Xanthohumol Explained

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.[1] Xanthohumol is a prenylated chalconoid, biosynthesized by a type III polyketide synthase (PKS) and subsequent modifying enzymes.[2] [3]

Biosynthesis

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.[4] [5] 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.[6] 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.[7] [8]

Beer

In commercial beers, the concentration of xanthohumol ranges from about 2 μg/L – 1.2 mg/L.[9] During the brewing process, xanthohumol and other prenylated flavonoids are lost as they are converted to the corresponding flavanones.[10] Different hop varieties and different beers contain varying quantities of xanthohumol.

Research

Xanthohumol is under basic research for its potential biological properties. Xanthohumol can be extracted with pressurized hot water.[11]

See also

Notes and References

  1. 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. 10.1016/j.phytochem.2004.04.025. 0031-9422. 15231405. 2004PChem..65.1317S .
  2. Goese. Markus. Kammhuber. Klaus. Bacher. Adelbert. Zenk. Meinhart H.. Eisenreich. Wolfgang. 1999-07-15. Biosynthesis of bitter acids in hops. European Journal of Biochemistry. en. 263. 2. 447–454. 10.1046/j.1432-1327.1999.00518.x. 10406953. 1432-1033. free.
  3. 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. 10.1104/pp.108.125187. 0032-0889. 2577278. 18775972.
  4. Book: M., Dewick, Paul. Medicinal natural products : a biosynthetic approach. 9 March 2009 . Wiley . 978-0-470-74168-9. 259265604.
  5. 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. 10.1105/tpc.107.055178. 1040-4651. 2254931. 18223037.
  6. 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. 10.1016/j.bbrc.2011.11.125. 1090-2104. 22166201.
  7. Khupse. Rahul S.. Erhardt. Paul W.. 2007-09-01. Total Synthesis of Xanthohumol. Journal of Natural Products. 70. 9. 1507–1509. 10.1021/np070158y. 17844997. 0163-3864.
  8. 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. 10.1021/jm5016507. 25629304. 0022-2623.
  9. Gerhäuser. Clarissa. September 2005. Beer constituents as potential cancer chemopreventive agents. European Journal of Cancer. 41. 13. 1941–1954. 10.1016/j.ejca.2005.04.012. 0959-8049. 15953717.
  10. 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. 10.1021/jf990101k. 10794646. 0021-8561.
  11. 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.

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