Phototoxin

Last updated

Phototoxins are toxins that can cause allergic reactions in particularly susceptible individuals and which can cause dangerous photosensitivity in a much broader range of subjects.

A toxin is a poisonous substance produced within living cells or organisms; synthetic toxicants created by artificial processes are thus excluded. The term was first used by organic chemist Ludwig Brieger (1849–1919), derived from the word toxic.

Photosensitivity is the amount to which an object reacts upon receiving photons, especially visible light. In medicine, the term is principally used for abnormal reactions of the skin, and two types are distinguished, photoallergy and phototoxicity. The photosensitive ganglion cells in the mammalian eye are a separate class of light-detecting cells from the photoreceptor cells that function in vision.

Contents

Phototoxins are common in:

Adaptation Trait with a current functional role in the life history of an organism maintained and evolved by natural selection

In biology, adaptation has three related meanings. Firstly, it is the dynamic evolutionary process that fits organisms to their environment, enhancing their evolutionary fitness. Secondly, it is a state reached by the population during that process. Thirdly, it is a phenotypic trait or adaptive trait, with a functional role in each individual organism, that is maintained and has evolved through natural selection.

<i>Citrus</i> genus of fruit-bearing plants (source of fruit such as lemons and oranges)

Citrus is a genus of flowering trees and shrubs in the rue family, Rutaceae. Plants in the genus produce citrus fruits, including important crops such as oranges, lemons, grapefruits, pomelos, and limes.

Essential oil hydrophobic liquid containing volatile aroma compounds from plants

An essential oil is a concentrated hydrophobic liquid containing volatile chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetherolea, or simply as the oil of the plant from which they were extracted, such as oil of clove. An essential oil is "essential" in the sense that it contains the "essence of" the plant's fragrance—the characteristic fragrance of the plant from which it is derived. The term essential used here does not mean indispensable as with the terms essential amino acid or essential fatty acid which are so called since they are nutritionally required by a given living organism. In contrast to fatty oils, essential oils typically evaporate completely without leaving a stain or residue.

Ingested medications may cause systemic photosensitivity and topically applied medications, cosmetics and essential oils may lead to local (or perhaps systemic) photosensitivity. Para-aminobenzoic acid (PABA), found in some sunscreens, can also cause photosensitivity.

4-Aminobenzoic acid (also known as para-aminobenzoic acid or PABA because the number 4 carbon in the benzene ring is also known as the para position) is an organic compound with the formula H2NC6H4CO2H. PABA is a white solid, although commercial samples can appear gray. It is slightly soluble in water. It consists of a benzene ring substituted with amino and carboxyl groups. The compound occurs naturally.

Upon exposure to light, notably light containing ultraviolet radiation, discolouration of the skin (whether as inflammation, lightening or darkening) or rashes may result. In extreme cases, blistering may also occur.

Ultraviolet Electromagnetic radiation with a wavelength shorter than that of visible light, but longer than X-rays

Ultraviolet (UV) designates a band of the electromagnetic spectrum with wavelength from 10 nm to 400 nm, shorter than that of visible light but longer than X-rays. UV radiation is present in sunlight, and contributes about 10% of the total light output of the Sun. It is also produced by electric arcs and specialized lights, such as mercury-vapor lamps, tanning lamps, and black lights. Although long-wavelength ultraviolet is not considered an ionizing radiation because its photons lack the energy to ionize atoms, it can cause chemical reactions and causes many substances to glow or fluoresce. Consequently, the chemical and biological effects of UV are greater than simple heating effects, and many practical applications of UV radiation derive from its interactions with organic molecules.

Uses

The marigold plant produces the phototoxin alpha-terthienyl, which functions as a nematicide. When exposed to near ultraviolet light, such as in sunlight, alpha-terthienyl generates the toxic singlet oxygen. [3] Alpha-terthienyl results in damage to the respiratory, digestive and nervous system of larvae, resulting in 100% death rates in concentrations of 33 ppb. [4] This makes it an interesting natural insecticide.

