represent a primitive nucleus from which a non-myricetin group may have evolved giving rise by subsequent eastward and westward expansion to two myricetin-lacking phytogeographic lines. This hypothesis is in agreement with current proposals for geographic evolution in the Chrysobalanaceae. W h e n first described by Aublet (1775), Parinari included two species, P. campestris a n d P. m o n t a n u m . As the genus grew it was allied to other chrysobalanoid genera but r e m a i n e d distinct in its possession o f bilocular carpels. T h e genus has grown with the discovery o f new taxa f r o m all three m a j o r tropical regions. Until recently it was a repository for all c h r y s o b a l a n o i d taxa with bilocular carpels, regardless o f their m o r e p r o p e r a s s i g n m e n t to newly recognized (e.g., Exellodendron Prance) or o t h e r established genera (e.g., Couepia Aubl., Hirtella L.). Parinari has been r e e x a m i n e d leading to a m o r e n a r r o w concept o f the genus a n d the C h r y s o b a l a n a c e a e as a whole, especially in the N e o t r o p i c s (Prance, 1967, 1972; Prance et al., 1969). T h e African species h a v e been discussed b y White (197 6b), Letouzey a n d White (19 7 6), C h a p m a n a n d White (19 70) a n d White and C h a p m a n (In prep.) a n d those in Asia b y K o s t e r m a n s (1965). A current review and circumscription o f the Chrysobalanaceae is also in progress (Prance & White, in prep.). O n the basis o f these studies a b o u t 35 taxa o f Parinari are currently recognized, the largest n u m b e r occurring in the N e o t r o p i c s with smaller groups in Africa a n d East Asia. Little or nothing is k n o w n o f the flavonoid chemistry o f Parinari or, for that matter, the C h r y s o b a l a n a c e a e in general. Earlier flavonoid aglycone surveys o f the Rosaceae (including the Chrysobalanaceae) showed the presence o f m y r i c e t i n in Chrysobalanus pellocarpus G. F. W. M e y e r (now C. icaco L.) a n d Licania rigida Benth., the two c h r y s o b a l a n o i d taxa e x a m i n e d (Bate-Smith, 1961, 1962). This flavonoid was f o u n d to be lacking in all other tribes o f the R o s a c e a e except the Rosoideae which suggested that a d o m i n a n t presence o f this flavonol in chrysobalanoid taxa m i g h t p r o v i d e a valuable c h e m i c a l m a r k e r delimiting the Chrysobalanaceae f r o m the Rosaceae (Harborne, 1967). Indeed, the suggestion that the true relationships o f the Chrysobalanaceae lie closer to the L e g n m i n o s a e (cf. H e y w o o d , 1971) derives s o m e tenuous support f r o m the presence o f myricetin and several 1To whom requests for reprints should be addressed. 170 BRITTONIA [VOL. 37 highly methylated derivatives in the Leguminosae (Gottlieb, 1975; Harborne & Williams, 1975). The presence of myricetin in Parinari (Giannasi et al., 1983) and several related genera suggests that it may be a common marker in the Chrysobalanaceae (Harborne, 1967). This work is the first in a series of studies describing the systematic and phytogeographic implications of flavonoids in the family. Materials and Methods Both leaves and flowers from herbarium specimens and dried field collections were sampled for chemical studies. Several collections of selected taxa were examined to test infraspecific variation and monitor the possibility of flavonoid profile alteration due to field collection techniques (cf. Coradin & Giannasi, 1980). The identity and geographic location of each sample are shown in Appendix I. Voucher specimens of each sample are at NY. Paper, thin layer, and column chromatographic studies of flavonoids of these plants followed the procedures of Mabry et al. (1970), Giannasi (1975), and Wilkins