Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Xanthohumol: Difference between pages

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| PIN = 2′,4,4′-Trihydroxy-6′-methoxy-3′-(3-methylbut-2-en-1-yl)chalcone

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| CASNo = 6754-58-1

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| ChEMBL_Ref = {{ebicite|correct|EBI}}

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| ChEBI = 66331

| RTECS = UD5574117

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| C=21 | H=22 | O=5

| Density = 1.24 g/cm³<ref name=scbt>[http://www.scbt.com/datasheet-301982.html Xanthohumol from hop (Humulus lupus)], Santa Cruz Biotechnology</ref>

| MeltingPtC = 157-159

| MeltingPt_ref = <ref name=scbt/>

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'''Xanthohumol''' is a [[natural product]] found in the female [[inflorescence]]s 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.<ref name=":0">{{Cite journal|last1=Stevens|first1=Jan F.|last2=Page|first2=Jonathan E.|date=May 2004|title=Xanthohumol and related prenylflavonoids from hops and beer: to your good health!|journal=Phytochemistry|volume=65|issue=10|pages=1317–1330|doi=10.1016/j.phytochem.2004.04.025|issn=0031-9422|pmid=15231405|bibcode=2004PChem..65.1317S }}</ref> Xanthohumol is a prenylated [[chalconoid]], biosynthesized by a type III [[polyketide synthase]] (PKS) and subsequent modifying [[enzyme]]s.<ref>{{Cite journal|last1=Goese|first1=Markus|last2=Kammhuber|first2=Klaus|last3=Bacher|first3=Adelbert|last4=Zenk|first4=Meinhart H.|last5=Eisenreich|first5=Wolfgang|date=1999-07-15|title=Biosynthesis of bitter acids in hops|journal=European Journal of Biochemistry|language=en|volume=263|issue=2|pages=447–454|doi=10.1046/j.1432-1327.1999.00518.x|pmid=10406953|issn=1432-1033|doi-access=free}}</ref><ref>{{Cite journal|last1=Wang|first1=Guodong|last2=Tian|first2=Li|last3=Aziz|first3=Naveed|last4=Broun|first4=Pierre|last5=Dai|first5=Xinbin|last6=He|first6=Ji|last7=King|first7=Andrew|last8=Zhao|first8=Patrick X.|last9=Dixon|first9=Richard A.|date=November 2008|title=Terpene biosynthesis in glandular trichomes of hop|journal=Plant Physiology|volume=148|issue=3|pages=1254–1266|doi=10.1104/pp.108.125187|issn=0032-0889|pmc=2577278|pmid=18775972}}</ref>

