Evolution of Sesquiterpene Lactones in Angiosperms*

Bkx~w-tdca/b'fs/ernat/cs and E~, Vol. 13, No. 2, pp. 145-166, 1985. 0305-1978/85 $3.00+0.00
Printed in Great Britain.
Pergamon Press Ltd.
Evolution of Sesquiterpene Lactones in Angiosperms*
VICENTE DE P. EMERENCIANO'r, MARIA AUXILIADORA C. KAPLAN¢ and OTTO R. GOTTLIEBI"
Tlnstituto de Quimica, Univeraidade de S~o Paulo, 05508 S&o Psulo, SP, Brazil;
tlnstituto de Quimica, Univemidede Federal Fluminanse, 24000 Niterbi, R J, Brazil
Key Word Index--Magnollaceae; Lauraceae; Apiaceae; Asteraceae; germacranes; seKluiterpena lectonas; skeletal specialization,
oxidation state; biochemical evolution.
AJ~t~act--The paper attempts to discover an outline Of the evolutionary tmnde of seScluiterpene lactones in angiosperms. The
working method involves the quantification Of skeletal specialization and oxidelJon state of the compounds and the assignment of
evolutionary advancement indices, based on such date, to texa. In the angiosperms as a whole, sesquitarpene lactone evolution
proceeds by divemification of structural types and by amplification of the oxidation state of the molecules. The opposite trend
appears to operate at lower hierarchical level, in the Asteracese. In this family, which contains most of the known compounds of the
class, sescluiterpene lactone evolution follows two parallel pathways in the tribes belonging to two groups of the subfamily Asteroideae.
Introduction
Two comprehensive collections of distributional
data and plausible biogenetic schemes for
germacrane acid (P) derived sesquiterpene
lactones have been published in recent years [2,
3]. An exhaustive discussion of the value of
sesquiterpene lactones as taxonomic characters
in the Asteraceae thus became possible [3]. The
present paper attempts to achieve, through
quantification of the published data and consideration
of the principles of micromolecular
systematics [4], a clear outline of the trends
accompanying the evolution of sesquiterpene
lactones in the angiosperms.
Experimental
Although seSClUiterpene lactona ring closure involves alternatively
carbons 6 and 8, for simplicity only the former cyclization
mode is featured in the representation of germacranolide (Fig.
1), guelanolide (Fig. 2), eudesmanolide (Fig. 3), eremophilanolide
(Fig. 4) and some rarer (Fig. 5) skeletal types. These types
are codified according to their position in a biogenetic scheme
(Fig. 6).
It has been emphasized that, although mechanistically
sound, the proposed steps Of the sesquiterpene lactone
*Part XXVII in the series "Chemosystematics and Phylogeny'.
For Part XXVI see ref. [1]. Based on the M.Sc. thesis
presented by V. de P. Emerencieno to Universidade de S~o
Paulo (1983).
(Received 23 March 1984)
biosynthetic pathways (Fig. 6) have not been established by
the usual labelling or enzyme studies [3]. Lack of detailed
biosynthetic knowledge, however, ceased to be a vulnerable
aspect [5] of our methodology [4]. It suffices that precursor
and derivatives be biosynthetically homologous in order that
their characteristics, such as skeletal specialization and
oxidation level, may be compared. It is now [1] the structural
difference between the precursor, in the present case
compound P, and a particular derivative which is being
measured, rather than, as previously [4], their biosynthetic
distance, as conveyed by the number of reaction steps defined
in the hypothetic biosyntheticel scheme.
The skeletal specialization of a compound (per carbon) (S)
with respect to a precursor is determined by counting the
number of bonds (to C) broken and the number of bonds (to C,
or to a heteroatom if this involves formation of a new cycle)
formed for each carbon of the compound; adding these
counts; and dividing the sum by the number of C-atoms of the
compound. The E--.Z isomerization of a double bond is considered
to involve breakage of a bond and formation of
another. The oxidation state Of a compound (again per carbon)
(Q is determined by counting, for each carbon of the
compound, -1 for each bond to H and +1 for each bond to a
heteroatom [6]; adding these counts; and dividing the sum by
the number of C-atoms of the compound. Loss of groups is
considered to operate through oxidized intermediates and for
each severed C-C bond which results in the loss of a molecular
moiety (in comparison with the precursor) 3 points are added
to the count. Such determinations are exemplified for five
selected compounds in Table 1. Their results for all sesquiterpene
lactones listed in references [2] and [3] are given in
Table 2.
A genus may contain several sesqulterpene iectones (Tables
3--6), each present in one or more species and each characterized
by S and 0 values (Table 2). The averages of these
values, weighted by the number of species in which the
compound occurs, are considered to represent the evolu-
145

146 VICENTE DE P. EMERENCIANO, MARIA AUXILIADORA C. KAPLAN AND O1"~'O R. GOI-I'UEB
! 9
~ p 0~/~ ~OH
1.3 1.4 1.6
FIG. 1. SKELETAL TYPES OF GERMACRANOLIDES.
~,
O
! .! .4
FIG. 2. SKELETAL TYPES OF GUAIANOUDES.

SESOUITERPENE LACTONES IN ANGIOSPERMS
147
% ~
0
1.2.2
FIG. 3. SKELETAL TYPES OF EUDESMANOUDES.
~ ~-~0
1.2.1 1.2.1.1
1.2.1.2
~.~0
0 ~ ~ 0
1.2.1.3
1.2.1.4
FIG. 4. SKELETAL TYPES OF EREMOPHILANOLIDES.
•
i
%.7 . 1 ~
i••
i.i~~0 O
FIG. 5. SKELETAL TYPES OF MISCELLANEOUS SESQUITERPENE LACTONES.

148 VICENTE DE P. EMERENClANO, MARIA AUXlLIADORA C. KAPLAN AND OTTO R. Go1-rUEB
1 : 1.1
= 1.2
] = 1.3
~
1.5
- i.~
!.7
1.8
!.~
I.!0
"-'•
i.1.1 -~~ 1.1J.l
- 1.1.2 1.1.1.2
i
I
= i.1.3 1.1.1.3
I = 1.1.4 1.1.1.4
1.2.2 1.2.1.2
I
- 1.2.1.3
~ 1,2.1A
FIG. 6. BIOGENETIC SCHEME FOR SKELETAL TYPES OF C,~RMACRANE
ACID DERIVED SESQUn'ERPENE LACTONES.
t~naW advencemam pamrn~ere (respectively EA s and EAo)
with respect to =escluiterpene lactone~ of the ~enem O'abte 7).
The EA s and F-Ao pamn'wtem of mxa of higher ranks are
calculllm:l is again indicated in Table 7. The ¢on~'ibu0on of the
character state of a particular cons'dtuem of the taxon to the
average is thus proportional to its frequency of distribution in
the taxon. The ~Pmadl between minimal and maximal Sand 0
values of compounds in texa Ire also given in Tabtes 8-10, as
are Spome's ~ i c a l advancement indices [7] in Table 8
and basic chromosome numbers [8] in Tables 9 and 10.
TABLE 1. EXAMPLES OF THE DETERMINATION OF SKELETAL SPECIALIZATION (S) AND OXIDATION STATE (O) VALUES FOR SESQUITERPENES LAC-
TONES NUMBERED AS IN REF. [3].
Formulae
Carbons with bonds S Numbers of bonds O
Broken (b) Formed (~) ~(b+~1 C--H C--O C--C ~ (o+3c--h)
At positions No. of C (h) (d (d No. of C
1 (C,s) 0
656 (C,s) 0
~0~ (c,~) 4:5
(total 2)
1348 (C,~) 5,6,10,14
(total 4)
1252 (C,,) 2,3,3A,4,15
(total 6)
(6,12) 2/15-0.13 20 4
(total 2)
5,6,10,12 4/15-0 ~.,6 20 4
(total 4)
1,5,5,6,12,15 8/I s--0.53 2o 6
(total 6)
5,5,8,I0,12,14 I0115--0,66 19 3
(total 6)
1,2A,5,5,6,12,15 14/14-1 .oo 17 9
(total 8)
-- -16/15,--1.06
-- -16115,-1.06
-- -14115--0.93
-- -16115--1.06
1 -5/14=--0.36
~ 12
a
~ ~ 0
~ OR
1 566 10~8 1348, R = ,4~e~lte
12~2

