5866 *

Biochemical SysremBal::s and Ecology. Vol. 15. No.4, pp. 433-439. 1987. D:105-197ll181 $3.OO+0 1987 Pergamon Joumals Ltd.

Seed Lipids of the Lythraceae

SHIRLEY A. GRAHAM* and ROBERT KLEIMANt ·Oepartment of Biological Sciences. Kent State University. Kent, OH 44242. U.SA.; tNorthem Regional Research Center, Agricultural Research Service, U.S. Department of Agriculture. Peoria, IL 61604, U.SA.

Key Word lndex-Lythraceae: seeds: lipid composition: fatty acids; t:hemotaxonomy. Abstract-Fatty acid composmon of seed lipids for 20 of the 26 genera in the Lythraceae and seed oil and protein content for nine genera are reported. The percent oil ranges from 2..7 to 34% of total weight and protein from '1.3 to 24.9%. Linoleic acid is the dominant fatty acid in seed lipids of all genera surveyed Variations in pattern emphasize palmitic or oleic acid or both as second most abundant lipid component There are three exceptions: in Dipluscdon capric acid ranks second in abundance: in Adensris lauric acid and oleic acid occur in approximately equal amounts as second most abundant fatty acid: in Decodon an unusual trienoic acid, previously reported only from the Compositae, is the main secondary component. Fatty acid composition of seeds in the genera is compared to that of the previously stUdied lythraceous genus Cuphea. Among all the genera. only Cuphea seed produces large quantities of lauric, capric. or caprylic acids. as well as a diversity of fatty acid patterns. No relation­ ship between oil content or seed weight and habit is apparent in any genus studied, nor are differences in seed morphology reflected in composition of the seed lipids. The fatty acid patterns are judged evolutionarily conservative, with the strong exception of Cuphea. which remains unique in the Lythraceae and among all angiosperms for the diversity of patterns displayed.

Introduction kingdom because of the diversity of major fatty As increasing attention is paid to discovery of acids produceq, as well as for the atypical . plant substances valued for human and emphasis on production of saturated medium industrial consumption around the world, there chain (8:0-14:0) fatty acids. Among 73 species is a concomitant developing awareness of the of Cuphea analyzed for fatty acid composition, paucity of information available on natural linoleic acid is the major component in a few of products produced by plants, especially those the most generalized species, lauric acid from warm regions of the globe. Oil-bearing predominates in the majority of the species, and seed plants provide an example of how little we capric and caprylic acids are restricted to the know about potentially exploitable plant species. most advanced species [5-7]. The abundance of Only nine species produce about 90% of the lauric acid, particularly, has recently stimulated world's vegetable oil crop [1]. Of an estimated research aimed at developing the genus as a 250 000 species of angiosperms, no more than new temperate oilseed crop [8J. 3% have received even a cursory analysis of Among other genera of the Lythraceae, fatty seed composition. The United States acid composition has been reported for only Department of Agriculture, in its search for new one, Lawsania [9J and the percentage of oil and industrial oils, has surveyed approximately 8000 protein in seeds is known for just three, species to date [2]. Lagerstroemia, Heimia, and Lythrum [10, llJ. We In general, the major fatty acid produced by report here the fatty acid composition for 29 oil seeds is linoleic acid [3J. Many unusual fatty species in 21 of the approximately 26 genera acids and lipid groups are also known, most of comprising the family. Among the 16 monotypic these having been identified only in recent or ditypic genera, 12 are reported in this study. years. A few taxa have been found to pro­ Data are not available for the monotypic Didiplis duce common fatty acids at levels much higher and Kaehneria, ditypic Crenea and Haitia, or for than normal [4J. One of these is Cuphea Hionanthera, a little known genus of four species (Lythraceae), a genus unique in the plant that is possibly synonymous with Ammannia [12]. Ammannia is reported here. The (R&eived5 September 1986) percentage of seed oil and protein is

