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{{Chembox {{Chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 416430236
| Watchedfields = changed
⚫ | verifiedrevid = 432005445
| ImageFile =Brevianamide A.svg | ImageFile =Brevianamide A.svg
| ImageSize =200px | ImageSize =
| ImageCaption = Brevianamide A | ImageCaption = Brevianamide A
| ImageFile1 =Brevianamide B.svg | ImageFile1 =Brevianamide B.svg
| ImageSize1 =200px | ImageSize1 =
| ImageCaption1 = Brevianamide B | ImageCaption1 = Brevianamide B
| IUPACName =Brevianamide A: (2'R,5aR,8aS,9aR)-8,8-dimethyl-2,3,8a,9-tetrahydrospiroindolizine-7,2'-indoline]-3',5,10(1H,6H,8H)-trione<br>Brevianamide B: (2'S,5aR,8aS,9aR)-8,8-dimethyl-2,3,8a,9-tetrahydrospiroindolizine-7,2'-indoline]-3',5,10(1H,6H,8H)-trione | IUPACName =Brevianamide A: (2{{prime}}''R'',5a''R'',8a''S'',9a''R'')-8,8-Dimethyl-2,3,8a,9-tetrahydrospiroindolizine-7,2'-indoline]-3',5,10(1''H'',6''H'',8''H'')-trione<br>Brevianamide B: (2{{prime}}''S'',5a''R'',8a''S'',9a''R'')-8,8-Dimethyl-2,3,8a,9-tetrahydrospiroindolizine-7,2'-indoline]-3',5,10(1''H'',6''H'',8''H'')-trione
⚫ | OtherNames = Brevianamid A; Brevianamid B
| IUPACName_hidden = yes
⚫ | OtherNames =Brevianamid A and brevianamid B
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| CASNo =23402-09-7 | CASNo =23402-09-7
| CASNo_Comment = (Brevianamid A) | CASNo_Comment = (Brevianamid A)
| CASNo_Ref = {{cascite|correct|CAS}} | CASNo_Ref = {{cascite|correct|CAS}}
| CASNo1 =38136-92-4 | CASNo1 =38136-92-4
| CASNo1_Comment = (Brevianamid B) | CASNo1_Comment = (Brevianamid B)
| CASNo1_Ref = {{cascite|correct|CAS}} | CASNo1_Ref = {{cascite|correct|CAS}}
| PubChem = | PubChem = 25163935
| PubChem_Comment = (Brevianamide A)
⚫ | SMILES = O=C12(NC3=O)C4(C(C)(C)2()C53N1CCC5)C(C6=CC=CC=C6N4)=O
| PubChem1 =99771
⚫ | SMILES_Comment = (Brevianamid A)
| PubChem1_Comment = (Brevianamide B)
⚫ | SMILES1 = O=C12(NC3=O)C4(C(C)(C)2()C53N1CCC5)C(C6=CC=CC=C6N4)=O
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | SMILES1_Comment = (Brevianamid B)}}
| UNII = L2S5E3NBIH
| UNII_Comment = (Brevianamide A)
| UNII1_Ref = {{fdacite|correct|FDA}}
| UNII1 = RTJ0M35T4U
| UNII1_Comment = (Brevianamide B)
⚫ | SMILES = O=C12(NC3=O)C4(C(C)(C)2()C53N1CCC5)C(C6=CC=CC=C6N4)=O
⚫ | SMILES_Comment = (Brevianamid A)
⚫ | SMILES1 = O=C12(NC3=O)C4(C(C)(C)2()C53N1CCC5)C(C6=CC=CC=C6N4)=O
⚫ | SMILES1_Comment = (Brevianamid B)
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 21447237
| ChemSpiderID_Comment = (Brevianamide A)
| ChemSpiderID1_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID1 = 21447236
| ChemSpiderID1_Comment = (Brevianamide B)
}}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=21 | H=23 | N=3 | O=3 | C=21 | H=23 | N=3 | O=3
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
| Solubility = }} | Solubility = }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| MainHazards = | MainHazards =
| FlashPt = | FlashPt =
| Autoignition = }} | AutoignitionPt = }}
}} }}