SESQUffERPENE LACTONES IN ANGIOSPERMS 149
TABLE 2. OXIDATION STATES (OVALUES) OF SESQUITERPENE LACTONES CLASSIFIED INTO GROUPS ACCORDING TO THEIR SKELETAL SPECIALI-
ZATION (S VALUES). THE NUMBERS 1-1350 AND THE ASTERISKED NUMBERS REFER TO STRUCTURAL FORMULAE LISTED UNDER THE SAME
NUMBERS IN REFS. [3] AND [2] RESPECTIVELY.
No. S O No. S O No. S O No. S O
1 0.13 -1.06 87 0.13 -0.93 114 0.13 -0.80 171 0.13 -0.80
2 0.13 -0.93 ,58 0.13 -0.93 115 0.13 -0.80 172 0.13 -0,80
3 0.13 -0~0 89 0.13 -0.93 116 0.13 -0.80 173 0.13 -0~0
4 0.13 -0.80 60 0.13 -0.93 117 0.13 --0.80 174 0.13 -0.80
5 0.13 -0.80 61 0.13 -0.93 118 0,13 --0.53 175 0.13 -0~0
6 0,13 -0.93 62 0.13 -0.80 119 0.13 -0.66 176 0,13 -0.80
7 0.13 -0~3 63 0.13 -0.80 120 0.13 -0.80 177 0.13 -0.~6
8 0.13 -0.93 64 0.13 -0.80 121 0.13 -0.80 178 0.13 --0.53
9 0.13 -0.93 65 0.13 -0.80 122 0.13 --0~0 179 0.26 -0.53
10 0.13 -0.93 66 0.13 -0.93 123 0.13 -0.66 180 0,13 -0~0
11 0,13 -0.93 67 0.13 -0.93 124 0.13 -0,80 181 0.13 -0.66
12 0.13 -0.93 68 0.13 -0.93 125 0.13 -0~6 182 0.13 -0~0
13 0.13 -0.93 69 0.13 -0.93 126 0.26 -0.26 183 0.26 -0.40
14 0.13 -0.93 70 0.13 -0.80 127 0.26 -0.26 184 0.26 -0.26
15 0.13 -0.93 71 0.13 -0.80 128 0.26 -0.26 185 0.26 -0.13
16 0.13 -0.93 72 0.13 -0~0 129 0.13 -0.80 186 0,13 -0.80
17 0.13 -0.80 73 0,13 -0.66 130 0.13 -0.66 187 0.13 -0.66
18 0.13 -0.80 74 0.13 -0.66 131 0.13 -0.53 188 0.13 -0.80
19 0.13 -0.80 75 0.13 -0.66 132 0.13 -0.53 188.5 0.13 -0.93
20 0.13 -0.80 76 0.13 -0.66 133 0.13 -0.53 189 0,13 -1.20
21 0.13 -0.80 77 0.13 -0.66 134 0.13 -0.66 190 0.13 -1.06
22 0.13 -0.66 78 0.13 -0.66 135 0.13 -0.66 191 0.13 -0.93
23 0,13 -0.66 79 0.13 -0.66 136 0,26 -0.53 192 0.13 -1.06
24 0.13 -0~0 80 0.13 -0.66 137 0.13 -1.20 193 0,26 -0.26
25 0.13 -0.93 81 0.13 -0.66 138 0.13 -1.06 194 0.26 -0.40
26 0.13 -0.93 82 0.13 -0.66 139 0.13 -1.06 195 0.13 -1.06
27 0.13 -0.93 83 0.13 -0.66 140 0.13 --0.93 196 0.13 -0.93
28 0.13 -0.93 84 0.13 -0.93 141 0.13 -1.06 197 0.13 -0.93
29 0.13 -0.80 85 0.13 -0.80 142 0.13 -1.06 198 0.13 -0.93
30 0.13 -0.80 86 0.13 -0.80 143 0.13 -0.93 199 0.13 -0.80
31 0.13 -0.80 87 0.13 -0.80 144 0.13 -0.93 200 0.13 -1.06
32 0.13 -0.80 88 0.13 -0.80 145 0.13 -1.06 201 0.13 -1.20
33 0.13 -0.80 89 0.13 -0.53 146 0.03 -1.06 202 0.40 -0.40
34 0.13 -0.66 90 0.13 -0.53 147 0.13 -0.80 203 0.40 -0.40
35 0.13 -0.93 91 0.13 -0.53 148 0.13 -0.96 204 0.40 -0.40
36 0.13 -0.93 92 0.13 -0.53 149 0.13 -1.06 205 0.40 -0.40
37 0.13 -0.93 93 0.26 -0.40 150 0.13 -0.66 206 0.40 --0.40
38 0.13 -0.93 94 0.26 -0.40 151 0.13 -0.80 207 0.40 -0.40
39 0.13 -0.93 95 0.26 -0.40 152 0.13 -0.93 208 0.40 -0.40
40 0.13 -0.80 96 0.26 -0.40 153 0.13 -0.93 209 0.40 --0.40
41 0.13 --0.66 97 0.26 -0.40 154 0.26 -0,40 210 0,40 -0.40
42 0.13 --0.80 98 0.13 --0.66 155 0.13 -0.80 211 0.40 -0.40
43 0.13 --0.80 99 0.13 --0.53 156 0.13 --0.93 212 0.40 --0.40
44 0.13 --0.93 I00 0.I 3 -0.40 158 0.I 3 -0.80 213 0.40 -0.40
45 0.13 -0.80 101 0.13 -0.53 159 0.13 --0.80 214 0.40 -0.40
46 0.13 -0.80 102 0.13 -0.80 160 0.13 -0.80 215 0.40 -0.40
47 0.13 -0.80 103 0.13 --0.80 161 0.13 -0.80 216 0.40 -0.40
47.5 0.13 -0.66 104 0.13 --0.66 162 0.13 -0.66 217 0.40 -0.40
48 0.13 -0.80 105 0.13 -0.66 163 0,13 --0.05 218 0.40 -0.40
49 0,13 --0.80 106 0.13 -0.66 164 0.13 --0.80 219 0.40 --0.40
50 0.13 -0~0 107 0.13 -0.66 164.5 0.13 --0.80 220 0.40 --0.40
51 0.13 -0.80 108 0,13 -0.66 165 0.13 -0.80 221 0.40 --0.40
52 0.13 -0.80 109 0.26 --0,40 166 0.13 -0.93 222 0.40 -0.40 "
53 0,13 -0.66 110 0.26 -0,40 167 0.13 -0.93 223 0.40 --0.26
54 0.13 -0.66 111 0.26 --0.40 168 0.13 --0.80 224 0.40 -0.53
55 0.13 -0.66 112 0.13 -0.93 169 0.13 --0.80 225 0.40 --0.40
56 0.13 --0,80 113 0.13 --0.80 170 0.13 -0.80 226 0.40 --0.40

150 VICENTE DE P. EMERENCIANO, MARIA AUXIUADORA C. KAPLAN AND OTI'O R. GOI"I"LIEB
TA~,.E 2--CONTINUED
No. S 0 NO. S O No. S O " No. S O
227 0.40 --0.40 281 0.40 -0.80 338 0.53 -0.26 39"7 0.66 -0.93
228 0.40 -0.40 282 0.40 -0.80 339 0.53 -0.26 398 0.66 -0.80
229 293 0.40 -0.80 340 0.53 -0.13 399 0.66 -0.40
230 284 0.40 -0.80 341 0.53 --0.I 3 400 0.66 -0.40
231 0.40 -0.40 285 0.40 -0.80 342 0.53 -0.13 401 0.66 -0.53
232 0.40 -0.46 286 0.40 -0.80 343 0.53 -0.26 402 0.66 -0.53
233 0.40 -0.40 297 0.40 -0.80 344 0.53 -0.26 403 0,66 -0.53
234 0.40 -0.26 288 0.40 -0.80 345 0.53 -0~6 404 0.66 -0.26
235 0.40 -0.26 289 0.40 -0.80 346 0.53 -0.40 405 0,66 -0.26
236 0.40 -0.53 290 0.40 -0.66 347 0.53 -0.26 406 0.66 -0.26
237 0.40 --0.53 291 0.40 -0.66 348 0.53 --0.26 407 0.66 -0.26
238 0.40 -0.53 292 0.40 -0.66 349 0.53 -0.26 40~ 0,66 -0.13
239 0.40 -0.53 263 0.40 -0.80 350 0.53 -0.40 409 0.66 -0.13
240 0.40 -0.53 294 0.40 -0.93 351 0.53 -0~6 410 0.66 -0.26
241 0.40 -0.40 295 0.40 -0.93 352 0.53 -0.26 411 0.66 -0.66
242 0.40 -0.53 296 0.40 -0.93 353 0.53 -0.26 412 0.66 --0.93
243 0.40 -0.53 296.5 0.40 -0.93 354 0.26 -0.26 413 0.13 --0.93
244 0.40 -0.40 297 0.40 -0.66 355 0.53 -0.53 414 0.13 -0.93
245 0.40 -0.53 298 0.40 -0.66 356 0.53 -0.53 415 0.13 -0.80
246 0.40 -0.40 299 0.40 -0.80 357 0.26 -0,66 416 0.13 --0.80
247 0.40 -0.40 300 0.40 -0.80 358 0.26 -0.80 417 0.13 -0.66
248 0.40 -0.40 301 0.40 -0.80 359 0.26 -0,80 418 0.13 -0.80
249 0.40 -0.40 302 0.40 -0.66 360 0.29 -0.53 419 0.13 --0.80
249.5 0.40 -0.40 303 0.40 -0.66 361 0.26 -0.93 420 0.13 -0.66
249.6 0.40 -0.26 304 0.40 -0.53 362 0.40 -0.53 421 0.13 -0.80
249.7 0.40 -0.26 305 0.40 --0.53 363 0.40 -0.66 422 0.13 -I .06
249.8 0.40 -0.40 306 0.40 -0.66 364 0.40 -0.66 423 0.13 -0.93
250 0.40 --0.13 306.5 0.40 -0.66 365 0.40 --0.66 424 0.40 --0.66
251 0.40 -0.13 30 0.40 -0.66 366 0.40 -0.66 425 0.13 -0.66
252 0.40 -0.13 308 0.40 -0.66 367 0.66 -0.46 426 0.13 -0.66
253 0.40 --0.13 309 0.40 -0.66 368 0.66 -0.46 42"7 0.13 -0.93
254 0.40 -0.13 310 0.40 -0.66 369 0.66 -0.46 428 0.13 -0.80
255 0.40 -0.13 311 0.40 -0.66 370 0.66 -0.46 429 0.13 -0.40
255.5 0.40 --0.13 312 0.40 -0.66 371 0.66 -0.46 430 0.13 -0.26
256 0.40 -0.26 313 0.40 -0.66 32 0.66 --0.46 431 0.40 -0.26
25 0.40 -0.26 314 0.40 -0.66 373 0.66 -0.60 432 0.40 -0.26
258 0.40 -0,26 315 0.40 --0.53 374 0.66 -0.60 433 0.40 -0.26
259 0.40 -0.26 316 0.40 -0.40 375 0.66 -0.60 434 0.40 -0.26
260 0.40 -0.26 317 0.40 -0.40 3"76 0.53 -0.26 435 0.13 -0.80
261 0.40 --0.26 318 0.40 -0.40 377 0.53 -0.26 436 0.13 -0.93
262 0.40 -0.13 319 0.53 --0.53 38 0.53 -0.13 437 0.13 --0.93
263 0.40 -0.00 320 0,53 --0.66 379 0.60 -0.20 438 0.13 -0.93
264 0.40 --0.40 321 0.53 -0.53 380 0.53 --0.26 439 0.13 -0.66
265 0.40 -0.53 322 0.53 -0.53 3~I 0.53 -0.26 440 0.13 --0.80
266 0.40 -0.53 323 0.53 -0,53 382 0.53 -0.26 441 0.40 -0.93
267 0.40 --0.40 324 0.53 --0.53 383 0.53 -0.13 442 0.40 -0.80
268 0.40 -0.40 325 0.53 -0.53 384 0.53 -0.13 443 0.40 -0.80
269 0.40 -0.66 326 0.53 -0.53 385 0.53 -0.13 4~, 0.40 -0.66
270 0.40 --0.53 327 0.53 -0.66 386 0.40 --0.80 445 0.40 --0.66
271 0.40 -0.53 328 0.53 -0.53 387 0.53 -0.40 446 0.40 --0.80
272 0.40 -0.80 329 0.53 -0.53 388 0.53 -0.26 447 0.26 -0.66
273 0.40 -0.80 330 0.53 --0.53 389 0.53 --0.40 448 0.26 -0.53
274 0.40 -0.29 331 0.53 -0.40 390 0.53 -0.40 449 0,26 -0.53
275 0.40 -0.26 332 0.53 -0.40 391 0.53 -0.40 450 0.26 -0.53
276 0.40 -0.26 333 0.53 -0.40 392 0.53 -0.26 451 "0.26 -0.93
277 0.40 -0.26 334 0.53 -0.40 393 0.53 -0.40 452 0.13 --0.53
278 0.13 --0.40 335 0.53 -0.40 394 0.53 -0.40 453 0.13 -0.53
279 0.40 -0.93 336 0.53 -0.40 395 0.26 -0.26 454 0,I 3 -0.66
280 0.40 -0.80 337 0.53 -0.40 396 0.66 --0.26 455 0.13 -0.53