433 SHIRLEY A. GRAHAM AND ROBERT KLEIMAN summarized for nine genera. Results reveal Diplusodon and Adenaria, patterns of composi­ whether other members of the family, besides tion are unique in their emphasis of other Cuphea, possess unusual patterns of seed oil secondary fatty acids. composition, and whether seed lipids offer new The most common pattern among the genera evidence, or corroborate earlier data from other surveyed emphasizes linoleic acid as the sources, in suggesting evolutionary relationships primary fatty acid and palmitic acid as the only among the taxa. secondary component constituting 10% or more of total fatty acid composition (Table 2). The Results pattern occurs in nine species of eight genera; Linoleic acid (18:2) is the dominant fatty acid in Ammannia auriculata and A. latifolia, Galpinia the seed lipids of all genera surveyed (Table 1). It transvaalica, Ginoria nudiflora, Heimia myrtifolia, ranges from 41.0% to 81.7% of total fatty acid Ne,saea cordata, Peplis erecta, Pleurophora composition with a mean of 70.5%. Second saccocarpa and Tetrataxis salicitolia. In the most important components are palmitic acid second most common pattern, 18:2 predomi­ (16:0) (x - 10.6%) and oleic acid (18:1) (x­ nates, with oleic and palmitic fatty acids more or 10.1 %). As in most other seed oils, stearic acid less comparably represented as fatty acids (18:0) does not accumulate in any quantity but second in importance to linoleic acid. Eight functions primarily as the substrate for the first species in seven genera have this pattern; desaturation step [13]. In three genera, Decodon, Lafoensia nummulariitolia, Lawsonia inermis,

TABLE 1. FATTY ACID COMPQsmON OF SEED UPtOS AS PERCENTAGE OF TOTAL FATlY AOO CONTeNT IN GENERA OF THE LYTHRACEAE

Fatty acid Genus and spei:ies 10:0 12:0 14:0 16:0 18:0 18:1 18:2 18:3 20:0 Others-

Adenans flonoundll1/1t B.O 0.5 7.2 2.6 B.5 64.B 0.6 7.6 AmmlJlJnia auricuJaca 25/2 tr 10.8 1.3 7.2 78.6 0.5 1.6 Ammsnnia Jarifolill 11.4 3.2 B.5 72.7 1.1 .3.0 0.1 Capuronill madagsscanen$i!$1/1 tr tr 7.B '.B . .. 11.2 76.2 Decodon wmicilJsCU:t 1/1 7.6 1.9 7.' 64.9 15.7 0.7 1.6 Diplusodon glaucl!scen!J 57/1 10.0 5.B 3.1 9.1 2.3 7.5 41.0 O.B 3.5 16.5 Galpinia rnm:1V88/ie8 1/1 1.1 D.• 11.8 3.5 6.6 70.4 0.3 1.5 '.0 Ginons nudiflora 15/1 18.6 2.9 9.1 65.1 1.3 1.5 1.5 Htlimia myrtifolia (aj 2/2 D.• 03 12.4 2.9 6.B 75.3 1.0 0.7 0.2 Heimia sa/icifolia 9.' 3.' 6.5 n.3 0.9 1.3 1.0 Lsfo4nsia nummuiIJnffolia 10/1 13,2 ••• 11.9 69.' 0.3 0.9 0.1 Lagel'$tJ'Oemis indica (aj 5312 B.6 1.6 9.7 79.7 0.1 LsgM'!JtTOemia tomt!l'lLO~ tr 6.9 3.B 7.2 n.3 1.6 0.9 2.3 Lawsonia inermi:lll1 0.1 12.7 3.1 7.9 74,5 0.1 1.2 D•• Lythrum ecurangulum 35/3 tr 10.3 2.1 .15.7 71.3 0.5 0.1 Lythrum hy$$Cpifolia tr 0.2 10.2 2.5 11,7 68.3 0.5 1.7 '.9 Lythrom saJic8ris (a) 6.1 1.2 10.7 81.7 0.1 0.1 0.1 Lythrum salicsria (bl tr 5.B 1.5 14.5 75.s 0.3 0.9 1.1 NtI!S8etJ a~ SO/2 9.2 2.6 7.3 78.6 0.7 1.7 0.1 N8S8etJ cordata 10.0 1.7 6.B 76.9 1.2 L7 1.. Pehris compaetlJ 1/1 0.2 0.1 B.6 '.0 B.l 75.9 0.3 O.B 2.0 Pemphi$ aciduJa 1/1 1.0 0.2 15.s 3.' 14.6 59.3 0.3 3.s 1.1 Pep& altemi/olia 3/3 7.1 1.1 15.8 73.2 O.s 1.0 0.3 PepIi:t ereem 0.3 13,0 1.7 9.2 73.6 1.s 0.1 Pep/CJ ".,..,,,, 11.9 1.0 14.1 73.0 Physocalyrnma scaberrims 111 1.5 14.8 7.1 22.5 48.6 1.6 2.0 1.5 Pfeurophora $lIccOCJJrps 11/1 13.1 1.6 B.s 71,0 D.• 3.6 0.9 Rosla ramosior4411 0.6 B.5 2.3 10,7 76.4 0.5 O.B Tetrllsxi:J salicifolia 1/1 14.2 2.7 9.5 68.1 1.0 2.3 1.B 'lrborifordia fruticO$1J 2/1 a.' 0.1 11.2 3.3 12.7 70.0 0.7 O.B

