37:
24:
385:
468:
in 1969, brevianamide A has shown insecticidal activity. Further studies showed that a minor secondary metabolite, brevianamide B, has an epimeric center at the spiro-indoxyl quaternary center. Both were found to fluoresce under long-wave ultraviolet radiation. Furthermore, under irradaton,
651:
Paterson, R. R. M.; Simmonds, M. J. S.; Kemmelmeier, C.; Blaney, W. M. (1990). "Effects of
Brevianamide A, its photolysis product brevianamide D, and ochratoxin A from two Penicillium strains on the insect pests Spodoptera frugiperda and Heliothis virescens".
865:
Schkeryantz, Jeffrey M.; Woo, Jonathan C. G.; Siliphaivanh, Phieng; Depew, Kristopher M.; Danishefsky, Samuel J. (1999). "Total
Synthesis of Gypsetin, Deoxybrevianamide E, Brevianamide E, and Tryprostatin B: Novel Constructions of 2,3-Disubstituted Indoles".
565:
sp. However, some insecticidal activity has been shown in one study, possibly showing some use as an insecticide for food crops. In mammalian (mice lung cell) studies, brevianamide A has shown to induce cytoxicity in cells. Furthermore,
185:
193:
760:
Maiya, S.; Grundmann, A.; Li, S. M. & Turner, G. (2006). "The fumitremorgin gene cluster of
Aspergillus fumigatus: identification of a gene encoding brevianamide F synthetase".
398:
803:
Bringmann G, Lang G, Steffens S, Schaumann K (2004). "Petrosifungins A and B, novel cyclodepsipeptides from a sponge-derived strain of
Penicillium brevicompactum".
838:
Williams, Robert M.; Glinka, Tomasz; Kwast, Ewa; Coffman, Hazel; Stille, James K. (1990). "Asymmetric, stereocontrolled total synthesis of (-)-brevianamide B".
719:"Inflammatory and Cytotoxic Responses in Mouse Lungs Exposed to Purified Toxins from Building Isolated Penicillium brevicompactum Dierckx and P. chrysogenum"
299:
679:
Williams RM, Cox RJ (2003). "Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report".
575:
611:
Borthwick AD (2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal
Chemistry, and Bioactive Natural Products".
405:
267:
571:
920:
Zhao, Liang; May, Jonathan P.; Huang, Jack; Perrin, David M. (2012). "Stereoselective
Synthesis of Brevianamide E".
971:
961:
976:
966:
893:
Kametani, Tetsuji; Kanaya, Naoaki; Ihara, Masataka (1980). "Asymmetric total synthesis of brevianamide E".
723:
429:
53:
425:
445:
141:
785:
937:
820:
777:
742:
696:
628:
449:
221:
213:
929:
902:
875:
847:
812:
769:
732:
688:
661:
620:
327:
284:
276:
159:
151:
506:
421:
509:
of several brevianamides have been reported, for brevianamide-B and for brevianamide-E.
452:
that contain a bicyclodiazoctane ring system. One of the major secondary metabolites in
591:
376:
665:
955:
579:
470:
247:
789:
582:(IL-6). Therefore, brevianamide A may not be a suitable insecticide in food crops.
482:
255:
717:
Thomas G. Rand; S. Giles; J. Flemming; J. David Miller & Eva
Puniani (2005).
567:
485:
has not been conclusively elucidated, brevianamide A and B are constructed from
440:
434:
486:
361:
204:
737:
718:
36:
23:
941:
824:
781:
773:
746:
700:
632:
312:(Brevianamid B): O=C12(NC3=O)C4(C(C)(C)2()C53N1CCC5)C(C6=CC=CC=C6N4)=O
307:(Brevianamid A): O=C12(NC3=O)C4(C(C)(C)2()C53N1CCC5)C(C6=CC=CC=C6N4)=O
109:)-8,8-Dimethyl-2,3,8a,9-tetrahydrospiroindolizine-7,2'-indoline]-3',5,10(1
76:)-8,8-Dimethyl-2,3,8a,9-tetrahydrospiroindolizine-7,2'-indoline]-3',5,10(1
494:
906:
851:
490:
234:
933:
879:
816:
692:
624:
456:
spores, they are responsible for inflammatory response in lung cells.
375:
Except where otherwise noted, data are given for materials in their
192:
184:
173:
537:
were negative. Also, no inhibitory action was shown against
393:
712:
710:
254:
246:
158:
150:
424:that belong to a class of naturally occurring
8:
517:Tests for antibiotic effectiveness against
646:
644:
642:
220:
212:
15:
736:
283:
275:
895:Journal of the American Chemical Society
868:Journal of the American Chemical Society
840:Journal of the American Chemical Society
603:
304:
7:
237:
14:
576:macrophage inflammatory protein-2
469:brevianamide A has been shown to
383:
345:
339:
35:
22:
379:(at 25 °C , 100 kPa).