SF.SQUffERPENE LACTONES IN ANGIOSPERMS : ; ~:~ 151
TABLE 2--CONTINUED
No. $ 0 No. $ 0 No. S 0 No. $ 0
456 0.13 "-0.53 511 0.40 .-0.66 563 0.66 --0.66 619 0.13 -1.06
457 0.13 --0.53 512 0.40 -0.53 564 0.66 -0.40 619.5 0.13 -I.06
458 0.13 -0.53 512.5 0.40 -0.66 595 0.66 -0.40 620 0,13 -1.06
459 0.13 -0.53 513 0.26 .-0.40 986 0.26 -1.06 621 0,13 -1.06
460 0.13 -0.53 514 0.13 --0.66 567 0.26 --0.93 622 0.13 -1.06
461 0.13 -0.53 515 0.13 -0.53 568 0,26 -0.93 623 0.13 -1.06
462 0.13 -0.40 515.5 0.26 -0.26 989 0.26 -0.93 624 0,13 -%06
463 0.13 -0.40 516 0.13 --0.80 570 0,26 -0.93 625 0.13 -I.06
464 0.13 -0.40 517 0.13 -0.66 571 0~6 -0.93 626 0.13 -I.06
4~5 0.13 -0.40 518 0.26 -0.53 571.5 0.26 -1.06 627 0.13 -0.93
466 0.13 -0.40 519.0 0.13 -0.80 572 0.26 -0.80 628 0.13 --0.93
467 0.13 -0.53 519.1 0.13 .-0.40 573 0,26 -0.80 629 0.13 .-0.93
467.4 0.13 --0.53 519.2 0,13 -0.40 574 0.26 -0,66 629.5 0.13 --1.26
467.5 0.13 -0.53 519,3 0.13 -0.40 575 0.26 -0.66 630 0.13 --1.06
467.6 0.13 -0.53 520 0.13 -0.40 576 0.26 -0.66 631 0.13 --1,00
468 0,26 -0.66 521 0.13 --1.20 577 0.26 -0.66 632 0.13 --1.20
469 0.26 -0.53 522 0.13 --1.06 578 0.26 -0.66 633 0.13 --1.06
470 0.13 -0.80 523 0.13 --1.06 579 0.26 -0.66 634 0.26 -0.80
471 0.13 -0.80 524 0.13 --0.93 580 0.26 -0.66 635 0.26 --1.02
472 0.26 --0.40 525 0.13 -0.80 581 0.26 -0.66 636 0,26 -0.80
473 0.26 -0.40 526 0.13 -0.80 582 0.26 -1.06 637 0.26 -0.80
474 0,26 -0.40 527 0.66 -0.66 583 0.26 -0.80 638 0.26 -1.02
475 0.26 -0,40 528 0.66 ,-0.53 584 0.26 --0.93 639 0.26 -1.02
476 0.26 -0.40 529 0.66 -0.53 585 0.26 -0.80 640 0.26 -0.93
47"/ 0.26 ,-0.40 530 0.13 -0.80 586 0.26 -0.80 641 0.26 -0.93
478 0.26 -0.40 530.5 0.13 -0.80 587 0.26 --0.80 642 0.26 -0.93
478.5 0.26 -0.40 530.6 0.13 -0.80 588 0.26 -0.66 643 0,26 --0.80
479 0.26 -0.66 531 0.13 --0.80 589 0.26 -0.80 644 0.26 -0.80
480 0.26 -0.66 532 0.26 -0.40 590 0.26 -0.80 645 0.26 -0.66
481 0.26 -0.40 533 0.26 -0.40 591 0.26 -0.93 645.5 0.26 -0.80
482 0.26 -0.53 534 0.13 -0.80 592 0.26 -0.80 646 0.26 -0.66
483 0.26 --0.53 535 0.13 --0.53 593 0,26 --1.06 647 0.26 --0.66
484 0.26 -0.53 536 0.13 -0.80 594 0.26 --0.93 648 0.26 -1.20
485 0.26 --0.40 537 0.13 --0.80 595 0.26 --0.80 649 0.26 -1.02
486 0.26 .-0.40 538 0.13 ,-0.80 596 0.26 -0.80 650 0.26 --0.93
487 0.26 -0.40 539 0,13 -0.80 597 0.26 --0.80 651 0.26 -0.93
488 0.26 -0.40 540 0.13 --0,93 598 0.26 -0.80 652 0.26 --0.93
489 0,26 -0.40 641 0.40 -0.66 599 0.26 -0.80 653 0.26 "--0.80
490 0.26 -0.40 642 0A0 -0.66 600 0.26 -0.80 654 0.26 --0.80
491 0.26 -0,40 543 0,40 -0.40 601 0.26 --0.80 655 0.26 --0.66
492 0.26 -0.40 544 0,26 -0.40 602 0.26 -0.80 656 0.26 -1,20
493 0.26 --0,40 645 0.53 -0.13 603 0.26 -0.80 657 0.26 -0.93
4~4 0,26 -0.46 546 0,53 --0.13 604 0.26 -0.80 658 0.26 -0.93
495 0.26 ---0.40 647 0.53 --0.26 6~4.5 0.26 -1.06 659 0.26 -0.93
49~ 0.26 --0.40 548 0.53 --0.26 605 0.26 -0.66 660 0.26 --0.93
497 0,40 --0.53 549 0.53 -0.26 606 0.26 --0.93 661 0.26 -1.02
4~ 0.40 -0.53 550 0.53 -0.26 607 0.26 --0.80 662 0.26 --0.93
498 0.13 --0.53 551 0.53 -0.26 606 0.26 -0.80 663 0.26 -0.93
500 0.13 --0.40 552 0.66 -0.40 609 0.26 -0.66 664 0.26 -0.80
501 0.26 -0.53 553 0A0 -0.26 610 0.26 -0.53 665 0,26 -0.93
502 0.26 -0.66 554 0.40 -0.53 611 0.26 -0.93 666 0.26 -1.02
503 0.26 -0.66 555 0.40 -0.53 612 0.26 -0.80 667 0.26 -0.93
~ 0.26 -0.66 ,556 0.40 -0.53 613 0.26 -1.06 668 0.26 -0.93
~ 0,13 --0.53 557 0.40 -0.53 614 0,26 -1.06 669 0.26 -0.80
506 0.13 -0.53 559 0.40 -0.53 615 0.26 -0.80 670 0.26 -0.93
507 0,40 -0.66 559 0.40 -0.53 616 0.26 -0.80 671 0.26 --0.93
508 0.40 .-0,66 560 0.40 -0.53 617 0.13 -0.66 672 0.26 -0,93
50~ 0,40 -0.53 561 0.40 -0.53 617.5 0.13 -0.93 673 0.26 -0.93
510 0.40 -0.66 562 0.26 -0.80 618 0.13 --1.26 674 0.26 --1.02

152 VICENI~ DE P. EMERENCIANO, MARIA AUXIUADORA C. KAPLAN AND OTTO R. GOTTUEB
TABLE 2--CONTINUED
No. S 0 No. S 0 No. S O No. $ 0
675 0.26 --0.93 731 0.26 --I .02 788.5 0.26 --0.66 845 0.26 -0.66
676 0.26 -0.80 732 0.26 --I .02 789 0.26 -0.80 846 0.26 -0.66
677 0.26 -0.80 733 0.26 -I .02 790 0.26 -0.66 84"/ 0.26 -0~56
678 0.26 -0.93 734 0.26 -0.93 791 0.26 -0.80 848 0.26 -0.66
679 0.26 -0.80 735 0.26 -0.93 792 0.26 -0.80 849 0.26 -0.66
680 0.26 -0.80 736 0.26 -I .02 793 0.26 -0.66 850 0.26 -0.80
681 0.26 -0.66 737 0.26 -1.02 793.5 0.26 I -0.66 851 0.26 -0.93
682 0.26 -0.80 738 0.46 -0.60 794 0.26 -0.66 852 0.26 -0.80
683 0.26 -0.80 739 0.40 -0.80 795 0.26 -0.80 853 0.26 -0.80
683.5 0.26 -033 740 0.40 -0.80 796 0.26 -0.40 854 0.26 -0.80
684 0.26 -0,93 741 0.40 -0.80 797 0.26 -0.40 855 0.26 -0.53
684.5 0.26 -0.93 742 0.40 -0.66 768 0.26 -0.66 856 0.26 -0~0
684.6 0.26 -0.93 743 0.40 -I .02 799 0.26 -0.53 857 0.26 -0~0
685 0.26 -0.66 744 0.66 -0.66 799.5 0.26 -0.53 858 0.26 -0.80
686 0.26 -I .02 "/45 0.53 -0.80 800 0.40 --0.53 859 0.26 --0.53
687 0.26 -0.96 746 0.40 -0.93 801 0.26 -0.40 860 0.26 -0.53
688 0.26 -0.80 74; 0.66 -0.66 802 0.26 -0.40 861 0.26 -0.53
689 0.26 -0.80 746 0.66 -0.68 803 0.26 -0.53 862 0.26 -0.53
690 0.26 -0.93 749 0.66 --0.66 804 0.26 -0.53 863 0.26 -0.80
691 0.26 -0.93 750 0.66 -0.66 805 0.26 --0.40 864 0.26 -0.53
692 0.26 -0.80 751 0.66 -0.66 806 0.26 -0.53 865 0.26 -0.53
683 0.26 -0.80 752 0.66 -0.66 807 0.26 -0.53 866 0.26 -0.53
694 0.26 -0.80 753 0.26 -0.80 80~ 0.26 -0.40 867 0.26 -0.53
695 0.26 -0.80 753.5 0.26 -0.80 809 0.26 -0.66 868 0/,6 --0.53
696 0.26 -0.60 754 " 0.26 -0.53 810 0.26 -0.66 869 0.26 -0.80
697 0.26 -0.93 755 0.26 --0.53 811 0.26 -0.66 870 0.26 -0.66
698 0.26 -0.93 756 0.26 -0.66 812 0.40 --0.26 8";I 0.26 -0.66
699 0.26 -0.93 757 0.26 -0.66 813 0.26 -0.93 872 0.26 -0.40
700 0.26 -0.66 758 0.26 -0.66 814 0.26 -0.26 873 0.26 -0.40
701 0.26 -0.80 759 0.26 -0.66 815 0.26 -0.40 874 0.26 -0.53
702 0.26 -0.80 760 0.26 -0.66 816 0.26 -0.40 875 0.26 -0.80
703 0.26 -0.80 761 0.26 -0.66 817 0.26 -0.40 876 0.26 -0.80
704 0.26 -1.06 762 0.26 -0.53 818 0.26 -0.40 877 0.26 -0.93
705 0.26 -1.06 763 0.26 -0.53 819 0.26 -0.26 878 0.26 --0.53
706 0.26 -1,06 754 0.26 -0.66 820 0.26 -0.40 879 0.26 -0.53
707 0.26 -0.93 765 0.26 -0.40 821 0.26 -0.26 880 0.26 -0.80
708 0.26 - 1.06 766 0.26 -0.26 822 0.26 -0.26 881 0.26 -0.80
709 0.26 --0.80 767 0.26 -0.66 823 0.40 -0.26 882 0.26 -0.80
710 0.26 --0.80 768 0.26 -0.66 824 0.40 --0.26 683 0.26 --0.53
711 0.26 -0.80 769 0.26 -0.80 825 0.26 -0.66 884 0.26 --0.53
712 0.26 -0.93 770 0.26 -0.66 826 0.26 --0.53 884.5 0.26 -0.53
713 0.26 --0.66 771 0,26 -0.53 827 0.26 -0.53 885 0.26 -0.40
714 0.26 -0.66 772 0~26 -0.53 828 0.26 -0.53 886 0.26 -0.40
715 0.26 -0.66 773 0.26 -0.40 829 0.26 -0.53 887 0.40 -0.53
716 0.40 --0.66 774 0.26 -0,40 830 0.26 -0.53 888 0.40 --0.40
717 0.26 -0.66 775 0.26 -0.66 631 0.26 --0.53 889 0.40 -0.53
718 0.26 --0.66 776 0.26 --0.53 832 0.26 -0.53 890 0.26 -0.26
719 0.26 --0.93 777 0.26 -0.66 833 0.26 -0.53 891 0.26 -0,40
720 0.26 -0.93 778 0.26 --0.66 834 0.26 --0,93 892 0.26 -0.66
721 0.26 -0.93 779 0.26 -0.53 835 0.26 --0.80 893 0.26 -0.53
722 0.26 --0.80 780 0.26 -0.53 836 0.26 -0.80 894 0.26 --0.53
723 0.26 -1.20 781 0.26 -0.26 837 0.26 -0.80 895 0.26 --0.53
724 0.26 -1.06 782 0.26 -0.93 838 0.26 -0.80 896 0.26 -0.40
725 0.26 -1.20 783 0.26 -0.80 83~ 0.26 --0.80 897 0.26 --0.40
726 0.26 .-0.93 784 0.26 -0.80 840 0.26 -0.80 898 " 0.26 --0.93
727 0.26 -0.93 795 0.26 --0.80 841 0.26 -0.66 899 0.26 -0.93
726 0.26 -0.80 786 0.26 -0.80 842 0.26 --0.80 900 0.26 -0.80
729 0.26 -1.02 787 0.26 -0.66 843 0.26 -0,80 901 0.26 -0.93
730 0.26 --0.93 788 0.26 -0.66 844 0.26 --0.66 902 0.26 -0.93

