Article

Lupine Alkaloids as Larval Feeding Deterrents for Spruce Budworm, Choristoneura fumiferana (Lepidoptera: Tortricidae)

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Abstract

Twelve lupine alkaloids, eight from Lupinus polyphyllus (Lindl), were tested in feeding bioassays against sixth instar spruce budworm, Choristoneura fumiferana (Clemens). Feeding deterrence was found in the alkaloid fraction of L. polyphyllus extracts. Eight lupine alkaloids shown to be present in the extract were tested at the rate of 25 μg per feeding disc. Of these compounds, 13-trans-cinnamoyloxylupanine and 13- tigloyloxylupanine were highly deterrent, whereas lupanine, sparteine, 13-hydroxylupanine, tetrahydrorhombifoline, angustifoline, and 17-oxolupanine, were not. Four alkaloids not present in L. polyphyllus, lupinine, epilupinine, α-isolupanine, and lupinyl-trans-cinnamate, were not active at 25 μg per feeding disc. Clearly, there is wide variability in the response of spruce budworm larvae, which are not adapted to feeding on alkaloids, to various alkaloids within the same structural class. If this variability in response is general among herbivores, perhaps the presence of an alkaloid is not significant with regard to defense, whereas diversity in structure of alkaloids may deter generalist grazers.

