Alkaloids from Animals

The presence of pyrrolizidine alkaloids in arctiid moths that had been reared on Senecio and Crotalaria species has been established by Rothschild et al.4S These alkaloids are stored in the moths, and serve as a deterrent to vertebrate predators and as precursors for insect sex pheromones. A pyrrolizidine alkaloid metabolite from the Cinnabar moth (Tyria jacobaea L.), named callimorphine, has been shown to have the structure (49) on the basis of mass-spectral and degradative evidence.46 The structure (49) was confirmed by synthesis of callimorphine and a diastereo-isomer by treatment of 9-chlororetronecine with the sodium salt of ( )-2-acetoxy-2-methylbutanoic acid. 

The venomous constituent of the cryptic thief ant, Solenopsis xenovenenum, has been identified as the 3-heptyl-5-methylpyrrolizidine (50) from its mass spectrum and the fact that a related pyrrolidine (51) has been isolated from another species of ant.47 This is the first reported occurrence of a 3,5-dialkyl-pyrrolizidine, and its structure was confirmed by synthesis. Reductive amination of the known triketone (52) with sodium cyanoborohydride and ammonium acetate gave a mixture of four isomers of 3-heptyl-5-methylpyrrolizidine, which were separated by preparative g.l.c. The stereochemistry of the ring-junction of each isomer was established from its i.r. and n.m.r. spectra. 

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Microcrystal tests can be performed to identify tropane alkaloids from animal tissues (57). 

Owing to the use of lupin seeds for feeding animals, much attention has been given to the selection of species free from the more toxic alkaloids of the group, particularly sparteine, to methods of removing alkaloids from the seeds, a subjeet on which there is an extensive literature and to methods of estimating alkaloids in lupins on which a critical review has been published by Brahm and Andresen. ... 

After 1960, many new isolations of these bases were reported, much chemistry and biology has been added to the original body, and about 80 new alkaloids from the vegetable and animal kingdoms have joined the list. These are the reasons why it was felt that the time had come to update the preceding reviews. 

Coincidental with the above developments, biomedical scientists in pharmaceutical companies were actively pursuing purified extracts and pure compounds derived from plants and animal sources (e.g., digitalis, rauwolfia alkaloids, and animal hormones) as human medicaments. Analogs and derivatives of these purified substances were also investigated... 

Nicotine is the principal psychoactive alkaloid from tobacco and has effects on cognition in animal and human studies. This is not surprising... 

The 4-acyl derivatives of 4-deacetylvinblastine (98) are among the earliest semi-synthetic compounds prepared in exploring the medicinal chemistry of the bisindole alkaloids from Catharanthus. By 1965, the clinical utility of vinblastine (1) and vincristine (2) was firmly established, and the naturally occurring congeners leurosine (3) and leurosidine (4) had been well characterized with respect to their experimental antitumor activity. Since these compounds were substantially less active in animal tumor... 

The chemical properties of water determine what compounds will leach out of soil and vegetation, and hence what chemicals other plants and animals will be exposed to. For instance, acidic water will extract alkaloids from plant materials. 

Quinazoline alkaloids contain more than 100 compounds. They have been isolated from animal and plant sources. The plant family Rutaceae is especially rich in these alkaloids. Typical quinazoline alkaloids include, for example, arborine, glomerin, homoglomerin, glycerine, glycosminine, febrifugine and... 

Alkaloids are active bioagents in animal tissues. There is clear scientific evidence of this. Crawford and Kocan" " have tested the toxicity of steroidal alkaloids from the potato Solanum tuberosum), such as a-chaconine, a-solanine, solanidine and solasodine, and Veratrum alkaloid, jervine on fish. The results of Crawford and Kocan s research proved that rainbow trout exhibited a toxic response to chaconine, solasidine and solanine, while medaka only did so to chaconine and solanine. Embryo mortality was observed as an effect of toxicity in both species. Many other alkaloids are known to disturb or cause disorder in animal reproductive systems. For example, gossypol from cotton-seed oil is known as a clear reducer of spermatogenesis and premature abortion of the embryo. 

Since the report by Bancroft (77) of an alkaloid from Crytocara bowiei, possibly cryptaustoline, which affected respiration of warm blooded animals and caused paralysis in frogs, no serious pharmacological studies with either cryptaustoline or crytowoline have been reported. 

Extraction from animals, microorganisms, or plants isolation and purification, used, for example, for alkaloids, antibacterials (especially penicillins), and steroids... 

