From Wikipedia, the free encyclopedia
Chemical compound
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.
[2] Xanthohumol is a prenylated
chalconoid , biosynthesized by a type III
polyketide synthase (PKS) and subsequent modifying
enzymes .
[3]
[4]
Biosynthesis
Xanthohumol is a prenylated chalconoid derived from a plant type III PKS, and is synthesized in the glandular trichromes of hop cones.
[2]
L-Phenylalanine serves as the starting material, which is converted to
cinnamic acid by the PLP-dependent
phenylalanine ammonia lyase .
[5]
[6] 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.
[5]
[6] This molecule is extended three times with
malonyl CoA , cyclized through a
Claisen condensation , and aromatized through
tautomerization to form
naringenin chalcone (chalconaringenin).
[5] This intermediate has the potential to form a variety of different products depending on the enzymes that modify the core structure.
[2]
[5] In the case of xanthohumol, a
prenyltransferase called Humulus lupulus prenyltransferase 1 (HlPT-1) attaches a molecule of
dimethylallyl pyrophosphate from the
DXP pathway .
[7] HlPT-1 has a broad substrate specificity and also participates in making other prenylated flavonoids in the hop plant.
[7] Finally, an
O-methyltransferase methylates a phenol substituent using
S-adenosyl methionine .
[6] Total syntheses of xanthohumol and derivatives have been achieved, though extraction from hops remains a primary source.
[8]
[9]
The biosynthesis of Xanthohumol utilizes building blocks from plant secondary metabolism, and is catalyzed by a type III PKS and accessory modifying enzymes.
Beer
In commercial beers, the concentration of xanthohumol ranges from about 2 μg/L – 1.2 mg/L.
[10] During the
brewing process, xanthohumol and other prenylated flavonoids are lost as they are converted to the corresponding
flavanones .
[11] Different hop varieties and different beers contain varying quantities of xanthohumol.
[2]
Research
Xanthohumol is under
basic research for its potential biological properties.
[10] Xanthohumol can be
extracted with pressurized hot water.
[12]
See also
References
^
a
b
Xanthohumol from hop (Humulus lupus) , Santa Cruz Biotechnology
^
a
b
c
d Stevens, Jan F.; Page, Jonathan E. (May 2004). "Xanthohumol and related prenylflavonoids from hops and beer: to your good health!". Phytochemistry . 65 (10): 1317–1330.
Bibcode :
2004PChem..65.1317S .
doi :
10.1016/j.phytochem.2004.04.025 .
ISSN
0031-9422 .
PMID
15231405 .
^ Goese, Markus; Kammhuber, Klaus; Bacher, Adelbert; Zenk, Meinhart H.; Eisenreich, Wolfgang (1999-07-15).
"Biosynthesis of bitter acids in hops" . European Journal of Biochemistry . 263 (2): 447–454.
doi :
10.1046/j.1432-1327.1999.00518.x .
ISSN
1432-1033 .
PMID
10406953 .
^ Wang, Guodong; Tian, Li; Aziz, Naveed; Broun, Pierre; Dai, Xinbin; He, Ji; King, Andrew; Zhao, Patrick X.; Dixon, Richard A. (November 2008).
"Terpene biosynthesis in glandular trichomes of hop" . Plant Physiology . 148 (3): 1254–1266.
doi :
10.1104/pp.108.125187 .
ISSN
0032-0889 .
PMC
2577278 .
PMID
18775972 .
^
a
b
c
d M., Dewick, Paul (9 March 2009). Medicinal natural products : a biosynthetic approach . Wiley.
ISBN
978-0-470-74168-9 .
OCLC
259265604 . {{
cite book }}
: CS1 maint: multiple names: authors list (
link )
^
a
b
c Nagel, Jana; Culley, Lana K.; Lu, Yuping; Liu, Enwu; Matthews, Paul D.; Stevens, Jan F.; Page, Jonathan E. (January 2008).
"EST analysis of hop glandular trichomes identifies an O-methyltransferase that catalyzes the biosynthesis of xanthohumol" . The Plant Cell . 20 (1): 186–200.
doi :
10.1105/tpc.107.055178 .
ISSN
1040-4651 .
PMC
2254931 .
PMID
18223037 .
^
a
b Tsurumaru, Yusuke; Sasaki, Kanako; Miyawaki, Tatsuya; Uto, Yoshihiro; Momma, Takayuki; Umemoto, Naoyuki; Momose, Masaki; Yazaki, Kazufumi (2012-01-06). "HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops". Biochemical and Biophysical Research Communications . 417 (1): 393–398.
doi :
10.1016/j.bbrc.2011.11.125 .
ISSN
1090-2104 .
PMID
22166201 .
^ Khupse, Rahul S.; Erhardt, Paul W. (2007-09-01).
"Total Synthesis of Xanthohumol" . Journal of Natural Products . 70 (9): 1507–1509.
doi :
10.1021/np070158y .
ISSN
0163-3864 .
PMID
17844997 .
^ Zhang, Baoxin; Duan, Dongzhu; Ge, Chunpo; Yao, Juan; Liu, Yaping; Li, Xinming; Fang, Jianguo (2015-02-26). "Synthesis of Xanthohumol Analogues and Discovery of Potent Thioredoxin Reductase Inhibitor as Potential Anticancer Agent". Journal of Medicinal Chemistry . 58 (4): 1795–1805.
doi :
10.1021/jm5016507 .
ISSN
0022-2623 .
PMID
25629304 .
^
a
b Gerhäuser, Clarissa (September 2005). "Beer constituents as potential cancer chemopreventive agents". European Journal of Cancer . 41 (13): 1941–1954.
doi :
10.1016/j.ejca.2005.04.012 .
ISSN
0959-8049 .
PMID
15953717 .
^ Stevens, Jan F.; Taylor, Alan W.; Clawson, Jeff E.; Deinzer, Max L. (1999-06-01). "Fate of Xanthohumol and Related Prenylflavonoids from Hops to Beer". Journal of Agricultural and Food Chemistry . 47 (6): 2421–2428.
doi :
10.1021/jf990101k .
ISSN
0021-8561 .
PMID
10794646 .
^ A. Gil-Ramírez, J.A. Mendiola, E. Arranz, A. Ruíz-Rodríguez, G. Reglero, E. Ibáñez, F.R. Marín.
Highly isoxanthohumol enriched hop extract obtained by pressurized hot water extraction (PHWE). Chemical and functional characterization . Innovative Food Science and Emerging Technologies 2012 October, vol 16 Pages 54-60.
doi: 10.1016/j.ifset.2012.04.006 .