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Revision as of 21:18, 17 August 2011 editRjwilmsi (talk | contribs)Extended confirmed users, Pending changes reviewers, Rollbackers931,971 editsm Journal cites:, added 1 DOI, using AWB (7794)← Previous edit Latest revision as of 23:06, 4 May 2023 edit undoLegionMammal978 (talk | contribs)Extended confirmed users7,894 edits add semisystematic name 
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{{chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 431371149
| Watchedfields = changed
⚫ | verifiedrevid = 445399695
| Name = Megaphone | Name = Megaphone
| ImageFile = megaphone chemical structure.png | ImageFile = megaphone chemical structure.png
| ImageSize = 200px
| ImageName = Chemical structure of megaphone | ImageName = Chemical structure of megaphone
| IUPACName = 6--4-methoxy-6-prop-2-enylcyclohex-2-en-1-one | IUPACName = (1′''R'',5′''R'',7''R'',8''S'')-7-Hydroxy-3,4,5,5′-methoxy-5′,6′-dihydro-2′''H''-8,1′-neolign-8′-en-2′-one
| SystematicName = (4''R'',6''R'')-6--4-methoxy-6-(prop-2-en-1-yl)cyclohex-2-en-1-one
| OtherNames = <!-- <br> --> | OtherNames = <!-- <br> -->
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 64332-37-2 | CASNo = 64332-37-2
| CASNo_Ref = | CASNoOther =
| UNII_Ref = {{fdacite|correct|FDA}}
| CASOther =
| UNII = 8J0BV7D5N9
| PubChem = 324150 | PubChem = 324150
| SMILES = O=C1C=C(OC)C1(CC=C)(C)(O)C2=CC(OC)=C(OC)C(OC)=C2 | SMILES = O=C1C=C(OC)C1(CC=C)(C)(O)C2=CC(OC)=C(OC)C(OC)=C2
| CASNo = | PubChem2 = 442908
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| PubChem = 442908
⚫ | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 391211 | ChemSpiderID = 391211
| StdInChI_Ref = {{stdinchicite|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 | 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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = JCRROBQLLRCCAV-SQKDIAQBSA-N | StdInChIKey = JCRROBQLLRCCAV-SQKDIAQBSA-N
| InChI = | InChI =
| MeSHName = | MeSHName =
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=22|H=30|O=6 | C=22 | H=30 | O=6
| ExactMass = 390.204239 u
| Appearance = | Appearance =
| Density = 1.242 g/cm<sup>3</sup> | Density = 1.242 g/cm<sup>3</sup>
| MeltingPt = 152 °C | MeltingPtC = 152
| MeltingPt_notes =
| BoilingPt = <!-- °C --> | BoilingPt =
| Solubility = | Solubility =
}} }}
}} }}


'''Megaphone''' is a ] ] obtained from '']'', a ] of ] 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> '''Megaphone''' is a ] ] obtained from '']'', a ] of ] which gave the compound its name. Megaphone has also been prepared synthetically.<ref>{{cite journal|last1=Zoretic|first1=P|title=Total synthesis of d,l-megaphone|journal=Tetrahedron Letters|volume=24|issue=11|pages=1125–1128|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|author1=Tomioka, Kiyoshi |author2=Kawasaki, Hisashi |author3=Iitaka, Yoichi |author4=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|issue=10|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 ] of the ]. In 1978, the active components of the extract were isolated using ] ], characterized and named as megaphone (C<sub>22</sub>H<sub>30</sub>O<sub>6</sub>, solid), megaphone ] (C<sub>24</sub>H<sub>32</sub>O<sub>7</sub>, oily liquid) and megaphyllone acetate (C<sub>23</sub>H<sub>28</sub>O<sub>7</sub>, oily liquid). For comparison, megaphone acetate was also produced synthetically by reacting megaphone with ] 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 ]-] solution.<ref name=j1/> They have monoclinic symmetry with ] ''P''2<sub>1</sub>, lattice constants ''a'' = 0.8757 nm, ''b'' = 1.1942 nm and ''c'' = 1.0177 nm and two ]s per ]. Megaphone and megaphone acetate molecules are ] and the reported extraction and synthesis procedures yielded their ]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 ], 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> 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 ] of the ]. In 1978, the active components of the extract were isolated using ] ], characterized and named as megaphone (C<sub>22</sub>H<sub>30</sub>O<sub>6</sub>, solid), megaphone ] (C<sub>24</sub>H<sub>32</sub>O<sub>7</sub>, oily liquid) and megaphyllone acetate (C<sub>23</sub>H<sub>28</sub>O<sub>7</sub>, oily liquid). For comparison, megaphone acetate was also produced synthetically by reacting megaphone with ] at 50&nbsp;°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 ]-] solution.<ref name=j1/> They have monoclinic symmetry with ] ''P''2<sub>1</sub>, lattice constants ''a'' = 0.8757&nbsp;nm, ''b'' = 1.1942&nbsp;nm and ''c'' = 1.0177&nbsp;nm and two ]s per ]. Megaphone and megaphone acetate molecules are ] and the reported extraction and synthesis procedures yielded their ]s.<ref name=j1>{{cite journal|doi = 10.1021/jo00398a013|author1=SM Kupchan |author2=KL Stevens |author3=EA Rohlfing |author4=BR Sickles |author5=AT Sneden |author6=RW Miller |author7=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 ], 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== == References ==
{{reflist}} {{reflist}}


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