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 Post subject: Plant Content
PostPosted: Wed Jan 22, 2014 2:15 am 
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CONTENT:

AMINO ACIDS
CARBOHYDRATES
LIPIDS
ALKALOIDS
VOLATILE OILS
STEROIDAL COMPOUNDS
TERPENOIDS
PHENOLS
GLYCOSIDES



AMINO ACIDS

In plants, amino acids are broken down into two groups, protein, and non-protein. Most protein is water and dilute alcohol soluble. There are twenty proteins, derived from the acid hydrolysates of plant proteins (as with animal proteins). Plant proteins are essential for carrying out specific cellular functions both internally and externally. Plant proteins are seed-based store-houses for nitrogen and guard against would-be predators. Some are toxic to humans, some are of daily necessity in the human diet. Some, furthermore, have been developed into specific drugs: L-Dopa, from fava beans and other Fabaceae/Leguminosae, is used in the treatment of Parkinson's disease; L-Cysteine, found in all plants, is used in eye drops and topical antibiotics. L-Arganine stimulates the pituitary gland to release growth hormone. L-Aspartic acid is present in coffee, liquorice, sugar cane, sugar beet, and is neuro-excitatory. It is the phytochemical responsible for so-called 'sugar highs,' and is in aspartame (Harborne, 61-67).


CARBOHYDRATES AND RELATED COMPOUNDS

Plant energy storage components are referred to as carbohydrates. The group which the term carbohydrates represents includes mono-(sucrose, lactose, etc.), and poly-(starch, inulin) saccharides, some acids which are produced after cellular carbohydrate respiration, alcohols such as sorbitol and cellulose; and gums and mucilages. For the purposes of therapeutics, usually the polysaccharide and gum/mucilage subgroups are most important.

Polysaccharides [] are produced through the linkage of simple or single sugars linked by ethers in various and complex ways, and are divided into two categories, water(sometimes hot) soluble or water non-soluble. Plant starch, gums, mucilage, cellulose (and sub-group hemicellulose) are all polysaccharides.

Cellulose, i.e., cotton, powdered cellulose, microcrystalline cellulose, and purified rayon, is another polysaccharide, whose derivatives, have been developed as bulking agents for the alleviation of constipation, as opthalmic solutions, topical emollients and protectants, and as agents meant to reduce the appetite (Tyler et al., 44-45).

It has been difficult for phytochemists to distinguish between gums (almost insoluble in alcohol) and mucilage categorically. Presently, it is generally agreed that while gums are water solvent and insoluble in alcohol, mucilage will become a slimy mass; and, that gums are pathologically formed while mucilages are physiological in origin (Tyler et al., 46).

Mucilage, therapeutically, can reduce bowel irritation, gut irritation, peristalsis, toxin absorption, cough, bronchial and urinary spasm. Mucilage can also increase expectoration (Cabrera, 35). As a gelating agent, the polysaccharide hydrocolloidal carrageenan often finds its way in ice cream; it is also used as a laxative ingredient. Perhaps the most common bulking agent derived from a polysaccharide comes from Plantago major, whose seed, the psyllium, can bulk itself up with the addition of water sufficiently to initiate peristalsis and evacuate the bowels (Tyler, 45-56).

LIPIDS

Fixed oils, fats, waxes, phosphatides, and lecithins, as members of the lipid group, are made up of esters of long-chain fatty acids and alcohols which contain carbon, hydrogen, and oxygen. Fixed oils are liquid at normal temperature, fats are solid; however this distinction does not always come through, especially with differences in climate.

Lipids are often a main constituent in drugs, separated by expression from the crude vegetable (plant) matter and presented as drugs in the refined state (Tyler, 82). Plant seeds are the largest source (e.g. sesame seeds,almonds, linseed) of lipids (Tyler, 83; Evans, 322). They are soluble in alcohol, ether, volatile oils or other fats. They are insoluble in water or glycerine. Heated in the presence of alkalies, they form soaps and one of the by-products is glycerine. Fats and fixed oils are obtained chiefly by the process of expression, such as castor oil, olive oil, cocoa butter. Waxes; compounds of fatty acids with certain alcohols. Differ from fats chiefly in containing no glycerol. Soluble in oils when heated.