351:
333:
1:
666:10.1016/S0953-7562(10)80017-6
129:Brevianamid A; Brevianamid B
805:Journal of Natural Products
572:tumor necrosis factor-alpha
444:. Structurally similar to
993:
570:showed elevated levels of
464:Originally isolated from
448:, they are a small class
373:
320:
295:
134:
126:
52:
47:
34:
21:
774:10.1002/cbic.200600003
724:Toxicological Sciences
432:of fungi in the genus
288: (Brevianamide B)
280: (Brevianamide A)
259: (Brevianamide B)
251: (Brevianamide A)
225: (Brevianamide B)
217: (Brevianamide A)
191:(Brevianamid B):
183:(Brevianamid A):
738:10.1093/toxsci/kfi223
466:Pennicillum compactum
430:secondary metabolites
426:2,5-diketopiperazines
163: (Brevianamid B)
155: (Brevianamid A)
907:10.1021/ja00531a061
874:(51): 11964–11975.
852:10.1021/ja00158a048
513:Biological activity
473:to brevianamide B.
369: g·mol
90:Brevianamide B: (2
18:
406:Infobox references
57:Brevianamide A: (2
16:
972:Diketopiperazines
934:10.1021/ol202880y
901:(11): 3974–3975.
880:10.1021/ja9925249
817:10.1021/np034015x
693:10.1021/ar020229e
625:10.1021/cr200398y
414:Chemical compound
412:
411:
194:Interactive image
186:Interactive image
984:
962:Indole alkaloids
946:
945:
917:
911:
910:
890:
884:
883:
862:
856:
855:
835:
829:
828:
800:
794:
793:
768:(7): 1062–1069.
757:
751:
750:
740:
714:
705:
704:
676:
670:
669:
648:
637:
636:
619:(7): 3641–3716.
613:Chemical Reviews
608:
422:indole alkaloids
396:
390:
387:
386:
368:
353:
347:
341:
335:
328:Chemical formula
287:
279:
258:
250:
239:
224:
216:
196:
188:
162:
154:
93:
60:
39:
26:
19:
992:
991:
987:
986:
985:
983:
982:
981:
977:Total synthesis
967:Spiro compounds
952:
951:
950:
949:
922:Organic Letters
919:
918:
914:
892:
891:
887:
864:
863:
859:
837:
836:
832:
802:
801:
797:
759:
758:
754:
716:
715:
708:
678:
677:
673:
650:
649:
640:
610:
609:
605:
600:
588:
515:
507:total synthesis
503:
501:Total synthesis
479:
462:
446:paraherquamides
415:
408:
403:
402:
401: ?)
392:
388:
384:
380:
366:
356:
350:
344:
338:
330:
316:
313:
308:
303:
302:
291:
262:
240:
228:
199:
177:
166:
144:
130:
122:
91:
89:
58:
43:
40:
30:
27:
12:
11:
5:
990:
988:
980:
979:
974:
969:
964:
954:
953:
948:
947:
912:
885:
857:
846:(2): 808–821.
830:
811:(3): 311–315.
795:
752:
731:(1): 213–222.
706:
687:(2): 127–139.
681:Acc. Chem. Res
671:
660:(4): 538–542.
