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Diindolyl methane glucosinolates

A whole range of cabbage varieties, especially flower, rose, red, green and white cabbage as well as broccoli, but also other types of cabbage and mustard oils contain plant substances that are very beneficial to health and are not found in other vegetables, or only rarely. These are the glucosinolates, a group of pungent sulphur-containing components that used to be known as vitamin U, among other things. They help plants to defend themselves against microorganisms, e.g. bacteria and molds, and thus protect them from diseases.

Glucosinolates - also healthy for humans

If the plant cells are divided, cut up or chopped during the production of cabbage meals, a decomposing process occurs with the help of the enzyme myrosinase (ß-thioglucosidase). This produces various decomposition products which the body utilizes further. Heating food reduces the amount of these products, while shredding cabbage plants increases them. It is therefore very healthy to eat cabbage raw.

The breakdown products of glucosinolates include isothiocyanates with a special form, sulforaphane, which has interesting health properties. Indoles are also among the breakdown products of glucosinolates. They are found in some types of cabbage and are a group of plant growth hormones. A special form is indole-3-carbinol, often abbreviated as I3C. Diindolylmethane, abbreviated DIM, can in turn be formed from this. Both have very interesting and health-promoting properties.

Glucosinolates and indoles - mainly found in cabbage varieties

Glucosinolates are found in many types of cabbage and are also present in some edible oils. If the plant tissue is destroyed during food preparation and/or consumption, the enzyme thioglucosidase is released. This hydrolyzes the glucosinolates, from which various degradation products can be formed. These include isothiocyanates and indoles.

Glucosinolates: cauliflower, broccoli, watercress, red, green and white cabbage, Brussels sprouts, horseradish, radishes, mustard oil, rapeseed oil Isothiocyanates: cabbage varieties, but also in soybeans and peanuts Sulforaphane: largest amounts in broccoli sprouts, but also in broccoli and cauliflower, red, green and white cabbage etc. Indoles: cauliflower, broccoli, red, green and white cabbage, Brussels sprouts, etc. I3C: cauliflower, broccoli, red, green and white cabbage, Brussels sprouts

Glucosinolates - the health effects

Glucosinolates have antioxidant properties and can help to inhibit the development of some types of cancer. They can eliminate harmful aflatoxin. This is a toxic substance (mycotoxin) produced by fungi, which can form when peanuts or potatoes are stored poorly, for example. Isothiocyanates, which belong to the degradation products of glucosinolates, contribute to the prevention of some types of cancer with their antioxidant properties. They can render carcinogens harmless and inhibit enzymes that contribute to the development of oesophageal cancer.

Sulforaphane

Sulforaphane is a special type of isothiocyanate that can help inhibit the development of cancer cells. Sulforaphane can promote enzymes that can block carcinogens. It also increases the activity of quinone reductase, an important enzyme in detoxification processes in the body.

Indoles

Indoles have antioxidant effects and support the immune system. They help to prevent various forms of cancer, including breast cancer. Indoles activate protective enzymes that can deactivate excessive oestrogen, which is involved in the development of breast cancer.

Indole-3-carbinol (I3C)

Among the indoles, I3C is particularly interesting because of its special properties. It can relieve some symptoms of chronic fatigue syndrome and fibromyalgia. I3C also stimulates the endogenous production of glutathione by liver cells (hepatocytes). It can render a number of toxic substances harmless, including dioxin, aflatoxin and heterocyclic aromatic amines, which can contribute to cancer and damage DNA. I3C can also prevent the formation of cancer with these functions. I3C also combines with vitamin C to form ascorbigen, another indole.

Diindolylmethane (DIM)

In the stomach, indole-3-carbinol is metabolized to DIM, which consists of two linked molecules of I3C. DIM is thought to be 10 times more potent per milligram than indole-3-carbinol. DIM can inhibit the metabolism of toxic aflatoxins. It also inhibits the conversion of estrone into its carcinogenic metabolites (16-hydroxyestrone). It ensures that estrone is converted into its safe metabolites (2-hydroxyestrone). In this way, DIM inhibits the development of some types of cancer, including breast, colon and prostate cancer.

Glucosinolates - generally safe to ingest

Glucosinolates and indoles are generally safe to use. However, excessive consumption of isothiocyanates can lead to gout or hypothyroidism, as it can inhibit the utilization of iodine and thus reduce the function of the thyroid gland. Pregnant women should not use I3C because of its effects on estrogen.