ALKALOIDS

Alkaloids are arguably the most potent therapeutic compounds and have been manufactured as various allopathic drugs, including the pain-killer morphine and the anti-malarial quinine. Derived from amino acids, alkaloids represent a varied and complex class of nitrogenous crystalline or oily compounds. Alkaloid levels in a given botanical change in the course of the day and are not homogeneous, which makes them difficult to define (Tyler et al., 186). Their presence appears to be most prevalent in the Fabaceae/Leguminosae, Papaveraceae, Ranunculaceae, Rubiaceae, Solanaceae, and Berberidacea families. Plant genera providing the highest yield of alkaloids are Nicotiana, Vinca, Strychnos, Papaver sominifera, and Rauwolfia serpentina (Evans, 545).

Pyrrolidine, tropane, or solanaceous alkaloids effect the peripheral nervous system, inhibiting the parasympathetic nervous system and stimulating the sympathetic. Pupils dilate, secretions slow, and the vagus nerve is inhibited (causing vasodilation, bronchial dilation, and reduced peristalsis) (Harborne and Baxter, 300-308).

Pyridine and piperidine alkaloids represent a class which affects the central nervous system, reduces appetite, and contains other properties usually diuretic or diaphoretic in action. Nicotine, lobeline, and coniine are examples. Coniine is extremely toxic (Harborne and Baxter, 243-254).

Pyrrolizidine alkaloids are under fire today as chemists and doctors try to determine the human hepatotoxicity of these agents which can damage liver veins, causing hepatic veno-occlusive disease (Awang, 20-22). Toxicity to livestock is demonstrated by the fact that 50% of livestock deaths occur through the ingestion of a plant that contains these alkaloids (Harborne and Baxter, 255). Because of five well-publicized deaths (one of which was the teratogenic poisoning of a fetus) following the consumption of an herb(comfrey) that had been regarded as safe, plant families in which pyrrolizidine alkaloids are most often found (Boraginacea, Asteraceae/Compositae, and Fabaceae/Leguminosae) are of immense concern to both herbalists and the FDA (Mattocks, 724).

Indole alkaloids are derived from tryptophan, and apart from the few with hallucinogenic effects, indoles such as serotonin, harmine and reserpine have a sedative effect on the central nervous system. Other constituents in this category are cytostatic, antileukemic, or are able to act on the ratio of oxygen and glucose to the cell, specifically increasing oxygen to deprived areas.

Quinoline alkaloids are named from quinoline in the cinchona plant, and refers to the quinoline alkaloids developed in the nucleus from tryptophan (Tyler et al., 202). Included in this group are quinine, the anti-malaria medication, and quinidine, which calms the heart in tachycardiasis and arrhythmia, and others. Chinchonine is an astringent and a bitter. Isoquinoline alkaloids are derived from tyrosine and phenylalanine. The therapeutic value of this class of alkaloid differs according to the sub-categories, which include simple, benzyl, Papaveraceae, codeine, protopine, protoberberine, and ipecac isoquinolines. The protoberberines, which include berberine, hydrastine, and canadine, are anti-bacterial, anti-protozoal, astringent, tonic, bitter tasting, and respiratory, vasomotor, and circulatory stimulants. Alkaloids unite with acids to form salts, in the manner of ammonia. Most alkaloids are somewhat soluble in alcohol (this will be enhanced by adding glycerine) and some are soluble in water. Some will form salts with vinegar.

VOLATILE OR ESSENTIAL OILS

Volatile oils are usually responsible for the odor of a plant. Volatile, or essential, oils evaporate with air. They can contain hundreds of constituents, the highest of which are terpenes. Hydrocarbons (as with acillin, from garlic), alcohols, aldehydes (this group includes cinnamon oil, orange oil, lemon peel, lemon oil, hamamelis water, and citronella oil, whose medicinal purposes include the astringent quality of witch hazel). Therapeutically, volatile oils have many uses. They can serve as a mode of transportation, to distribute a medicine equally throughout the body. They can act as antiseptics. Volatile oils tend to stimulate tissues they come in contact with, hence they can be rubefacients, counter-irritants, and/or vasodilators. Internally, volatile oils may cause an increase in saliva, perspiration, peristalsis, and/or stimulate the heart muscle (Cabrera, 40). Soluble in alcohol, slightly in water and some fixed oils.

