Benzylisoquinoline: Difference between revisions

| Watchedfields = changed

| verifiedrevid =

| PIN = 1-Benzylisoquinoline

| = 1-(Phenylmethyl)isoquinoline

| CASNo_Ref = {{cascite||??}}

| CASNo = 6907-59-1

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = UF5CSU3HA6

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| ChemSpiderID_Ref = {{chemspidercite||chemspider}}

| Appearance =

| Density =

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'''1-[[]] of [[]] a wide variety of , [[papaverine]], [[noscapine]], [[codeine]], [[morphine]], [[apomorphine]], [[berberine]], [[tubocurarine]].

(''S'')-[[Norcoclaurine]] ([[higenamine]]) has been identified as the central 1-benzyl-tetrahydro-isoquinoline precursor<ref name=":0">{{Cite journal|last1=Stadler|first1=Richard|last2=Kutchan|first2=Toni M|last3=Zenk|first3=Meinhart H|date=1989|title=(S)-Norcoclaurine is the central intermediate in benzylisoquinoline alkaloid biosynthesis|journal=Phytochemistry|volume=28|pages=1083–1086}}</ref><ref>{{Cite journal|last1=Hagel|first1=Jillian M|last2=Morris|first2=Jeremy S|last3=Lee|first3=Eun-Jeong|last4=Desgagne-Penix|first4=Isabel|last5=Bross|first5=Crystal D|last6=Chang|first6=Limei|last7=Chen|first7=Xue|last8=Farrow|first8=Scott C|last9=Zhang|first9=Ye|date=2015|title=Transcriptome analysis of 20 taxonomically related benzylisoquinoline alkaloid-producing plants|journal=BMC Plant Biol|volume=15|pages=227|doi=10.1186/s12870-015-0596-0|pmid=26384972|pmc=4575454 |doi-access=free }}</ref> from which numerous complex biosynthetic pathways eventually emerge. These pathways collectively lead to the structurally disparate compounds comprising the broad classification of plant natural products referred to as benzylisoquinoline alkaloids (BIA), which have been comprehensively discussed by Hagel.<ref>{{Cite journal|last1=Hagel|first1=Jillian M|last2=Facchini|first2=Peter J|date=2013|title=Benzylisoquinoline alkaloid metabolism: A century of discovery and a brave new world|journal=Plant Cell Physiol.|volume=54|issue=5 |pages=647–672|doi=10.1093/pcp/pct020|pmid=23385146|doi-access=free}}</ref> The biosynthesis of [[(S)-norcoclaurine]], which is catalyzed by [[(S)-norcoclaurine synthase|(''S'')-norcoclaurine synthase]], is accomplished by the stereoselective condensation of [[dopamine]] and 4-hydroxyphenylacetaldehyde (4-HPAA); each of these compounds is prepared by multiple enzymatic transformations from [[L-Tyrosine|L-tyrosine]].

It is of interest to note that early studies initially identified norlaudanosoline ([[tetrahydropapaveroline]]) as the purported central precursor for the biosynthesis of BIAs.<ref>{{Cite journal|last1=Battersby|first1=A. R.|last2=Binks|first2=R.|last3=Francis|first3=R. J.|last4=McCaldin|first4=D. J.|last5=Ramuz|first5=H.|date=1964|title=Alkaloid biosynthesis> Part IV. 1-Benzylisoquinolines as precursors of thebaine, codeine, and morphine|journal=J Chem Soc|pages=3600}}</ref> However, more than two decades later it was finely unequivocally established that [[(S)-norcoclaurine|(''S'')-norcoclaurine]] was the central precursor for the biosynthesis of the structurally diverse BIAs.<ref name=":0" />

:Benzylisoquinoline structure in Papaverin.svg|[[Papaverine]]

:Benzylisoquinoline structure in Apomorphone.svg|[[Apomorphine]] ''(one additional ring closure)''

:.svg|[[Morphine]] ''(two additional ring closures)''

:Benzylisoquinoline structure in Berberine.svg|[[Berberine]] ''(one additional ring closure with incorporated N-methyl)''

:Benzylisoquinoline in .svg|[[]] ''( )''

==See also==

*[[Morphinan]]

*[[Indole]]

*[[Indolizidine]]

{{Reflist}}

[[Category:]]