Diindolylmethane discovered as an active ingredient

Researchers at the University of Berkeley have discovered a positive effect against prostate cancer in broccoli. This is due to a substance formed during the digestion of this vegetable that blocks the growth of cancer cells.

The same effect occurs with other cruciferous vegetables of the genus Brassica genus such as cabbage, cauliflower and cabbage sprouts. These vegetables are rich in indole-3-carbinol, which is converted into 3,3-diindolylmethane (DIM) during digestion, write the researchers, led by nutritionist and toxicologist Leonard Bjeldanes, in the online edition of the Journal of Biological Chemistry. DIM acts as an anti-androgen. Androgen is important for the normal development and function of the prostate, but also plays a central role in the early prostate cancer phase. Normally, the cancer is treated with anti-androgenic drugs during this phase. In most cases of prostate cancer, the cancer cells are resistant to androgen and grow independently of the hormone in the later phase of the disease. In the current study, the team carried out comparative tests between DIM and androgen-dependent prostate cancer cells. It turned out that the cancer cells treated with DIM showed 70 percent less growth. At the same time, the levels of prostate-specific antigen (PSA) fell. PSA is a growth factor in prostate cancer.

Glucosinolates - as a dietary supplement

Glucosinolates, especially sulforaphane, and indoles are used in some multi-nutrient preparations. Indoles are mainly used as food supplements or for preventive and therapeutic purposes. Daily doses range from 100 to 300 mg per day. I3C and DIM are also offered as monopreparations or in special combinations. I3C is usually dosed at 400 to 800 mg daily; more specific doses in therapy depend on body weight. DIM is usually used in doses of 100 to 400 mg daily.

Safety and side effects

Diindolylmethane and sulforaphane are safe and harmless when consumed in the amounts that occur naturally in food. It is not known if supplements containing larger amounts are safe and harmless.

Precautions and warnings

Pregnancy and lactation: Diindolylmethane and sulforaphane are safe and harmless during pregnancy and lactation at normal dietary levels. It is not known whether larger amounts are safe for pregnant and breastfeeding women.

Hormone-sensitive conditions such as breast cancer, uterine cancer, ovarian cancer and endometriosis: There is evidence that diindolylmethane may act like estrogen, so there are concerns that it may exacerbate hormone-sensitive conditions. These conditions include breast, uterine and ovarian cancer and endometriosis. However, recent research also suggests that diindolylmethane may counteract the effects of estrogen and possibly protect against hormone-dependent cancers. Until more is known, it is best to err on the side of caution and not use diindolylmethane if you have a hormone-sensitive condition.

Interactions

Care should be taken when combining sulforaphane with the following medications:

Medications that are broken down by the liver (cytochrome P450 1A2 (CYP1A2) substrates).

Some drugs are broken down by the liver. Sulforaphane can reduce the rate at which the liver breaks down certain drugs. Taking sulforaphane in combination with drugs that are broken down by the liver can increase the effects and side effects of some drugs. For this reason, you should consult your doctor before taking sulforaphane if you are taking medication that is broken down by the liver.

Care should be taken when combining diindolylmethane with the following medications:

Drugs that are broken down by the liver (cytochrome P450 1A2 (CYP1A2) substrates).

Some drugs are broken down by the liver. Diindolylmethane may accelerate the rate at which the liver breaks down certain drugs. Taking diindolylmethane in combination with drugs that are broken down by the liver may reduce the effects of some drugs. For this reason, you should consult your doctor before taking diindolylmethane if you are taking medications that are broken down by the liver.

References

  1. Chang, Y.-C., Riby, J., Chang, G.H.-F., Peng, B., Firestone, G., Bjeldanes, L.F. Cytostatic and antiestrogenic effects of 2-(indol-3-ylmethyl)-3,3'- diindolylmethane, a major in vivoproduct of dietary indole-3-carbinol - Detection in vivo and enzyme induction in vitro. BIOCHEMICAL PHARMACOLOGY; ISSN: 0006-2952 (1999); VOL 58; NUMBER 5; 825-834
  2. Leibelt, Dustin A. (2004) Chronic exposure of rodents to indole-3-carbinol and 3,3'-diindolylmethane: Implications for drug metabolism, chemoprevention and human health. OREGON STATE UNIVERSITY
  3. Xue, Ling (2004), Immunomodulatory effects and molecular mechanisms of the dietary component, 3,3'-diindolylmethane in vivo and in cell culture. UNIVERSITY OF CALIFORNIA, BERKELEY