A nematicide is a type of chemical pesticide used to kill plant-parasitic nematodes. Nematicides have tended to be broad-spectrum toxicants possessing high volatility or other properties promoting migration through the soil. Aldicarb (Temik), a carbamate insecticide marketed by Bayer CropScience, is an example of a commonly used commercial nematicide. It is important in potato production, where it has been used for control of soil-borne nematodes. Aldicarb is a cholinesterase inhibitor, which prevents the breakdown of acetylcholine in the synapse. In case of severe poisoning, the victim dies of respiratory failure. It is no longer authorised for use in the EU and, in August 2010, Bayer CropScience announced that it planned to discontinue aldicarb by 2014. Human health safety and environmental concerns have resulted in the widespread deregistration of several other agronomically important nematicides. Prior to 1985, the persistent halocarbon DBCP was a widely used nematicide and soil fumigant. However, it was banned from use after being linked to sterility among male workers; the Dow Chemical company was subsequently found liable for more than $600 million in damages.

Singlet oxygen, systematically named dioxygen(singlet) and dioxidene, is a gaseous inorganic chemical with the formula O=O, which is in a quantum state where all electrons are spin paired. It is kinetically unstable at ambient temperature, however the rate of decay is slow.

Rose bengal and other singlet oxygen generating phototoxins are also used in synthetic organic chemistry. They have also found use in photodynamic therapy, where the toxin is activated by intense light to destroy cancer cells.

Related Research Articles

Bay leaf aromatic leaf of Laurus nobilis

The Bay leaf is an aromatic leaf commonly used in cooking. It can be used whole, or as dried and ground.

Luminescence emission of light by a substance not resulting from heat

Luminescence is spontaneous emission of light by a substance not resulting from heat; it is thus a form of cold-body radiation. It can be caused by chemical reactions, electrical energy, subatomic motions or stress on a crystal. This distinguishes luminescence from incandescence, which is light emitted by a substance as a result of heating. Historically, radioactivity was thought of as a form of "radio-luminescence", although it is today considered to be separate since it involves more than electromagnetic radiation.

Insecticide pesticide used against insects

Insecticides are substances used to kill insects. They include ovicides and larvicides used against insect eggs and larvae, respectively. Insecticides are used in agriculture, medicine, industry and by consumers. Insecticides are claimed to be a major factor behind the increase in the 20th-century's agricultural productivity. Nearly all insecticides have the potential to significantly alter ecosystems; many are toxic to humans and/or animals; some become concentrated as they spread along the food chain.

Photochemistry sub-discipline of chemistry

Photochemistry is the branch of chemistry concerned with the chemical effects of light. Generally, this term is used to describe a chemical reaction caused by absorption of ultraviolet, visible light (400–750 nm) or infrared radiation (750–2500 nm).

Photodynamic therapy (PDT), is a form of phototherapy involving light and a photosensitizing chemical substance, used in conjunction with molecular oxygen to elicit cell death (phototoxicity). PDT has proven ability to kill microbial cells, including bacteria, fungi and viruses. PDT is popularly used in treating acne. It is used clinically to treat a wide range of medical conditions, including wet age-related macular degeneration, psoriasis, atherosclerosis and has shown some efficacy in anti-viral treatments, including herpes. It also treats malignant cancers including head and neck, lung, bladder and particular skin. The technology has also been tested for treatment of prostate cancer, both in a dog model and in human prostate cancer patients.

Photodermatitis Human disease

Photodermatitis, sometimes referred to as sun poisoning or photoallergy, is a form of allergic contact dermatitis in which the allergen must be activated by light to sensitize the allergic response, and to cause a rash or other systemic effects on subsequent exposure. The second and subsequent exposures produce photoallergic skin conditions which are often eczematous. It is distinct from sunburn.

Light sensitivity or photosensitivity refers to a notable or increased reactivity to light. Apart from vision, human beings have many physiological and psychological responses to light. In rare individuals an atypical response may result in serious discomfort, disease, or injury. Some drugs have a photosensitizing effect. Properties of natural or artificial light that may abnormally affect people include:

Phototoxicity

Phototoxicity, also called photoirritation, is a chemically induced skin irritation, requiring light, that does not involve the immune system. It is a type of photosensitivity.

