Evolution of Sesquiterpene Lactones in Angiosperms*

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.