Sekikaic acid is an

organic compound Some chemical authorities define an organic compound as a chemical compound that contains a carbon–hydrogen or carbon–carbon bond; others consider an organic compound to be any chemical compound that contains carbon. For example, carbon-co ...

in the structural class of chemicals known as

depside A depside is a type of polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester group. Depsides are most often found in lichens, but have also been isolated from higher plants, including species of the Ericaceae, ...

s. It is found in some

lichen A lichen ( , ) is a hybrid colony (biology), colony of algae or cyanobacteria living symbiotically among hypha, filaments of multiple fungus species, along with yeasts and bacteria embedded in the cortex or "skin", in a mutualism (biology), m ...

s. First isolated from '' Ramalina sekika'', it is a fairly common

lichen product Lichen products, also known as lichen substances, are organic compounds produced by a lichen. Specifically, they are secondary metabolites. Lichen products are represented in several different chemical classes, including terpenoids, orcinol deri ...

in ''

Ramalina ''Ramalina'' is a genus of greenish fruticose lichens that grow in the form of flattened, strap-like branches. Members of the genus are commonly called strap lichensField Guide to California Lichens, Stephen Sharnoff, Yale University Press, 201 ...

'' and ''

Cladonia ''Cladonia'' is a genus of moss-like lichenized fungi in the family Cladoniaceae. They are the primary food source for reindeer/caribou. ''Cladonia'' species are of economic importance to reindeer-herders, such as the Sami in Scandinavia or th ...

'', both

genera Genus (; : genera ) is a taxonomic rank above species and below family as used in the biological classification of living and fossil organisms as well as viruses. In binomial nomenclature, the genus name forms the first part of the binomial s ...

of lichen-forming fungi. The

species epithet Specific name may refer to: * in Database management systems, a system-assigned name that is unique within a particular database In Taxonomy (biology), taxonomy, either of these two meanings, each with its own set of rules: * Specific name (botany) ...

of the powdery lichen '' Lepraria sekikaica'' refers to the presence of this substance—a rarity in genus ''

Lepraria ''Lepraria'' is a genus of leprose (powdery) crustose lichens that grows on its substrate like patches of granular, caked up, mealy dust grains.A taxonomic revision of the North American species of Lepraria s.l. that produce divaricatic acid, w ...

''.

Properties

In its purified form, sekikaic acid exists as colourless rectangular prisms or rhombic plates. Its

molecular formula A chemical formula is a way of presenting information about the chemical proportions of atoms that constitute a particular chemical compound or molecule, using chemical element symbols, numbers, and sometimes also other symbols, such as paren ...

is C₂₂H₂₆0₈. It has a

melting point The melting point (or, rarely, liquefaction point) of a substance is the temperature at which it changes state of matter, state from solid to liquid. At the melting point the solid and liquid phase (matter), phase exist in Thermodynamic equilib ...

of . An

ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...

ic solution of sekikaic acid reacts with

iron(III) chloride Iron(III) chloride describes the inorganic compounds with the formula (H2O)x. Also called ferric chloride, these compounds are some of the most important and commonplace compounds of iron. They are available both in anhydrous and in hydrated f ...

to produce a violet colour. Its ultraviolet spectrum has three peaks of maximum absorption (λ_max) at 219, 263, and 303 nm. Sekikaic acid has been demonstrated to have several biological activities in laboratory experiments. These include

antioxidant Antioxidants are Chemical compound, compounds that inhibit Redox, oxidation, a chemical reaction that can produce Radical (chemistry), free radicals. Autoxidation leads to degradation of organic compounds, including living matter. Antioxidants ...

activity, inhibition of the enzymes

α-glucosidase In biochemistry, glycoside hydrolases (also called glycosidases or glycosyl hydrolases) are a class of enzymes which catalyze the hydrolysis of glycosidic bonds in complex sugars. They are extremely common enzymes, with roles in nature includi ...

and α-amylase,

hypoglycemic Hypoglycemia (American English), also spelled hypoglycaemia or hypoglycæmia (British English), sometimes called low blood sugar, is a fall in blood sugar to levels below normal, typically below 70 mg/dL (3.9 mmol/L). Whipple's tria ...

activity, and lipid-lowering activity. It also has

antiviral Antiviral drugs are a class of medication used for treating viral infections. Most antivirals target specific viruses, while a broad-spectrum antiviral is effective against a wide range of viruses. Antiviral drugs are a class of antimicrobials ...

activity against

Respiratory syncytial virus Respiratory syncytial virus (RSV), also called human respiratory syncytial virus (hRSV) and human orthopneumovirus, is a virus that causes infections of the respiratory tract. It is a negative-sense, single-stranded RNA virus. Its name is derive ...

, even more so than the standard antiviral medication

ribavirin Ribavirin, also known as tribavirin, is an antiviral medication used to treat illness caused by respiratory syncytial virus (RSV) and hepatitis C virus (HCV) infections, as well as some viral hemorrhagic fevers. For HCV, it is used in combi ...

Related compounds

The sekikaic acid contains similar compounds that are metabolically related to sekikaic acid. It comprises sekikaic acid as the major compound, and 4''O''-demethylsekikaic and homosekikaic acids as satellite metabolites.

References

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