SESQUITERPENE LACTONES IN ANGIOSI~RMS .... 153
TABLE 2--CONTINUED
No. $ 0 No. S 0 No. $ 0 No. S 0
903 0.26 --0.80 961 0.26 --0.93 1018 0.40 --0.80 1073.6 0.40 -0.53
904 0.26 --0.66 962 0.26 -0.93 1019 0.40 -0.80 1074 0.40 -0.40
905 0.26 -0.66 963 0.40 --0.73 1020 0.40 -0.93 1075 0.40 -0.40
906 0.26 -0.66 964 0.40 -0.93 1021 0.13 -0.80 1076 0.40 -0A0
907 0.26 -0.53 965 0.40 --0.93 1021.5 0.13 -1.20 1077 0.40 -0,40
90e 0,26 -0.53 966 0.53 -0.53 1022 0.40 -0.93 1078 0.40 -0.40
S0~) 0~6 -0.53 967 0.40 -1.06 1023 0A0 -0.93 1079 0.40 -0A0
~10 0.26 -0.53 968 0.40 -0.80 1024 0.40 --0~0 1080 0.40 --0.40
911 0.26 -0.93 969 0A0 -0.66 1025 0A0 -0~0 1061 0.40 -0A0
911.5 0~,6 -1.06 970 0.40 -0.80 1026 0A0 -0.66 1062 0.40 --0.40
912 0.26 -0.80 971 0.40 -0.66 1027 0~0 -0.80 1083 0A0 -0.40
913 0.26 -0.66 972 0.26 -0.40 1026 0A0 -0.93 1084 0.40 -0.40
914 0.26 -0.66 973 0.26 -0.53 1029 0.40 -0.93 1085 0.66 -0,40
915 0~6 -0.66 974 0.26 -0.66 1030 0.40 -1.06 I0~6 0.53 -0.53
916 0.26 -0.80 975 0.26 -0.53 1031 0.40 -0.93 1067 0.53 -0.40
917 0.26 -0.80 976 0.26 -0.53 1032 0.40 --0.93 1088 0.40 -I .06
918 0.26 -0.80 976.5 0.26 -0.53 1033 0.40 -0.93 1089 0.40 -I .06
919 0.26 -0.80 977 0.26 -0.66 1034 0.40 -0.80 1090 0.40 -I .06
920 0.26 -0.80 978 0.26 -0.66 1035 0.40 -I .06 1091 0.40 -1.06
921 0~6 -0.66 979 0.26 -0.80 1036 0.40 -0.80 1092 0.40 -0.66
922 0.26 -0.66 980 0~ -0.80 1037 0.40 -0.93 1093 0.40 -0.80
923 0.26 -0.66 981 0.26 -0.93 1038 0.40 -1.06 1094 0.40 -0.80
924 0.26 -0.53 982 0.40 -0.66 1039 0.40 -0.93 1095 0.40 -0.93
925 0.26 -0.53 983 0.26 -0.66 1040 0.40 -0.93 1096 0.40 -I ~0
926 0.26 -0.53 984 0.26 -0.53 1041 0.40 -0.93 1097 0.40 -0.40
927 0.26 -0.53 985 0.26 -0.80 1042 0.40 -0.80 I0~ 0.53 -0.93
928 0.26 -0.93 986 0.26 -0.80 1043 0.40 -0.80 1099 0.53 -0.80
929 0.26 -0.66 987 0.26 -0.93 1044 0.40 -0.80 1100 0.53 -0.66
930 0.26 -0.66 988 0.26 -0.53 1045 0.53 -1.06 1101 0.53 -0.66
931 0.26 --0.66 989 0.26 -0.80 1046 0.40 -0.93 1102 0.53 -0.66
932 0.26 -0,93 990 0.26 -0.80 1047 0.93 -0,53 1103 0,53 -0.80
933 0.26 -0.80 991 0.26 -0.66 1048 0.93 -0.66 1104 0.53 -0.80
934 0.26 -0.66 992 0.26 -0.93 1049 0.53 -0.93 1104.5 0.53 -0.66
935 0,26 -0,53 993 0.26 -1.06 1049.5 0.53 -0.93 1105 0.53 -0.80
936 0.26 -0,80 994 0.26 -0.40 1050 0A0 --1.20 1106 0.53 -0.80
937 0.26 --0,40 995 0,26 -0.80 1051 0,40 --1.06 1107 0.53 -0,80
938 0.26 -0.40 996 0.26 -0.93 1052 0,53 -1.06 1108 0.53 -0.80
939 0.26 -0.80 997 0.26 -0.80 1053 0.40 -0.80 1109 0.53 --0.90
940 0.26 -0.93 998 0.26 --0,93 1054 0.40 -0.80 1110 0.66 -0.53
941 0.26 -0.93 999 0.26 --0,66 1055 0.40 --0.93 1111 0.53 --0.80
942 0.26 -0.80 1000 0.26 -0.93 1056 0.40 -0.80 1112,5 0.53 -0.66
943 0.26 -0.80 1001 0.26 --0.93 1057 0.40 --0.66 1113 0.53 -0.66
944 0.26 -0.66 1002 0.26 -0.80 1058 0.53 -0.40 1114 0.53 -0.53
945 0,26 -0.80 1003 0.26 -0.80 1059 0,53 -0.40 1115 0.53 -0.66
946 0.26 -1.06 1004 0,26 -0,80 1060 0.53 -0,13 1116 0,53 -0.66
947 0.26 --1.06 1005 0.26 -1.06 1061 0.53 -0.66 1117 0.53 -0.80
948 0.26 -0.66 1006 0.26 -0.66 1062 0.40 -1.20 1118 0.53 -0.93
949 0.26 -0.66 1007 0.26 -0,93 1063 0.40 "-0.93 1119 0.53 -0.93
950 0.26 -0.66 1008 0.26 -0,93 1064 0.40 -0.93 1120 0,53 -1.06
951 0.26 -0.66 1009 0.26 -0.93 1065 0.40 -0.93 1121 0.53 -0.80
952 0,26 -0.80 1010 0.26 -0.93 1066 0.40 -1.06 1122 0.53 -0.80
953 0.26 -0.93 1011 0,26 -0.80 1067 0.53 -0.40 1123 0.53 --0.80
994 0.26 -0.93 1012 0.26 -0.80 1068 0.53 -0.40 1124 0.53 -0.80
955 0.26 -0,93 1013 0.26 -0.80 1069 0.66 -0.26 1125 0.53 -0.93
9~6 0.26 -0.93 1013.5 0,26 -0.80 1070 0.40 -0.53 1126 0.53 -0.93
957 0.26 -0.80 1014 0.26 --0.80 1071 0.40 -0.53 1127 0.53 -0.66
958 0.26 -0.80 1015 0.26 -0.93 1072 0.40 -0,53 1126 0.53 -0.93
959 0.26 -0.80 1016 0.26 -0.80 1073 0A0 -0.53 1129 0.53 -0.93
960 0.26 -0.80 1017 0.26 -0.66 1073.5 0.40 -0.53 1130 0.53 --1.06

