Testosterone plants

Folmar, L.C., Denslow, N.D., Rao, V. et al. (1996). Vitellogenin induction and reduced serum testosterone concentrations in feral male carp (Cyprinus carpio) captured near a major metropohtan sewage treatment plant. Environmental Health Perspectives 104, 1096-1101. 

Androgenic compounds occur in various plants. Celery stalks and parsnip roots contain trace amounts of androstenedione (Fig. 11.12), the same compound found in boar odor (Claus and Hoppen, 1979). Testosterone is also found in pollen of Scots pine Pinus sylvestris). 

Tribulus terrestris — A plant found throughout Australia, Asia, Africa, and North and South America. It contains saponins, polysaccharides, sterols, flavonoids, and fatty acids, many of which are indicated to have general health benefits. Tribulus terrestris is a natural testosterone enhancer, shown in clinical studies to increase testosterone levels by aiding in the production of the luteinizing hormone (LH), a hormone that influences sex drive. Tribulus terrestris has been used to increase fertility and aid impotence. 

If as above we simply represent alicyclic rings sharing two Gs by a vertical line, then we can represent the basic tetracyclic structure of lanosterol as G61G61 G6 C5 (noting that there are two double bonds and various alkyl substituents and also a 3-hydroxyl on the first of the alicyclic rings). Many subsequent reactions yield cholesterol, a major triterpene membrane component that modifies the fluidity of animal cell membranes and is a precursor for synthesis of animal bile acids (fat solubilizing amphipathic detergents) plant triterpenes and steroid hormones such as the corticosteroids cortisol and cortisone, the mineralocorticoid aldosterone and the sex hormones testosterone and 17-(3-oestradiol. The structure and bioactivity of the plant terpenes is sketched below. 

In addition to the many hundreds of steroids isolated from plants and animals, thousands more have been synthesized in pharmaceutical laboratories in a search for new drugs. Among the best-known synthetic steroids are the oral contraceptives and anabolic agents. Most birth-control pills are a mixture of two compounds, a synthetic estrogen, such as ethynylestradiol, and a synthetic progestin, such as norethindrone. Anabolic steroids, such as stanozolol and methandrostenolone (Dianabol), are synthetic androgens that mimic the tissue-building effects of natural testosterone. 

The conventional definition of the endocrine system is the collection of ductless glands that secrete small amounts of hormones directly into the blood of vertebrates. The hormones are transported to other parts of the body where they have a profound effect on biological processes. Perhaps the best examples are the sex hormones oestrogen and testosterone, but there are many others. Hormones are also produced by invertebrates (e.g. moulting hormones) and even by plants (e.g. growth hormones). 

Takahashi, T., 320, 330, 331 Tea decaffeination plant, 7 Temperature-entropy diagram, 138 Temperature rising elution fractionation (TREF), 197, 202-203 Ternary mixtures, phase diagrams, 71-84 Testosterone, 340 Tetracyclic steroids, 293 Thermodynamic modeling, 99-134 Thies, M. C., 88-90... 

Progesterone is synthesized from either cholesterol or alkylated plant sterols by a pathway similar to that in animals. Hydroxylation at C-20 and C-22 is a prerequisite for removal of the C-6 residue of the side chain (A, B, C, Fig. 16). The product pregnenolone is then reduced to progesterone (D, Fig. 16). Traces of oestrone, testosterone, deoxycorticosterone and closely related compounds have been found in plants but nothing is known of their biosynthesis. 

FIGURE 18-6 Chemical structures of major sterols and cholesterol derivatives. The major sterols in animals (cholesterol), fungi (ergosterol), and plants (stigmasterol) differ slightly in structure, but all serve as key components of cellular membranes. Cholesterol is stored as cholesteryl esters in which a fatty acyl chain (R = hydrocarbon portion of fatty acid) is esterified to the hydroxyl group. Excess cholesterol is converted by liver cells into bile acids (e.g., deoxycholic acid), which are secreted into the bile. Specialized endocrine cells synthesize steroid hormones (e.g., testosterone) from cholesterol, and photochemical and enzymatic reactions in the skin and kidneys produce vitamin D. 

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