232:
24:
366:
492:
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
126:
592:
Tomioka, Kiyoshi; Kawasaki, Hisashi; Iitaka, Yoichi; Koga, Kenji (1985). "Enantiospecific total synthesis of (-)-megaphone by a highly controlled consecutive 1,4- and 1,3-asymmetric induction".
379:
649:
SM Kupchan; KL Stevens; EA Rohlfing; BR Sickles; AT Sneden; RW Miller; RF Bryan (1978). "Tumor inhibitors. 126. New cytotoxic neolignans from Aniba megaphylla Mez".
255:
InChI=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
271:
548:, using chromatography of ethanolic solution. It showed inhibitory activity against cells of crown gall tumor and human lung, breast and colon carcinomas.
1150:
1119:
1124:
23:
246:
884:
729:
386:
189:
210:
1155:
488:, oily liquid). For comparison, megaphone acetate was also produced synthetically by reacting megaphone with
1165:
1160:
986:
981:
533:
66:
36:
1079:
1075:
1071:
1067:
1063:
1059:
769:
765:
1019:
1014:
839:
722:
1009:
227:
1034:
918:
819:
92:
1029:
804:
799:
676:
Ma, WW; Kozlowski, JF; McLaughlin, JL (1991). "Bioactive neolignans from
Endlicheria dysodantha".
1104:
1089:
1024:
976:
1114:
1109:
1099:
1054:
1049:
961:
1084:
1044:
1039:
774:
693:
425:
Studies carried out in the 1960s demonstrated that an alcoholic extract of the ground root of
1145:
685:
658:
628:
601:
574:
489:
410:
294:
146:
198:
102:
834:
715:
537:
415:
231:
923:
445:
357:
605:
578:
1139:
1004:
996:
956:
913:
908:
494:
345:
941:
895:
814:
779:
525:
402:
178:
171:
422:
which gave the compound its name. Megaphone has also been prepared synthetically.
829:
824:
502:
438:
903:
854:
809:
760:
498:
442:
322:
137:
1094:
946:
933:
865:
849:
794:
784:
545:
529:
434:
419:
405:
697:
966:
951:
878:
789:
755:
689:
662:
632:
873:
844:
461:
335:
158:
747:
739:
619:
Buechi, George; Chu, Ping-Sun (1981). "The
Synthesis of Megaphone".
441:. In 1978, the active components of the extract were isolated using
356:
Except where otherwise noted, data are given for materials in their
707:
536:
and the reported extraction and synthesis procedures yielded their
125:
115:
711:
215:
565:
Zoretic, P (1983). "Total synthesis of d,l-megaphone".
540:. Megaphone acetate was also isolated from the root of
374:
79:)-6--4-methoxy-6-(prop-2-en-1-yl)cyclohex-2-en-1-one
995:
932:
894:
863:
746:
1120:Tricin 4'-O-(erythro-beta-guaiacylglyceryl) ether
532:. Megaphone and megaphone acetate molecules are
279:O=C1C=C(OC)C1(CC=C)(C)(O)C2=CC(OC)=C(OC)C(OC)=C2
177:
170:
1125:Tricin 4'-O-(threo-beta-guaiacylglyceryl) ether
101:
723:
501:solution. They have monoclinic symmetry with
56:)-7-Hydroxy-3,4,5,5′-methoxy-5′,6′-dihydro-2′
8:
730:
716:
708:
476:, oily liquid) and megaphyllone acetate (C
230:
145:
15:
448:, characterized and named as megaphone (C
197:
621:Journal of the American Chemical Society
557:
276:
251:
226:
881:(isolariciresinol-9'-rhamnopyranoside)
350:152 °C (306 °F; 425 K)
433:, growth of cells derived from human
258:Key: JCRROBQLLRCCAV-SQKDIAQBSA-N
7:
644:
642:
161:
14:
896:Mammalian lignans (enterolignans)
885:Secoisolariciresinol diglucoside
364:
306:
22:
360:(at 25 °C , 100 kPa).