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

156 VICENTE DE P. EMERENCIANO. MARIA AUXlUADORA C. KAPLAN AND O'1-1"O R. GOI"t'LIEB
TABLE 6. OCCURRENCE OF SESQUITERPENE LACTONES IN GENERA, CLASSIFIED IN TRIBES. OF ASTERACEAE INDICATED BY NUMBERS WHICH
REFER TO SI~UCTURAL FORMULAE GIVEN IN REF. [3J/NUMBER OF SPECIES IN WHICH "rile COMPOUND HAS BEEN FOUND
I. Lactuceae
C4~orkzm 97211' 97311; H),pochoer/s 63911, 083/I, 26411' 004.511, 90311' 91211, 262/1' 9~311; L.acluca 76311' 97213, 973•3; Picridium 77711, 90512,
936/2; ,,~onchus 60~/1' 63512, 26314; 7ar~x~um 9811' 14711' 66011, 66111, 97311; Urosperrnum 9011, 9111.
2. Arcototeae
A~tob~s 112/2, 82512, 55911, 95211. 96611, 96811; Berkhe, ya 4811; G~zan/a 60611' 60711; P/atycarpha 5711, 14611 ; I/~u~/um 87011.
3, Liabeae
~ 753.5/1' 778/1, 788/1' 7~8.5/1, 79011' 79311; Fen~y~n=hu~ 97911; G/echom~ 20011; L~bum 112, 26611' 83411; Mumm=~ 43611.
4. Muti$ieae
C-ochnatiinae and Mutilsinae
~ 7011, 79/1, 83711; D~coma 17711. 17811, 55611, 64811; D/no$er~ 706; Cm~tm~ 1~/1' 17011, 17211,173/1. 174/1, 17~/1, 41111; M ~
~11, 61311. 648/1; Pert~ ~5~1; Wunder/~h~ 161/1.
5. Cardueae
Carduinae
Ac~oliton~2~ll, ~2911, ~3311, ~511, 26211, 26811; Am~m 4914, 50/1; ~mB3411' 94611; Cy~re82611, 84112, 870/1; Ju~b~ 4~/1, 53/1, 5511,
r=611,19111, ~28/1, ~30/1, ~3/1, 93911, 95711; Onopordurn 50/3, 6411' 6511, 10~4/1, 10~5/1; PCTo,~n ~32/2, 94412; S~aBum~ 111' 11711, ~4/1'
~41/1, ~67/1, 946/1, 97711, g7~12. 106211.
Centaureinae
Atrdmt~me ~41 I1, 844/1, ~63/1, r/o/l, 95411. 95511, ~/1; Cen~uma 111, 48/1, 5216, 11711. 16~/1, 17011. 17614, 19112, 61212, ~2~/1' 929/9, ~33/1,
84112, ~4411, ~47/1, 848/4, B49/9, B/2, ~60/2, ~6112, ~62/9, ~64/1. 86511, 86611, 94~/1, 94911, 95611, 1053/1, 10~/2, 1063/1, 10~1/4; C/~u~ 4~/1,
52/1.
Cadineae
A~ac~#ode$1349/1, 135011; Xeranthemum 9~011.
G~mer= not ==~igned to =ubtrlbes.
(:Y~rm/e/~ 870/1; Gtt~=he/ma 87012.
6. Vemonieae
Cen~r~herum 267/1, 26211, 71B4/1' ~54/1; Chr~ 488/1, 48~/1, 51811 ; Eleph~n~Ol~$ 93/2, 12611, ~1/1, 12711, 15411, 12711, 50111, B~/1. B~/1, 515,5/1,
~611, 98711 ; F, mm~nthu$1 I1, 36713, 26~12, 9~/2, 3"/0/1, 37411, 37511, 26711. 388/1, :~911, ~0/1, 455/10 451 I1, ~211, 7~12, ~11, ~0/1, 940/1;
Er~ngea 42911, 43011, 779/1, 787/1, 519.3/1 ; Hefemcoma 78211; Lychno~hora 112, ~911' 37111, ~11, ~413, 7~2/9, 7~11' ~411, ~/1, ~111,
88211. 95311 ; Marffeldanthus 171 I1 ; P~loc~rp~ 4g011, 491/1, 49211, 493/1, 49411, 49511; P ~ 44811, 467/1;/~=L~ 37111, 37211, ~111,
39212; Rol~ndm 49711, 49811. 49911, 50011; $~t~ke=/~ 47"//1, 47~/1, 478.5/1, 48611. 4~7/1, 83411. 85011; Ven///~ 111, 52/1, 9111, 92/1, 387/1.
26812, ~/2, 7~2/2; M~rnon~ 112, 54/1, 58/1, 59/1. 13111, 132/1, 133/3, 13419, 13512, 19611, 473/2, 47411, 475/1, 476/1, 479/1, 4~0/1, 4~J3, 483/2,
4~4/1' 48512, 513/1, 51711, 519.1/22, 519.2/27, 52011, 52712, 52811, 52911, 73812, 783/1. 825/3, ~'/11. ~31/1' ~34/3, ~35/1, B~7/9, ~B/4, ~40/1' ~/1,
~11, 95111.
7. Eupatorieae
,4~er~tk~ 617.5/1, 629,511, ~02/1; Agr~n~u= ~06/1, 81911; Aual~N~tdce//~ 761/1; Chrom~ 28611 ; C o ~ 351/1, 35212; ~ 112,
604.§/1. 671.511; ~ela98911; Di~lnaphia346II, 51911. 55311, 106011; Eupatorium312. 412, 1111, 14/1,15/1, 1711, 18/1' 1911, 20/1. 2111, ~1/1,
33/1, 3411, 4511.4611, 47.511. 51/2. 99/1, 11612. 118/3, 119/9, 12211, 12313, 12414. 15011, 15111, 28211' 28312, 286/1, 2~/1, ~0/1. 29111' 29711, 29911,
30012, 44112, 44213, 51012, 51111. 51212. 512.511, 76511, 76611, 781/1. 79112, 79611, 79711, 79912, 799.5/1, 80111, ~02/1, ~0311' 814/1, ~1711' 81811,
~20/1, 821/1, ~22/1' 823/2, 82411, 87211, r/3/1, 26011, 93711, 93811, 974/1. 97511. 97611. 976.511, ~4/1; Gra~=~ 532/1, r~3311, ~4/10 535/1, ~=36/1,
537/1, 83811, r~9/1, ~4111, 81211; Guevar~ 77311; H~.ft~Wg/h/~ 36311, 36411; L~cn~ 12/1, 3211. 28911, 29311, 29411, ~11, ~1611, ~17/I, ~15/1, ~/1,
26111, 26211, ~02/3, 503/1, 50411, 55211, ~)4/1' ~5513, 807/1, 80~11, ~15/1' 97411, 87811, 87911. 109111; Lo~e/g~ 261/1; Mil~nia~6/1, 67/1. 55/1'
68/1, 1~3/1' 18411.1~5/5, 193/5, 19411, 98111. 10~8/1, 108511; Oxylobu$111, 56611. ~2/1, ~/1, ~26/1; ~ 14011, 79111. 792/2, 79511, r~/1'
94111' 114011; Tr/~n~ 54411, 54611, 54711, 54~/1, 54911, r~o/1, 551 I1, 554/1, 55511, ~11, 55711, ~/1' ~/1, 55011, ~61/1. F~3/1' 56411,
56511.
8. Heliantheae
8.1. Mellmpodiinae
Acen~oermum 2~611, 2~BI1. 23~/1' 241/1, 24211, 243/1, 244/1, 24511. 24611, 24711. 24811, 24911, 400/1, 401/1, 40311, 543/1, 55211 ; Melarnl~dium
7511, 7611, 7711, 7~11, 10011, 12511. 223/1. 22411. 22711, 25011, 25111. 25211' 25311, 25413, 25511. 255.5/1, 25611, 2~0/12, ~o211. 26311, 26511, 2~/1,
26712, 26~20 27413, 27514. 276/1, 27711, 27~/2, 30211, 30311, 40411. 40511. 40611, 40711.40811, 40911' 410/1, 99111; Po/ymn= 168/1, 69011; $igesbeotia
23111, 23211, 249.811, 51611; Sm~/~n~hu= 202/1, 20311. 22511, 22611, 22811, 2~3/2, 249.511, 249.6/1' 249.7/1, 255/1, 25511, 2~0/1' 26111, 26911, 27011.
271/1, 6~6/1; Tetragono~heca 205/1. 20611. 20711. 20~/1, 20911. 21011, 211/1, 21211, 21311. 21411, 21,511, 21611, 21711, 21~/1' 21911. 22011, 221/1. 22211,
22611. 23411. 23511. 25611. 43111, 43211. 433/2.
8.2. Zinniinae
~ 2611, 7~2/1, 7~5/1, 7~6/1, ~711, 83~11, 8~9112, ~13/2, 85711, 55~/1, g~ll, 106~11, 1070/2,107112, 107212, 107~/2, 107~.~/1, 107Z1.6/1, 107412,
107511, 107611, 107711,1078/1, 107911. 10~0/1' 10~111,126211, 10~3/1, 10~4/1, 10~911,10~0/1, 10~4/1. 1085/1.
8.3. Ecliptinae
~ 3511, 70011, 70111. 70211. 70311; B~/nv///e~ 95/1. 5511' 9711, 13611, 24011, 26411, 32611; ~ 25711, 25~11, 2~O/1; ~ 6~011, 71611.
71711, 71911, 1230/1, 123111, 1232/1, 123311, 123411.