Photosensitizer Drugs that are pharmacologically inactive but when exposed to ultraviolet radiation or sunlight are converted to their active metabolite to produce a beneficial reaction affecting the diseased tissue. These compounds can be administered topically or

A photosensitizer is a molecule that produces a chemical change in another molecule in a photochemical process. Photosensitizers are commonly used in polymer chemistry in reactions such as photopolymerization, photocrosslinking, and photodegradation. Photosensitizers are also used to generate triplet excited states in organic molecules with uses in photocatalysis, photon upconversion and photodynamic therapy. Photosensitizers generally act by absorbing ultraviolet or visible region of electromagnetic radiation and transferring it to adjacent molecules. Photosensitizers usually have large de-localized π systems, which lower the energy of HOMO orbitals and its absorption of light might be able to ionize the molecule. There are also examples of using semiconductor quantum dots as photosensitizers.

Eucalyptol chemical compound

Eucalyptol is a natural organic compound that is a colorless liquid. It is a cyclic ether and a monoterpenoid.

Allergic contact dermatitis medical condition

Allergic contact dermatitis (ACD) is a form of contact dermatitis that is the manifestation of an allergic response caused by contact with a substance; the other type being irritant contact dermatitis (ICD).

<i>Calendula officinalis</i> species of plant

Calendula officinalis, the pot marigold, ruddles, common marigold or Scotch marigold, is a plant in the genus Calendula of the family Asteraceae. It is probably native to southern Europe, though its long history of cultivation makes its precise origin unknown, and it may possibly be of garden origin. It is also widely naturalised farther north in Europe and elsewhere in warm temperate regions of the world.

Photoinhibition

Photoinhibition is light-induced reduction in the photosynthetic capacity of a plant, alga, or cyanobacterium. Photosystem II (PSII) is more sensitive to light than the rest of the photosynthetic machinery, and most researchers define the term as light-induced damage to PSII. In living organisms, photoinhibited PSII centres are continuously repaired via degradation and synthesis of the D1 protein of the photosynthetic reaction center of PSII. Photoinhibition is also used in a wider sense, as dynamic photoinhibition, to describe all reactions that decrease the efficiency of photosynthesis when plants are exposed to light.

The aging of natural and artificial polymeric materials is a natural phenomenon in metals, glass, minerals and other inorganic materials. The main environmental parameters influencing the degradation of polymeric materials is daylight combined with the effects of temperature, moisture and oxygen. These act as the main parameters of stress for outdoor weathering.

Photoaging or photoageing is a term used for the characteristic changes to skin induced by chronic UVA and UVB exposure. Tretinoin is the best studied retinoid in the treatment of photoaging

Clostridium novyi (oedematiens) a Gram-positive, endospore- forming, obligate anaerobic bacteria of the class clostridia. It is ubiquitous, being found in the soil and faeces. It is pathogenic, causing a wide variety of diseases in man and animals. It comes in three types, labelled A, B, and a non-pathogenic type C distinguished by the range of toxins they produce. Some authors include Clostridium haemolyticum as Clostridium novyi type D. C novyi is closely related to Clostridium botulinum types C and D as Yoshimasa Sasaki et al. have demonstrated by 16S rDNA sequence analysis.

Bergamot essential oil cold-pressed essential oil

Bergamot essential oil is a cold-pressed essential oil produced by cells inside the rind of a bergamot orange fruit. It is a common flavoring and top note in perfumes. The scent of bergamot essential oil is similar to a sweet light orange peel oil with a floral note.

References

  1. http://journaltimes.com/lifestyles/food-and-cooking/the-root-of-it-all-plants-to-avoid/article_89b6ef96-ec30-11e3-a868-001a4bcf887a.html
  2. http://zimbabweflora.co.zw/speciesdata/note-display.php?note_id=2
  3. J. Bakker, F. J. Gommers, I. Nieuwenhuis and H. Wynberg. Photoactivation of the nematicidal compound alpha-terthienyl from roots of marigolds (Tagetes species). A possible singlet oxygen role. JBC, Vol. 254, Issue 6, 1841-1844, Mar, 1979. http://www.jbc.org/cgi/content/abstract/254/6/1841
  4. Manish Nivsarkar, Bapu Cherian and Harish Padh. Alpha-terthienyl: A plant-derived new generation insecticide. Current Science, Vol. 81, No. 6, 25 September 2001. http://www.ias.ac.in/currsci/sep252001/667.pdf

See also