3D model (JSmol)
|Molar mass||354.40 g·mol−1|
|Melting point||157–159 °C (315–318 °F; 430–432 K) |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|what is ?)(|
Xanthohumol is a natural product found in the female inflorescences of Humulus lupulus, also known as hops. This compound is also found in beer and belongs to a class of compounds that contribute to the bitterness and flavor of hops. Xanthohumol is a prenylated chalconoid, biosynthesized by a type III polyketide synthase (PKS) and subsequent modifying enzymes.
Xanthohumol is a prenylated chalconoid derived from a plant type III PKS, and is synthesized in the glandular trichromes of hop cones. L-Phenylalanine serves as the starting material, which is converted to cinnamic acid by the PLP-dependent phenylalanine ammonia lyase. Cinnamic acid is oxidized by cinnamate-4-hydroxylase and loaded onto Coenzyme A (CoA) by 4-coumarate CoA ligase to yield 4-hydroxy-cinnamoyl CoA, the starter unit for PKS extension. This molecule is extended three times with malonyl CoA, cyclized through a Claisen condensation, and aromatized through tautomerization to form naringenin chalcone (chalconaringenin). This intermediate has the potential to form a variety of different products depending on the enzymes that modify the core structure. In the case of xanthohumol, a prenyltransferase called Humulus lupulus prenyltransferase 1 (HlPT-1) attaches a molecule of dimethylallyl pyrophosphate from the DXP pathway. HlPT-1 has a broad substrate specificity and also participates in making other prenylated flavonoids in the hop plant. Finally, an O-methyltransferase methylates a phenol substituent using S-adenosyl methionine. Total syntheses of xanthohumol and derivatives have been achieved, though extraction from hops remains a primary source.
In commercial beers, the concentration of xanthohumol ranges from about 2 μg/L – 1.2 mg/L. During the brewing process, xanthohumol and other prenylated flavonoids are lost as they are converted to the corresponding flavanones. Different hop varieties and different beers contain varying quantities of xanthohumol.
- Isoxanthohumol, the corresponding prenylated flavanone
- 8-Prenylnaringenin, a related prenylflavanoid with anti-estrogenic activity
- Alpha acids, a class of bitter compounds in hops
- Myrcene, humulene, and caryophyllene, essential oils in hops
- Xanthohumol from hop (Humulus lupus), Santa Cruz Biotechnology
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