Parietin

Last updated
Parietin
Parietin.svg
Parietin molecule ball.png
Names
Preferred IUPAC name
1,8-Dihydroxy-3-methoxy-6-methylanthracene-9,10 dione
Other names
Physcion(e), rheochrysidin, methoxyemodin
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.007.561 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3 X mark.svgN
    Key: FFWOKTFYGVYKIR-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C16H12O5/c1-7-3-9-13(11(17)4-7)16(20)14-10(15(9)19)5-8(21-2)6-12(14)18/h3-6,17-18H,1-2H3
    Key: FFWOKTFYGVYKIR-UHFFFAOYAX
  • Oc1cc(OC)cc(C2=O)c1C(=O)c3c2cc(C)cc3O
Properties
C16H12O5
Molar mass 284.26348 g/mol
AppearanceOrange/yellow
Related compounds
Related compounds
Emodin
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Parietin is the predominant cortical pigment of lichens in the genus Caloplaca , a secondary product of the lichen Xanthoria parietina , and a pigment found in the roots of curled dock (Rumex crispus). It has an orange-yellow color and absorbs blue light.

It is also known as physcion.

It has also been shown to protect lichens against UV-B light, at high altitudes in alpine regions. The UV-B light stimulates production of parietin and the parietin protects the lichens from damage. Lichens in arctic regions such as Svalbard retain this capability though they do not encounter damaging levels of UV-B, a capability that could help protect the lichens in case of ozone layer thinning. [1] [2] [3]

It has also shown anti-fungal activity against barley powdery mildew and cucumber powdery mildew, more efficiently in the latter case than treatments with fenarimol and polyoxin B. [4]

It reacts with KOH to form a deep, reddish-magenta compound.

Effect on human cancer cells

Also found in rhubarb, [5] the orange compound appears to have potential to suppress 6-phosphogluconate dehydrogenase, or 6PGD. 6PGD is the third enzyme of the pentose phosphate pathway, or PPP, an oxidative process fueling growth in a still-relatively-unknown way. But it appears that arresting the chemical machinery at its third step could be promising for oncology. The parietin, identified from an FDA database of 2,000 known suppressors of 6PGD, killed half the human leukemia cells over two days in the laboratory. The pigment also slowed the growth of other human cancer cells in mouse models, according to the study. A more-potent derivative of the parietin called S3 may even cut the growth of lung cancer cells implanted in mice by two-thirds, over the course of 11 days. The compound also appears to be non-toxic to healthy cells. [6] [7]

Related Research Articles

<span class="mw-page-title-main">Powdery mildew</span> Fungal plant disease

Powdery mildew is a fungal disease that affects a wide range of plants. Powdery mildew diseases are caused by many different species of ascomycete fungi in the order Erysiphales. Powdery mildew is one of the easier plant diseases to identify, as its symptoms are quite distinctive. Infected plants display white powdery spots on the leaves and stems. The lower leaves are the most affected, but the mildew can appear on any above-ground part of the plant. As the disease progresses, the spots get larger and denser as large numbers of asexual spores are formed, and the mildew may spread up and down the length of the plant.

<span class="mw-page-title-main">Lichenometry</span>

In archaeology, palaeontology, and geomorphology, lichenometry is a geomorphic method of geochronologic dating that uses lichen growth to determine the age of exposed rock, based on a presumed specific rate of increase in radial size over time. Measuring the diameter of the largest lichen of a species on a rock surface can therefore be used to determine the length of time the rock has been exposed. Lichen can be preserved on old rock faces for up to 10,000 years, providing the maximum age limit of the technique, though it is most accurate when applied to surfaces that have been exposed for less than 1,000 years. Lichenometry is especially useful for dating surfaces less than 500 years old, as radiocarbon dating techniques are less accurate over this period. The lichens most commonly used for lichenometry are those of the genera Rhizocarpon and Xanthoria. The measured growth rates of R. geographicum tends to fall within the range of 0.9–0.3 millimeter per year, depending on several factors, including the size of the lichen patch.