STEROIDAL COMPOUNDS

Steroids are a natural product class of widely distributed compounds. Steroids develop and control the reproductive tract in humans, molt insects, induce sexual reproduction in aquatic fungi. Therapeutically, steroids contribute cardiotonics (digitoxin), Vitamin D precursors, oral contraceptives (semi-synthetic progestins), antiinflammatory agents (corticosteroids) and anabolic agents (androgens).The phytochemical make up of this group of plant glycosides always includes a 4-membered hydrocarbon ring. This is true in animal-derived steroids and synthesized steroids as well.

In plants, steroidal content is divided into steroid saponins (soluble in water), which are very similar to triterpenoid saponins in the terpenoid group; or, they may be compounds which render them steroid alkaloids, from the alkaloid group(Harborne and Baxter, 290, 689). Steroidal compounds serve many functions both for the plant and also for humans: Combined steroids derived from plants have proven and continue to be valuable for medicinal purposes that range from topical antibiotics to relieving dysmenorrhea (ibid.; Evans, 480-488). See:terpenoid saponins, steroid saponins, steroid alkaloids.

TERPENOIDS

Terpenoids form the largest group of plant products and are the most common ingredient in volatile oils. They include camphor, Beta-carotene, and digitalin, for example, and are sometimes referred to as isoprenoids, due to the fact that all terpenoids are derived from a 5-carbon precursor isoprene (Harborne and Baxter, 552). Terpenoids are categorized as monoterpenoids and monoterpenoid lactones, sesquiterpenoids and sesquiterpenoid lactones, diterpenoids, and triterpenoids. Of these four groups, triterpenoids forms the largest. Carotenoids are formed through a head-to-tail combination of geranylgeranyl pyrophosphate, the same precursor to monoterpenoids (ibid.).

Monoterpene, sesquiterpene, and diterpene alkaloids, as well as steroidal alkaloids, are classified as alkaloids due to the presence of nitrogen in their structure. Despite that classification, those alkaloids, and some phenols as well (for instance, rotenone), may contain terpenoidal atoms or compounds or isoprenoid derivatives (ibid.).

Monoterpenoids have a head-to-tail formation of their ten-carbon precursor, geranyl pyrophosphate (Harborne and Baxter, 555). These constituents are present in volatile oils. Monoterpenoids often have a strong smell; they are the source of such scents as spearmint (carvone), bergamot and lavendar (both of which contain linalyl acetate), and sweet rose (nerol) (ibid, PD2042, PD2059, PD2065; Evans, 321). Monoterpenoids occur in insect pheromones as well. Monoterpenoids vary in pharmacological use, as expectorants, anthelmintics, anticholesteremics, insecticides, and antiseptics.

The phrase bitter principles (Soluble in water and alcohol), which refers to the bitter-tasting monoterpenoid lactones known as iridoids are also components of volatile oils and have been used to stimulate actions within the body, such as mucosal or gastric secretion. The attachment of a glucose to a hydroxyl group on the lactone ring is the determining factor in recognizing a lactone. These isoflavonoid polyphenols are sometimes also referred to as iridoid glycosides, because they are often present in glycosidic form . Iridoids usually occur in angiosperms, especially valerian, gentian, blue flag, and orris root, and can have, aside from the therapeutic actions described above, antimicrobial and antileukemic properties (Harborne and Baxter, 555, 569).

Sesquiterpenoids occur with monoterpenoids in plant essential oils, especially in the families Labiatae, Myrtaceae, Pinaceae, and Rutaceae. They also occur in micro-organisms, marine animals, fighting insects, and insect pheromonal secretions. Some are very toxic, but sesquiterpenes can be used as antifungals, carminatives, insecticides, or as an antibiotic. This latter action has been successfully demonstrated against staphylococcus areus and candida albicans, by sesquiterpenes found in marine alga (Duke, 584, Harborne and Baxter, PD2141). A sesquiterpenes found in chamomile, is an antiinflammatory agent (Harborne and Baxter, PD2123).

With the addition of a y-lactone sesquiterpenoids become sesquiterpene lactones such as those found in absynthe and arnica (Harborne and Baxter,599). The cytotoxicity of sesquiterpene lactones prevents their widespread use but encourages research into antitumor applications. Often these are the components causing contact dermatitis and some are lethal (ibid.).

