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Lichexanthone information


Lichexanthone
Names
IUPAC name
1-Hydroxy-3,6-dimethoxy-8-methyl-9H-xanthen-9-one
Other names
Lichenxanthone,
1-hydroxy-3,6-dimethoxy-8-methylxanthen-9-one
Identifiers
CAS Number
  • 15222-53-4 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:67821 checkY
ChEMBL
  • ChEMBL470650 checkY
ChemSpider
  • 4513972 checkY
PubChem CID
  • 5358904
CompTox Dashboard (EPA)
  • DTXSID80164977 Edit this at Wikidata
InChI
  • InChI=1S/C16H14O5/c1-8-4-9(19-2)6-12-14(8)16(18)15-11(17)5-10(20-3)7-13(15)21-12/h4-7,17H,1-3H3 checkY
    Key: QDLAGTHXVHQKRE-UHFFFAOYSA-N checkY
SMILES
  • CC1=CC(=CC2=C1C(=O)C3=C(C=C(C=C3O2)OC)O)OC
Properties
Chemical formula
C16H14O5
Molar mass 286.283 g·mol−1
Appearance long yellow prismatic crystals
Density 1.323 g/cm3
Melting point 189–190 °C (372–374 °F; 462–463 K)
Boiling point 494 °C (921 °F)
Structure[1]
Crystal structure
Monoclinic
Space group
P21/c (No. 14)
Lattice constant
a = 11.6405 Å, b = 7.5444 Å, c = 15.2341 Å
Lattice volume (V)
1307.26 Å3
Formula units (Z)
4
Hazards
Flash point 186.9 °C (368.4 °F)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Lichexanthone is an organic compound in the structural class of chemicals known as xanthones. Lichexanthone was first isolated and identified by Japanese chemists from a species of leafy lichen in the 1940s. The compound is known to occur in many lichens, and it is important in the taxonomy of species in several genera, such as Pertusaria and Pyxine. More than a dozen lichen species have a variation of the word lichexanthone incorporated as part of their binomial name. The presence of lichexanthone in lichens causes them to fluoresce a greenish-yellow colour under long-wavelength UV light; this feature is used to help identify some species. Lichexanthone is also found in several plants (many are from the families Annonaceae and Rutaceae), and some species of fungi that do not form lichens.

In lichens, the biosynthesis of lichexanthone occurs through a set of enzymatic reactions that start with the molecule acetyl-CoA and sequentially add successive units, forming a longer chain that is cyclized into a double-ring structure. Although it has been suggested that lichexanthone functions in nature as a photoprotectant—protecting resident algal populations (photobionts) in lichens from high-intensity solar radiation—its complete ecological function is not fully understood. Some biological activities of lichexanthone that have been demonstrated in the laboratory include antibacterial, larvicidal, and sperm motility-enhancing activities. Many lichexanthone derivatives are known, some produced naturally in lichens, and others created synthetically; like lichexanthone, some of these derivatives are also biologically active.

  1. ^ Cite error: The named reference Buitrago Díaz et al. 2010 was invoked but never defined (see the help page).

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Lichexanthone

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Lichexanthone is an organic compound in the structural class of chemicals known as xanthones. Lichexanthone was first isolated and identified by Japanese...

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Minquartia

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Suriname, and Venezuela. One of the phytochemicals it contains is lichexanthone. Americas Regional Workshop (Conservation & Sustainable Management of...

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Caprettia lichexanthotricha

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a patchy yellow when shone with a UV light, due to the presence of lichexanthone, a secondary chemical for which the lichen is named. Caprettia lichexanthotricha...

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Wirthiotrema xanthopustulatum

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diameter. It contains the secondary compounds protocetraric acid and lichexanthone. This latter compound causes the lichen thallus to fluoresce a yellow...

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Astrothelium gyalostiolatum

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Astrothelium bicolor but uniquely characterized by the presence of lichexanthone exclusively around the ostioles. The lichen has a dull, dirty ochraceous...

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Chiodecton xanthonosorediatum

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xanthonosorediatum is characterized by its thallus and soredia containing lichexanthone and trentepohlioid green algae. The lichen has a crustose, granular...

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Enterographa lichexanthonica

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sheath surrounding them. The specific epithet lichexanthonica refers to lichexanthone, a secondary chemical that occurs in the cortex of the lichen. This...

