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Xanthohumol

April 13, 2024

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]

Xanthohumol
Names
Preferred IUPAC name
2′,4,4′-Trihydroxy-6′-methoxy-3′-(3-methylbut-2-en-1-yl)chalcone
Identifiers
  • 6754-58-1 N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:66331 N
ChEMBL
  • ChEMBL253896 Y
ChemSpider
  • 555077 Y
ECHA InfoCard 100.123.285
  • 639665
RTECS number
  • UD5574117
UNII
  • T4467YT1NT Y
  • DTXSID00893171
  • InChI=1S/C21H22O5/c1-13(2)4-10-16-18(24)12-19(26-3)20(21(16)25)17(23)11-7-14-5-8-15(22)9-6-14/h4-9,11-12,22,24-25H,10H2,1-3H3/b11-7+ Y
    Key: ORXQGKIUCDPEAJ-YRNVUSSQSA-N Y
  • O=C(c1c(OC)cc(O)c(c1O)C/C=C(\C)C)\C=C\c2ccc(O)cc2
Properties
C21H22O5
Molar mass 354.402 g·mol−1
Density 1.24 g/cm3[1]
Melting point 157–159 °C (315–318 °F; 430–432 K)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Biosynthesis edit

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 edit

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 edit

Xanthohumol is under basic research for its potential biological properties.[10] Xanthohumol can be extracted with pressurized hot water.[12]

See also edit

References edit

  1. ^ a b Xanthohumol from hop (Humulus lupus), Santa Cruz Biotechnology
  2. ^ 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.
  3. ^ 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.
  4. ^ 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.
  5. ^ 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)
  6. ^ 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.
  7. ^ 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.
  8. ^ 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.
  9. ^ 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.
  10. ^ 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.
  11. ^ 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.
  12. ^ 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.

April 13, 2024
xanthohumol, natural, product, found, female, inflorescences, humulus, lupulus, also, known, hops, this, compound, also, found, beer, belongs, class, compounds, that, contribute, bitterness, flavor, hops, prenylated, chalconoid, biosynthesized, type, polyketid. 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 Xanthohumol NamesPreferred IUPAC name 2 4 4 Trihydroxy 6 methoxy 3 3 methylbut 2 en 1 yl chalconeIdentifiersCAS Number 6754 58 1 N3D model JSmol Interactive imageChEBI CHEBI 66331 NChEMBL ChEMBL253896 YChemSpider 555077 YECHA InfoCard 100 123 285PubChem CID 639665RTECS number UD5574117UNII T4467YT1NT YCompTox Dashboard EPA DTXSID00893171InChI InChI 1S C21H22O5 c1 13 2 4 10 16 18 24 12 19 26 3 20 21 16 25 17 23 11 7 14 5 8 15 22 9 6 14 h4 9 11 12 22 24 25H 10H2 1 3H3 b11 7 YKey ORXQGKIUCDPEAJ YRNVUSSQSA N YSMILES O C c1c OC cc O c c1O C C C C C C C c2ccc O cc2PropertiesChemical formula C 21H 22O 5Molar mass 354 402 g mol 1Density 1 24 g cm3 1 Melting point 157 159 C 315 318 F 430 432 K 1 Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Biosynthesis 2 Beer 3 Research 4 See also 5 ReferencesBiosynthesis editXanthohumol 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 nbsp The biosynthesis of Xanthohumol utilizes building blocks from plant secondary metabolism and is catalyzed by a type III PKS and accessory modifying enzymes Beer editIn commercial beers the concentration of xanthohumol ranges from about 2 mg 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 editXanthohumol is under basic research for its potential biological properties 10 Xanthohumol can be extracted with pressurized hot water 12 See also editIsoxanthohumol 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 hopsReferences edit 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 a href Template Cite book html title Template Cite book cite book a 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 Gerhauser 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 Ramirez J A Mendiola E Arranz A Ruiz Rodriguez G Reglero E Ibanez F R Marin 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 Retrieved from https en wikipedia org w index php title Xanthohumol amp oldid 1211957566, wikipedia, wiki, book, books, library,

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