Evolution of Sesquiterpene Lactones in Angiosperms*

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154 V1CENTE DE P. EMERENCIANO, MARIA AUXlLIADORA C. KAPLAN AND OTtO R. GO1-1"LIEB rABLE 2--CONTINUED ~Vo. S O No. $ O No. S O No. S O 1131 0.53 -0.93 1186 0.53 -0.66 1244 0.80 -0.66 1300 0.80 -1.06 1132 0.53 -0.93 1187 0.53 -0,53 1245 0.80 -0,80 1301 0.80 -I .06 1132,5 0.53 -0.93 1188 0.53 -0,66 1246 0.80 -0.80 1302 0.53 -0.66 1133 0.53 -0.93 1189 0.53 --0.93 1247 0.80 -0.93 1303 O. 53 -0.66 1134 0.53 -0.80 1190 0.53 -0.68 1248 0.80 -1.20 1309 0.66 -0.93 1135 0.53 -0.66 1191 0.53 -0,66 1249 0.80 -0.93 1310 0.66 -0.66 1136 0.53 -0.80 1192 0.53 -0.80 1250 0.60 --0.73 1311 0.26 -1.06 1137 0.53 -0.93 1193 0.66 -0.66 1251 0.60 -0.66 1312 0.26 -0.80 1138 0.53 -0.93 1194 0.53 -0.80 1252 1.00 -0.36 1313 0.26 -0.93 1139 0.53 -0.93 1195 0.53 -0.66 1253 0.53 -0.53 1314 0.26 -0.93 1140 0.53 -0.93 1196 0.53 -0,66 1254 0.53 -0,66 1315 0.26 "-0.53 1141 0.53 -0.93 1197 0.53 -0.66 1255 0.66 -.0.93 1316 0.26 -0.80 1142 0.53 -0.93 1198 0.53 -0,66 1256 0.66 -0.93 1317 0.26 -0.80 1143 0.53 -0.93 1199 0.53 -0.53 1257 0.71 -0.47 1318 0.26 -0.80 t144 0.53 -1.06 1200 0,53 -0.66 1258 0.71 -0.60 1319 0.26 -0.80 1145 0.53 -0.80 1201 0.53 -0.66 1259 0.53 -1.06 1320 0.26 -1.06 1146 0.53 -1.06 1202 0,53 "-0.93 1260 0.53 -1.06 1321 0.26 -0.80 1147 0.53 -0,93 1203 0.53 -0.80 1261 0.53 -1,20 1322 0.26 -0.93 1148 0.53 -0.93 1204 0.53 -0.93 1261,5 0.40 -1.06 1325 0.53 -1.33 1149 0.53 -0.93 1205 0.53 -0.93 1261,6 0.40 -1.06 1326 0.53 -1,20 1149.5 0.66 -0.53 1205.5 0.53 -0.80 1261.7 0.40 -1.20 1327 0.53 -1.06 1150 0.80 -0.66 1206 0.53 -0.80 1262 0.53 -0.80 1328 0.53 -1.06 1151 0.80 -0.66 1207 0.53 -0,80 1263 0.53 -0.66 1329 0.53 -1.06 1151.5 0.80 -0.80 1208 0.53 -0.80 1264 0.53 -0.66 1330 0,53 -1.06 1152 0,80 -0.80 1209 0.53 -0.80 1265 0.53 -0.66 1331 0.53 -0.93 1153 0.80 -0.66 1210 0.53 -0.80 1266 0.53 -0.66 1332 0.53 -0.80 1154 0.66 -0.66 1211 0.53 -0.80 1267 0.53 -0.93 1333 0.53 -1.20 1155 0.80 -0.40 1212 0.53 -0.80 1268 0.53 -0.80 1334 0.53 -0.93 1156 0.80 -0.40 1213 0,53 -0.80 1269 0.53 -0.80 1335 0.53 -0.80 1157 0.80 -0.66 1214 0.53 -0.66 1270 0,53 -0.80 1336 0.53 -1.20 1158 0.93 -0,66 1215 0.53 -0.93 1271 0.53 - 1.20 1337 0.53 -0.93 1159 0.53 -0.93 1216 0,53 -0.80 1272 0.53 -1.06 1338 0.53 -0.80 1160 0.53 -0.80 1217 0.53 -0.80 1273 0.53 -1.06 1339 0.53 -0.80 1161 0,53 -0,80 1218 0.53 -0.93 1274 0.53 - 1.06 1340 0.53 -0.80 1162 0,53 -0,53 1219 0,53 -0.93 1275 0.53 -1,06 1341 0.66 "-0.93 1163 0.53 -0.80 1220 0.66 -0.80 1276 0.53 -1.06 1342 0.66 -0.93 1164 0.53 -0.53 1221 0.53 -0.93 1277 0.53 --0.93 1343 0.66 -0.80 1165 0.53 -0.53 1222 0.53 -0.80 1278 0,53 -1.06 1344 0,66 -0.80 1166 0.53 -0,53 1223 0.53 -0.40 1279 0.53 -1.06 1345 0,66 -0.66 1167 0.53 -0,53 1224 0.53 -040 1280 0.53 -0.93 1346 0.53 -1.20 1168 0.53 -0.53 1225 0.66 -0.53 1281 0.53 -0.93 1347 0.40 --0.93 1169 0.53 --0.66 1226 0.53 --0.66 1282 0.66 -0.66 1348 0,66 --1.06 1169.5 0.53 -0.80 1227 0.53 -0.80 1283 0.66 -0.53 1349 0.53 -1.06 1170 0.53 -0.66 1228 0.53 -0.93 1284 0.53 -0.80 1350 0.53 - 1.06 1171 0.53 --0.66 1229 0.53 --0.66 1285 0.53 -0.80 17* 0.13 -1.06 1172 0.53 -0,80 1230 0,53 -0.80 1286 0.53 -0.80 38" 0.13 -0.93 1173 0.53 -0.93 1231 0.53 -0,80 1287 0.66 -0.80 39" 0.13 -0.93 1174 0.53 --0.80 1232 0.53 -0,80 1288 0.66 --0.53 80 ° 0.13 --0,80 1175 0.53 --0.66 1233 0.53 --0.80 1289 0.66 -0,40 83" 0.13 --0.80 1176 0.53 --0.80 1234 0.53 --0,80 1290 0.60 --1.00 93* 0.13 -0.93 1177 0.53 -0.80 1235 0,53 --0.80 1291 0.60 --1.00 105" 0.13 --0.93 1178 0.53 --0.66 1236 0.53 -0.66 1292 0.80 --1.20 233" 0.26 --0.66 1179 0.53 -0.66 1237 0.80 --0.80 1293 0.80 --0.93 234* 0.26 --0.53 1180 0.53 --0.66 1238 0.80 --0,80 1294 0.80 --0.93 235" 0.26 --0.66 1181 0.53 --0.80 1239 0.80 --0.80 1295 0.80 --0.93 236" 0.26 -0.53 1182 0.53 --0.80 1240 0.80 -0.80 1296 0.80 -0.93 237" 0,26 --0.53 1183 0.53 --0.80 1241 0.80 -0,66 1297 0.80 --0.93 238" 0.26 --0.53 1184 0.53 -0.66 1242 0.80 --0,66 1298 0.80 -0.93 239 ° 0.26 --0.40 1185 0.53 --0.66 1243 0.80 --0.66 1299 0.80 --1.06 240" 0.26 --0.26
SESQUITERPENE LACTONES IN ANGIOSPERMS 155 TABLE 2--CONTINUED No. S O No. S O No. S O No. S 0 241 * 0~6 -'0.40 398" 0.26 --I .06 623* 0~6 --0.53 700" 0.26 -0~0 242* 0~6 -0.26 3~9" 0.26 --I.06 624" 0.26 -0,53 728* 0.26 -0~6 243* 0.26 -0.53 408°a 0.26 -0.66 625," 0.26 -0.53 "/29 ° 0.26 -0.66 244" 0.26 --0.40 414" 0.26 -0.93 633," 0.26 --I.06 793" 0.40 -0.93 246 ° 0.13 -0.93 415" 0.26 -0.80 634* 0.26 -0.66 807* 0.40 --I.06 248" 0.13 -0.93 428* 0~6 -0.93 635* 0~6 -0.53 808* 0.40 --0.93 249* 0~6 -1.06 429* 0.26 --0.93 626" 0.26 -0.53 809' 0.40 -0.66 253" 0,13 -0,66 430" 0.26 -0.66 63"/* 0.26 -0.53 810" 0.40 --0.53 2M* 0.13 "--0.66 434" 0.26 -0.80 649* 0.26 -0.53 1005" 0,53 -0.80 3~2" 0.40 -0.66 478," O.Z~ -0.93 659* 0.26 -0.93 1146" 0.13 -0.80 354* 0.40 -'0.93 479* 0.26 -0.80 660" 0.26 -0.93 1217" O~ -0.66 365* 0.26 -0.93 483* 0~6 -0.80 666 ° 0.26 -0.80 1227" 0.26 -0.93 370"a 0.Z,6 -0.80 577" 0,26 -0.80 667* 0.26 -0.66 1240" 0~,6 --1.06 374* 0~6 -0.93 587* 0.26 -0.66 692" 0~6 --1.06 1242" 0.26 -0.80 384* 0~6 -0.66 5~2" 0.26 -0.66 696" 0.26 -0.53 1254" 0.53 -0.80 385* 0.26 -0.80 613" 0.26 --0.93 658* 0.26 -0.80 1261 = 0.29 -0.80 397* 0~,6 --1.06 621 * 0.26 -0.53 699* 0.26 -0.80 TABLE 3. OCCURRENCE OF SESQUITERPENE LACTONES IN GENERA OF MAGNOLIACEAE INDICATED BY ASTERISKED NUMBERS WHICH REFER TO STRUCTURAL FORMULAE GIVEN IN REF. [2]/NUMBERS OF SPECIES IN WHICH THE COMPOUND HAS BEEN FOUND Liriodendn~38=ll, 3S*ll, 83*ll, 93*ll, 