SESOUrTERPENE LACTONES IN ANGIOSPERMS 157
T,~LE 6-- CON~'~ED
8A. Vertmtnin~e
Dk~mslWna 57511, 577/2, 57~/2, §7~/1, ~11, ~ I1; ~ 1~1; ~ ~1, ~1, 2~1, ~/1, 4111, 1~ 1~1, ~/1; ~ m
~I, ~11, ~I, ~11; ~ ~ ~11, ~1, ~I, ~I, ~I; ~ ~.511, ~.611; ~ I~I, 1~11; ~ ~11,
~11, ~11, ~711, ~/I, ~11, ~I, ~I, ~11, ~11.
8.5. ~ n ~
~ ~/2, ~/1, ~, ~; ~ ~.5/~ 1~1; ~ ~4, 4/1, 42/1. ~1, ~/1, ~.~1, ~ ~/1. ~/1, ~/1, ~/1,
~2, ~2, ~/1, ~/1, ~/1. ~/1, ~1, ~1. ~7/1, ~7.~ ~/1, ~.5/1, ~.6/1, ~/1. ~1, ~.~1; ~ ~1, ~/1, 11~1,
1~7/1, 1~/1, 1~/1; S~ 1~/1; ~ 5/1, ~1,1~/1, 1~1, 1~/1, ~/1, 1~/1, ~/1. ~2/1, ~9/1, ~4/1, ~1, ~/1, ~1, ~/2, ~7/1,
~1, ~/1, ~/1, 5~/1, ~/1, ~/1; ~/1,1~/1, ~1, ~0/1, ~1/1, ~2, ~1, ~ ~.
8.6. Gai~
~ 2 , I~I/~, 11~I. I~/2,11~/I, I~/I, 11~, 11~/2,11~2. I~/~ I~/I, I~I, I~I; ~ 11~/I. 11~/I, I~I, I~/I.
~7. ~ ~
~ : ~ / ~ .
82. F ~
~/~, ~/I, ~/I, ~I, ~/I. ~2/I, ~/I.
8.9. 5ahiln~
~ ~/I. ~/I. ~I, ~/I, ~/I, 7~I, 7~I. 7~/I, ~I; ~ ~/~ ~I, ~.S/1, ~.~I.
8.10. ~d;i~
8.11. Ga~in~
~ I~, ~/~, ~/I, ~/~, ~/I, ~/I, ~/2. ~/~, ~I/I. ~, ~/I, ~/I. ~7/~, ~/I. ~/I, ~/I, ~2, ~/I, ~/I, 3~/2,
~/2, ~/2, ~/I, ~/I. ~/I, ~5/I. ~/I, 4~/I, ~I, 4~/2, ~7/I, ~/I, ~/I, ~/I, ~/I, ~/I, ~. ~/I, ~5/~, ~/I, ~7.5/I.
~.6/I; ~ ~/I, ~I, ~I. M/I, ~/I, ~I, ~I. ~/I, ~/I, ~7/~.
• 12. ~u~n~n~
~ ~/I, ~5/I; ~ I/I, 10/I, ~I, ~/I, ~/~. ~/2, ~3, ~I/2, I~2, ~9/2.
8.13. E~Imsn~n~
~/I, ~I; ~ I~/I ; ~ ~/~.
8.~. ~i~ae
~ I / ~ 2/I. ~2, I~2, ~2, ~2, 112/4, ~/~, ~, I~.~I. ~/2, ~/2, ~/6, ~I, 5~I, ~/3. ~8/2. 6~2, ~/~, ~/~, ~/~,
~7/I, ~/2, ~/I, I~/I, I~/I, I~. I~/6, 1107/I, 11~3. 11~/2, ~I~, ~2/~, 1113/I. 1116/I. 1117/I, I~18/I, 1119/I. 11~/2,11~/~, 11~/~,
11~/~ 11~/I. I~/3, 11~3, ~I~/~, I~/3, ~/~. I~/~, ~5/~, I~/~, I~.~/~, ~I~, ~151/I, 1151.5/~, 11~/~0, ~53/7, ~/I. 11~/~, I~57/~.
I~/I; ~ I/I. 61~2, I~/I, 1111/I, 111~I, I~17/2, ~I~/I, 11~/I, 11~/I ; ~ ~/I, ~/2. ~/2, ~, ~2~, ~/~. ~/I, ~/2,
I~/I. I~/I~ I~/I. I0~/I, I0~I. I0~/I, I0~/~, I0~/~, I~/I, I~/I, I~/I, I~11/2. 11~2/I, 1117/~: ~ I~I; ~ 1~/~,
~3/I, I~. I~/3, 11~/6, I~01/5, 11~/I, 11~/4, 11~/~. 11~.5/I, ~I~/I, ~110/2, ~111/I. 1112/I, ~113/I, 11~/3. 1115/I, ~7/2, 11~/5, 11~,
11~, ~I~I. 11~3. 11~/I, 1127~, 11~/~; ~ 10~/2, I0~/I, I0~/5, ~0~/9. I0~/I, I~/~, I~2/4, I~/7, I~/I, I~/~, I~/I.
~.15. Milte~ilnae
~ ~/I; ~ I~/I, I~/~, I~/I.
9. ~n~
~ ~/I, ~/2. ~0/2, ~/I; ~ I~/~, ~/2, ~3/2. ~/I, ~5/~, ~/~. I~/~, 11~/I, 11~/I, 11~/I, I~2, I~/I, 11~/~, 11~/I,
1174/I. 11~/5. 11~/I, ~I~/~. I~/2, 11~/~. 11~I, ~/I, 11~/I. ~I~3, I~/~, ~9/I, I~/I; ~m~/1, ~I, ~/~, I~/I. I~/I,
I~/~, I~/~, 30~0/~, I014/~, ~0~5/~, I017/I, I~9/2, 11~/2, 1163/6, 11~/3, 11~/5, IM.~I, I~70/I, 11~/~, 1172/I, I~74/2, I~/~, 11~/I. ~18~/~.
~/2. 11~/I. 1191/I, 11~/I, 11~/I, 11~/13, 11~I, I~I/2, I~3/~, I~/2, I~0/I, ~2/I, ~, I~2, i~7/2, I~/12, I~/~. I~/I,
I~/I, 12~I, 1251/I, 12~/3, I~7/3, 12~/I: ~ 11~/I, 1167/I. 11~/3, ~/~. I~/I, ~/I, I~.5/I, ~4/I, I~8/I, 32~/I, I~/I,
I~7/I, 12~, ~/I, I~/I, I~/I, 1247/~, 12~/~. ~249/~, 12M/I ; ~ 11~/~, I~/I. I~/~, 1241/I, I~2/I, 12~I, 12~/I, I~.
10. ~emae
~rT~/~, ~/~. ~/~, ~/~, ~/~, ~7/~, I~/I; ~p~on ~/~.
I~. inu~ae
~ 11~/~ ~ Ag~,f~us ~0~/I: ~n~en~r~ I~/~ ; ~/oce~a/us ~/~. ~/~. ~016/I; Ca~es~um ~/~. 6~/2, ~/~, ~9/~, I~5/2, I~4/2;
~ / ~ , ~01~2, I~7/2, 3~7/2, I~/2, I~2, 12~/2; ~ m ~ 1 , I~/I; ~ I/I. 7/I, ~2, ~I. ~/I, ~, ~2, ~/~, 112/~.
~/I, I~/~, I~/2, 2~/I, 412/I, 427/I, ~/~. 4~/I. 4~/~, S~S/~. 6~/I, ~/I. ~/I, ~4/2, 675/~, ~/5. ~7/I, ~/I, ~/~. ~/I. ~/~, ~7/I,
~/I. ~/5, 7~/I, 707/I. ~/I, 7~/I, 7~2, 725/2, ~/~. ~/~, 7~/I. ~/~. ~/2, I~I, I~/3. I~, I~I, I~I/2, 1~5/I, I~/I,
I~3/~, ~3~/I, I~/I. 1227/I, I~5/I. ~/I, 3~/3, ~322/3: ~c~n~ 6~/~, ~/I; ~ 574/~ ; ~ 7~/3, I~/~. I0~/I, I0~/~,
I~/3. ~/~, I~/~, I~/3, I~/I, 11~/I; Te~ ~/I, ~7/I, ~/~, 723/3, 11~/~, 11~/~; ~m~ I~I.~.
12. ~m~ae
~ ~/~, 142/I. ~/I, ~I, ~/~, ~/I. ~3. ~/I, 912/3. 9~3, 915/~. ~/I, I~2/4; ~ M/I ; ~ 112/I, ~/I, I~/~. ~/~,
~/I, ~/I, ~7/I, ~/I, ~4/I. I~.5/I ; ~ ~/2, ~I. 6/I, 8/I, 25/~, 27/2,1~/~. ~I/~, I~/I, ~/I, ~/I. I~I, ~4, ~/4, ~/I, 41~2,
415/4. 4~6/I, 4~7~, 4~/I, 4~/I. ~/I, 42~I, ~, ~/4, ~/I, ~/I, ~7/2, ~I/I, ~2/~, ~3/3, ~/4, ~/3, ~/I, 572/I, ~, ~/2, ~I,
~/~, ~/I, ~I/6. ~/2, ~2, ~/~, ~/I, ~/3, ~3~, ~5/I, 61~2. ~/2, ~/I. ~I, ~/I, ~/3, ~I/I. ~2/I, ~3/24, ~/~2, ~.5/17,
~/3. ~/I. ~7.~I. ~/I, ~3, ~I~, ~/2, ~, ~S/1. ~/2, ~7/I, ~/~, ~/I, ~/I, 672/I, ~/~, ~7/I, ~0/I, 7~. ~/3. ~/~,
~/3, ~7/~, M/I, ~/I, ~4/~, ~/2, ~, M/~, ~/I, M/I. ~/I, 8~2, ~/I. 8~/2, ~I, ~/I. ~2. ~/5, ~/I, ~/I. ~4. ~/I,
~/14. ~S, 912/4. ~3/I, 9~/I. 9~/~, 9~/~, ~2/4. ~/~, ~/~, 9~/~, ~2/I, ~2. ~I, ~/I, ~/2. ~/2. ~/I; ~ / I , M/I,

158
VICENTE DE P. EMERENCIANO, MARIA AUXILIADORA C. KAPLAN AND OTTO R. GOTTUEB
TABLE 6.--CONTINUED
75611. 757/1, 760/1. 762/1, 88711, 88811, 8~9/1; C/mmaeme/um 28111; ~nthemum 1/2, 112/2. 166/1, 18012, 397/1, 42611. 588/1, 59411,
56211, 67711, 678/1, T/0/1, T/6/2, 79511. 895/2, 912/1. ~6/1, S82/1 ; Co~/a 111, 44'1, 76112. 79511 ; Handelia 25/1, 876/1. 985/1, 96311 ; Lidbectua 761/1 ;
Ma~r~ 111, 120/1, 753/1, g03/1, 905/1, 906/1, 912/1, 932/1, 933/1, 1312/1 ; Osm/Iof~ 813/1.967/1, ~6/1; Penm;a 775/1; Peymusea 761/1;
Tanace~um 112/t, 182/1, 27~/1, 425/1, 440/1, 58811, ~0/1, ~=84/1, 611/1, 682/1, 67711, 6"/9/1. 875/1, r/6/1. 102o/1; (Am/n/a 156/1, 158/1, 156.5/1, 157/1,
351/1.
13. Amicineee
Anna 104912,1049.§/1, 1190/2, 11~5/1, 11S7/1,1206/1, 1207/2,1206/1, 1209/1, 1211/1, 121511; C/menac~ 11/2; EnOphy//um 11/1, 80/1, 81/1, 83/1,
304/1. 30511, 306/1, 31511, 524/1, 62511, 74011, 74111, 106111;/.a~t~w/e ~S/2, ~6/1. 1Z~1.712; Peucepht4um 285/1.
14. Senecione~e
Bedford= 1050/1.1051/1, 1290/1. 1291/1 ; CacaJb 12~2/2, 134111. 1347/1; Eu~t~os 1267/1,126~/1; Homo91~e 1~92/1. 12¢J~/1. 1300/1; Lygu~r~ 127011.
127612, 1277/1, 12~2/1, 1283/1, 12~8/2. 12~9/1. 1292/30 129S/1. 130011; Pemw~s 1271/2, 1272/1. 1273/2. 1274/2, 1275/2, 1276/3,127711, 1292/4.
1293/1. 129411. 128511. 1297/1, 12S8/1, 130111, 134611; Se~ck, 747/1. 74811, 748/1. ~0/1, 7~1/1, 75211, 126211. 1263/1, 126411,1~6/1, 1278/1. 12"/9/1,
1280/1. 1286/1, 12~7/1. 12~2/1.
TABLE 7. EVOLUTIONARY ADVANCEMENT PARAMETERS OF TAXA
WITH RESPECT TO SKELETAL SiIECJALIZATION AND OXIDATION LEVEL
OF SESQUWERPENE LACTONES
Genera
Taxa EA5 F, Ao
Tribes or families (except Astersceee)
Family (Asteraceae)
TEA5 of tribe
[F-Ao of tribe
t !
S--ikeletal q~cialization, O--oxidltion level of I com¢x)und, n--
number of i~ecies of the taxo~ in which the compound occurs,
t--number of tribes.
additionally produces type 1.5 is even more
similar to the Apiaceee, chiefly if the Vemonieae
are considered to be peripheral. The sasquiterpene
lactone data of this tribe are close to the
data for Eupetorieee, which, although it was
formerly indeed considered to be akin to Vernonieae
[10], is placed in Asteroideae group 2 by
Wagenitz [9]. In this group affinities can be
detected easily by inspection of the registry of
the skeletal types (Table 12). Heliantheae, Inuleae
and Anthemideee are definitively very different
from Senecioneas where eremophilanolidas are
formed exclusively.
An EAslEA o correlation (Fig. 9) provides a
dynamic picture of this situation, revealing not
only the affinity of Cichorioideee and Asteroideae,
group 1, the distance of Anthemidase from
Asteroideee, group 2 [9], and the relationship of
Amicineae and Heliantheee [11], all anticipated
on morphological grounds, but also the existence
of two major directions of sesquiterpene
lactone development. One direction encompasses
the tribes of Asteroideee, group 1 and
Cichorioideae, and the pair Vernonieae-Eupetorieae
is indeed situated on one of its extremes.
The other direction encompasses the tribes of
Asteroideae, group 2, to which Senecioneae is
only distantly related.
Also in a/~s//~ o correlation clustering of points
representing tribes is observed (Fig. 10). Structural
variation of sesquiterpene lactones is
TABLE 8. EX1REME S N~ID O VALUES OF SESQUITERPENE LACTONES AND EVOL~Y
ANGIOSPERMS
ADVANCEMENT PARAMETERS FOR FAMlUES OF
~ex s s /~ EA= O 0 ~o EA~
[7] min max min max
Megnolieceae 25 0.13 0.26 0.13 0.20 -1.06 -0.~6 0.40 -0.90
Laursceee 52 0.26 0A0 0.14 0.30 -1.06 -0.26 0.80 -0.83
A~=/~ace~e 51 0.13 0.53 0.40 0,28 -1.06 -0.53 0.53 -0.70
Alterm 72 0.13 0~10" 0.67" 0.32 --1.20 0.00 1.20 --0.78
"The extraordinarily high S v~ue$, 0.93 and 1.00, for two r.oml~ourRb we~ excluded.