Resins are non volatile secretions or excretions, some said to be oxidation products of essential oils. Soluble in alcohol,fixed oils and volatile oils. Oleo-Gum resins; milky exudates from plants which are composed of a gum or gums partly or wholly soluble in water, and a resin or resins soluble in alcohol. Gum-resins, when mixed in with water, yield emulsions, the gum more or less dissolving while the resin becomes suspended in the solution.

Oleo-resins; natural solutions of resins in essential oils, where the latter can be separated by distillation.

Balsams; resins or oleo resins with aromatic substances. They may be liquid or solid and are soluble in alcohol.

Many resin acids, termed diterpenoid acids are included in this group, as are plant hormones called gibberellins. Many of the diterpenoids are toxic, similar to sesquiterpenoids, but some have antibiotic, antiviral, antiinflammatory, and bitter tonic uses (ibid). Ginkgolides, diterpenoids from the Ginkgo biloba plant, are fast becoming one of today's most highly-esteemed phytochemicals, finding use in the treatment of memory loss, allergies, asthma, brain injury, and more (DeFeudis, 1991; Harborne and Baxter, PD2447; Petkov et al., 106).

Triterpenoid saponins, or sapogenins, are plant glycosides which lather in water and are used in detergents, or as foaming agents or emulsifiers, and have enormous medical implications due to their antifungal, antimicrobial, and adaptogenic properties. Glycyrrhizin, from licorice root, is an example of a saponin used for antiinflammatory purposes in place of cortisone (Harborne and Baxter, PD2536).

Steroid saponins are similar to the sapogenins and related to the cardiac glycosides Therapeutically, steroidal saponins their ability to interact medically and beneficially with the cardiac glycosides, sex hormones, Vitamin D, and other factors, render these phytochemicals components of great medical significance (Evans, 481). For instance, diosgenin, from Wild Yam, was used in the development of the first oral contraceptive (Harborne and Baxter, 689).

Phytosterols are necessary to plant membranes and plant cell growth. Sitosterol, stigmasterol, and campesterol are the most common (Harborne and Baxter, 712). It has been demonstrated that B-sitosterol decreases the risk of atherosclerosis by lowering plasma concentrations of LDL's (low-density lipoproteins) (Lehninger, 614). Ergosterol, combined with ultra violet light, becomes vitamin D2. Vitamin D3, mentioned in the first issue of The Protocol Journal of Botanical Medicines as a topical treatment for psoriasis, is obtained from 7-dehydrocholesterol (Tyler et al., 161).

Carotenoids, or forty-carbon tetraterpenoids, are lipid-soluble terpenes found in all forms of plants. Their value to animals comes from the splitting of the C40 molecule into the twenty-carbon isoprenoid alcohol known as Vitamin A, a process which occursafter the substance has been ingested (Guyton, 867; Harborne and Baxter, 745).

PHENOLS
Phenols, which are also called polyphenols or phenolic compounds, are plant substances which have an aromatic ring bearing one or more hydroxyl groups (Harborne and Baxter, 324). Phenols are widely splattered throughout the plant kingdom. Food and drink owe their actions on our senses to phenols. To many other phytochemical classifications this is the parent group, but phenols may also be contained as constituents in compounds through which a botanical phytochemical exists under a different classification.

The flavonoids constitute about one-half of the eight-thousand or so recognized phenols. The rest are broken down into phenylpropanoids, anthones, stilbenoids, and quinones. The compounds have a myriad of medical functions. From the perspective of the plant kingdom, polyphenolic compounds are important contributors to the survival of plant species through the insurance of successful pollination, and also provide plants with an unpleasant taste so that possibly threatening herbivores are repelled (ibid.).

Flavonoids are molecules responsible for the color of fruit and flowers. They are beneficial to man as powerful antioxidants, stress modifiers, anti-allergic agents, anti-viral compounds and anti-carcinogens (Evans,420). Some are able to stimulate protein synthesis, and some are known antiinflammatory agents. Still others have demonstrated vaso-protective activity. Some are diuretic, antispasmodic, antibacterial,and antifungal (Harborne and Baxter, 367-415).

While some flavonoids may be classified as flavonoid glycosides, all are phenols, but flavonoids, flavonals, flavanones, isoflavones, and xanthones, all stem from flavones. Flavones have effectively been used to tone blood cell walls and bloodcells. Anthocyanidins and anthocyanins are related flavonoids. These, and flavones in general, occur most frequently as glycosides.