-Components other- than fany acid methyl esters eluting from the GC columns. tEach name followed by the number of species in the genus/number of species.sampled in this study. SEED UPIOS OF THE LYTHRACEAE 435

TABLE 2. FATTY ACID· PAmANS IN LYTHRACEAE SEeD UPIOS. acid (14:0) and longer-chained fatty acids (20:0, EXCLUDING CUPHEA 20: 1) are present in many genera. In Ammannia Pattern- X Range No. Gen.lNo. Spp, /atifo/ia, Dip/usodon, Pemphis and P/europhora, arachidic acid (20:0) represents between 3-4% 1. 18:2 72.4 65.1-78.6 819 16:0 12.8 10.0-18.6 of total fatty acid composition. 2. 18:2 65.1 48.6-73.0 7/8 Trans-3, cis-9, c/s-12-octadecatrienoic acid is 18:1 14.4 11.7-22.5 found in Decodon, where it constitutes 15.7% of 16:0 12.5 10.2:-15.9 total fatty acid composition. This fatty acid has 3. 18:2 75.6 64.8-79.7 5/8 been found previously as a seed oil constituent 4. 18:2 76.7 73.2-81.7 4/4 only from a number of species of Compositae 18:1 12.6 10.7-15.8 [14-17]. 5. 18.2 41.0 The percent oil in seeds of Lythraceae 10:0 10.0 '" analyzed ranges from 2.7 to 26.8% and protein 6. 18:2 64.9 from 11.3 to 24.9% (Table 3). Mean percentage 18:3 15.7 '" of oil in Cuphea [18] is included in the table for

'"The firm fatty acid listed, linoleic acid (18:2) is the dominant fany purposes of comparison. Seeds in the family are acid in all patterns. Subsequent fatty acids listed are the secondary characteristically numerous but most are small components constituting 10% or more of the total fattY acid in size (3 mm long or less) and weight Difficulty composition. in obtaining the quantities of seeds necessary for determining oil and protein fractions limits Lythrum acutangu/um, Lythrum hyssopifo//a, the data presented on oil and protein composi­ Pemphis acidu/a, Pep/is portu/a, Physocalymma tion. The largest seeds are the winged ones scaberrima and Woodfordia fruticosa. Our found among members of the tree genera findings for Liiwsonia differ from an earlier Lagerstroemia and Lafoensia (as large as 30 x published report for the genus [9] in which the 13 mm in Lafoensia Vande//iana Cham. & Schldl). seeds of the species are said to contain 4% Seeds of Cuphea are considerably smaller, from linolenic acid. In a third pattern, no fatty acid, 0.3 to 3 mm long, but are heavy in relation to except linoleic acid, occurs in quantities their size. Hirsinger and Knowles [18, 19J report a reaching 10% of total fatty acid composition. weight range for Cuphea seeds of 0.16 to 4.45. Included in this category are six species in five gm/l000 seed, with lipids, on the average genera; Adenaria f1oribunda, Heimia sa/icifo/ia, accounting for 34% of total seed weight [19]. Lagerstroemia indica and Lagerstroemia tomentosa, Nesaea aspera and Pehria compacta.