and Bohm (1976). Purification and UV spectral analysis of flavonoid glycosides and aglycones were carried out according to Mabry et al. (1970). Sugar analysis of the glycosides followed the procedures of Wilkins and Bohm (1976), and Giannasi and Mickel (1979). The identity of the flavonoid glycosides along with pertinent spectral data are listed in Table I. Results Twenty-five flavonoid spots (Table I) were recorded for the 31 species that were examined. Some of the compounds occurred in trace amounts or were sporadic in occurrence, often being restricted to a single population of a taxon. About 19 compounds occurred regularly and in quantities suitable for at least partial or complete identification. The distribution of all of the compounds is shown in Table II. Infraspecific flavonoid variation ranged from highly variable in P. excelsa (e.g., glycoflavone in some but not all African collections and absent in Neotropical collections) to very little in P. curatellifofia. A number of taxa were only available as single population (herbarium) samples and their flavonoid profiles are here treated only as tentative listings. The tables do, however, show that flavonols predominate, with several or more glycoside combinations, each of myricetin, kaempferol, and especially quercetin. Flavones (in the form of glycoflavone) are rare, occurring only in one species. While present in only four species of Parinari, the occurrence of myricetin glycosides adds the genus to the list of chrysobalanoid taxa which produce this flavonol. This limited occurrence of myricetin gains significance, however, when the phytogeography of the genus is examined in relation to the distribution of the compound. Parinari in Africa Six species are found in Africa (Appendix I) and a seventh in Madagascar. The systematics and biology of these taxa have been discussed in considerable detail by White (1976b) and elegant distribution maps are also available (White, 1976a; Prance, 1'979). Each of the six mainland taxa is morphologically distinct and while sympatric with one or more other taxa, is probably ecologically distinct as well. Based on the presence or absence of myricetin glycosides, however, two chemical groups may be recognized (Table II). The first consists of Parinari curatellifolia, P. ca- 19 8 5 ] 171 C O R A D I N ET AL." PARINARI TABLE I IDENTITY AND PERTINENT CHROMATOGRAPHIC AND SPECTRAL DATA OF FLAVONOIDS IN Compound No. Identity Solvent Colors Parinari" Spectral maxima" I I1 UV NH3 MeOH AIC13 HCI 361 258 361 255 352 257 . 355 b 314 355 b 314 355 256 332 b 291 332 b 228 345 256 358 256 359 256 348 267 356 257 347 258 351 266 . . 360 257 352 256 333 271 351 265 359 256 358 265 366 256 434 406 414 270 379 435 408 423 274 383 432 402 402 269 370 1. Q-3-O-arabinoside .51 .39 P YG 2. Q-3 -O-glucosylgalactoside .53 .48 P YG 3. Q-3-O-rharnnoside .64 .56 P G 4. 5. Unknown K-3,4-di-O-glycoside .67 .67 .42 .42 P P G G 6. K-3,4-di-O-glucoside .74 .36 P DG 7. Q-3-O-glycoside .58 .45 P G 8. T-3-O-xylosylarabinoside .80 .73 P P 9. T-3-O-arabinoside .83 .67 P P 10. K-3-O-triglycoside .40 .75 P G 11. Q-3-O-triglycoside .36 .69 P Y 12. Q-3-O-triglycoside .29 .63 P Y 13. K-3-O-glycoside? •67 .57 P DG 14. Q-3-O-glycoside? .65 .70 P G 15. Q-3-O-glueoside .53 .51 P YG 16. K-3-O-glucoside .65 .57 P G 17. 18. .60 .17 19. Unknown Unknown Q-3-O-rutinoside .47 .60 Y P P Y G YG 20. Q-O-glycoside .25 .48 P D 21. A-6,8-di-C-glycoside .36 .61 P G 22. K-3-O-rutinoside .54 P G 23. M-3-O-rhanmoside .57 .51 P Y 24. M-3-O-glycoside? .45 .40 P Y 25. M-3-O-galaetoside .52 .40 P Y NaOMe NaOAc H3BO3 . . . 401 398 . . 372 276 400 398 372 275 428 401 405 275 375 378 328 332 374 370 325 314 413 393 401 258 333 b 290 334 b 291 353 432 403 417 265 375 427 401 423 270 377 . . . . . . . . . . 