254"11,3"/0a*/I; ,Y,~gno~il~O*/1, 246"11, 248"11.253"11,365"11, 374"11; Mk:he//a17*11, 80°11,249"11,385"12,374=12, 1149"11, 1227"/I, 1240°11. TABLE 4. OCCURRENCE OF SESQUITERPENE LACTONES IN GENERA OF LAURACEAE INDICATED AS IN TABLE 3 Lindera 233= /1, 235"/1, 238"/1, 262"/1, 354"/1, 478"11, 4"/9"/1, 483"/1, 807"/1, 808"/1; Neo/~ea 234"/1, 236"/1, 237"/1, 239"/1, 240"/1, 241 ,'/1, 242"/1, 243=/1o 244=/1, 809"/1, ~10"/1; Ocorea 126'/1. TABLE 5. OCCURRENCE OF SESOUITERPENE LACTONES IN GENERA OF APIACEAE INDICATED AS IN TABLE 3 Feru/a 384"12, 385"12, 3~9=12, 414*11, 415"12, 432*11,433*11, 434"11, 621"11. 623"11, 633°11, 634"11, 635=11, 636"11, 637°11, 728"11, 729*11; Laser 429*11, 696"/I, 793"11 ; Laserpitium428*ll, 613=11, 621 °11, 624"11, 625*11, 649*11, 698"11, 700"11, 1242*11 ; Me/anosenium 397"11, 398°11, 408a*11, 430"11 ; Smyrnium 1005"/I, 1254"11. Results The distribution of sesquiterpene lactones, classified into structural types, in taxa of angiosperms is given in Tables 11, 12 and 13. Presence (-t-) signs are inserted whenever a structural type, although not actually represented by an isolated derivative, must nevertheless be present, even if only transitorily, _ since it functions as a biosynthetic intermediate to an isolated metabolite. Only the most common structural types 1, 1.1 and 1.2 of sesquiterpene lactones have so far been located in Magnoliaceae (Table 11). Diversification of types occurs from here on in two directions, one towards the Lauraceae which produce characteristically furanogermacranolides (1 F) and one towards the Apiaceae-Asteraceae which both develop mainly the guaianolide and eudesmanolide themes. A correlation of the EA s and EA o parameters (Fig. 7) also can best be interpreted in the light of this two-directional evolution of sesquiterpene lactones. Clearly the Magnoliaceae contain biosynthetically much simpler and less oxidized compounds of this class than the Lauraceae on one hand and the Apiaceae- Asteraceae on the other (Fig. 7). Indeed the EA s and EA o values, and perhaps even better the/~s and/~o values (Fig. 8), for sesquiterpene lactones of these families correlate well with their evolutionary advancement, as measured by Sporne indices [7] based on morphological criteria. The distribution of sesquiterpene lactones in the Asteraceae is quite heterogeneous (Table 12). Only the common types 1, 1.1 and 1.2 have been found in the Cichorioideae, a subfamily which in this respect resembles the Magnoliaceae or, more closely, if EA s and EA o values are also considered (cf. Table 8 and 9), the Apiaceae. The subfamily Asteroideae group 1 [9] which
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Evolution of Sesquiterpene Lactones in Angiosperms*

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