'''Brevianamides''' are a class of ]s produced as ] of fungi in the genus '']'' and '']''.<ref name=Paterson>{{cite journal | author = Paterson, R. R. M.; Simmonds, M. J. S.; Kemmelmeier, C.; Blaney, W. M. | year = 1990 | title = 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 | journal = Mycol. Res. | volume = 94 | pages = 538–542 | doi = 10.1016/S0953-7562(10)80017-6 | issue = 4}}</ref> Structurally similar to ]s, they are a small class ] that contain a bicyclodiazoctane ring system.<ref>{{cite journal | author = Williams RM, Cox RJ | year = 2003 | title = Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report | journal = Acc. Chem. Res. | volume = 36 | issue = 2 | pages = 127–139 | doi = 10.1021/ar020229e | pmid = 12589698}}</ref> One of the major secondary metabolites in ''Penicillium'' spores, they are responsible for inflammatory response in lung cells.<ref name="Thomas G. Rand 2005">{{cite journal | author = Thomas G. Rand, S. Giles, J. Flemming, J. David Miller, and Eva Puniani | year = 2005 | title = Inflammatory and Cytotoxic Responses in Mouse Lungs Exposed to Purified Toxins from Building Isolated Penicillium brevicompactum Dierckx and P. chrysogenum | journal = Toxicological Sciences | volume = 87 | issue = 1 | pages = 213–222 | doi = 10.1093/toxsci/kfi223 | pmid = 15958659}}</ref> '''Brevianamides''' are ]s that belong to a class of naturally occurring ]<ref>{{Cite journal | title = 2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products | author = Borthwick AD | journal = Chemical Reviews | year = 2012 | volume = 112 | issue = 7 | pages = 3641–3716 | doi = 10.1021/cr200398y | pmid = 22575049}}</ref> produced as ] of fungi in the genus '']'' and '']''.<ref name=Paterson>{{cite journal | author = Paterson, R. R. M. | author2 = Simmonds, M. J. S. | author3 = Kemmelmeier, C. | author4 = Blaney, W. M. | year = 1990 | title = 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 | journal = Mycol. Res. | volume = 94 | pages = 538–542 | doi = 10.1016/S0953-7562(10)80017-6 | issue = 4}}</ref> Structurally similar to ]s, they are a small class ] that contain a bicyclodiazoctane ring system.<ref>{{cite journal | vauthors = Williams RM, Cox RJ | year = 2003 | title = Paraherquamides, brevianamides, and asperparalines: laboratory synthesis and biosynthesis. An interim report | journal = Acc. Chem. Res. | volume = 36 | issue = 2 | pages = 127–139 | doi = 10.1021/ar020229e | pmid = 12589698}}</ref> One of the major secondary metabolites in ''Penicillium'' spores, they are responsible for inflammatory response in lung cells.<ref name="Thomas G. Rand 2005">{{cite journal | author = Thomas G. Rand | author2 = S. Giles | author3 = J. Flemming| author4 = J. David Miller | author5 = Eva Puniani | name-list-style = amp | year = 2005 | title = Inflammatory and Cytotoxic Responses in Mouse Lungs Exposed to Purified Toxins from Building Isolated Penicillium brevicompactum Dierckx and P. chrysogenum | journal = ] | volume = 87 | issue = 1 | pages = 213–222 | doi = 10.1093/toxsci/kfi223 | pmid = 15958659| doi-access = free }}</ref>


==History== ==History==
Originally isolated from ''Pennicillum compactum'' in 1969, brevianamide A has shown insecticidal activity.<ref name=Paterson/><ref>{{cite journal | author = Maiya, S., Grundmann, A., Li, S. M. & Turner, G. | year = 2006 | title = The fumitremorgin gene cluster of Aspergillus fumigatus: identification of a gene encoding brevianamide F synthetase | journal = ChemBioChem | volume = 7 | pages = 1062–1069 | doi = 10.1002/cbic.200600003 | pmid = 16755625 | issue = 7}}</ref> 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, brevianamide A has been shown to ] to brevianamide B. Originally isolated from ''Pennicillum compactum'' in 1969, brevianamide A has shown insecticidal activity.<ref name=Paterson/><ref>{{cite journal | author = Maiya, S. | author2 = Grundmann, A. | author3 = Li, S. M. | author4 = Turner, G. | name-list-style = amp | year = 2006 | title = The fumitremorgin gene cluster of Aspergillus fumigatus: identification of a gene encoding brevianamide F synthetase | journal = ChemBioChem | volume = 7 | pages = 1062–1069 | doi = 10.1002/cbic.200600003 | pmid = 16755625 | issue = 7| s2cid = 28967158 }}</ref> 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, brevianamide A has been shown to ] to brevianamide B.


