Cerevisterol (5α-ergosta-7,22-diene-3β,5,6β-triol) is a

sterol Sterol is an organic compound with formula , whose molecule is derived from that of gonane by replacement of a hydrogen atom in position 3 by a hydroxyl group. It is therefore an alcohol of gonane. More generally, any compounds that contain the go ...

. Originally described in the 1930s from the yeast '' Saccharomyces cerevisiae'', it has since been found in several other fungi and, recently, in deep water coral. Cerevisterol has some '' in vitro'' bioactive properties, including

cytotoxic Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are an immune cell or some types of venom, e.g. from the puff adder (''Bitis arietans'') or brown recluse spider (''Loxosceles reclusa''). Cell physiology Treating cells ...

ity to some mammalian

cell line An immortalised cell line is a population of cells from a multicellular organism which would normally not proliferate indefinitely but, due to mutation, have evaded normal cellular senescence and instead can keep undergoing division. The cell ...

Discovery and properties

Cerevisterol was first discovered in 1928 as a component of crude yeast ('' Saccharomyces cerevisiae'') sterols remaining from the manufacture of the related

ergosterol Ergosterol (ergosta-5,7,22-trien-3β-ol) is a sterol found in cell membranes of fungi and protozoa, serving many of the same functions that cholesterol serves in animal cells. Because many fungi and protozoa cannot survive without ergosterol, the ...

. Chemists Edna M. Honeywell and Charles E. Bills purified the compound and reported some of its properties in a 1932 publication. They noted its high melting point (265.3 °C) relative to other sterols, and insolubility in the organic solvent hexane. These characteristics facilitated its purification, and they were able to obtain of cerevisterol from of dry yeast. The following year, they determined its chemical formula to be C₂₆H₄₆O₃, with two

double bonds In chemistry, a double bond is a covalent bond between two atoms involving four bonding electrons as opposed to two in a single bond. Double bonds occur most commonly between two carbon atoms, for example in alkenes. Many double bonds exist betwee ...

, and with two of the oxygen molecules occurring in hydroxyl groups. Its structure was determined in 1954 by comparison with a sample that was chemically synthesized from ergosterol. Purified cerevisterol has the form of a white amorphous solid. When crystallized in ethyl alcohol, it forms elongated prisms, while crystallization in acetone or ethyl acetate produces broad hexagonal prisms. Its UV

absorption spectrum Absorption spectroscopy refers to spectroscopic techniques that measure the absorption of radiation, as a function of frequency or wavelength, due to its interaction with a sample. The sample absorbs energy, i.e., photons, from the radiating f ...

shows a maximum at about 248 nm. Cerevisterol is a stable molecule, showing no discoloration or change in melting point even after several weeks of exposure to light and air.

Occurrence

Cerevisterol is widely distributed in the fungal kingdom. In the division

Basidiomycota Basidiomycota () is one of two large divisions that, together with the Ascomycota, constitute the subkingdom Dikarya (often referred to as the "higher fungi") within the kingdom Fungi. Members are known as basidiomycetes. More specifically, Basi ...

, it occurs in several members of the fungal family Boletaceae, the

edible mushroom Edible mushrooms are the fleshy and edible fruit bodies of several species of macrofungi (fungi which bear fruiting structures that are large enough to be seen with the naked eye). They can appear either below ground (hypogeous) or above ground ...

s '' Cantharellus cibarius'', '' Volvariella volvacea'', '' Pleurotus sajor-caju'', '' Laetiporus sulphureus'', and '' Suillus luteus'', in the milk mushroom '' Lactarius hatsudake'', and the coral fungus '' Ramaria botrytis''. In the division

Ascomycota Ascomycota is a phylum of the kingdom Fungi that, together with the Basidiomycota, forms the subkingdom Dikarya. Its members are commonly known as the sac fungi or ascomycetes. It is the largest phylum of Fungi, with over 64,000 species. The def ...

, it has been reported in ''

Auricularia polytricha ''Auricularia cornea'' (毛木耳, maomuer or cloud ear) is a species of fungus in the order Auriculariales. It is commercially cultivated for food in China. The species was previously referred to ''Auricularia polytricha'', but the latter speci ...

'', ''

Bulgaria inquinans ''Bulgaria inquinans'' is a fungus in the family Phacidiaceae. It is commonly known by the name black bulgar and black jelly drops. It grows on branches and bark of dead oak and hornbeam. It has also been growing on ash trees due to ash diebac ...

'', ''

Engleromyces goetzei ''Engleromyces'' is a genus of fungi in the family Xylariaceae. The genus contains two species, the type ''Engleromyces goetzei'' (found in Africa and Asia) and ''E. sinensis'' (found in China), described as new in 2010. The genus was circ ...

'', '' Acremonium luzulae'', and '' Pencillium herquei'', as well as the lichens '' Ramalina hierrensis'' and ''

Stereocaulon azoreum ''Stereocaulon'' is a genus of lichens. Members of ''Stereocaulon'' are commonly called snow lichens. Species *''Stereocaulon alpinum'' *'' Stereocaulon apocalypticum'' *'' Stereocaulon arcticum'' *'' Stereocaulon arenarium'' *'' Stereocaul ...

''. It has also been found in the endophytes '' Alternaria brassicicola'', '' Fusarium oxysporum'', and a strain of ''

Gliocladium ''Gliocladium''Corda (1840) ''Icon. fung. (Prague)'' 4: 30. is an asexual fungal genus in the Hypocreaceae. Certain other species including ''Gliocladium virens'' were recently transferred to the genus ''Trichoderma'' and ''G. roseum'' became '' ...

'', and the deep-sea fungus '' Aspergillus sydowi''. In 2013, the sterol was reported in the South China Sea gorgonian coral '' Muriceoopsis flavida''. A 9-hydroxylated analogue of cerevisterol was found in ''R. botrytis''. A modified version of the compound, (22''E'', 24''R'')-cerevisterol, has been reported from the coral '' Subergorgia mollis''. It was shown to be moderately

to embryos of the zebrafish '' Danio rerio''.

Bioactivity

Cerevisterol inhibits the eukaryotic enzyme DNA polymerase alpha, and it is also a potent inhibitor of NF-kappa B activation. The sterol is cytotoxic to mouse

P388 The NCI-60 cancer cell line panel is a group of 60 human cancer cell lines used by the National Cancer Institute (NCI) for the screening of compounds to detect potential anticancer activity. Purpose The screening procedure is called the NCI- ...

leukemia cells and A549 human

alveolar Alveolus (; pl. alveoli, adj. alveolar) is a general anatomical term for a concave cavity or pit. Uses in anatomy and zoology * Pulmonary alveolus, an air sac in the lungs ** Alveolar cell or pneumocyte ** Alveolar duct ** Alveolar macrophage * ...

epithelial cells grown in culture.

References

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