352 b 310 355 b 314 370 436 406 407 268 377 398 397 402 273 355 . . 405 . . . . 414 275 380 433 b 399 408 262 365 385 385 400 280 339 400 400 403 274 356 426 405 270 377 -- -- -- -- 428 411 406 dec. 390 dec. 399 dee. 272 388 . . . . 434 a C o m p o u n d abbreviations: A = apigenin, L = luteolin, K = kaempferol, Q = quercetin, M = myricetin, T = taxifolin; Solvents: I - - t e r t - b u t a n o l : acetic acid : water (3:1:1, v/v); II--acetie acid: water (15:85, v/v); C o m p o u n d colors: P = purple, Y = yellow, G = green, D = dark; Spectral m a x i m a : All m a x i m a are B a n d I (visible) except for M e O H w h i c h includes B a n d II for calculation o f shift against B a n d II in N a O A e for 7-hydroxyl position; dec. = d e c o m p o s e s . b Shoulder or inflection. 172 BRITTONIA [VOL. 37 q-4" -I- + + + ÷ ll I q_ -t-+ + +++++ + + + ++++ ++~++ + -t-+ 4-+ 6 ++ + + ++++ ++++ I:I o + +++++ +++ +÷++ ++ + + + + + + + + + + + + ++ ++ ++ ++ ++ ++ ++++ + + -t- + + -b +++++ II m "~ g~ O ++ + II + o r~ z + e~ +++++ + + + + + "~ -t- + ++ o > + + + + + ÷ + + + + +++ ++ +-4-+ ~+ • .. ~ + ÷ '.-' -I- + ! *-. o z e ~l~u + + + + + + + + + ÷ + + + ÷ + + + ÷ + + + + + + + + + + + + + + +++++ + + + + + + + + + + + + + + + + + +++ +++++ + + + + + + + + + + + + + + ++÷ +++++ ~o H~ +÷+ +++ +++÷ ++++ -~.~ ++++ .'~ U o ~eqeq "~ e q e q e q e q e q e q e q ~ 1985] CORADIN ET AL.: PARINARI 173 pensis (with two varieties), and P. congolana, all of which possess the myricetin glycosides. The Madagascan disjunct, P. chapelieri, also is a myricetin-producer within whose range occur a few naturalized populations of P. curatellifolia. This grouping by flavonoids is not unexpected, since White (1976b) indicates that P. curatellifolia is closely related to P. capensis and that P. chapelieri is probably conspecific with P. curatellifolia, despite the disjunction and some differing morphological characters ofP. chapelieri. In fact, populations within both of the latter taxa (including mainland P. curatellifolia) overlap with each other morphologically. Parinari congolana also appears to fall within this first chemical group although White (1976b) states no specific relationships for this morphologically distinct taxon. The second chemical group includes Parinari excelsa, P. congensis, and the newly described P. hypochrysea (Letouzey & White, 1976) all of which lack myricetin glycosides but produce only the more common kaempferol and quercetin glycosides. The flavonoid profile of P. congensis is like that of P. excelsa (i.e., lacking myricetin) as is that of P. hypochrysea although both taxa are chemically much simpler than P. excelsa and do possess one compound unique to each taxon. Parinari in South America The Neotropical portion of the genus consists of some sixteen species most of which actually differ by only a few morphological characters. The greatest and perhaps more reliable distinctions rest on differences in habit and ecology (Prance, 1967). This portion of the genus represents what Prance terms a species "complex" of very closely related taxa. The flavonoid profiles of all the taxa would certainly support their close relationship and adds a further note of homogeneity. Flavonoid distributions in these taxa (Table II) do suggest some chemical differences between several groups of species. Although an earlier study (Giannasi et al., 1983) had suggested the presence of myricetin in Neotropical taxa, a reexamination shows that in contrast to the situation in the African taxa, myricetin is lacking in the Neotropical species. Infraspecific flavonoid variation in P. excelsa is unusual in that chromatographic patterns of individual collections are often similar to the profiles of distinct species