Thujaplicinol is either of two

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formula – that is, the same number of atoms of each element (chemistry), element – but distinct arrangements of atoms in space. ''Isomerism'' refers to the exi ...

ic tropolone-related

natural product A natural product is a natural compound or substance produced by a living organism—that is, found in nature. In the broadest sense, natural products include any substance produced by life. Natural products can also be prepared by chemical s ...

s. They are found in tree species primarily in bark, needles, xylem, of the family of ''

Cupressaceae Cupressaceae or the cypress family is a family of conifers. The family includes 27–30 genera (17 monotypic), which include the junipers and redwoods, with about 130–140 species in total. They are monoecious, subdioecious or (rarely) dioecio ...

'' like the ''Cupressus, Thuja, Juniperus'' and ''Thujopsis''. The thujaplicinols are structurally equivalent to the thujaplicins with an additional

hydroxyl group In chemistry, a hydroxy or hydroxyl group is a functional group with the chemical formula and composed of one oxygen atom covalently bonded to one hydrogen atom. In organic chemistry, alcohols and carboxylic acids contain one or more hydroxy ...

. They belong to the class of natural

terpenoid The terpenoids, also known as isoprenoids, are a class of naturally occurring organic compound, organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeabl ...

s having two free hydroxyl groups at C3 and C5 position. The thujaplicinols are highly volatile compounds. It is known that the presence of such tropolones, including alpha-tropolone and its isopropyl derivatives, result in the high natural durability of wood species, such as

western red cedar ''Thuja plicata'' is a large evergreen coniferous tree in the family Cupressaceae, native to the Pacific Northwest of North America. Its common name is western redcedar in the U.S. or western red cedar in the UK, and it is also called pacific re ...

, juniper and

cypress Cypress is a common name for various coniferous trees or shrubs from the ''Cupressus'' genus of the '' Cupressaceae'' family, typically found in temperate climates and subtropical regions of Asia, Europe, and North America. The word ''cypress'' ...

Uses

''Alpha-thujaplicinol'', an isomer of thujaplicinol, is often encountered in the Asian species of '' Thujopsis dolabrata'', and exhibits high antibacterial and antifungal activities. It has been found to be effective against ''Enterococcus faecalis'' and ''Legionella pneumophila'', even at low inhibitory concentrations (1.56 to 50 mg/ml). In a 2004 study, α-thujaplicinol showed to have high cytotoxic effects upon several cancer cell lines, such as human stomach cancer and murine lymphocytic leukemia. The other isomer of the compound is called ''β-thujaplicinol''. A recent study found out that it inhibited the development of hepatocellular carcinoma cells because it triggered the autophagic cell death and a subsequent apoptosis. Earlier studies have shown that β-thujaplicinol can addiotionally suppress estrogen-dependent breast cancer by regulating the estrogen receptor signaling.

References

{{Authority control Natural products Monoterpenes Tropolones Isopropyl compounds