Four species in four genera produce oleic acid TABLE 3. SEeD WEIGHT AND OIL AND PROTEIN COMPOsmON FOR alone as second most important fatty acid SOME GENERA OF THE LYTHRACEAE component; Capuronia madagascariensis, Dry basis % Lythrum sa/icaria, Pep/is altemifo/ia and Rota/a W1 Genus and species Igm/l000 seedl Oil Protein ramosior. In the six genera where more than one species has been analyzed, four· are hetero­ Ammsnnis auricu/ata 0.05 15.2 16.1 geneous with respect to the secondary compo­ Cuphesspp.- 1.94 34.0 Heimis myrtifo/iB {hI 0.10 14.7 16.0 nents, i.e. Heimia, Nesaea, Lythrum and Pep/is; H. sa/icifo/is 0.05 26.8 21.6 two, Lagerstroemia and Ammannia, are Lagel'$tlTJemis indies (hI 2.40 18.9 24.9 homogeneous. L tomentrJ$lJ 2.7 13,7 Seed lipids of Dip/usodon and Adenaria are of LawsqniB inennis 0.40 9.6 8.8 Lyr!lrom acutangu/um 2.80 8.1 11.6 special interest. Dip/usodon is the only genus L hyssopifo/ia 2.40 7.1 11.3 surveyed that produces capric acid in greater L sa/fearis lal 0.10 22.2 20.8 than trace amounts. It also produces L sa/icans (hI 0.10 25.4 17.0 measurable amounts of lauric acid (5.8%). Pep/is ereeta 0.05 17.6 17.2 Adenaria produces 8% lauric acid, a quantity x 0.94 16.9 16,3 significantly greater than in all other genera - Cuphes data. included for comparison. are given as the mean of 30 investigated (Table 1). Small amounts of myristic specias {19J. 436 SHIRLEY A. GRAHAM AND ROBERT KLEIMAN

Discussion and Conclusions of their production of greater amounts of The Lythraceae is a family of world-wide medium chain saturated fatty acids. For distribution, occurring primarily in subtropical comparison, a sample of seed oils from seven and tropical areas. It is believed to have an Old species of Cuphea analyzed earlier is presented World, warm-temperate origin, possibly in east in Table 4; the sample is representative of the Africa, and to have subsequently dispersed unusual diversity of pattems occurring in this throughout the world [20, 21]. Today the family genus. How these saturated fatty acids is represented by a few moderate-sized genera accumulate in quantity is not yet completely and several, small, relic genera. The largest understood but it is apparently not by chain­ genus is Cuphea (ca 260 spp.), distantly followed shortening. It may depend on the presence of by Diplusodon (ca 57 spp.), Lagerstroemia (53 increased amounts of acetyl transacylase in spp.), Nesaea rca 50 spp.) and Rotala (44 spp.). relation to malonyl-ACP early in the fatty acid The first two genera are New World, the last biosynthetic process, with the amount of the three are Old World, in distribution. The enzyme present determining the chain length remaining genera average 16 species. produced [Po Stumpf. Cuphea Research and Knowledge of seed lipid composition is thus Development Meeting, unpubl. data. 1984]. Fatty complete or adequate for slightly more than half acid biosynthesis in Cuphea is in early stages of the genera surveyed. investigation [22]. The common pattem of fatty acid composi­ To generate patterns emphasizing a variety of tion in Lythraceae seed oils is the one common medium chain saturated fatty acids would seem to most angiosperm seed oils. Linoleic acid is to necessitate genetic changes or control beyond the primary component, and palmitic acid or that required to regulate the degree of desatura­ oleic acid is frequently the secondary compo­ tion in the 18-earbon chain. The mechanism for nent To complete the pattern, a number of fatty acid production in Lythraceae seed lipids. other fatty acids are found in amounts equalling therefore, appears to be generally an less than 10% of the total [4]. Deviations from evolutionarily conservative one. but remarkable this composition in most of the Iythraceous exceptions are found in Cuphea, Diplusodon. . genera analyzed are" apparently due to the more Adenaria and Decodon. complete conversion of palmitic acid to the The usefulness of fatty acid composition of desaturated forms of oleic, linoleic and/or Lythraceae seed oils in determining phylogeny linolenic acids. This conversion occurs in a two­ of the genera appears minimal. Patterns. with step fashion, first by elongation from the 16:0 to the noted exceptions, are very similar. Clusters the 18:0 form, then via a separate desaturation of genera associated through evidence from system in which oleic, linoleic, or linolenic acids floral morphology, anatomy. or palynology may may be formed consecutively from the stearic .or may not share a common fatty acid pattern. acid precursor [13J. The New World monotypic genera Adenaria and Cuphea, and to a lesser degree, Diplusodon Pehria. for example. are related on the basis of and Adenaria, are atypical in the family because similar advanced floral and pollen morphology