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... Alkaloids: Many alkaloids interfere with nerve acetylcholine receptors (e.g., nicotine) or membrane sodium channels (e.g., veratridine) of the insects. It is well known that alkaloids also can exert a feeding deterrent action against numerous insects, such as Choristoneura fumiferana [71] and Spodoptera littoralis [72]. Other alkaloids such as harmaline and hermidine again affect the growth and development of insects, including Tribolium castaneum, but their modes of action are not fully understood [73]. ...
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Chapter
The role of plant secondary natural products and their interactions with insect herbivores have been focal points for research by chemists, botanists, and entomologists for several years and is the topic of several excellent reviews (1,2, 3,4). For example, Hedin et al. (5) have an early review of modifications in insect behavior due to host plant secondary natural products. Included among the classes of compounds listed as feeding stimulants, repellents, or deterrents are: flavonoids, terpenoids, phospholipids, glycosides, acids, esters, phenolics, and alkaloids. In general, alkaloids and their glycosides seem to be most often involved as feeding repellents or deterrents, although there are examples when alkaloids are specific feeding cues. Barbosa et al. (6) have linked the presence of alkaloids in deciduous trees with feeding avoidance by the polyphagous feeding gypsy moth Lymantria dispar. They have shown that when the major groups of plant secondary natural products are examined, alkaloids rank the lowest in feeding preference (7). In this paper we will examine potential relationships between the chemistry of alkaloids in the host plants and effects that these compounds may have on insect herbivores. In many cases the specific alkaloid that is produced by a particular plant has different effects on different insects. When the data are available, specific associations between the plant alkaloids and the feeding behavior of the insect herbivore will be made.
Chapter
Quinolizidine alkaloids (QA), of which more than 170 structures have been reported (overviews in: Mears and Mabry 1971; Kinghorn and Balandrin 1984; Salatino and Gottlieb 1980; Wink 1993), are distinct from other alkaloids in that they contain at least one quinolizidine ring system. According to the degree of substitution at least seven different groups can be distinguished: (1) the lupinine-type, (2) the Leontidine-type, (3) the sparteine/lupanine/ multiflorine-type, (4) the alpha-pyridone-type, (5) the matrine-type, (6) the Ormosia-type, and (7) piperidine and dipiperidines, which often occur together with QA (Fig. 1).
Thesis
Bisquinolizidine alkaloids are a fascinating natural product class of secondary metabolites with about 50 members. The most prominent ones are (−)-sparteine (9), which can be isolated from scotch broom and serves as the ligand of choice in several asymmetric reactions, but also has antiarrhythmic and oxytocic properties, and cytisine (13), which is a partial agonist of the nicotinic acetylcholine receptor and pharmaceutically marketed for smoking cessation. Common structural element of all bisquinolizidine natural products is a 3,7-diazabicyclo[3.3.1]-nonane skeleton, which builds the chiral core and appears in nature in both enantiomeric forms (7S/9S and 7R/9R series). Combinations of an α,N-fused pyridone, endo- or exo-α,N-annulated piperidin(on)es, and an exo-allyl substituent can be attached to it. To date, several elegant, enantioselective total syntheses are described, but these are all based on an “outside-in” strategy. The periphery, in which the natural products are differing, is constructed first and the common bispidine core is closed in a later stage. This usually limits the applicability of the approach to particular target molecules. A flexible route, as required for the efficient total synthesis of bisquinolizidine natural products and for the synthesis of new bispidine ligands, is still missing. Main goal of this work was the development of a modular, enantioselective “inside-out”-strategy for the synthesis of tri- and tetracyclic bisquinolizidine alkaloids. The achiral tetraoxobispidine 7 was desymmetrized in the first key step, which delivered the dioxobispidine 6 or, optionally, its enatiomer ent-6 in 34% yield and >99% ee over five steps. The installation of the α,N-fused pyridone 123, which exclusively occurs in the 7R/9R-series, was the second key step and achieved, after selective modification of only one of the two imide groups, via an enamine-bromoacrylic acid strategy. Six steps were needed for that, giving the pyridone 123 in an overall yield of 35% and >99% ee. The enantiomeric pyridone was hydrogenated to provide the key intermediate 122 of the 7S/9S-series. By choice of the reaction sequence endo-substituents were attached via addition and subsequent reduc¬tion, while exo-substituents were installed via reduction and following addition. In conclusion, a modular and broadly applicable route to bisquinolizidine alkaloids was developed. The versatility was proven in the asymmetric synthesis of 21 natural products, inclu¬ding the first enantioselective total syntheses of angustifoline (14), α-isosparteine (15), ther¬mospsine (16), anagyrine (17), (+)- and (−)-lupanine (23 and ent-23), tetrahydrorhombifoline (37), 11-allylcytisine (125), 11-oxocytisine (133), tinctorine (135), isolupanine (140), and N-methylangustifoline (142). The second project was the synthesis of baptifoline (19) and epibaptifoline (epi-19) and the unambiguous elucidation of their configuration at C13. The configuration suggested by CAS/scifinder is based on a 50-year-old assignment, which was done on basis of IR spectroscopy, by using the wavenumber of the OH vibration. In other literature, however, the opposite configuration is given. To unambiguously determine the correct stereochemistry, epi-bapti¬foline (epi-19) was synthesized from allylcytisine (125) in 86% yield (>98:2 dr) and converted via an oxidation/reduction-sequence into baptifoline (19, 50% yield, dr >98:2). By hydration to ent,epi-18, the enantiomer of 13β-hydroxylupanine (epi-18), NMR spectroscopic studies, and X-ray analysis, the configuration at C13 bearing the alcohol function was unequivocally determined: it is equatorial in epibaptifoline (epi-19) and axial in baptifoline (19). A side project dealt with the modular, stereoselective synthesis of new bispidine ligands derived from key intermediate 124, which was synthesized in five steps and 48% yield. Endo-substituents were introduced via addition followed by reduction. By doing so, the three new ligands 11a,b and 12 as well as the known (−)-sparteine surrogate (10) were synthesized. Under optimized conditions, ligand 11b delivered the β-nitroalcohols 154 in enantioselective, Cu-catalyzed Henry reactions with 2-4 mol% catalyst in 80-99% yield and 96-99% ee (ten examples). Enantioselective and diastereoselective Henry reactions of 152 with nitroethane or nitropropane were done on six examples, giving 51-99% yield, 96-99% ee, and up to 86:14 d.r. Thus, diamine 11b is the most efficient bispidine derived ligand for this reaction.
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