<span class="mw-page-title-main">Biological soil crust</span> Communities of living organisms on the soil surface in arid and semi-arid ecosystems

Biological soil crusts are communities of living organisms on the soil surface in arid and semi-arid ecosystems. They are found throughout the world with varying species composition and cover depending on topography, soil characteristics, climate, plant community, microhabitats, and disturbance regimes. Biological soil crusts perform important ecological roles including carbon fixation, nitrogen fixation and soil stabilization; they alter soil albedo and water relations and affect germination and nutrient levels in vascular plants. They can be damaged by fire, recreational activity, grazing and other disturbances and can require long time periods to recover composition and function. Biological soil crusts are also known as biocrusts or as cryptogamic, microbiotic, microphytic, or cryptobiotic soils.

<i>Xanthoria parietina</i> Species of lichen

Xanthoria parietina is a foliose lichen in the family Teloschistaceae. It has wide distribution, and many common names such as common orange lichen, yellow scale, maritime sunburst lichen and shore lichen. It can be found near the shore on rocks or walls, and also on inland rocks, walls, or tree bark. It was chosen as a model organism for genomic sequencing by the US Department of Energy Joint Genome Institute (JGI).

<i>Lobaria</i> Genus of lichens

Lobaria is a genus of foliose lichens, formerly classified in the family Lobariaceae, but now placed in the Peltigeraceae. They are commonly known as "lung wort" or "lungmoss" as their physical shape somewhat resembles a lung, and their ecological niche is similar to that of moss.

<i>Chlamydomonas nivalis</i> Species of alga

Chlamydomonas nivalis, also referred to as Chloromonas typhlos, is a unicellular red-coloured photosynthetic green alga that is found in the snowfields of the alps and polar regions all over the world. They are one of the main algae responsible for causing the phenomenon of watermelon snow, where patches of snow appear red or pink. The first account of microbial communities that form red snow was made by Aristotle. Researchers have been active in studying this organism for over 100 years.

Photoprotection is the biochemical process that helps organisms cope with molecular damage caused by sunlight. Plants and other oxygenic phototrophs have developed a suite of photoprotective mechanisms to prevent photoinhibition and oxidative stress caused by excess or fluctuating light conditions. Humans and other animals have also developed photoprotective mechanisms to avoid UV photodamage to the skin, prevent DNA damage, and minimize the downstream effects of oxidative stress.

<i>Trebouxia</i> Genus of algae

Trebouxia is a unicellular green alga. It is a photosynthetic organism that can exist in almost all habitats found in polar, tropical, and temperate regions. It can either exist in a symbiotic relationship with fungi in the form of lichen or it can survive independently as a free-living organism alone or in colonies. Trebouxia is the most common photobiont in extant lichens. It is a primary producer of marine, freshwater and terrestrial ecosystems. It uses carotenoids and chlorophyll a and b to harvest energy from the sun and provide nutrients to various animals and insects.

<span class="mw-page-title-main">Vulpinic acid</span> Chemical compound

Vulpinic acid is a natural product first found in and important in the symbiosis underlying the biology of lichens. It is a simple methyl ester derivative of its parent compound, pulvinic acid, and a close relative of pulvinone, both of which derive from aromatic amino acids such as phenylalanine via secondary metabolism. The roles of vulpinic acid are not fully established, but may include properties that make it an antifeedant for herbivores. The compound is relatively toxic to mammals.

<i>Lobaria pulmonaria</i> Species of lichen

Lobaria pulmonaria is a large epiphytic lichen consisting of an ascomycete fungus and a green algal partner living together in a symbiotic relationship with a cyanobacterium—a symbiosis involving members of three kingdoms of organisms. Commonly known by various names like tree lungwort, lung lichen, lung moss, lungwort lichen, oak lungs or oak lungwort, it is sensitive to air pollution and is also harmed by habitat loss and changes in forestry practices. Its population has declined across Europe and L. pulmonaria is considered endangered in many lowland areas. The species has a history of use in herbal medicines, and recent research has corroborated some medicinal properties of lichen extracts.

