Natural substances

(This is the last subchapter and the last section of this chemistry course “Free Level”)

Among the natural substances mainly there are: Terpenes, Steroids, Vitamins and Alkaloids

Terpenes

Terpenes are certain hydrocarbons with branched methyl groups, from which special alcohols, ethers, aldehydes and ketones are derived and mostly occur in flowers and fruits. In the chapter organic chemistry some examples have already been mentioned. Many terpenes are among the fragrances. Also mucolytic cough chewable tablets belong to the terpenes, example Mentol. In the paint industry, turpentine is used as a cleaning agent.

Steroids

Most steroids are hormones and are circulated by glands. Steroids act as catalysts (biocatalysts = enzymes) to trigger certain reactions in the organism. The basic structure of steroids consists of three six-membered rings and a five-membered ring. Steroids differ by positions of alkyl, OH and keto groups. Important steroids:

• Testosterone, is the most important male sex hormone.
• progesterone and estradiol, are the most essential female sex hormones.
• Costisol and corticosterone are hormones of the adrenal cortices. These two steroids degrade glycose in the liver from glycogen.
• Cholesterol serves as a messenger of the cell membrane and is present in the tissue in addition to the brain and spinal cord. 95% of this steroid is in cells. Excess quantities in gallstones occur as degradation substance. Since about 90% of the body’s own cholesterol is produced, there is a risk that too much of it is ingested via animal foods, which can lead to cardiovascular diseases such as arteriosclerosis, as this hormone settles on the walls of the atrium. Since cholesterol, a polycyclic alcohol, has only been produced with oxygen since the beginning of existence and, according to research, only thanks to oxygen, there is no cholesterol in plants, mushrooms and bacteria.

Vitamins

Vitamins are co-enzymes and take on catalytic functions in the human and animal organism. Most vitamins have to be ingested regularly by humans and animals. A and L-vitamins are terpenes. D-vitamins (linoleic acids) whose overdoses can be deadly! are steroids.  

Vitamin C

Vitamin C (L-ascorbic acid, to remember: L = leftfurning) Is a chiral compound found throughout the plant and animal kingdoms. According to Linus Pauling, a mountain goat synthesizes 12-14 g of vitamin C per day and is produced in the liver by a 4-step synthesis:

D-glucose →  D-glucuronic acid → D-glucuronic acid-γ-lactone → L-glutonic acid-γ-lactone → L-ascorbic acid = vitamin C.

The enzyme required for the last reaction stage, L-gulonolactone oxidase, is absent in humans, some monkeys, guinea pigs and birds. This is probably due to a defective gene that was said to have occurred in a mutation about 60 million years ago. Thus, the human must take vitamin C from outside. Vitamin C is extremely unstable, especially the oxygen ring is easily destroyed by light and heat.  Since vitamin C is water-soluble, and thus has a dipole, this substance is rapidly degraded. That’s why you can barely take enough.

The recommended daily minimum dose is 60mg according to Michel Bontemps, Reuille Publishing. Smokers should take as large amounts of vitamin C as possible, a cigarette destroys about 25 mg of vitamin C! As already mentioned, thanks to its oxygen ring, vitamin C can protect the body against bacterial and viral infections. (Cold, flu). Its anti-inflammatory properties and active involvement in collagen construction help wound healing. In addition, vitamin C along with other antioxidants such as selenium and vitamin E may delay the aging process.

Natural vitamin C suppliers are fresh fruits, namely black currant, lemons, oranges, grapefruit, kiwi, rosehip and fresh vegetables such as Brussels sprouts, broccoli, parsley, peppers and potatoes.

Deficiency symptoms of vitamin C are scurvy. Today, this disease rarely occurs. However, vitamin C deficiency is manifested by fatigue, malaise, headache, bone pain and increased susceptibility to infection.

Vitamin A

Vitamin A (The structural formula can be found under the subchapter hydrocarbons in the chapter Organic Chemistry) Vitamin A is a biological degradation product of the dye beta-carotene, among others it is included in vegetables, especially in carrots. Vitamin A is also called retinol, must be taken from the outside and is responsible for the visual process. Lack of vitamin A can lead to night blindness. In the living organism the following mechanisms take place, very simplified:

 Vitamin A, retinol → trans-retinal → cis-retinal → rhodopsin.

The first isomerization to the trans retinal occurs with the enzyme, retinol dehydrogenase. The second step to cis retinal is by using the enzyme retinol isomerase. In the last step, a protein comes into play, the opsin, (molar mass about 38,000). The final reaction step leads to imine, rhodopsin. If a photon hits rhodopsin, the trans retinal is returned. In this process in picoseconds a nerve signal! is created that is perceived as light. The trans-retinal again produces cis-retinal and rhodopsin and the same process will be repeated continously.