with which it is locally sympatric. This phenomenon is not unique to Parinari and has been observed in the widespread weedy taxon Dahlia coccinea Cav. (Compositae) and other species in the genus (Giannasi, 1975), and is also observed in sesquiterpene patterns of the legume genus Hymenaea. Here the widespread H. courbaril L. often shows closer chemical and habit similarities with sympatric local species, producing regional chemical homogeneity which would otherwise be specific to ecologically and interspecifically distinct taxa (Martin & Langenheim, 1976; Langenheim et al., 1978). Parinari in Asia The Asian taxa sampled are chemically similar in pattern to the Neotropical species in their lack of myricetin (at least in those examined). Quercetin and kaempferol glycosides predominate and in a few cases several taxa do possess additional unique compounds. In general, however, the flavonoid pattern is quite similar to that of the South American species although a few taxa remain to be examined (Kostermans, 1965). Discussion Relative homogeneity in the predominant flavonol patterns is observed in the majority of Parinari species. This is perhaps not unexpected and is especially 174 BRITTONIA [VOL. 37 apparent in the Neotropical (and Asian) taxa, since Parinari appears to consist of closely related species whose distinction as taxonomic and biological units, even in the less homogeneous African taxa, depends a great deal on consistency in habit as well as habitat. As Prance (1967) suggests, Parinari represents a single species complex (superspecies), even the different phytogeographical nuclei (especially Neotropical and African) showing greater or lesser degrees of parallel inter- and infraspecific variation. This is unlike the situation in Couepia Aubl. which possesses several such clear-cut species complexes, and in Licania Aubl. where clear-cut subgeneric groups are quite obvious. Indeed, a preliminary flavonoid survey of a dozen species each of Couepia and Licania show greater interspecific and intergeneric differences in flavonoid profiles than that observed in Parinari (Giannasi & Coradin, unpubl.). Thus, chemical patterns would appear to parallel the generic concepts developed by Prance (1967). O f particular interest is the chemical dichotomy between presence or absence of myricetin in the African taxa. The presence of this flavonol has long been thought to be indicative of primitive chemical status (Bate-Smith, 1961, 1962; Harborne, 1977). Its absence (loss?) then would represent a derived feature. Although neither Prance (1972) nor White (1976b) ascribe evolutionary relationships to the species or phytogeographical groups of Parinari based on non-chemical characters, the presence ofmyricetin in P. curatellifolia, P. capensis, P. congolana, and P. chapelieri would represent an archaic (primitive) character retained by these taxa. The absence of myricetin synthesis in P. excelsa, P. congensis, and P. hypochrysea apparently represents a derived feature (Harborne, 1967, 1977). The absence of myricetin (at least in the current study) in both Neotropical and Asian species of Parinari suggests that their affinities lie closer to the non-myricetin producing African taxa (e.g., P. excelsa). Prance (1972), for example, feels that the African P. excelsa in fact is conspecific with the Neotropical P. brachystachya Benth. White (1976b) disputes this citing differences in fruit character. Flavonoid distributions suggest some subspecific differences (Table II) but observed infraspecific chemical variation (Neotropical and African) indicates that a more detailed flavonoid survey is needed to determine if this apparent difference is legitimate. Among American collections of P. brachystachya (= P. excelsa, sensu Prance, 