== Biosynthesis ==

Xanthohumol is a prenylated chalconoid derived from a plant type III PKS, and is synthesized in the glandular trichromes of hop cones.<ref name=":0" /> [[Phenylalanine|L-Phenylalanine]] serves as the starting material, which is converted to [[cinnamic acid]] by the PLP-dependent [[Phenylalanine ammonia-lyase|phenylalanine ammonia lyase]].<ref name=":1">{{Cite book|title=Medicinal natural products : a biosynthetic approach|last=M.|first=Dewick, Paul|date=9 March 2009 |publisher=Wiley |isbn=978-0-470-74168-9|oclc=259265604}}</ref><ref name=":2">{{Cite journal|last1=Nagel|first1=Jana|last2=Culley|first2=Lana K.|last3=Lu|first3=Yuping|last4=Liu|first4=Enwu|last5=Matthews|first5=Paul D.|last6=Stevens|first6=Jan F.|last7=Page|first7=Jonathan E.|date=January 2008|title=EST analysis of hop glandular trichomes identifies an O-methyltransferase that catalyzes the biosynthesis of xanthohumol|journal=The Plant Cell|volume=20|issue=1|pages=186–200|doi=10.1105/tpc.107.055178|issn=1040-4651|pmc=2254931|pmid=18223037}}</ref> Cinnamic acid is oxidized by [[Trans-cinnamate 4-monooxygenase|cinnamate-4-hydroxylase]] and loaded onto [[Coenzyme A]] (CoA) by [[4-Coumarate-CoA ligase|4-coumarate CoA ligase]] to yield [[Coumaroyl-CoA|4-hydroxy-cinnamoyl CoA]], the starter unit for PKS extension.<ref name=":1" /><ref name=":2" /> This molecule is extended three times with [[Malonyl-CoA|malonyl CoA]], cyclized through a [[Claisen condensation]], and aromatized through [[tautomer]]ization to form [[naringenin chalcone]] (chalconaringenin).<ref name=":1" /> This intermediate has the potential to form a variety of different products depending on the enzymes that modify the core structure.<ref name=":0" /><ref name=":1" /> In the case of xanthohumol, a [[prenyltransferase]] called ''Humulus lupulus'' prenyltransferase 1 (HlPT-1) attaches a molecule of [[dimethylallyl pyrophosphate]] from the [[Non-mevalonate pathway|DXP pathway]].<ref name=":3">{{Cite journal|last1=Tsurumaru|first1=Yusuke|last2=Sasaki|first2=Kanako|last3=Miyawaki|first3=Tatsuya|last4=Uto|first4=Yoshihiro|last5=Momma|first5=Takayuki|last6=Umemoto|first6=Naoyuki|last7=Momose|first7=Masaki|last8=Yazaki|first8=Kazufumi|date=2012-01-06|title=HlPT-1, a membrane-bound prenyltransferase responsible for the biosynthesis of bitter acids in hops|journal=Biochemical and Biophysical Research Communications|volume=417|issue=1|pages=393–398|doi=10.1016/j.bbrc.2011.11.125|issn=1090-2104|pmid=22166201}}</ref> HlPT-1 has a broad substrate specificity and also participates in making other prenylated flavonoids in the hop plant.<ref name=":3" /> Finally, an [[O-methyltransferase]] methylates a phenol substituent using [[S-Adenosyl methionine|S-adenosyl methionine]].<ref name=":2" /> Total syntheses of xanthohumol and derivatives have been achieved, though extraction from hops remains a primary source.<ref>{{Cite journal|last1=Khupse|first1=Rahul S.|last2=Erhardt|first2=Paul W.|date=2007-09-01|title=Total Synthesis of Xanthohumol|journal=Journal of Natural Products|volume=70|issue=9|pages=1507–1509|doi=10.1021/np070158y|pmid=17844997|issn=0163-3864|url=https://figshare.com/articles/Total_Synthesis_of_Xanthohumol/2983579}}</ref><ref>{{Cite journal|last1=Zhang|first1=Baoxin|last2=Duan|first2=Dongzhu|last3=Ge|first3=Chunpo|last4=Yao|first4=Juan|last5=Liu|first5=Yaping|last6=Li|first6=Xinming|last7=Fang|first7=Jianguo|date=2015-02-26|title=Synthesis of Xanthohumol Analogues and Discovery of Potent Thioredoxin Reductase Inhibitor as Potential Anticancer Agent|journal=Journal of Medicinal Chemistry|volume=58|issue=4|pages=1795–1805|doi=10.1021/jm5016507|pmid=25629304|issn=0022-2623}}</ref>

[[File:Xanthohumol Biosynthesis v2.jpg|center|700x700px|The biosynthesis of Xanthohumol utilizes building blocks from plant secondary metabolism, and is catalyzed by a type III PKS and accessory modifying enzymes.|frameless]]

== Beer ==

In commercial beers, the concentration of xanthohumol ranges from about 2 μg/L – 1.2&nbsp;mg/L.<ref name=":4">{{Cite journal|last=Gerhäuser|first=Clarissa|date=September 2005|title=Beer constituents as potential cancer chemopreventive agents|journal=European Journal of Cancer|volume=41|issue=13|pages=1941–1954|doi=10.1016/j.ejca.2005.04.012|issn=0959-8049|pmid=15953717}}</ref> During the [[brewing]] process, xanthohumol and other prenylated flavonoids are lost as they are converted to the corresponding [[flavanone]]s.<ref>{{Cite journal|last1=Stevens|first1=Jan F.|last2=Taylor|first2=Alan W.|last3=Clawson|first3=Jeff E.|last4=Deinzer|first4=Max L.|date=1999-06-01|title=Fate of Xanthohumol and Related Prenylflavonoids from Hops to Beer|journal=Journal of Agricultural and Food Chemistry|volume=47|issue=6|pages=2421–2428|doi=10.1021/jf990101k|pmid=10794646|issn=0021-8561}}</ref> Different hop varieties and different beers contain varying quantities of xanthohumol.<ref name=":0" />

==Research==

Xanthohumol is under [[basic research]] for its potential biological properties.<ref name=":4" /> Xanthohumol can be [[extract|extracted]] with pressurized hot water.<ref>A. Gil-Ramírez, J.A. Mendiola, E. Arranz, A. Ruíz-Rodríguez, G. Reglero, E. Ibáñez, F.R. Marín. [https://doi.org/10.1016/j.ifset.2012.04.006 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. [https://www.sciencedirect.com/science/article/pii/S1466856412000549 doi: 10.1016/j.ifset.2012.04.006].</ref>

== See also ==

* [[Isoxanthohumol]], the corresponding prenylated flavanone

* [[8-Prenylnaringenin]], a related prenylflavanoid with anti-estrogenic activity

* [[Alpha acid]]s, a class of bitter compounds in hops

* [[Myrcene]], [[humulene]], and [[caryophyllene]], essential oils in hops

== References ==

{{reflist|30em}}

[[Category:Chalconoids]]

[[Category:O-methylated natural phenols]]

[[Category:Humulus]]