<span class="mw-page-title-main">Teloschistaceae</span> Family of lichen-forming fungi

The Teloschistaceae are a large family of mostly lichen-forming fungi belonging to the class Lecanoromycetes in the division Ascomycota. Many members of the Teloschistaceae are readily identifiable by their vibrant orange to yellow hue, a result of its frequent anthraquinone content. The presence of these anthraquinone pigments, which confer protection from ultraviolet light, enabled this group to expand from shaded forest habitats to harsher environmental conditions of sunny and arid ecosystems during the Late Cretaceous. Collectively, the family has a cosmopolitan distribution, although members occur predominantly in subtropical and temperate regions. Although most members either live on rock or on bark, about 40 species are lichenicolous–meaning they live on other lichens.

<i>Rusavskia elegans</i> Species of lichenised fungus

Rusavskia elegans, commonly known as the elegant sunburst lichen, is a lichenized species of fungus in the genus Rusavskia, family Teloschistaceae. Recognized by its bright orange or red pigmentation, this species grows on rocks, often near bird or rodent perches. It has a circumpolar and alpine distribution. It was one of the first lichens to be used for the rock-face dating method known as lichenometry.

<i>Pseudocyphellaria</i> Genus of lichens

Pseudocyphellaria is a genus of large, leafy lichens that are sometimes referred to as "specklebelly" lichens. The genus has a widespread distribution, especially in south temperate regions, and contains about 170 species. They resemble Lobaria, except that most species of Pseudocyphellaria have conspicuous pseudocyphellae on their lower surface, a characteristic that was once considered unique to this genus. Some species contain pulvinic acid-related pigments; in these species the soredia and pseudocyphellae can be bright yellow.

<span class="mw-page-title-main">Crustose lichen</span> Growth form of lichen as a continuously adherent crust

Crustose lichens are lichens that form a crust which strongly adheres to the substrate, making separation from the substrate impossible without destruction. The basic structure of crustose lichens consists of a cortex layer, an algal layer, and a medulla. The upper cortex layer is differentiated and is usually pigmented. The algal layer lies beneath the cortex. The medulla fastens the lichen to the substrate and is made up of fungal hyphae. The surface of crustose lichens is characterized by branching cracks that periodically close in response to climatic variations such as alternate wetting and drying regimes.

<i>Hydropunctaria maura</i> Species of lichen

Hydropunctaria maura, still often called by the older name Verrucaria maura and commonly known as tar lichen, is a species of saxicolous (rock-dwelling), crustose lichen belonging to the family Verrucariaceae. A perennial species that does not experience seasonal variations, it is the type species of the genus Hydropunctaria. The medulla is a black basal layer that forms columns to the upper surface and isolates the algae into pockets near the upper surface. The black band formed by H. maura can often be seen at a distance as a marker of the high water point.

Gallowayella aphrodites is a species of corticolous (bark-dwelling), foliose (leafy) lichen in the family Teloschistaceae. It is found in the Mediterranean countries Greece, Cyprus, and Italy. Characteristics of the lichen include its small thallus, the disposition of the rhizines on the thallus undersurface, and the lack of vegetative propagules.

Astrothelium aeneoides is a species of corticolous (bark-dwelling), crustose lichen in the family Trypetheliaceae. It is found in Brazil, Guyana, and Puerto Rico, where it grows on the smooth bark of rainforest trees.

<i>Xanthoria aureola</i> Species of fungus in the family Teloschistaceae

Xanthoria aureola, commonly known as the seaside sunburst lichen, is a lichenized species of fungus in the family Teloschistaceae and phylum Ascomycota. X. aureola can be recognized by its bright yellow-orange pigmentation and abundant strap-shaped lobes. It is usually found growing on exposed, nutrient-rich rocks in sunny, maritime habitats. It is largely restricted to European coasts, stretching from Portugal to Norway.

Ochrolechia insularis is a rare species of crustose lichen in the family Ochrolechiaceae. Found only on Kangaroo Island in South Australia, it forms an intricate crust on granite rocks near the sea, providing a habitat for a diverse range of species.