1972), for example, we found a few collections with fruit characters like those of African P. excelsa. Thus, the differences between the two taxa may not be as unequivocal as White (1976b) has suggested and indicate that further studies of these latter taxa are needed. Regardless of precise taxonomic assignment, both chemical and morphological data support a relationship between the non-myricetin African species, particularly P. excelsa (sensu White, 1976b) and the complex of ecotypically differentiated species of Parinari in the Neotropics. Less is known of the Asian taxa, but these appear to represent a second evolutionary line in Parinari. If as Raven and Axelrod (1974) state, the Chrysobalanceae originated in Africa with subsequent eastward and westward expansion and diversification, then the patterns of flavonoid development are what would be expected even considering various modes of dispersal (Thorne, 1973). Similar chemical/phytogeographic correlations between the major continental areas are well documented in other plant groups using several types of secondary metabolites (Bate-Smith, 1973, 1976; Bate-Smith & Richens, 1973; Bell & Evans, 1978; Culberson & Hale, 1973; Harborne & Williams, 1971; Kelsey & Shafizadeh, 1979; Mabry et al., 1975; Scora, 1975; Scora & Malik, 1970; Williams, 1978; Williams & Harborne, 1977) and also include several direct comparisons between related fossil and extant taxa (Giannasi & Niklas, 1981; Niklas & Giannasi, 1978). Parinari is the only chrysobalanoid genus with major representation throughout 1985] CORADIN ET AL." PARINARI 175 the tropics. O t h e r g e n e r a are e i t h e r m a i n l y A f r i c a n (Maranthes B l u m e , Magnistipula Engl.) or m a i n l y N e o t r o p i c a l (Licania A u b l . , Hirtella L.) o r e x c l u s i v e l y N e o t r o p i c a l (Couepia A u b l . , Exellodendron). T h u s , it w o u l d b e o f i n t e r e s t to d e t e r m i n e i f these v a r i o u s m o r p h o l o g i c a l l y a n d o f t e n p h y t o g e o g r a p h i c a l l y d i s t i n c t g e n e r a s h o w a f l a v o n o i d c h e m i s t r y i n m a c r o c o s m p a r a l l e l to t h a t o b s e r v e d i n m i c r o c o s m i n Parinari. T h e o c c u r r e n c e o f m y r i c e t i n i n Chrysobalanus icaco is n o t u n e x p e c t e d as t h e t a x o n is r e p r e s e n t e d i n b o t h the N e o t r o p i c s a n d A f r i c a a n d t h u s a clear p h y t o g e o g r a p h i c r e l a t i o n s h i p is p r o b a b l e ( P r a n c e , 1972). H o w e v e r , the o c c u r r e n c e o f m y r i c e t i n i n Licania rigida, a N e o t r o p i c a l t a x o n , suggests that c h e m i c a l / p h y t o g e o g r a p h i c c o r r e l a t i o n s b e t w e e n a n d w i t h i n g e n e r a are p r o b a b l y m o r e c o m p l e x t h a n t h a t o b s e r v e d i n Parinari. Acknowledgments W e w i s h to t h a n k Mrs. R i t a R i c h a r d s o n a n d Mrs. L y n n H i l l for t e c h n i c a l a s s i s t a n c e i n t h e c h r o m a t o g r a p h i c a n a l y s e s . T h i s w o r k was s u p p o r t e d b y N S F G r a n t s D E B 7 8 - 2 4 0 6 3 a n d D E B . 8 1 - 2 0 5 1 5 a w a r d e d to D. E. G i a n n a s i . A s always we are i n d e b t e d to D r . P. K. H o l m g r e n for h e r k i n d p e r m i s s i o n to o b t a i n h e r b a r i u m m a t e r i a l f r o m t h e N e w Y o r k B o t a n i c a l G a r d e n for s o m e o f o u r c h e m i c a l studies. Literature Cited Aublet, F. 1775. Histoire des plantes de la Guiane Franfoise, vols. 1 and 2. Bate-Smith, E• C. 1961. Chromatography and taxonomy in the Rosaceae with special reference to Potentilla and Prunus. J. Lima. Soc., Bot. 58: 39-54. • 1962. The phenolic constituents of plants and their taxonomic significance. I. Dicotyledons. J. Lima. Soc., Bot. 58: 95-73. • 1973. Chemotaxonomy of Geranium. J. Linn. Soc., Bot. 67: 347-359. • 1976. Chemistry and taxonomy ofRibes. Bioch. Syst. Ecol. 4: 13-23. - & R. H. Richens. 