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Aggregatorygma lichexanthonicum

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Graphidaceae. Found in Brazil, it is characterised by the presence of lichexanthone in its thallus. The lichen was formally described in 2022 by the Dutch...

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Pertusaria lichexanthoimmersa

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specific epithet lichexanthoimmersa refers both to the presence of lichexanthone as a secondary chemical, and the apothecia, which are immersed in the...

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Bathelium flavostiolatum

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pseudostromata ostioles (pores) have nearby white spots that contain lichexanthone; this is a lichen product that causes these spots to fluoresce yellow...

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Soursop

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alkaloid containing a quaternary ammonium group. The plant also contains lichexanthone, a compound in the xanthone class. The Memorial Sloan-Kettering Cancer...

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Astrothelium fijiense

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(2 in) in diameter. Both the thallus and the pseudostromata contain lichexanthone, a lichen product that causes these structures to fluoresce a yellow...

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Graphis stipitata

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The lichen contains three secondary metabolites (lichen products): lichexanthone as a major metabolite, norstictic acid as a minor component, and trace...

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Lecanora lichexanthoxylina

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Maria Fernanda Souza. The specific epithet refers to the presence of lichexanthone, a secondary chemical. List of Lecanora species Aptroot, André; Souza...

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Caloplaca sipmanii

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volume featuring this species was dedicated. Caloplaca sipmanii contains lichexanthone as a major lichen product. List of Caloplaca species Kondratyuk, Sergiy...

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Polymeridium albidovarians

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ornamentation. The lichen's chemistry is characterized by the presence of lichexanthone. "Polymeridium albidovarians Aptroot". Catalogue of Life. Species 2000:...

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Astrothelium flavoduplex

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immersed in the bark tissue as pseudostromata. The thallus contains lichexanthone, a lichen product that causes the thallus surface to fluoresce yellow...

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Architrypethelium hyalinum

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lichens in the Trypetheliaceae. Both the thallus and ascomata contain lichexanthone, a lichen product that causes these structures to glow yellow when lit...

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Carbacanthographis subchionophora

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Carbacanthographis chionophora, but unlike that lichen, it does not contain lichexanthone. The specific epithet subchionophora refers to its resemblance with...

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Bathelium pruinosum

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in a lowland Amazon forest surrounded by Beni savanna. It contains lichexanthone, a lichen product that causes it to fluoresce yellow when lit with a...

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Platythecium verrucoareolatum

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products: consalazinic acid, hypostictic acid, norstictic acid, and lichexanthone; the latter substance causes the thallus of the lichen to fluoresce...

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Pyxine albovirens

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lichen has lobes with distinctly round, laminal soralia. It contains lichexanthone, a lichen product that causes the cortex to fluoresce bright yellow...

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Lepra lichexanthonorstictica

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tree. The lichen is named after its two major secondary compounds, lichexanthone and norstictic acid. Lepra lichexanthonorstictica has a thin, smooth...

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Astrothelium miniannulare

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characterized by its corticolous (bark-dwelling) habitat and presence of lichexanthone. Characteristics of the lichen include the whitish ring around its ostiole...

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Vismia baccifera

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rapid death of cancer cells. One of the phytochemicals it contains is lichexanthone. The antitumour mechanism of an Amazonian plant in human cancer cells...

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Astrothelium sinuosum

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largely immersed in the bark tissue. The area of the ostioles contains lichexanthone, a lichen product that causes these structures to fluoresce yellow when...

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Architrypethelium penuriixanthum

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Architrypethelium hyalinum, but unlike that species, does not have lichexanthone in its thallus. The species epithet penuriixanthum alludes to the absence...

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Cryptothecia evergladensis

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compounds, including psoromic acid, 2-O-methylperlatolic acid, and lichexanthone. The last compound, when present in the lichen at sufficient amounts...

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Astrothelium corallinum

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this is due to the presence of lichexanthone, a lichen product. The thallus, however, does not contain lichexanthone, which distinguishes it from the...

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Pertusaria lichexanthoverrucosa

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specific epithet lichexanthoverrucosa refers to both the presence of lichexanthone as well as the verrucose (warty) thallus. List of Pertusaria species...

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