The daily dose of vitamin A is 0.2 mg to 0.5 mg according to Michel Bontemps, Reuille Publishing. This dose can be taken up to sixfold.  However according to Michel Bontemps, health guide for the family, Reuille Verlag, Nyon, the 6-fold dose should not be exceeded, otherwise vitamin A will be toxic. Overdoses of vitamin A can cause nausea, hair loss, headaches and blurred vision. Pregnant and kidney patients are also advised not to consume vitamin A in high doses. In addition to carrots and cabbage, vitamin A suppliers are mainly halibut liver oil 1500 mg per 100 g food and cod liver oil of 22 mg per 100 g food. Furthermore, pork or beef liver, summer butter, cheese, eggs, kidneys, herring and cow’s milk also contain vitamin A.

 

The Vitamins of the B-group:

All B vitamins are water soluble.

Natural sources of all B vitamins are brewer’s yeast, liver and unpeeled cereals. Beware of vegetarians taking vitamin B 12, cobalamin! According to Michel Bontemps, plant-based foods contain no vitamin B12 and the daily requirement can not be met with a vegetarian diet. However, in the first script “Long Lifes” by Prof. Dr. Robert Toquet, Reuille Pulishing, Versoix, Switzerland, it is written that vitamin B12 is abundant in brewer’s yeast. Smaller amounts of it are also present in cow’s milk and cheese.

 

Vitamin B1, Thiamine

Thiamine, an organic salt, consists of a pyridine ring and a thiazole ring.

Like vitamin C, thiamine is water-soluble and must be given daily as it is not stored in the body. By drinking coffee and alcohol and taking birth control pills, vitamin B1 can be destroyed according to Michel Bontemps, Reuille Verlag. Therefore, the need for vitamin B1 is increased in these circumstances. This also applies to smoking and over-consumption of sweets.
Deficiency can cause indigestion, fatigue and depression.
Vitamin B1 supports the nervous system and strengthens the vessels of the circulation. Thiamine is found mainly in yeast, wheat germ and unpeeled cereals. According to Michel Bontemps, the daily requirement for adults is 1.5 mg children 0.5 mg to 1 mg.

Vitamin B2, Riboflavin (Picture below)

A ribose-unit is bound onto the heterocyclic 3-ring. To the heterocyclic three-ring, a benzene-labeled pteridine (with o-xylene) is a monosaccharide bound to the ribose.

Riboflavin is found in plant and animal tissues, is involved as a coenzyme in cellular respiration and acts on carbohydrate-, protein and fat metabolism. According to Michel Bontemps, vitamin B2 is important for eyesight and the skin and is thought to have a healing effect on dental disease. Recommended daily dose according to Michel Bontemps is 1.6 mg, pregnant and nursing women 2 – 10 mg. Since riboflavin is water-soluble, no signs of intoxication are known.

Vitamin B3 (picture below)

PP means “pellagra prevention” due to the disease pellagra. Vitamin B3 can be made from the essential amino acid tryptophan, Trp, in the body itself. According to Michel Bontemps, the daily requirement is 15 mg to 20 mg children 6 mg to 8 mg. Overdoses of 100 mg or more can cause symptoms of intoxication: itching, burning skin and nausea.

Vitamin B5, pantothenic acid (picture below)

Vitamin B5 is a metabolism vitamin. It turns fats and carbohydrates into energy, aids in the formation of adrenal hormones, and relieves stress and tiredness. Because this vitamin is involved in building up the antibodies, it also promotes the immune system. According to Michel Bontemps, the daily dose is 10 mg, up to 100 mg can be taken safely. Vitamin B5 is quite common in nature, except in royal jelly, e.g. in honey, milk, eggs, poultry, beef and spinach.

Vitamin B6, Pyridoxine (picture below)

Vitamin B6 is one of the heterocycles, it is an aromatic or a pyridine, which is water-soluble and quite heat-resistant, but sensitive to light and oxygen.

According to Michel Bontemps, vitamin B6 is essential for people who often consume meat. Pyridoxine is produced in certain amounts in the intestine by intestinal bacteria and supports the absorption of magnesium, Mg, and the conversion of the essential amino acid tryptophan, Trp, into vitamin B3, niacin. According to Michel Bontemps, this vitamin is very valuable for women, as it relieves menstrual problems, nausea during pregnancy and unpleasant side effects of birth control pills. According to Michel Bontemps, 2 mg of vitamin B6 are enough per day. In case of pregnancy and excessive consumption of meat, the dose per day can safely be 250 mg to 500 mg. In nature, vitamin B6 is abundant in yeast, egg yolks, liver, kidneys and fresh fruits.