1973. Flavonoid chemistry and taxonomy in Ulmus. Bioch. Syst. Ecol. I: 141-146. Bell, E. A. & C. S. Evans. 1978. Biochemical evidence of a former link between Australia and the Mascarene Islands. Nature 273: 295-296• Chapman, J. D. & F. White. 1970. The evergreen forests of Malawi. Commonwealth Forestry Institute, Oxford• Coradin, L. & D. E. Giannasi. 1980. The effects of chemical preservations on plant collections to be used in chemotaxonomic surveys. Taxon 29: 33-40• Culberson, C. F. & M. E. Hale. 1973. Chemical and morphological evolution in Parmelia sect. Hypotrachyna: product of ancient hybridization? Brittonia 25:162-173. Giannasi, D.E. 1975. The flavonoid systematics of the genus Dahlia (Compositae). Mem. New York. Bot. Gard. 26: 1-125• - & J. T. Mickel. 1979. Systematic implications of flavonoid pigments in the fern genus Hemionitis (Adiantiaceae). Brittonia 31: 405-412. - & K. J. Niklas. 1981. Comparative paleobiochemistry of some fossil and extant Fagaceae. Amer. J. Bot. 68: 762-770• --, G. T. Prance & L. Coradin. 1983. Flavonoids in Parinari (Chrysobalanaceae). [Abstract] Amer. J. Bot. 70(5) Pt. 2:115. Gottlieb, O. R. 1975. Flavonols. Pages 296-375. In: J. B. Harborne, T. J. Mabry & H. Mabry, editors. The flavonoids. Chapman and Hall, London. Harborne, J.B. 1967. Comparative biochemistry of the flavonoids. Academic Press, London. --. 1977. Flavonoids and the evolution of the angiosperms. Bioch. Syst. Ecol. 5: 7-22. - & C. A. Williams. 1971. Leaf survey of flavonoids and simple phenols in the genus Rhododendron. Phytochemistry 10: 2727-2744. - & . 1975. Flavone and flavonol glycosides. Pages 376-441• In: J. B. Harborne, T. J. Mabry & H. Mabry, editors. The flavonoids. Chapman and Hall, London. Heywood, V.H. 1971. The Leguminosae--a systematic purview. Pages 1-29. ln: J. B. Harborne, 176 BRITTONIA [VOL. 37 D. Boulter & B. L. Turner, editors. Chemotaxonomy of the Leguminosae. Academic Press, London. Kelsey, R. G. & F. Shafizadeh. 1979. Sesquiterpene lactones and systematics of the genus Artemisia. Phytocbemistry 18:1591-1611. Kostermans, A. J. G . H . 1965. A monograph of the genus Parinari Aubl. (Rosaceae-Chrysobalanoideae) in Asia and Pacific Region. Reinwardtia 7: 147-213. Langenbeim, J. H., W. H. Stubblebine, D. E. Lincoln & C. E. Foster. 1978. Implications of variation in resin composition among organs, tissues and populations in the tropical legume Hymenaea. Bioch. Syst. Ecol. 6: 299-313. Letouzey, R. & F. White. 1976. Chrysobalanac6es nouvelles du Cameroun et du Gabon. Adansonia 16: 229-243. Mabry, T. J., K. R. Markham & M. B. Thomas. 1970. The systematic identification of flavonoids. Springer-Verlag, New York. , Z. Abdel-Baset, G. Padolina & S. B• Jones. 1975. Systematic implications offlavonoids and sesquiterpenc lactones in species of Vernonia. Bioch. Syst. Ecol. 2:185-192. Martin, S. S., J. H. Langenbeim & E. Zavarin. 1976. Quantitative variation in leaf pocket resin composition in Hymenaea. Bioch. Syst. Ecol. 4: 181-191. Nildas, K. J. & D. E. Giannasi. 1978. Angiosperm paleobiocbemistry of the Succor Creek Flora (Miocene), Oregon, U.S.A. Amer. J. Bot. 65: 943-952. Prance, G . T . 1967. The taxonomy and ecology of the Chrysobalanaceac of the Amazon Basin. Atas do Simp6sio s6bre a Biota Amaz6nica 4: 209-228. 1972. Chrysobalanaceae. Flora Neotropica 9: 1-410. Hafner, New York. • 1979. Distribution patterns of lowland Neotropical species with relation to history, dispersal and ecology, with special reference to Chrysobalanceae, Caryocaraceae and Lecythidaceae. Pages 59-87. In: K. Larsen & L. B. Holm-Nielsen, editors. Tropical botany. Academic Press, London. •, D. J. Rogers & F. White. 