TABLE 4. FATlY ACtO COMPOsmON OF seee UPiDS AS PERCENTAGE OF TOTAL FATlY ACID CONTENT IN SELECTED SPECtES OF CUPHEA·

Species 8:0 10;0 12:0 14:0 .16:0 18:0 18:1 18:2 Others!

Cn=n=a 0.1 0.2 15.3 1.7 17.4 58.8 6.5 C cartllagtJtJensi$ 0.3 8.0 B2.5 ,3.. 3.5 5.2 5.7 1.4 e. hy=opifolitl 0.2 7.3 78.5 4.8 1.5 0.2 2.4 3.8 1.3 C ra/tJesna 23.0 63.3 4.5 1.B 1.9 5.0 0.5 C. PllUCJfHtt111tJ '.2 87•• 2.0 O.B 1.9 I.B 4.0 0.9 C ",""". 87.8 24.' 1.4 2.4 3.1 0.9 C_ '9.7 1.4 2.0 63.7 6.7 3.0 2.9 0.6

·Specie, examples selected from [5]: primary and secondary fatty acids are indicated by bold type. tAdditional components un~med. SEeo UPIOS OF THE LYTHRACEAE 437 and shared specialized glandular hair types [21. unusual wealth of environmental factors. a 23]. They are not closely related to the Old combination not met with in any other genus of World Lagerstroemia. yet share the same basic the family. fatty acid pattern in which only linoleic acid Seed oil composition of other core families in accumulates in quantity. Likewise, Ammannia the order Myrtales is insufficiently known to and Nesaea, closely related genera of wet allow comparison with the Lytihraceae. The habitats in Africa [24], with actinomorphic, closely related Onagraceae are characterized as 4-merous flowers, share a fatty acid composition linoleic-rich [25], and the Myrtaceae as also similar to Pleurophora, a South American genus linoleic-rich, but data for other families are of dry areas, with zygomorphic, 6-merous meagre or absent [4]. flowers. Pleurophora is closely related to Cuphea, Levin [26] has pointed out some generalized as attested to by its zygomorphic floral relationships of seed oil content and seed condition, unusual. spirally twisted seed coat weight to habit and habitat He found oil content hairs. and other shared, specialized trichome and seed weight increased with woodiness. and types (Graham, unpubl. data). It is the one genus with decreasing illumination of the habitat In that would be most likely to display a fatty acid Lytihraceae no pattern related to habit is composition similar to that of Cuphea, an apparent The heaviest seeds occur in the tree expectation not borne out by the data. genera Lagerstroemia and Lafoensia and in the The isolation of the genus Cuphea in the herbaceous genus Cuphea. The percentage of family, suggested by the fatty acid data from this oil content is less than 27% in all genera survey, is supported by distinctive embryo­ analyzed, woody and herbaceous. except in logical data [Tobe, in prep.] and unique pollen Cuphea (Table 3). The data base is insufficient to morphology [23]. Among the genera investiga­ allow determination of whether the variability in ted, only, Cuphea produces lauric acid (12:0) in the oil percentage within a genus or species is quantity, only Cuphea produces caprylic acid, affected by habitat illumination. (It is generally (8:0) and only Cuphea and Diplusodon, produce known, however, that low temperature during capric;. acid (10:0). Further investigation of seed development results in deqreased oil Diplusodon seed Iipids'is needed to establish the content. so illumination as it affects temperature degree of composition diversity in this large is. certainly, at least one environmental factor of genus. Since diversity in fatty acid composition consequence.) has evolved with extensive speciation in Fatty acid patterns were examined further in Cuphea, diversity might also be anticipated in relation to pollination and dispersal Diplusodon but to a lesser degree because the mechanisms. Specific seed oil patterns are not genus is about a