312:
300:
1:
606:10.1016/S0040-4039(00)61960-3
579:10.1016/S0040-4039(00)86382-0
1151:O-methylated natural phenols
678:Journal of Natural Products
1182:
60:-8,1′-neolign-8′-en-2′-one
524:= 1.0177 nm and two
354:
287:
267:
242:
85:
65:
35:
30:
21:
542:Endlicheria dysodantha
520:= 1.1942 nm and
67:Systematic IUPAC name
840:Secoisolariciresinol
512:, lattice constants
460:, solid), megaphone
919:Hydroxymatairesinol
690:10.1021/np50076a045
663:10.1021/jo00398a013
633:10.1021/ja00400a039
594:Tetrahedron Letters
567:Tetrahedron Letters
544:, another plant of
330: g·mol
18:
987:Rhaphidecursinol B
982:Rhaphidecursinol A
977:4-O-Methylhonokiol
516:= 0.8757 nm,
387:Infobox references
16:
1133:
1132:
1060:Scutellaprostin A
573:(11): 1125–1128.
395:Chemical compound
393:
392:
211:CompTox Dashboard
127:Interactive image
1173:
766:Chamaecypanone A
732:
725:
718:
709:
702:
701:
673:
667:
666:
646:
637:
636:
616:
610:
609:
589:
583:
582:
562:
538:racemic mixtures
490:acetic anhydride
427:Aniba megaphylla
411:Aniba megaphylla
377:
371:
368:
367:
329:
314:
308:
302:
295:Chemical formula
235:
234:
219:
217:
201:
181:
174:
163:
149:
129:
105:
26:
19:
1181:
1180:
1176:
1175:
1174:
1172:
1171:
1170:
1156:Total synthesis
1136:
1135:
1134:
1129:
1020:Deoxysilydianin
1015:Deoxysilycistin
991:
928:
890:
859:
835:Podophyllotoxin
742:
736:
706:
705:
675:
674:
670:
648:
647:
640:
618:
617:
613:
591:
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586:
564:
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487:
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471:
467:
459:
455:
451:
416:flowering plant
396:
389:
384:
383:
382: ?)
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369:
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361:
327:
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305:
297:
283:
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184:
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132:
119:
108:
95:
81:
80:
61:
12:
11:
5:
1179:
1177:
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1163:
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1153:
1148:
1138:
1137:
1131:
1130:
1128:
1127:
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1117:
1112:
1107:
1102:
1097:
1092:
1087:
1082:
1057:
1052:
1047:
1042:
1037:
1032:
1027:
1022:
1017:
1012:
1010:Dehydrosilybin
1007:
1001:
999:
997:Flavonolignans
993:
992:
990:
989:
984:
979:
974:
969:
964:
959:
954:
949:
944:
938:
936:
930:
929:
927:
926:
924:Syringaresinol
921:
916:
911:
906:
900:
898:
892:
891:
889:
888:
882:
876:
870:
868:
861:
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837:
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827:
822:
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797:
792:
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777:
772:
763:
758:
752:
750:
744:
743:
737:
735:
734:
727:
720:
712:
704:
703:
668:
657:(4): 586–590.
638:
611:
600:(7): 903–906.
584:
556:
555:
553:
550:
509:
493:grown from an
485:
481:
477:
473:
469:
465:
457:
453:
449:
446:chromatography
408:obtained from
394:
391:
390:
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363:
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358:standard state
355:
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228:DTXSID80214542
223:
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10:
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3:
2:
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1126:
1123:
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1088:
1086:
1083:
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1077:
1073:
1069:
1065:
1061:
1058:
1056:
1053:
1051:
1048:
1046:
1043:
1041:
1038:
1036:
1035:Neosilyhermin
1033:
1031:
1028:
1026:
1023:
1021:
1018:
1016:
1013:
1011:
1008:
1006:
1005:Cinchonain-Ib
1003:
1002:
1000:
998:
994:
988:
985:
983:
980:
978:
975:
973:
970:
968:
965:
963:
960:
958:
957:Interiotherin
955:
953:
950:
948:
945:
943:
940:
939:
937:
935:
931:
925:
922:
920:
917:
915:
914:Lariciresinol
912:
910:
909:Enterolactone
907:
905:
902:
901:
899:
897:
893:
886:
883:
880:
877:
875:
872:
871:
869:
867:
862:
856:
853:
851:
848:
846:
843:
841:
838:
836:
833:
831:
828:
826:
823:
821:
820:Obtulignolide
818:
816:
813:
811:
808:
806:
803:
801:
798:
796:
793:
791:
788:
786:
783:
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771:
767:
764:
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757:
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751:
749:
745:
741:
733:
728:
726:
721:
719:
714:
713:
710:
699:
695:
691:
687:
684:(4): 1153–8.