Isoflavones occur less frequently as glycosides, more often in their free state, and have a higher degree of structural variation(Harborne and Baxter, 415).

Tannins are polyphenolic compounds and are divided into two groups, i.e., the hydrolyzable and non-hydrolyzable tannins, and the condensed tannins. Hydrolyzable tannins are thought to be hepatotoxic with overuse; condensed tannins appear not to have this action.

In general, tannins are astringent and antiseptic. Hamamelitannin, from witch hazel bark is a source of pharmacologically-used tannin (Evans, 386-388) and often found in men's aftershave lotions. A polyphenol classified as a napthaquinone, plumbagin, for example, found in the Round Leaved Sundew (Drosera rotundifolia) a plant indigenous to coastal Maine, has shown anti-bacterial properties and continues to be researched for its anti-cancer actions (Evans, 672).

GLYCOSIDES

Glycosides, or sugar ethers, are a complex grouping which can be broken down to yield one or more sugars (glycones), plus a non-sugar component (aglycones). It is important to note that glycosides are not a major classification of phytochemicals, as are alkaloids, carbohydrates, phenols and terpenoids. However, it is often when a phytochemical is in its glycosidic form that a constituent may have a specific therapeutic action. Neucleotide glycosides, in combination with particular compounds, create specific glycosides in plants, the distinction between which is signified by a C-, S-, N-, or O-. The letters indicate that the formation of the glycoside is dependent on interaction with Carbon, Sulphur, Nitrogen, or alcohol/phenol components, respectively (Evans, 281). Given this mutability, glycosides can occur in any of the major phytochemical classifications, because a sugar ether can bind itself to molecules in a myriad of ways. Glycosides are most commonly classified according to the chemical nature of the aglycone, and have vast medicinal applications as they are found in almost every therapeutic class.

Some phytochemical groups, such as anthraquinone phenols, normally do contain glycosides, so they are nicknamed anthraquinone glycosides. Alcohol glycosides have been used as antirheumatics and analgesics. Salicin, from Salix spp., is the glycosidic precursor to what is transformed to salicylic acid in our bodies. Salicylic acid is an anodyne: Ultimately, salicylic acid was synthesized to become today's aspirin. Glycosides are soluble in alcohol and water.

Known primarily for their laxative actions, anthraquinone glycosides were found after the aglycones (a non-sugar component) of anthraquinones had been obtained upon hydrolysis. Both glycones and aglycones of anthracene derivation are polyphenols containing the red or purple pigment found in senna, cascara, rheum, and aloe, for example.

Flavonoid glycosides are yellow pigments in flowers and plants which have demonstrated antiinflammatory, anti-allergic effects, antithrombotic and vasoprotective properties. These plant constituents exert antioxidant effects on free radicals in the body. Related to flavonoid glycosides are the anthocyanidins and anthocyanins, mentioned under the phenol heading.

Lactone glycosides, a.k.a. Coumarin glycosides are very fragrant: they are the source, for instance, of freshly-mown hay scents (ibid.). Medicinally, coumarin glycosides have been shown to have hemorrhagic, antifungicidal, and antitumor activities. The lactone glycoside dicumarol is known as an anticoagulant.

Cardiac glycosides, come from triterpenoid groups and their action on the heart is still under investigation. It is known, however, that the cardiac glycosides do exert a specific action on the myocardial muscle and allay myocardial infarction. Digitalis, from the foxglove plant, is an allopathic prescription. (Planta Medica, 1993, 539.)

Cyanogenic glycosides, which initially contain hydrogen cyanide (HCN) compounds, are toxic to unadapted farm animals and humans. However, some have been found to be of cytotoxic interest in cancer research. Originally, these glycosides were probably developed so that a plant could defend itself from herbivores. The cyanide content, referred to as a bound toxin, only occurs in some of the 1000 or so plants which initially produce cyanohydrin upon hydrolysis (Harborne and Baxter, 84). Detection of the presence of cyanide is accomplished through smell or by its yellow to brownish-red reaction with moist picrate paper. Prunasin, to illustrate, is a cyanogenic glycoside occurring in Wild Cherry Bark, a botanical which has been used since the late 1700's as a cough sedative and medicinal flavorant (Evans, 538).

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