quarter of the size of Cuphea. correlated with seed morphological types in the Although not closely related, both genera have family. For example, genera with winged seeds centers of speciation in the same temperate, '(Galpinia), seeds with floats (Ammannia) and upland regions of eastern Brazil. Similar non-specialized seed types (Heimia, Tetrataxis) environmental factors, if these are of share a common pattern. In addition, the same consequence in selection of fatty acid patterns. generalized fatty acid pattern is shared by bat­ could be operating during speciation events. pollinated Lafoensia which has large. Cuphea differs from Diplusodon, however, in compressed, winged seeds, and by self­ having a major secondary center of speciation pollinated Peplis which has minute, nearly in Mexico. There Cuphea has evolved under a orbicular seeds. Pemphis. a strand plant of the much greater array of orogenic, physiographic Indian and Pacific Oceans. has the same pattem and altitudinal situations than are present in the as Lythrum sallearia, a marsh plant of northern. Brazilian center, and it is in Mexico that the temperate regions. greatest diversity of Cuphea seed oil composi­ In conclusion. the seed lipids of Lytihraceae tion occurs. The unique fatty acid diversity in are typical of angiosperms seeds generally in Cuphea may well be due to the fortuitous emphasizing linoleic acid as the dominant fatty combination of a highly plastic and actively acid component. The number of fatty acid changing genetic pool being acted on by an patterns is limited among the genera and seed 438 SHIRLEY A. GRAHAM AND ROBERT i<;LEIMAN lipid composition is considered evolutionarily 63813 Capuronia madagascadensis Lour. Madagascar: D~rcy conservative, with the major exceptions of 15439IMO). Cuphea and, to a lesser degree, Diplu50don, 64205 Decodon verticillatus En. USA: Ohio, Graham 917 (KE· G). Adenaria and Decodon. In spite of hopes that 64191 Diplusodon glaucescens DC. Brazil: Minas Gerais. seed oil composition would prove of value in Graham 874IKE-G}. chemotaxonomy and phylogenetics as more 64192 Galpinia transvaalica N. E. Br., South Africa: Cult data became available [4, 27J, its usefulness at Pretoria Bot Inst. no. 238. 1983. V1/n ~k 6932 (KE-G). 64193 Ginona nudiflora Koehne. Mexico: Oaxaca, ~ndt 3203 the generic level in this family is minimal due to IKE-G). the commonality of the pattems found. The 64194 Heirma myrtifolia Cham. & Schld!. (a). Brazil: Cult major revelation of the study is the uniqueness FairChild Bot Gard. FG-61-31S. Gillis 8536 (KE-G). in pattem and the diversity of the seed oils 44634 Heimia myrtifolia Cham. & Schldl. Ib}. Uruguay: USDA produced by the largest genus of the family, no. 4142. 42928 Heim/a salicifolia Link. Uruguay: USDA no. 3439. Cuphea. 64195 Lafoensia nummulariifolia St.·Hil. Brazil: Parana. Graham 912IKE-G). Experimental 41054 Lagerstroemia indica L (a). USA: Florida, cult. Godfrey 6ll347IFSU). Seeds were obtained in the wild and from recently collected 45887 Lagerstroemia indica L. {bl. Pakistan: USDA no. 3244. herbarium specimens. Collection data and location of 40655 Lagersrroemia tomentosa Pres!. USA: Aorida. cult, herbarium voucher specimens are listed in Appendix I. Gentry & Barclay s.n. Analyses were perfonned at the USDA Northern Regional 64196 Lawsonia inennis L. Nicaragua: Dept Managua, Guzman Research Center, Peoria. llo. U.SA Seeds were ground in & Castro 189 IKE-G}. redistilled pentane and placed on a rotary shaker for 1 h. The 47249 Lythrum acurangulum Lag. Spain: USDA no. 480 solvent was evaporated to dryness and the