638:
602:
601:
599:
596:
595:
594:
592:Brevianamide F
587:
584:
555:F. moniliforme
551:F. graminearum
514:
511:
502:
499:
478:
475:
461:
458:
413:
410:
409:
404:
382:
381:
377:standard state
374:
371:
370:
364:
358:
357:
354:
348:
342:
336:
331:
326:
323:
322:
318:
317:
315:
314:
311:
309:
306:
298:
297:
296:
293:
292:
290:
289:
281:
272:
270:
264:
263:
261:
260:
252:
243:
241:
233:
230:
229:
227:
226:
218:
209:
207:
201:
200:
198:
197:
189:
180:
178:
171:
168:
167:
165:
164:
156:
147:
145:
140:
137:
136:
132:
131:
128:
124:
123:
56:
50:
49:
45:
44:
42:Brevianamide B
41:
32:
31:
29:Brevianamide A
28:
13:
10:
9:
6:
4:
3:
2:
989:
978:
975:
973:
970:
968:
965:
963:
960:
959:
957:
943:
939:
935:
931:
927:
923:
916:
913:
908:
904:
900:
896:
889:
886:
881:
877:
873:
869:
861:
858:
853:
849:
845:
841:
834:
831:
826:
822:
818:
814:
810:
806:
799:
796:
791:
787:
783:
779:
775:
771:
767:
763:
756:
753:
748:
744:
739:
734:
730:
726:
725:
720:
713:
711:
707:
702:
698:
694:
690:
686:
682:
675:
672:
667:
663:
659:
655:
647:
645:
643:
639:
634:
630:
626:
622:
618:
614:
607:
604:
597:
593:
590:
589:
585:
583:
581:
580:interleukin 6
578:(MIP-2), and
577:
573:
569:
564:
560:
556:
552:
548:
544:
540:
536:
535:P. aeruginosa
532:
528:
524:
520:
512:
510:
508:
500:
498:
496:
492:
488:
484:
476:
474:
472:
467:
459:
457:
455:
451:
447:
443:
442:
437:
436:
431:
427:
423:
419:
418:Brevianamides
407:
400:
395:
378:
372:
365:
363:
360:
359:
332:
329:
325:
324:
319:
310:
305:
301:
294:
286:
282:
278:
274:
273:
271:
269:
266:
265:
257:
253:
249:
245:
244:
242:
236:
232:
231:
223:
219:
215:
211:
210:
208:
206:
203:
202:
195:
190:
187:
182:
181:
179:
175:
170:
169:
161:
157:
153:
149:
148:
146:
143:
139:
138:
133:
125:
120:
116:
112:
108:
104:
100:
96:
87:
83:
79:
75:
71:
67:
63:
55:
51:
46:
38:
33:
25:
20:
17:Brevianamide
928:(1): 90–93.
925:
921:
915:
898:
894:
888:
871:
867:
860:
843:
839:
833:
808:
804:
798:
765:
761:
755:
728:
722:
684:
680:
674:
657:
653:
616:
612:
606:
568:ELISA assays
563:Cladosporium
562:
558:
554:
550:
547:P. crustosum
546:
542:
538:
534:
530:
526:
522:
518:
516:
504:
483:biosynthesis
480:
477:Biosynthesis
465:
463:
453:
439:
433:
428:produced as
417:
416:
135:Identifiers
127:Other names
118:
114:
110:
106:
102:
98:
94:
85:
81:
77:
73:
69:
65:
61:
762:ChemBioChem
527:B. subtilis
454:Penicillium
441:Aspergillus
435:Penicillium
321:Properties
54:IUPAC names
956:Categories
654:Mycol. Res
598:References
523:A. fecalis
487:tryptophan
481:While the
362:Molar mass
285:RTJ0M35T4U
277:L2S5E3NBIH
205:ChemSpider
172:3D model (
160:38136-92-4
152:23402-09-7
142:CAS Number
574:(TNF-A),
561:sp., and
559:Alternara
543:A. flavis
531:S. aureus
493:, and an
471:isomerize
450:compounds
942:22126228
825:15043401
790:28967158
782:16755625
747:15958659
701:12589698
633:22575049
586:See also
539:A. niger
495:isoprene
248:25163935
222:21447236
214:21447237
121:)-trione
88:)-trione
519:E. coli
491:proline
460:History
399:what is
397: (
367:365.433
235:PubChem
940:
823:
788:
780:
745:
699:
631:
533:, and
497:unit.
394:verify
391:
300:SMILES
48:Names
786:S2CID
256:99771
174:JSmol
938:PMID
821:PMID
778:PMID
743:PMID
697:PMID
629:PMID
505:The
438:and
420:are
268:UNII
930:doi
903:doi
899:102
876:doi
872:121
848:doi
844:112
813:doi
770:doi
733:doi
689:doi
662:doi
621:doi
617:112
238:CID
105:,9a
101:,8a
97:,5a
72:,9a
68:,8a
64:,5a
958::
936:.
926:14
924:.
897:.
870:.
842:.
819:.
809:67
807:.
784:.
776:.
764:.
741:.
729:87
727:.
721:.
709:^
695:.
685:36
683:.
658:94
656:.
641:^
627:.
615:.
557:,
553:,
549:,
545:,
541:,
529:,
525:,
521:,
489:,
343:23
337:21
117:,8
113:,6
84:,8
80:,6
944:.
932::
909:.
905::
882:.
878::
854:.
850::
827:.
815::
792:.
772::
766:7
749:.
735::
703:.
691::
668:.
664::
635:.
623::
389:N
355:3
352:O
349:3
346:N
340:H
334:C
176:)
119:H
115:H
111:H
107:R
103:S
99:R
95:S
92:′
86:H
82:H
78:H
74:R
70:S
66:R
62:R
59:′
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
