Chemistry of Acacia's from South Texas
Acacia species in south Texas contain numerous chemical compounds, many of which have negative effects on animal performance.
Alkaloids, phenolic amines, phytoestrogens, and tannis have been identified in south Texas acacias.
Many of the acacias of south Texas are considered to be valuable forage for deer and domestic livestock. It is known, however, that at least one species, guajillo (Acacia berlandieri) will produce a paralytic condition in sheep and goats called "guajillo wobbles." As part of a larger study investigating the chemistry of south Texas range plants, we determined the chemical composition of the leaves of several south Texas acacias.
Most woody plants contain a variety of chemical compounds a number of which have the advantage to the plant of being toxic to animals that consume them. Many of these defensive compounds are nitrogen-based, though there also are a significant number of nonnitrogenous toxic compounds. Additionally, plants produce compounds which may be repellent or, as in the case of tannins, lower the nutritional value of the plant. Early research, using paper and thin-layer chromatographic techniques, identified several phenolic amines in A. berlandieri, including n-methyl-phenethylamine (NMP), tyramine, nmethyltyramine and hordenine.
The alkaloid fractions (those extractable with 10% HCL) of A. berlandieri and A. rigidula contained a complex mixture of alkaloids including nicotine, nornicotine, anhalamine, mescaline, and 3,4,5-trihydroxy-phenethylamine (demethylated mescaline).
The phenolic amines, such as tyramine, hordenine and N-methyl-B-phenethylamine are powerful activators of the sympathetic nervous system causing the release of cortisol and adrenocorticotropic hormone. In addition to the alkaloids, the plants were also found to contain intricate mixtures of tannins and flavenoids including catechin, fisetin and quercetin.
While tannins and their antinutritional effects have been the subject of much research in recent years, little attention has been paid to the negative effects of consumption of other secondary compounds that are not acutely toxic. However, recent research has shown the negative effects on fertility of consumption of amine-containing forage. Consumption of guajillo and blackbrush was shown to reduce fertility in male goats, and to reduce their ability to handle stressful situations such as transportation.
Table 1. Major Chemical Compounds in South Texas Acacias :
Amines and Alkaloids:
phenethylamine
N,N-dimethylphenethylamine
N,N-dimethyl-"-methylphenethylamine
p-hydroxyamphetamine
tyramine
3-5-dimethoxytyramine
3,4-dimethoxy-5-hydroxy-$-phenethylamine
hordenine
N,N-dimethyldopamine
tryptamine
N,N-dimethyltryptamine
N-methylmescaline
nicotine
anhalamine
peyophorine
nortryptyline
3-"-cumyl-1,3,4-oxadiazolidine-2,5-dione
p-hydroxypipecolamide
4-methyl-2-pyridinamine
N-methylphenethylamine
amphetamine
methamphetamine
p-methoxyamphetamine
N-methyltyramine
candicine
dopamine
N-methyldopamine
3-methoxytyramine
N-methyltryptamine
mescaline
trichocereine
nornicotine
anahalidine
mimosine (methyl ester)
musk ambrette
pipecolamide
1,4-benzezediamine
Phytoestrogens:
octylphenol \
aristolone
(Z)-9-octadecenoic acid
(Z,Z,Z)-9,12,15-octadecatrienoic acid
3b-acetoxy-17-methyl-5a-18-abeoandrost-13-ene
nonylphenol
3b-cholest-5-en-3-ol
(Z,Z)-9,12,-octadecanoic acid
FULL VERSION:
http://uvalde.tamu.edu/pdf/chemtdaf.pdf Last but not least some more on toxicology:
Toxic amines and alkaloids from acacia rigidula
Acacia rigidula Benth., blackbrush, is a shrub found growing on rocky ridges in west and southwest Texas and northern Mexico. Consumption of blackbrush and a related species guajillo, Acacia berlandieri Benth., has been associated with a locomotor ataxia known as "limber leg".
A. rigidula has been shown to contain appreciable levels of toxic alkaloids. Sheep and goats grazing on a related species, Acacia berlandieri Benth., guajillo, during periods of drought in the Rio Grande Plains of Texas have developed a locomotor ataxia referred to as "guajillo wobbles" or "limber leg" [2]. Previous analysis of blackbrush had detected and identifed four amines, N-methyl-b-phenethylamine (NMPEA), tyramine, N-methyltyramine, and hordenine, which were also found in guajillo [3].
As a result of this study, an intensive chemical analysis of A. rigidula Benth. was undertaken to identify the amines and alkaloids present in the leaves and stems that would comprise browse material.
Forty-four amines and alkaloids, including the four previously encountered amines, N-methyl-b-phenethylamine, tyramine, N-methyltyramine, and hordenine, were identifed by GC-MS.
The majority of the isolated alkaloids, 18 of the 33 identifed, were related to the parent compound b-phenethylamine. These compounds generally varied in the degree of N-methylation, x-methylation (amphetamine family), and in oxygenation of the aromatic ring (tyramine, dopamine, and mescaline families). The 2-cyclohexylethylamine and the N-cyclohexylethyl-N-methylamine are the saturated analogs of the phenethylamine and NMPEA respectively. Tryptamine, N-methyltryptamine, and N,N-dimethyltryptamine were also isolated from blackbrush.
Other noteworthy alkaloids found in blackbrush include nicotine, nornicotine, and four tetrahydroisoquinoline alkaloids, anhalamine, anhalidine, anhalonidine, and peyophorine. The amides of the amino acids pipecolic acid and p-hydroxypipecolic acid were also detected.
As was previously found with NMPEA the foliage collected in the autumn contained higher quantities of amines and alkaloids [10]. There was also a distinct increase in the number and quantity of methylated analogs present (Table 1).
Several as yet unidentifed amine-containing compounds have been detected but have not yet been identifed. It is also probable that several biosynthetic precursors are present in the mixture but as yet are unresolved and are below the threshold of GC-MS detection.
Phenolic amines, as a group, impact the hypothalamic-pituitary-adrenal axis [11]. The consequent release of ACTH and cortisol results in symphathomimetic action. The number of phenolic amines reported in Table 1 and their concentrations in the plant indicate a substantial toxic load to animals consuming blackbrush. The toxicity of nicotine and nornicotine has been well established [12], as has the psychoactivity of mescaline and its derivatives. None of the compounds identifed appear to have been implicated in locomotor ataxia. However the presence of the amphetamines suggests the possibility for a reduction of monoamine oxidase activity [13]. FULL VERSION:
http://www.erowid.org/ar.../rhodiu...a.rigidula.pdf The difficulty of performing a given task is directly proportional to a persons capability for confusion![color=red]