Vitamin B7, Biotin (picture below)

Biotin plays an essential role in the protein, fat and carbohydrate metabolism. Therefore, biotin acts according to Prof. Dr. Robert Toquet against hair loss and according to Michel Bontemps against acne, eczema and other skin diseases. In addition to the brewer’s yeast, natural sources include egg yolk, dried peas, black chocolate, egg yolks, spinach and peanuts.
The daily dose amounts to 100 μg to 300 μg according to M. Bontemps.

 

Vitamin B9, Folic acid (Picture below)

The double ring on the left is a pteridine, a 1,3,5,8-tetraazanaphthalene. Attached to it in the middle there is a para-aminobenzenecarboxylic acid part. On the right there is the glutamic acid part (S-2-aminopentanoic acid)

Folic acid has a derivative structurally similar to it. Methotrexate, it is an important drug in the chemotherapy of cancer, which acts as an inhibitor in cell division processes.
According to Michel Bontemps, folic acid protects against intestinal parasites and symptoms of intoxication and delays the formation of white hair together with vitamin B5, pantothenic acid. Together with vitamin B12, folic acid acts against anemia. Michel Bontemps recommends folic acid especially pregnant women.
Recommended daily dose according to Michel Bontemps is 400 microgram. Deficiency symptoms are intestinal complaints and anemia.

Vitamin B10 (picture below)

Vitamin 10 absorbes in the UV spectrum at 289 nm = λmax and has an extinction coefficient of 18600. With this property, this vitamin can also be used as a sunscreen lotion. According to Prof. R. Tocquet, vitamin 10 is indispensable for the proper functioning of the glands.

Vitamin B11, carnitine

L-carnitine, a hermaphrodite ion, is levorotatory (left turning) and arises from the two essential amino acids, lysine, lys, and methionine, Met in the living organism.

Carnitine transports fatty acids to the cell organelles or to the mitochondria and is responsible for the energy metabolism. According to WIKIPEDIA, the human body absorbs carnitine from the amino acids lysine and methionine mainly via meat and is also used as a fat burner. Since the two amino acids Lys and Met must be taken from the outside, L-carnitine is also commercially available (drugstore, wholesalers). In the industrial process, carnitine is produced by biosynthesis using special bacteria (rhizobia).

Vitamin B12, cobalamin, a metalorganic complex compound with cobalt as the central atom. (Picture below)

Vitamin B15, Pangamic (picture below)

Vitamin B15 – more common name: Pangaminic acid or pangamic acid, an ester of dimethylglycine and gluconic acid – is an intermediate in the body’s synthesis of the amino acid, glycine.
Choline → betaine → pangamic acid → sarcosine → glycine.

An interesting vitamin for athletes who feel tired during the day. According to Michel Bontemps, this vitamin provides oxygen to the tissues by helping the body to break down and optimally utilize high-energy glycogen. In addition, vitamin B15 protects against environmental toxins.

Vitamin B15 was discovered in apricot kernels. Pangamic acid is also found in rice bran, (or unpolished rice), pumpkin seeds, sesame seeds and chickpeas according to WIKIPEDIA.
In the USA, a daily dose of 50 μg has been set for several years. However, since the body itself produces pangamic acid or vitamin B15, athletes are advised to visit a doctor if symptoms of tiredness appear.

 

Vitamins, D, E, F and K are liposoluble

 

Vitamin D, Calcipherol, (picture below)

 

Vitamin D, calciferol is got by photolysis of ergosterol. a steroid (h * ν, h = planck effect quantum, ν = frequency,1 / s) of ergosterol, a steroid.

Provitamin D is produced first and then by H-shift vitamin D is built up. In winter, where not only the days are shorter but also foggy and cloudy, causing the absence of daylight, significant vitamin D deficiency can occur. Deficiency symptoms include rickets and arthritis. However, according to Prof. Dr. med. Robert Toquet, Long Lifes, Reuille Publishing, Versoix, Vitamin D taken in excess even lead to death! So take care especially with this vitamin.  According to Michel Bontemps, the daily dose is 400 IU (1 IU = 0.025 micrograms). Vitamin capsules contain less than 100 IU of vitamin D per capsule. The risk of overdose is thus somewhat counteracted.