683:
679:
672:
669:
664:
660:
656:
652:
645:
643:
639:
634:
630:
626:
622:
615:
612:
607:
603:
599:
595:
588:
585:
580:
576:
572:
568:
561:
558:
551:
549:
547:
546:Laurel family
543:
539:
535:
531:
527:
526:formula units
523:
519:
515:
507:
504:
500:
496:
491:
463:
447:
444:
440:
436:
432:
428:
423:
421:
420:Laurel family
417:
413:
412:
407:
404:
400:
388:
381:
376:
359:
353:
349:
347:
346:Melting point
344:
343:
339:
337:
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333:
326:
324:
321:
320:
299:
296:
292:
291:
286:
277:
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68:
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55:
51:
47:
43:
38:
34:
29:
25:
20:
1166:Plant toxins
1161:Cyclohexenes
1030:Hydnowightin
971:
942:Balanophonin
815:Matairesinol
805:Lyoniresinol
800:Isootobanone
780:Globoidnan A
681:
677:
671:
654:
651:J. Org. Chem
650:
627:(10): 2718.
624:
620:
614:
597:
593:
587:
570:
566:
560:
541:
521:
517:
513:
505:
430:
426:
424:
409:
398:
397:
86:Identifiers
76:
72:
57:
53:
49:
45:
41:
1105:Silicristin
1090:Silyamandin
1025:Hydnocarpin
830:Pluviatilol
825:Pinoresinol
503:space group
439:nasopharynx
429:inhibited,
340:1.242 g/cm
288:Properties
1140:Categories
1115:Silyhermin
1110:Silydianin
1100:Silybinome
1055:Salcolin B
1050:Salcolin A
962:Linderin A
934:Neolignans
904:Enterodiol
866:glycosides
855:Steganacin
810:Macelignan
761:Arctigenin
552:References
499:chloroform
443:silica gel
323:Molar mass
199:8J0BV7D5N9
138:ChemSpider
114:3D model (
103:64332-37-2
93:CAS Number
37:IUPAC name
17:Megaphone
1095:Silibinin
1085:Silandrin
1045:Rhodiolin
1040:Palstatin
972:Megaphone
947:Eusiderin
850:Sesamolin
795:Gummadiol
785:Gmelanone
738:Types of
530:unit cell
435:carcinoma
406:neolignan
403:cytotoxic
399:Megaphone
967:Magnolol
952:Honokiol
879:Aviculin
790:Gmelinol
775:Eudesmin
756:Arboreol
431:in vitro
1146:Lignans
874:Arctiin
864:Lignan
845:Sesamin
748:Lignans
740:lignans
698:1665173
462:acetate
437:of the
380:what is
378: (
336:Density
328:390.476
159:PubChem
696:
534:chiral
375:verify
372:
272:SMILES
179:442908
172:324150
147:391211
31:Names
887:(SDG)
495:ether
401:is a
247:InChI
116:JSmol
1078:and
768:and
694:PMID
528:per
414:, a
190:UNII
686:doi
659:doi
629:doi
625:103
602:doi
575:doi
418:of
216:EPA
162:CID
44:,5′
40:(1′
1142::
1074:,
1070:,
1066:,
1062:,
692:.
682:54
680:.
655:43
653:.
641:^
623:.
598:26
596:.
571:24
569:.
482:28
478:23
470:32
466:24
464:(C
454:30
450:22
310:30
304:22
75:,6
71:(4
52:,8
48:,7
1080:F
1076:E
1072:D
1068:C
1064:B
770:B
731:e
724:t
717:v
700:.
688::
665:.
661::
635:.
631::
608:.
604::
581:.
577::
522:c
518:b
514:a
510:1
508:2
506:P
497:-
486:7
484:O
480:H
474:7
472:O
468:H
458:6
456:O
452:H
370:N
316:6
313:O
307:H
301:C
218:)
214:(
118:)
77:R
73:R
58:H
54:S
50:R
46:R
42:R
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