References

  1. "Xanthoria parietina is a widespread lichen coloured by the orange cortical pigment parietin (= physcion). We studied the pigment content in 60 thalli sampled in 4 habitats along a sun–shade gradient from evergreen boreal forests through open deciduous stands to sea cliffs. The significant positive regression between contents of parietin per unit area and site factors (reflecting the openness of the canopy relative to an open sky) across sampled habitats suggested a photoprotective role of parietin at UV-B and/or blue wavelengths, the two absorbance maxima of parietin. UV-B susceptibility of X. parietina, measured as permanent reductions in photosystem II, decreased highly significantly with increasing parietin content per thallus area. However, as much as three-fold greater UV-B irradiances than ambient daily summer maxima, maintained continuously for 240 h were required to cause UV-B damage even in thalli of shaded habitats. Since a previous study has documented a high PAR susceptibility of parietin-deficient X. parietina in the absence of UV-B, there are reasons to believe that the blue light screening of parietin is functionally more important than the UV-B screening. A strong positive relationship between parietin content per unit area and reflectance at 500 nm allows the parietin content in X. parietina thalli to be assessed non-destructively by reflectance measurements" Gauslaa Yngvar, Margrete Ustvedt Elin (2003). "Is parietin a UV-B or a blue-light screening pigment in the lichen Xanthoria parietina?". Photochem. Photobiol. Sci. 2 (4): 424–432. doi: 10.1039/b212532c . PMID   12760542.
  2. "This study reports UV screening pigments in the upper cortices of two widespread lichens collected in three sun-exposed locations along a latitudinal gradient from the Arctic lowland to alpine sites of the Central European Alps. Populations from the Alps receive 3–5 times higher UV-B irradiance than their Arctic counterparts from Svalbard because of latitudinal and altitudinal gradients in UV-B irradiance.... This implies that Arctic populations maintain a high level of screening pigments in spite of low ambient UV-B, and that the studied lichen species presumably may tolerate an increase in UV-B radiation due to the predicted thinning of the ozone layer over polar areas" Nybakken Line; Asbjørn Solhaug Knut; Bilger Wolfgang; Gauslaa Yngvar (2004). "The lichens Xanthoria elegans and Cetraria islandica maintain a high protection against UV-B radiation in Arctic habitats". Oecologia. 140 (2): 211–216. Bibcode:2004Oecol.140..211N. doi:10.1007/s00442-004-1583-6. PMID   15138881. S2CID   22917119.
  3. Asbjorn Solhaug Knut (2003). "UV-induction of sun-screening pigments in lichens". New Phytologist. 158 (1): 91–100. doi: 10.1046/j.1469-8137.2003.00708.x .
  4. Gyung Ja Choi; Seon-Woo Lee; Kyoung Soo Jang; Jin-Seog Kim; Kwang Yun Cho; Jin-Cheol Kim (December 2004). "Effects of chrysophanol, parietin, and nepodin of Rumex crispus on barley and cucumber powdery mildews". Crop Protection. 23 (12): 1215–1221. doi:10.1016/j.cropro.2004.05.005.
  5. "Cancer Growth Could be Slowed by Little-known Pigment in Rhubarb". Laboratory Equipment. 2015-10-22. Retrieved 2015-10-24.
  6. "Orange lichens are source for potential anticancer drug". news.emory.edu. 2015-10-21. Retrieved 2015-10-24.
  7. Basile, Adriana; Rigano, Daniela; Loppi, Stefano; Di Santi, Annalisa; Nebbioso, Angela; Sorbo, Sergio; Conte, Barbara; Paoli, Luca; De Ruberto, Francesca (2015-04-09). "Antiproliferative, Antibacterial and Antifungal Activity of the Lichen Xanthoria parietina and Its Secondary Metabolite Parietin". International Journal of Molecular Sciences. 16 (4): 7861–7875. doi: 10.3390/ijms16047861 . ISSN   1422-0067. PMC   4425054 . PMID   25860944.