oil residue then 46502 Lyrhrum hyssopifolia L Spain: USDA s.n. dissolved in 2 drops of benzene; 5 ml of 5% Hel in MaOH 45589 Lyrhrum salicaria L (al. Spain: USDA 5.n. were added. and the solution was. refluxed for 1h. The 62778 Lythrum saliearia L (b). USA: Illinois, I. M. Cull s.n. resulting methyl esters were extracted with pentane and the 64197 Nesaea aspera (Guill. et Perr.) Koehne. Africa: R. 8. pentane evaporated off with a stream of N2, The fatty acid Drummond 11446 (MOl. methyl esters were analyzed using suitable standards by GLC 64198 Nesaea cordata Hiern. Africa: R. 8. Drummond 11447 (f.Ld.), temperature programmed from 75" to 210- at4-/min. A IMO). sample of Cuphea wrightJlwith known fatty acid composition, 63658 Pehria compac~ (Rusby) Sprague. Venezuela: R (Jerry was run to allow comparison of data obtained earlier from this s.n. in 1979 (KE-Gj.· - genus with the other genera of the family analyzed. 64199 Pemphis aeidula Forst. Guam: Tarague Beach•. L. Analysis of Decodon methyl esters on a 60 meter capillary Raulerson s.n. in 1982 {MOl. SP~2340 column coated with revealed an unknown 64200 Peplis altemifolia M. Bieb. USSR: Voronezh Prov.• N. component that eluted between methyl linoleate and Tz:velev & E. Petehenyuk s.n. in 1983 (MOl. Jinolenate. GC-MS in the El mode. produced a spectrum with 46452 Pep/is erecta Aeq. Israel: USDA s.n. ions at 260 [M-32] and 218 [M-74], besides many low mass 64201 Peplis ponula L Portugal: J. Montezuma s.n. in 1983 ions from this same component. In the Cl mode. the only IMO). significant ions were at 219 [MH-74J. 261 [MH-321 and 293 64206 Physocalymma scaberrima Poh!. Brazil: Amazonas. 8. (MH). These ions would be expected from a methyl ester of Nelson 1332 (MOl. an oetadecatrienolc acid, but the absence of a molecular ion 64202 Pleurophora saecocarpa Koehne. Argentina: Corrientes. (292) in the EI mode and the large loss of 74 from the Schinini et al. 22540 (KE..(3I. eis~ molecular ion distinguish it from the more common all 64203 Rasia ramosior (L.l Koehne. USA: North Carolina. 9,12.15-0etadecatrienoic acid usually found in seed oils. MS Graham 447 (KE-Gl. analysis of methyls trans·3, eis·9, cls·12-octadecatrienoate. 64204 TetraSxls salieifolia (Tul.) Baker. Mauritius: D. Lorence found in methyl esters of Stenachaenium macrocephalum. 1231 (KE-G). produced spectra identical to the unknown in both EI and CI •Abbreviations in parentheses represent herbaria holding modes, along with 'the same GC retention characteristics. The voucher specimens; abbreviations fallow recommendations unusual component was isolated from the mixed Decodon of Index Herbariorum (1981) Bohn. Scheltema. and Holkema. methyl esters by HPLC using C'll·bondpak and acetonitrile. IR Utrecht. KE-G represents Iythraceous collections of S. Graham J and l C and IHNMR confirmed its identity as methyl trans~ at KE. 3.cis~9,cls·12·octadecatrienoate.

Acknowfedgements-The study is supported in part by NSF Appendix I-Accession Ust­ grant BSA 8314366 to the first author. We wish to thank Peter USDA Accession Number Raven, Missouri Botanical Garden, for arranging procurement 64189 Adenaria floribunda H. B. K. Mexico: Chiapas, Breedlove of seed samples of some rare. or otherwise difficult to obtain, 38133IMO}. genera. We also thank A. E. van Wyk and 8. Nelson for 47473 Ammannia audeulata Willd. Pakistan: USDA no. 4325. providing seed samples for analysis and Tomya Wilson for 64190 Ammannia larifolia L. Puerto Rico: Liogier 10314 (MICHl. technical assistance. • SEED LIPIDS OF THE LYTHRACEAE 439

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