Cacalia

Cacalia hastata, 601 Cacotheline, 566 Cactaceae, 154 Cadaverine, 518 Calabar bean alkaloids, 539 Calabarine, 540 Calabash curare, 373 alkaloids, 380... 

Oreina cacaliae) to damaged host plants. Journal of Chemical Ecology 27 647-661. 

Oreina leaf beetles (Chrysomelidae, Coleoptera) synthesize cardenolides as part of their defensive secretions that are released from specialized exocrine glands.139,140 Some Oreina beetles sequester and secrete PAs, which are taken directly as N-oxides from their Asteraceae food plants.59 It is assumed that PA acquisition evolved in species that already possessed the ability to synthesize and store cardenolides for efficient defense.14 O. cacaliae is the only species in this family that lost the ability to synthesize cardenolides autogenously. Instead the plant-derived PA A-oxides are stored in the body (primarily in the hemolymph) and... 

Six new compounds (418)—(423) have been isolated from Cacalia species and identified as derivatives of the co-metabolites cacalol (417) and the nor-sesquiterpenoid maturinone (424) cf. Vol. 1, p. 102). Compounds of this type are... 

Cacalol (596), a major constituent of Cacalia delfiniifolia Sieb. et Zucc., was oxidized with iodine (1 equiv.) and NaOMe in MeOH to give 11-methoxycacalol (597) in 62% yield. With 2 equivalents of iodine, a similar reaction provided cacalal (598), another sesquiterpene isolated from the same plant, although the yield (0.8%) was very low (Scheme 114). 

Betula species.49 The efficient conversion of (20S,24i )-20,24-epoxydammarane-3a, 12(3,25-triol into the 25-0-,3-D-glucoside has been reported.50 The seed oil of Cacalia atriplicifolia (Compositae) is a rich source of esters of dammarenediol II.51... 

Petasinine (43) and petasinoside (44) were isolated from Petasites japonic us Maxim. " Jacoline (48) was isolated from Cirsium wallichii D.C. collected from India and identified as O-acetyljacoline. Yamataimine (49) was isolated from Cacalia yatabei Maxim. ... 

The absolute configuration of (-i-)-cacalol (519) has been deduced by oxidative degradation to (5)-(+)-2-methylhexanedioic acid, and the corresponding aldehyde, cacalal (520), has been identified as a further constituent of Cacalia species (cf. Vol. 8, p. 117). Cacalane derivatives (521) and (522), structurally... 

C19H27NO7 S. erraticus Bert. spp. barbaraeifolius Krock (65) Cacalia floridana (23) ... 

Cacalia cordifolia C. decomposita (i, Note 7) Both of these composites are known as peyotes in Mexico—the former is known as PeyotlXochimilcensi (Di az 197 , Schultes 193 7b). However, they are used as medicinal plants and there is no evidence that they arc entheogenic. Sesquiterpene lactones and alkaloids are knotvn from the genus (Schultes Hofinann 1980). 

Cabiparaensis (Jussieu) Grisebach-211, 219,262-3,271,405,412 Cabomba aquatica Aublet-271 Cacalia cordifoiia L. /.-io8,422 Cacalia decomposita-io%,y2.z Caesalpinia echinata Lam.-2i7,270,40 5 Caesalpinia sepiaria RDxburgh-404 Colathea veitchiana Veitch ex Hooker ).-216,271... 

Hastacine was extracted from Cacalia hastata in 0.085% yield. 

A new alkaloid, yamataimine (28), has been isolated from the roots of Cacalia yatabei Maxim, by Hikichi etaO The H n.m.r. spectrum of (28) was typical of a twelve-membered macrocyclic diester of retronecine, particularly in the chemical... 

Pasteels, j. M., M. Rowell-Rahier, T. Randoux, J. C. Braek-MAN, and D. Daloze, Pyrrolozidine alkaloids of probable host-plant origin in the pronotal and elytral secretion of the leaf beetle Oreina cacaliae, Ent. Exp. Appl, 49, 55-58 (1988). 

Larvae of the chrysomelid beetle Oreina cacaliae produce seniciphylline A -oxide (12) as a part of their defensive secretions. This pyrrolizidine alkaloid probably is derived from the alkaloids of the host plant Adenostyles leucophylla (Asteraceae Senecioneae) (Pasteels et al., 1988). 

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