SESOUrrERI=ENE LACTONES IN ANGIOSPERMS
159
TABLE 9. EXTREME SAND OVALUES OF SESQUITERPENE LACTONES FOR TRIBES OF ASTERACEAE
Basic
chromosome $ S /~s EAt O O
numbers rain rrax rain max
Is]
Cichorioideae
Lactuceae 9, 6, 8, 7 0.13 0.26 0.13 0.25 -1.06 0.40 0.66 -0.68
Am~oid~e, group 1
Vernonieae 10, 8, 9 0.13 0.66 0.52 0.28 -1.06 -0~,6 0.80 -0,56
Liabeae 0.13 0.40 0.27 0~.5 -1.06 -0.66 0.40 -0.82
Mutisieae 9 0.13
,
0.66 0.53 0.21 -1.20 0.53 0.67 -0.85
Cardueae 12, 13, 10 0.13 0.53 0.40 0.24 -1.20 -0.53 0.67 -0.72
Arctoteae 9 0.13 0.26 0.13 0.20 -1.06 -0,66 0.40 -0.85
Asteroideae, group 2
Eupatorie~e 10 0.13 0.66 0.53 0.29 -1.20 -0.13 1.07 -0.61
Helientheae 18, 17, 12, 15 0.13 0.93 0~0 0.40 -1~0 0.00 1.20 -0.72
Helenieae 19, 18 0.26 0.80 0.54 0.53 -1.20 -0.13 1.07 -0.73
Amicineae - 0.13 0.53 0.40 0.36 -0.93 -0.53 0.40 -0.80
" A~tereae 9, 5 0.26 0.53 0.27 0.32 --1.06 -0.26 0.80 -0.92
I~uleae 10, 7, 9 0.13 0.93 0.80 0.33 --1.20 -0.53 0.67 -0.86
Senecloneae 10 0.40 0~0 0.80 0.59 -1 ~0 -0.53 0.67 --0.96
Anthemidese 9 0.13 0.80 0.67 0.27 -1.20 -0.26 0.80 --0.81
TABLE 10. EXTREME SAND OVALUES OF SESQUITERPENE LACTONES AND EVOLUTIONARY ADVANCEMENT PARAMETERS FOR SUBTRIBES OF
THE TRIBE HELIANTHEAE (ASTERACEAE)
Basic
chromosome
numbers $ S /~ s EAs 0 0
[8] rain max min max
/~o
EAo
Melampodiin~e 10, 15 0.13 0.66 0.53 0.40 -1.20 0.00 1.20 --038
Zinniinae 11, 14 0.13 0.53 0.40 0.35 -1.06 -0.40 0.66 -0.63
Ecliptinae 15, 16 0.13 0.66 0.53 0.35 --0.93 -0.26 0.67 -0.63
Verbe$ininae 15, 16, 17 0.13 0.53 0.40 0.26 -0.93 -0.26 0.67 -0.75
Helianthinae 17, 18 0.13 0.53 0.40 0.32 -1.20 -0.26 0.54 -0.72
Gaillardiinae 15. 16, 17. 19 0.26 0.80 0.54 0.54 -1.20 -0.13 1.07 -0.73
Coreopsidinae 12 0.13 0.13 0.00 0.13 -1.06 -0.93 0.13 -1.02
Fitchiinae 0.13 0.26 0.13 0.19 --0.93 -0.80 0.13 -0.90
Bahiinae 8, 9, 10, 12 0.26 0.66 0.40 0.38 --1.06 --0.26 0.80 -0.68
Gelin$oginae 8, 9 0.13 0.53 0.40 0.39 -0.80 -0.13 0.67 -0.41
Neurolaeninae 8, 9 0.13 0.40 0.26 0.26 -1.06 -0.53 0.53 -0.85
Engetmaniinae 9 0.26 0.53 0.27 0.33 -1.06 -0.53 0.53 -0.80
Ambrosiinae 18 0.13 0.93 0.80 0.47 -1.20 " -0.40 0.80 -0.82
Milteriinae 8, 12. 15 0.13 0.53 0.40 0.13 -0.93 -0.66 0.27 -0.81
smaller for Cichorioideae and Asteroideae,
group 1, than for Asteroideae, group 2. Again
Anthemideae constitute a borderline case and
Vernonieae is clearly peripheral to group 1. Here,
however, the situation of Eupatorieae in group 2
admits no doubts.
Many of the sesquiterpene lactone types have
been located in the subtribes of the Heliantheae
(Table 13), one of the largest tribes of the Aster-
aceae. With respect to their basic chromosome
numbers, the subtribes were classified into four
groups. Two major ones, grouped around Verbesinae
(x-15, 16, 17) and Galinsoginae (x--8,
9), and two minor ones with Coreopsidinae
(x-12) and Milleriinae (x-12) [8] (Table 10). The
EAslEA o correlation indicates that, although EA o
is consistently higher for representatives of the
former major group, parallel evolution of sesqui-

160 VICENTE DE P. EMERENCIANO, MARIA AUXlLIADORA C. KAPLAN AND O1"1"O R. GoI"rLIEB
TABLE 11. NUMBER OF SESQUITERPENE LACTONES, CLASSIFIED INTO
STRUCTURAL TYPES (FIG. 6), DISTRIBUTED IN FAMILIES OF THE
ANGIOSPERMS
Asteraceae
MAG LAU API ClC AST 1 AST 2
1 8 + + 4 190 291
1F 14 +
1.1 1 24 23 144 288
1.1-- 482
1.2 7 3 9 3 14 309
1.2.1 1 36
1.2.1~ 37
1.2.2 7
1.3 1 183
1.4, 1.7, 1.8. 1.10 100
1.5 1 13 34
1.6 1 33
1.9 2
MAG Magnoli~ceae, LAU Lauraceae, API Apiaceme. Subfamilies of the
Asteraceae: CIC Ciehorioideae, AST Asteroldeae groups 1 and 2.
terpene lactone characteristics has occurred in
both groups (Fig. 11). Especially the EA s parameter
is considerably lower for representatives
of the minor gmups. The dependence of
chromosome numbers and secondary products
chemistry becomes especially convincing upon
inspection of the /~s//~o plot (Fig. 12). This
evidences a positive relation to exist for the
t~ansition of x 12--,9-,15-,18 and the structural
variation of sesquiterpene lactones.
Discussion
It is not intended to suggest that sesquiterpene
lactone data establish a close relationship
between Magnoliaceae and Asteraceae,
although the topic has been discussed [5]. The
relationship between Apiaceae and Asteraceae,
however, has been proposed on micromolecular
TABLE 12. NUMBER OF SESQUITERPENE LACTONES, CLASSIFIED INTO Sll:tUCTURAL TYPES (FIG. 6). DISTRIBUTED IN TRIBES OF THE SUBFAMILIES
CICHORIOIDEAE (CIC) AND ASTEROIDEAE (FAMILY ASTERACEAE)
ClC Asteroideae, group 1 Ast~roideae, group 2
LAC MUT ARC LIA CAR VER EUP ANT HELl HELE ARN INU AST SEN
1
1.1
1.1.1
1.1.1.1
1.1.1.2
1.1.1.3
1.1.1.4
1.1.2
1.1.3
1 .I .4
1.2
1.2.1
1.2.1.1
1.2.1.2
1.2.1.3
1.2.1.4
1.2.2
1.3
1,4
1.5
1.6
1.7
1.8
1.9
1.10
4 12 4 4 39 130 66 70 128 1 8 18 + +
23 2 7 11 82 42 53 153 47 16 3 15 +
1 + 159 117 11 9
2 51 4
2 34 17
4
1 4
1
43 1 3 16 3
4
1
3 5 2 4 3 8 166 71 8 1 49 6
4 1 1
.
5 2
1 33 39 7 98 1 5
2 ~4
7 6 2 30 1 1
1 2 20 1
31
2O
6
6
5
LAC L~"tuce~e, ARC Arcto~ae, LIA Liebe~, MUT Mu~le~e, CAR C~rdu~e0 V~R Vemonleae, EUP Eul~tm'i~e, HEU I.IMienthel~e, HELE Helenieae,
AST Astem~e, INU Inuteae, ANT Aedhemideae, ARN Amicine~e, SEN SenecloneM.

S~SOUITERPI~N~ LACTONES IN ANGIOSI:I~RMS 161
TABLE 13, NUMBER OF SESQUITERPENE LACTONES, CLASSIFIED INTO STRUCTURAL TYPES (FIG 6), DISTRIBUTED IN SUBTRIBES OF THE TRIBE
HEUANTtdE~ (FAMCY ASTER~E)
MEL 71N ECL V~R HEL GAI COR FIT BAH MAD GAL. N£U ENG AMB MIL
1.
1.1
1.1.1
1.1.1.1
1.1.1.3
1,1.2
1.1A
13
13.1
1~3
13
1A
1.5
1~
1~
26 6 4 13 31 2 3 2 + 18 4 19
11 + 4 + 1 3 2 11 10
5 2 4 18 140
8
1 1
2 17 16 21 8 2 3
3
2 5 30 9 39
80 5
27
12 I 3 I
41
1 21
1 2
2
MEL Melampodiinae, ZlN Zinniirme, ECL Ecliptinae, VER Vedoeainae, HEL H~lian~inae, GA] Gaillardiin~e, COR Co~inae,
Bllhiinae, MAD Madiinae, GAL Galinsoginae. NEU Neurolaeninae. ENG Engelmaniinae, AMB AmbroeiinH, MIL Mtll~riinae.
FIT Fitc~iinae, BAH
eI.Au
eAP*
OA~T
emJ~
I t !
o.m*O 0.~'~ ~A s 0.~0
FIG. 7. CORRELA'rlON OF EA~ AND EAo PARAMETERS FOR FAMILIES OF ANGIOSPERMS CHARACTERIZED BY THEIR SPORNE INDEXES (cf. Table 8).
For a glossary of the three-le~er acronyms see Table 11.
[12, 13] and macromolecular [14] grounds, in the
face of criticism based on morphological criteria
[15]. Magnoliaceae and Asteracsee were plotted
in Figs. 7 and 8 in the hope that they might be of
assistance in the solution of the remaining
problem: the evolutionary polarity of the Asteraceae
tribes along the two lines of sesquiterpene
lactone development. Does it proceed in the
sense of structural diversification or simplification
Considering the location of the point
representing the Magnoliaceae, it appears that
the former prevails, i.e. that the sequence of
primitive to advanced tribes involves
Mutisieae-,Vemonieae-Eupatorieae and Astereae-,Heliantheae.
This, however, is unlikely
upon consideration of the point representing the
Apiaceae (Fig. 9). Its central location, between
the two Asteraceae lineages, makes it improbable
that Mutisieae and Astereae constitute the
basic tribes. Indeed the sesquiterpene lactone
chemistry of Apiaceae may have been ancestral
with respect to the analogous chemistry of
Asteraceae. In this case evolution of groups 1
and 2 got under way by increase in oxidation