Tyrosine-derived metabolites in this section do not include spiro-cyclohexadienyl-isoxazolines and related compounds (Sect. 3.22.3.3) or bastadins (Sect. 3.22.3.4), but they do include tyrosine-derived alkaloids that were covered in the Alkaloids section in the first survey (1). The prolific bryozoan Amathia convoluta, collected in Tasmania, has yielded amathamide G (1953) (1814), the latest of several amath-amide alkaloids from the genus Amathia (1). A Florida collection of this animal furnished the new convolutamines A-E (1954—1958) (1815), F (1959), and G (1960) (1425), and a Tasmanian sample of this bryozoan afforded convolutamine H (1961) (1319). A study of Amathia convoluta from the North Carolina coast has yielded volutamides A-E (1962-1966) (1816). Volutamides B and C reduce feeding by the pinfish (Lagodon rhomboids) and the urchin (Arbacia punctulata), respectively, and volutamides B and D are toxic toward larvae of the hydroid Eudendrium carneum. The New Zealand Amathia wilsoni contains the six novel amathaspiramides A-F (1967-1972) (1817). 

Nemerteans are slow-moving predators that can subdue prey of considerable size by means of a proboscis. A nicotine-like alkaloid from the integument has been described it was observed that the metabolite is not used to subdue prey.130 It would appear that the animals have evolved a... 

Of much interest is the recent discovery of substances closely related to the harmala alkaloids in animals. One of these is adrenoglomerulotropine, a hormone of the pineal body, the chemical identity of which has been indicated as 2,3,4,9-tetrahydro-6-methoxy-i-methyl-iH-pyrido (3,4,6) indole. This substance is identical to 6-methoxyletrahydroharman which has been shown to be formed in vivo from 5-methoxy tryptamine and acetaldehyde. 6-methoxytetrahydroharman is an isomer of tetrahydro-harmine, one of the alkaloids in Banisteriopsis, and in the African Leptactinia densillora. One more substance, 6-methoxyharmalan, has been shown to derive, at least in vitro, from melatonin, which results from the methylation of acetylserotonin. The enzyme which makes this possible, hydroxyindole O-methyl transferase, has only been found in the pineal body. (Naranjo, in Efron et al. 

Gunatilaka AA. Natural products from plant-associated microorganisms distribution, structural diversity, bioactivity, and imph-cations of their occurrence. J. Nat. Prod. 2006 69 509-526. Porter JK. Ergot alkaloids and alkaloids from other endophytes, responsible for causing toxic syndrome in cattle after eating contaminated grass. Prikl. Biokhim. Mikrobiol. 1993 29 51-55. Porter JK. Analysis of endophyte toxins fescue and other grasses toxic to livestock. J. Anim. Sci. 1995 73 871-880. 

Histrionicotoxin, one of the spiropiperidine alkaloids from the skin of the Colombian frog Dendrobates histrionicus, containing two c/s-but-3-en-l-yne groups, is the first acetylenic alkaloid and also the first acetylene of animal origin. (The acid 12, present in the secretion of the soldier beetle, ChauHognatus lecontei. ... 

Leaching or solid-liquid extraction are terms that describe the extraction of soluble constituents from a solid or semisolid by means of suitable solvents. The process, which is used whenever tea or coffee is made, is an important stage in the production of many fine chemicals found naturally in animal and vegetable tissue. Examples are found in the extraction of fixed oils from seeds, in the preparation of alkaloids, such as strychnine from Nux vomica beans or quinine from Cinchona bark and in the isolation of enzymes, such as rennin, and hormones, such as insulin, from animal sources. In the past, a wider importance attended the process because the products of simple extraction procedures, known as galenicals, formed the major part of the ingredients used to fulfill a doctor s prescription. 

COtinine [inn] is an alkaloid from leaf tobacco (Nicotiana tabacum) and is also detected in Duboisia hopwoodii (Solanaceae). It is a nicotine metabolite, used as a biomarker for exposure to cigarette smoke. It shows ANTIDEPRESSANT and other behavioural effects in animals, cothromboplastin factorVII. 

OCtOdrine [inn, usan] is a vasoconstrictor that formerly was used in the treatment of hypotensive states, octopamine [inn] (norsynephrlne noroxedrine) is a phenylethylamine alkaloid from Capsicum frutescens, Citrus spp., Cyperus spp. (Solanaceae, Rutaceae, Cyperaceae). It occurs in many animal tissues found in high concentrations in the posterior salivary gland of Octopus vulgaris. It serves as an invertebrate neurotransmitter. It is predominantly an O-ADRENOCEPTOR AGONIST, and has been used as a hypertensive to treat hypotensive states. 

These alkaloids are extracted from animal tissues with the universal buffer solution or with acid solution at pH 4 to 5 (using oxalic or tartaric acid). The alkaloids are then identified micro crystallographically by reaction with Rieneck s salt and by Vitali s reaction (57). 

Since the yields of active dimeric alkaloids from Catharanthus roseus is the lowest of any medicinally useful compounds (yield of VCR == 3 x 10 " %), material for studies of structure-activity relations has been scarce. Nevertheless, such studies were performed with VLB and it has been claimed that some of the products of molecular modification are more active in animal tests than VLB itself. 

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