1969. A taximetric study of an angiosperm family: generic delimitation in the Chrysobalanaceae. New PhytoL 68: 1203-1234. Raven, P. R. & D. I. Axelrod. 1974. Angiosperm biogeography and past continental movements. Ann. Missouri Bot. Gard. 61: 539-673. Scora, R . W . 1975. Volatile oil components in Citrus taxonomy. Internat. Flavors 11/12: 342-346. & M. M. Malik. 1970. Chemical characterization of Citrus as a tool in phylogeny. Taxon 19: 215-228. Thorne, R . F . 1973. Floristic relationships between tropical Africa and tropical America. Pages 2747. In: B. J. Meggers, E. S. Ayensu & W. D. Duckworth, editors. Tropical forest ecosystems in Africa and South America: a comparative review. Smithsonian Institution Press, Washington. White, F. 1976a. Chrysobalanaceae. Pages 283-334. Distributiones plantarum Africanarum. Jard. Bot. Nat. Belg./Nat. Plantentuin Belg. Brussels (U.N.E.S.C.O.). 1976b. The taxonomy, ecology and chorology of Afdcan Chrysobalanaceae (excluding Acioa). Bull. Jard. Bot. Nat. Belg./Bull. Nat. Plantentuin Belg. 46: 265-350. Wilkins, C. K. & B. A. Bohm. 1976. Chemotaxonomic studies ofHeuchera micrantha var. diversifolia. Canad. J. Bot. 54: 2133-2140. Williams, C . A . 1978. The systematic implications of the complexity of leaf flavonoids in the Bromeliaceae. Phytocbemistry 17: 729-734. & J. B. Harborne. 1977. Flavonoid chemistry and plant geography in the Cyperaccae. Bioch. Syst. Ecol. 5: 45-51. Appendix I VOUCHERS OF PariHt2ri SPECIES USED IN CHEMICAL ANALYSISa Africa and Madagascar Parinari curatellifolia Planch. ex Benth. Malawi: Brass 17377, 17467. ZaJre Beige: Taton 1403, Devred 2040. South Africa: Burtt-Davy 20322. Zimbabwe: Corby 30087, Lovemare 57; Kyimbila Dist., Stolz 1663. Tanzania: Stolz 469. Zaire: Katanga Prov., Huant 83. Ruanda: Troupin 8377; Kasungu Dist., Brass 17423. Burundi: Christiansen 2475. a All voucher specimens at NY. Species sequence as in Table II. 1985] CORADIN ET AL.: PARINARI 177 Parinari capensis Harv. South Africa: Pretoria, Schlieben 2060; Transvaal, Meebold 12259; Swaziland, Ross 1764. Parinari congolana Th. & H. Zaire: Chapin 570. Parinari chapelieri Baill. Madagascar: Capuron 903. Parinari congensis F. Didr. Zaire: Dubois 229, Lebrun 844, 1276. Parinari hypochrysea Mildbr. ex Letouzey & White Cameroun: Letouzey 12538, Hedin 1592. Parinari excelsa Sabine Zaire: Louis 9590, Pierlot 3327, Gerard 4089, Leonard 5438. South America Parinari excelsa (also under Africa; P. brachystachya Benth.) Brazil: Prance et al. 13693, 13404, Riedel 1667, Armond 175, Ducke 1347, 2145, Fr6es 26532, Prance et al. P3157, Pires & Cavalcante 52476, Fr6es 1909, 1982, Berg et al. P18678. Guyana: Forest Dept. 3406. Venezuela: de Bruijn 1696. Parinari campestris Aublet French Guiana: Martins s.n. Venezuela: Steyermark 87493. Suriname: Irwin et al. 55226, 55995. Parinari montana Aublet emend. Ducke Brazil: Ducke 2279, Oliveira 4563. Parinari rodolphii Huber Venezuela: Bernardi 2127, Blanco 484. Parinari occidentalis Prance Brazil: Krukoff 5650. Bolivia: Krukoff11278. Parinari sprucei Hooker f. Brazil: Silva et al. 1465. Parinari pachyphylla Rusby Venezuela: Aristeguieta 6771, de Bruijn 1252. Parinari brasiliensis (Schott) Hooker f. Brazil: Rio de Janeiro, R. Foviro 4382. Parinari klugii Prance Peru: Croat 20443, Klug 3870. Parinari maguirei Prance Guyana: Cowan & Soderstrom 2180. Parinari littoralis Prance Brazil: Beldm 1833. Parinari parvifolia Sandwith Guyana: Jenman 3992. Parinari parilis Maebride Peru: Croat 20367. Parinari chocoensis Prance Colombia: Fuchs & Zanella 21793. Parinari obtusifolia Hooker f. Brazil: Irwin et al. 14469, Heringer 8671. Parinari cardiophylla Ducke Brazil: Ducke s. n. (RB24183). Asia Parinari anamensis Hance China: Cochin, Harmand 109. Parinari oblongifolia Hooker f. Malaysia: Malay Peninsula, Henderson 21976. Borneo: Kostermans 6544, 10191. Parinari bicolor Mess. Philippines: Surigao, Razon F. B. 23022. Parinari canarioides Kostermans Borneo: Borneo, Kostermans 8646; Balikpapan, Kostermans 10017. Parinari costata (Korth.) Blume Philippines: Phillippines, Herre 1014. Parinari insularum A. Gray Fiji: Nasinu, Gillespie 3619, Prance 26624. 