Megaphone (molecule): Difference between revisions

{{chembox

| verifiedrevid = 431371149

| ImageSize = 200px

| IUPACName = 6-[1-hydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl]-4-methoxy-6-prop-2-enylcyclohex-2-en-1-one

|Section1= {{Chembox Identifiers

| CASNo_Ref =

| CASOther =

| CASNo =

| PubChem = 442908

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

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

| StdInChI=1S/C22H30O6/c1-7-10-22(13-16(25-3)8-9-19(22)23)14(2)20(24)15-11-17(26-4)21(28-6)18(12-15)27-5/h7-9,11-12,14,16,20,24H,1,10,13H2,2-6H3/t14-,16+,20-,22-/m1/s1

}}

|Section2= {{Chembox Properties

| C=22|H=30|O=6

| ExactMass = 390.204239 u

| MeltingPt = 152 °C

| BoilingPt = <!-- °C -->

}}

'''Megaphone''' is a [[Cytotoxicity|cytotoxic]] [[neolignan]] obtained from ''[[Aniba megaphylla]]'', a [[flowering plant]] of [[Lauraceae|Laurel family]] which gave the compound its name. Megaphone has also been prepared synthetically.<ref>{{cite journal|last1=Zoretic|first1=P|title=Total synthesis of d,1-megaphone|journal=Tetrahedron Letters|volume=24|pages=1125|year=1983|doi=10.1016/S0040-4039(00)86382-0}}</ref><ref>{{Cite journal|doi = 10.1016/S0040-4039(00)61960-3|title = Enantiospecific total synthesis of (-)-megaphone by a highly controlled consecutive 1,4- and 1,3-asymmetric induction|author = Tomioka, Kiyoshi; Kawasaki, Hisashi; Iitaka, Yoichi; Koga, Kenji|journal = Tetrahedron Letters |year = 1985|volume = 26|issue = 7|pages = 903–906}}</ref><ref>{{cite journal|doi=10.1021/ja00400a039|last1=Buechi|first1=George|year=1981|pages=2718|volume=103|journal=Journal of the American Chemical Society|last2=Chu|first2=Ping-Sun|title=The Synthesis of Megaphone}}</ref>

Studies carried out in the 1960s demonstrated that an alcoholic extract of the ground root of ''Aniba megaphylla'' inhibited, ''in vitro'', growth of cells derived from human [[carcinoma]] of the [[nasopharynx]]. In 1978, the active components of the extract were isolated using [[silica gel]] [[chromatography]], characterized and named as megaphone (C₂₂H₃₀O₆, solid), megaphone [[acetate]] (C₂₄H₃₂O₇, oily liquid) and megaphyllone acetate (C₂₃H₂₈O₇, oily liquid). For comparison, megaphone acetate was also produced synthetically by reacting megaphone with [[acetic anhydride]] at 50 °C for 6 hours. Stirring an alcoholic solution of megaphone (megaphone acetate), with added palladium catalyst, in hydrogen atmosphere, followed by evaporation of the solvent yields tetrahydromegaphone (tetrahydromegaphone acetate) as an oil. Millimeter-sized crystals of megaphone can be grown from an [[ether]]-[[chloroform]] solution.<ref name=j1/> They have monoclinic symmetry with [[space group]] ''P''2₁, lattice constants ''a'' = 0.8757 nm, ''b'' = 1.1942 nm and ''c'' = 1.0177 nm and two [[formula unit]]s per [[unit cell]]. Megaphone and megaphone acetate molecules are [[Chirality (chemistry)|chiral]] and the reported extraction and synthesis procedures yielded their [[racemic mixture]]s.<ref name=j1>{{cite journal|doi = 10.1021/jo00398a013|author = SM Kupchan, KL Stevens, EA Rohlfing, BR Sickles, AT Sneden, RW Miller, RF Bryan|title = Tumor inhibitors. 126. New cytotoxic neolignans from Aniba megaphylla Mez|journal = J. Org. Chem.|volume = 43|issue = 4|year = 1978|pages = 586–590}}</ref> Megaphone acetate was also isolated from the root of ''Endlicheria dysodantha'', another plant of [[Lauraceae|Laurel family]], using chromatography of ethanolic solution. It showed inhibitory activity against cells of crown gall tumor and human lung, breast and colon carcinomas.<ref>{{cite journal|pmid=1665173|last1=Ma|first1=WW|year=1991|pages=1153–8|issue=4|last2=Kozlowski|volume=54|journal=Journal of natural products|first2=JF|last3=McLaughlin|first3=JL|title=Bioactive neolignans from Endlicheria dysodantha|doi=10.1021/np50076a045}}</ref>

==References==

[[Category:Phenol ethers]]

[[Category:Alcohols]]

[[Category:Alkenes]]

[[Category:Ketones]]

[[Category:Ethers]]