 

 Vitamin E (picture below)

Vitamin E is preferentially stored in the liver by a transport protein (TTP). Larger amounts also occur in the fatty tissue, in the adrenal gland, the uterus, the testes and in the pituitary gland. Main function of vitamin E is the protection of tissues and cells from oxidation or destruction by oxygen. According to Michel Bontemps, this vitamin is supposed to slow down the aging process and even prevent tumor disease. The daily dose recommended by Michel Bontemps for adults is 30 IU to 200 IU. (1 IU = 0.025 microgram)

 

Vitamin F, essential unsaturated (double-bond) fatty acids: Examples: linoleic acid, gamma-linoleic acid, linolenic acid, arachidonic acid, eicosapentaenoic acid.

With vitamin F, the tissue hormones (prostaglandins) that are important for the organism are formed. These hormones work to build up the cell walls and muscles and prevent cardiovascular disease. Vitamin F also prevents cholesterol deposits in the blood vessels.
The different oils of vitamin F are mainly found in vegetable oils pressed in first from sunflower seeds and wheat germ, as well as soybeans and peanuts. Linoleic acid is found mainly in nuts and avocado, gamma linoleic acid in evening primrose and cucumber oil and linolenic acid in fish oils. Symptoms of vitamin F deficiency include fragile fingernails. With increased consumption of animal fat you should take more vitamin F according to Michel Bontemps.

Vitamin K (picture below), coagulum vitamin, fat soluble derivatives of naphthoquinone: vitamin K1 = phylloquinone, Vitamin K2 = menaquinone, Vitamin K3 = menadione

Vitamin K helps to build up prothrombin in the blood and thus promotes blood clotting. Vitamin K is therefore given before surgery and childbirth. In addition, vitamin K is good for the bones, it activates the bone protein, osteocalcin.
Vitamin K1 is mainly found in green leafy vegetables and is responsible for its photosynthesis. A good vitamin K supplier is also fishmeal.
Because vitamin K has blood clotting activity, causing blood clots and clogging of the blood vessels, it is not permitted for high blood pressure and for diseases that require blood thinning.
Otherwise, according to Michel Bontemps, a daily dose of 1 mg (milligrams) is recommended for normal health.

 

Alkaloids

Alkaloids are heterocyclic salts of organic acids and occur in certain plants. Because of the nitrogen, they are bases. Already taken in small amounts, alkaloids can cause physiological symptoms such as feelings of well-being, intoxication or even hallucinations and are used as a stimulant and intoxicant. Some are incorporated as mental remedies in appropriate drugs (psychotropic drugs). Moderate permitted alkaloids include caffeine and nicotine, the narcotic drugs such as cocaine, morphine and heroin are prohibited. Heroin is the ester of morphine. Morphine may only be used medically. The most common intoxicant is cannabis (tetrahydrocannabinol, THC from the hemp plant). THC is not an alkaloid, it does not contain nitrogen.

Deadly alkaloids are strychnine and brucine. The lethal dose is about 5 – 10 mg / kg in animals.

 

Lecithine

Lecithin is a hermaphrodite ion, a so-called phosphatide. It consists of 3 ester groups: 2 carboxylic acid esters (2 tail groups) and an ester of phosphoric acid as anion and a tertiary amine as cation (head group). (The head group is a hermaphrodite ion, consisting of the phosphoric acid as an anion and the tertiary amine as a cation.) Lecithin is a phospholipid. Lipids are among the waxes and fats, they are not water soluble. However, since lecithin consists of a polar phosphoric acid ester with a tertiary amino group (head group) and 2 nonpolar carboxylic acid esters (2 tail groups), micelle formation occurs in aqueous solution. The head groups are solvated with water, the 2 carboxylic acid esters are inside the micelle.

Lecithin occurs in the cell membrane of plants and animals. Almost all cells consist of a double-layered membrane. For most bacteria you will not find any lecithin. Lecithin is used primarily for lipid metabolism. Lecithin is mainly derived from soybeans.

 

Literature

• K. Peter C. Vollhart, Organic Chemistry, VCH Publishing Company, D-6940 Weinheim (BRD) 1988, 1990
• Charles E. Mortimer, The basic knowledge of chemistry, Georg Thieme Publishing Company, Stuttgart . New York 1987, 5th Edition
• James E. Huheey, Inorganic chemistry, Harper & Row, Publishers, Inc. New York, N.Y. 10022 USA, 3rd Edition 1988
• Michel Bontemps, The health guide for the Family, Reuille Publishing Company, Grand-Montfleury 6, CH-1290 Versoix GE,  1995 German Edition
• Prof. Dr. Robert Tocquet, Long Lifes, Reuille Publishing Company, Grand Montfleury 6, CH-1290 Versoix GE, 1988 German Edition

 

 

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