178 BRITTONIA [VOL. 37 Parinari honda F. V. M. ex Benth. New Guinea: Papua, Brass 5979. Australia:Prance 26601. Parinari rubiginosa Ridley Borneo: Sandakan, Puasa 669. Parinari sumatrana (Jack) Benth. Java: Bureau of Ag. 4791, Kostermans 21859. BOOK REVIEW Scala Millettiearum: A Survey of the Genera of the Tribe Millettieae (Legum.Pap.), with Methodological Considerations. By Robert Geesink. Leiden Botanical Series, volume 8. E. J. Brill Printers and Publishers, P.O. Box 1305, Long Island City, NY 11101. ISBN 90-04-07498-8. 1984. 131 pp. 56 guilders. In 1981 Dr. Robert Geesink, the well-known authority on Leguminosae of Southeast Asia, contributed to Part I of Advances in L e g u m e Systematics (the report of the First Legume Conference held at Kew in 1978) a generic survey of the notoriously controversial tribe Papilionoideae Tephrosieae. This was admittedly a preliminary census in need of refinement and elaboration. The present small but richly detailed book recounts the author's further search for a taxonomic scheme compatible with probable phylogeny. The epithet Millettieae Miq. of the title is merely a prior taxonomic synonym of Tephrosieae (Benth.) Hutch. The Scala is divided into two parts of approximately equal length. In the first Geesink discusses the available taxonomic characters and their manipulation; in the second he provides a descriptive synopsis of 43 accepted genera. The first part summarizes a struggle to disentangle pure lineages (or natural genera) from a matrix of false or possibly false clues and a priori evaluations of character-weight. Despite much effort expended on cladistic and compatibility analyses the goal proved elusive, and the pot of gold still lies inviolate at the far end of the rainbow; but for those who find the journey as engaging as the destination these pages will make fascinating reading. The taxonomic part consists of descriptions defining the accepted genera, a key to them (non-indented, one notes with regret), and, where appropriate, commentary on morphology, history, relationships, and dispersal. Because no unambiguous division of the tribe was found, the genera appear here in alphabetic, not systematic order. Especially notable features of the taxonomy are: restricted concepts of Derris, Lonchocarpus, and Millettia; disappearance o f Muellera into Lonchocarpus and o f P o n g a m i a into Millettia; and the disposal of the vexed American derrises into Deguelia Aubl. But a short review cannot begin to list the points of concern to specialists in this group. Five plates elegantly illustrate the diversity of fruits and seeds of Millettieae. The word scala in the title is susceptible to two interpretations according to its etymology: a balanced measure or simply a balance, if derived from Scandinavian root, or a progressive sequence, if from low Latin. The first might allude to the search for scientific method in taxonomy, the second to an orderly hierarchy achieved by that method. Whatever the author's intention may be, Scala Millettiearum will be of unambiguous interest to students of either theoretical or practical classification in any particular field. No leguminologist can afford to miss it. -- RUPERT C. BARNEBY,New York Botanical Garden.