162 VICENTE DE P. EMERENClANO, MARIA AUXILIADORA C, KAPLAN AND 01-tO R, GOTTLIEB
Is, O
~0
UO
OLAU
OAPi
OAa~
O.40 O~m~O
I ..... I
O.OO ¢1~0 ~ s O.O0
FIG. 8. CORRELATION OF /~= AND ~o VALUES FOR FAMIUES OF
ANGIOSPERMS CHARAC~RIZED BY THEIR SFGflNE INDEXES (of. Table
8). F(x a glossary of the th~e-lmt~r ~onyml m Tolde 11.
state (in Vemonieae) and skeletal specialization
(in Heliantheae) respectively. Reduction of oxidation
state and loss of skeletal specialization
followed in both cases (towards Mutisieae and
Astereae, respectively). This, however, is only a
working hypothesis. It will be necessary to insert
into this frame other micromolecular data
appearing as replacement characters, in order to
arrive at a clearer picture.
Finally, it was deemed desirable to verify the
strength of the present analysis in face of the
permanent flow of new information. A prioriit is
hoped that the system involving structural types
and averages of chemical characters, rather than
single compounds, should lead to more durable
conclusions. This seems to be the case.
The present analysis is based on data assembled
by Fischer et al. [2] and by Seaman [3]
which reviewed the literature up to 1982. Table 14
lists 50 species of Asteraceae the composition of
which became known subsequently. A comparison
of their sesquiterpene lactone types and
their EA s and EA o parameters with the analogous
data registered in Tables 12 and 9 is instructive.
Among the eight new species of Mutisieae
(Table 14) predominate compounds of type 1, a
feature shared indeed by Mutisieae, Vernonieae
and Heliantheae (Table 12). The two latter tribes,
however, are characterized by considerably
higher EA s and EA o values (Table 9). Among the
three new species of Vemonieae predominate
compounds of types 1 and 1.3. This feature and
the high EA o values of the species are indeed
consistent with the general characteristics of the
tribe, as well as of Eupatorieae and Heliantheae,
the species of the latter, however, possessing
higher F_A s values. Among the seven new
species of Eupatorieae predominate again compounds
of type 1.3 and, reciprocally,
differentiation from Vernonieae is difficult. The 10
new species of Heliantheae are distinguished, as
~.o(
OvIM
~l[up,
~.LAG~
X
OcA~
BHEU
~H~'l.j
~OmT
~R~
#L Ej~i., r IDA~N
,~
Iollu
IANT
~ e
0.,1~o ~ lEA=
FIG. 9. CORRELATION OF F..A, AND £A= PARAMETERS FOR TRIOES OF ASTERACEAE BELONGING TO THE SUBFAMIUES CIO4ORIOIDEAE (~) AND
ASTEROIDEAE GROUP 1 ~) AND 2 (~|; ANO FOR APIACEAE (X). For a glossary of she ~4otmr ac~mtyms ~e Ta~e 12.

SESOUITERPENE LACTONES IN ANGIOSPERMS 163
TABLE 14. SESOUITERPENE LACTONE DATA FOR RECENTLY ANALYSED SPECIES OF THE ASTERACEAE. FOR A GLOSSARY OF THE THREE-LETI'ER
ACRONYMS SEE TABLE 12
Structural type/
Species Tribe Ref. No. of compounds i$oieted EA 5 F_.,4 o
Ano~3ra/a p/nrmt/fida LAC [19] 1.1/1 0.26 --0.53
f.A,~p~c~n ~ s L~C [41] 1A/2 0.40 --0.53
A.~/ea ~gr=ns MUT [28] 1.1/5 0.26 -0.90
D/coma anoma/a ~ub =p. anoma/a MUT [23] 1.3/1 0.13 -0.53
k~m, =ub =p. ckck~des MUT [23] 114, 1.1/2, 1~/3 0~) -0.63
D/coma m~croce/~a/a MUT [23] 113 0.13 -0.80
O. tomentosa MUT [28] 1/4, 1.4/6 0.29 ---0,69
D. schinzii MUT [23] 1/3, 1.2/3 0.20 -0,73
D. zeyheri MUT [23] 1.1/1 0.26 -0.53
Gochna= pardcu/a~a MUT [44] 1.1/1.1.114,1.2/1 0.28 -0.78
Centaurea behen CAR [42] 1.115 0.26 -0.77
Ereman~hus cro=noides VER [16} 1.3/9 0.60 -0.43
E. g/oumeratus VER [16] 1.112 0.40 -0.60
Vemon~ na~a~ens~ VER [31] 1/4 0.13 -0.60
Eupatorium scabridum EUP [35] 1/4, 1.1/4 0.20 --0.61
Li~tris acMota EUP [47] 1.316 0.40 --0.53
L. a~era EUP [47] 1.3/4 0.13 -0~0
L. mucronata EUP [47] 1.3/4 0.40 -0.53
~tev~ monardaefol~a EUP [45] 1.3/1 0.40 -0,93
$. myr~denia EUP [21] 1.1/2 0.28 -0.80
Tni=hogon/o~ mon'i EUP [24] 1/3, 1.211, 1.3/3 0.28 -0.55
Calea angusta HELl [27] 1.3/2 0.53 --0.20
C hymeno/eps~s HELl 128] 1/2 0.33 -0.33
C. ~enuifolia HELl [32] 1/3 0.13 -0.62
C v#losa HELl ]39] 1/2, 1.3/5 0.42 -0.42
Enhyclra fluctuan$ HELl I17] 1.4/6 0.40 --0.28
Hetianthus ant)us HELl [38] 1.3/4 0.33 -0.56
Ich~hyoz~ere terminMis HELl [331 1.4/2 0.46 -0.13
Monanoa tomentosa HELl [25] 1.3/2 0.40 --0.73
Parlhenium hyterophoru$ HELl [20] 1.1.1/2 0.53 -0.80
Wedelia hookeriana HELl [34] 1/4, 1.1/4 0.26 -0.66
Gaillardia arislata HELE [48] 1.1.1/4 0.53 -0.66
Calostel~hane divaricata INU [22] 1.2/5 .0.28 -0.66
Geigeria a~oera vat. asoera INU [18] 1.1/5. 1.2/4, 1.1.2/3, 1.2.1/1 0.38 -0.90
G. brevifolia INU [18] 1.2/4, 1.2.1/1 0.34 -1.06
G burkeisub sp. burkei INU [18] 1.2/2 0.35 -1.15
idem, var. elata INU [18] 1.1.2/1 0.53 -0.93
idem, var. interrnedia INU [18] 1.1/1, 1.1.1/1, 1.1.2/3 0.48 -0.88
/dern, var. zeyheri INU [18] 1.1/1, 1.1.1/1 0.46 --1.06
G. burkeisub ~. diffusa INU [18] 1.2/2. 1.1.2/2 0.53 -0.60
Artemisia herba alba ANT [43] 1/3 0.13 --0.97
A. herba alba ANT [43] 1/3 0.13 -0.97
Inezia integrifolia ANT [41] 1.1/1.1.2/3 0.28 -0.83
O~anthu$ mari~mu$ ANT [46] 1.1/4 0.28 -0.66
Tanacetum par~eniurn ANT [37] 1.8/1.1.1/10.1.2/1 0.27 -0.74
Lopholaena distichia SEN [30] 1.2.1/5 0.53 -1.17
L. segmentata SEN [30] 1.2.1/6 0.53 -1.08
L. tomentosa SEN [30] 1.2.1/6 0.53 --1.06
Senecio corormtus SEN [36] 1.2.1/9 0.53 -0.61
$. glandulo.pilosus SEN [40] 1.2.1/2 0.53 -1.00

164 VICENTE DE P. EMERENCIANO. MARIA AUXILIADORA C. KAPLAN AND O1-I"O R. GoI-rLJEB
i.+l. o
lHmu
l.OC
mlKuP
mNm'L.ml
~,
~,~
mA|T OYEm m.~r,
&m.~ OoAo ~m~ Im, u
I
B~m~¢ O~A mJmN
m ~.o o.a~ m
~ ~
RG. lO. ~ f l ~ ~ ~s ~D ~ V~UES ~ ~[S ~ ~ BE~GI~ ~ ~E S~I~S C ~ l ~ ~) ~D
~ ~ GR~ 1 ~) ~ 2 ~). F~ m O ~ ~ ~ m ~ r m~n~ m Tm~ 12.
expected, by compounds of type 1.4 and by
uniformly high EA s values. The eight new
species of Inuleae contain compounds of various
types, including type 1.2 and possess low EA o
values. The situation for the five new species of
Anthemideae with respect to type 1.2 is similar,
but F-A s values are considerably lower. All five
new species of Senecioneae contain types 1.2.1.
This distinctive feature, together with very low
EA o and very high F_A s values, make recognitions
in this group especially easy.
The global analysis of the presem paper thus
not only reveals valid trends, but also shows that
the way is paved to a useful chemosystematic
device for the cla=sification of the Asteraceae.
Ackn~me~t--Con~lho Nacional de De~envolvirnento
Cientifico • Tecnolbgi¢o (CNPq) provided a graduate fellowship
(to V. de P, E.).
References
1. Silva, M. F. das G. Fo, Go~iieb00. Ft. sm~ Oreyer0 0. L. (1984)
~ochem. $~st ~co/. 12, 299.
~o
~,film'L
BOiL
~!
mA
Z*N~
h~.
~¥~
~,w.~
~
m,,,mu
B ~
B ~
&~OT
AOOel
o~1,o ~ =~. ~-J
~,~. ~. co~e~ o~ ~, ~o ~ ~ M ~ r~ SuO~lOeS o~ .eu~'r.e,oz. C~,~CTe~'O O~ ~e.~ O~C C.~OMO~O~
NUMBERS, BELONGING TO THE GROUPS CENTERED IN VERBE$1MNA~ t~), GAUNSOGINAE ~), COREOPSIDINAE (~) AND MILLERIINAE (Z~). For a
Oloa~ary of the ~me4Ottor acronyms see Tatde 11.

SESQUITERPENE LACTONES IN ANGIOSPERMS 165
OmEL
O.N
0o41
~H|L
0.~'0
nBAH
VBN
nAml
GM~L
&FIT
=~,o o.~o o.&o oJ~
'~s
FIG. 12. ~RRE~ON ~ ~s ~D ~ V~UES FOR SUB~tBES OF flELIA~E~, C~R~R~D BY ~EIR B~IC CHRO~ME NU~ERS,
BEL~I~ TO ~E GR~ ~ED IN VERBESlNIN~ (~), G~INS~I~ ~), C~E~IB~ (~) AND MI~ERIIN~ ~). F~ a glo~w ~ ~
~ r acmn~s ~ Tab~ 11.
2. Rscher, N. H., Olivier, E. J. and Fischer, H. D. (1979) Prog. 22. Bohlmann, F., Jakupovic, J. and Ahmed, M (1962) Phy~o-
Chem. Org. A/eL Prod. :~, 48.
chemistry 21, 2027.
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166 VICENTE DE P. EMERENCIANO, MARIA AUXILIADORA C. KAPLAN AND OTtO R. GOI-rLJEB
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