==Biosynthesis== == Biosynthesis ==
While the ] has not been conclusively elucidated, brevianamide A and B are constructed from ], ], and an ] unit.<ref>{{cite journal | author = Bringmann G, Lang G, Steffens S, Schaumann K. | year = 2004 | title = Petrosifungins A and B, novel cyclodepsipeptides from a sponge-derived strain of Penicillium brevicompactum | journal = Journal of Natural Products | volume = 67 | issue = 3 | pages = 311–315 | doi = 10.1021/np034015x | pmid = 15043401}}</ref> While the ] has not been conclusively elucidated, brevianamide A and B are constructed from ], ], and an ] unit.<ref>{{cite journal | vauthors = Bringmann G, Lang G, Steffens S, Schaumann K | year = 2004 | title = Petrosifungins A and B, novel cyclodepsipeptides from a sponge-derived strain of Penicillium brevicompactum | journal = Journal of Natural Products | volume = 67 | issue = 3 | pages = 311–315 | doi = 10.1021/np034015x | pmid = 15043401}}</ref>


==Biological activity== ==Total synthesis==
The ] of several brevianamides have been reported, for brevianamide-B <ref>{{Cite journal | doi = 10.1021/ja00158a048| title = Asymmetric, stereocontrolled total synthesis of (-)-brevianamide B| journal = Journal of the American Chemical Society| volume = 112| issue = 2| pages = 808–821| year = 1990| last1 = Williams| first1 = Robert M.| last2 = Glinka| first2 = Tomasz| last3 = Kwast| first3 = Ewa| last4 = Coffman| first4 = Hazel| last5 = Stille| first5 = James K.}}</ref> and for brevianamide-E.<ref>{{Cite journal | doi = 10.1021/ja9925249| title = Total Synthesis of Gypsetin, Deoxybrevianamide E, Brevianamide E, and Tryprostatin B: Novel Constructions of 2,3-Disubstituted Indoles| journal = Journal of the American Chemical Society| volume = 121| issue = 51| pages = 11964–11975| year = 1999| last1 = Schkeryantz| first1 = Jeffrey M.| last2 = Woo| first2 = Jonathan C. G.| last3 = Siliphaivanh| first3 = Phieng| last4 = Depew| first4 = Kristopher M.| last5 = Danishefsky| first5 = Samuel J.}}</ref><ref>{{Cite journal | doi = 10.1021/ja00531a061| title = Asymmetric total synthesis of brevianamide E| journal = Journal of the American Chemical Society| volume = 102| issue = 11| pages = 3974–3975| year = 1980| last1 = Kametani| first1 = Tetsuji| last2 = Kanaya| first2 = Naoaki| last3 = Ihara| first3 = Masataka}}</ref><ref>{{Cite journal | doi = 10.1021/ol202880y| title = Stereoselective Synthesis of Brevianamide E| journal = Organic Letters| volume = 14| pages = 90–93| year = 2012| last1 = Zhao| first1 = Liang| last2 = May| first2 = Jonathan P.| last3 = Huang| first3 = Jack| last4 = Perrin| first4 = David M.| issue = 1| pmid = 22126228}}</ref>
⚫ Tests for antibiotic effectiveness against ''E. coli'', ''A. fecalis'', ''B. subtilis'', ''S. aureus'', and ''P. aeruginosa'' were negative. Also, no inhibitory action was shown against ''A. niger'', ''A. flavis'', ''P. crustosum'', ''F. graminearum'', ''F. moniliforme'', ''Alternara'' sp., and ''Cladosporium'' sp. However, some insectidal activity has been shown in one study, possibly showing some use as an insecticide for food crops.<ref name=Paterson/> In mamamalian (mice lung cell) studies, brevianamide A has shown to induce cytoxicity in cells.<ref name="Thomas G. Rand 2005"/> Furthermore, ]s showed elevated levels of ] (TNF-A), ] (MIP-2), and ] (IL-6). Therefore, brevianamide A may not be a suitable insecticide in food crops.


== Biological activity ==
⚫ ==References==
⚫ Tests for antibiotic effectiveness against ''E. coli'', ''A. fecalis'', ''B. subtilis'', ''S. aureus'', and ''P. aeruginosa'' were negative. Also, no inhibitory action was shown against ''A. niger'', ''A. flavis'', ''P. crustosum'', ''F. graminearum'', ''F. moniliforme'', ''Alternara'' sp., and ''Cladosporium'' sp. However, some insecticidal activity has been shown in one study, possibly showing some use as an insecticide for food crops.<ref name=Paterson/> In mammalian (mice lung cell) studies, brevianamide A has shown to induce cytoxicity in cells.<ref name="Thomas G. Rand 2005"/> Furthermore, ]s showed elevated levels of ] (TNF-A), ] (MIP-2), and ] (IL-6). Therefore, brevianamide A may not be a suitable insecticide in food crops.
⚫ {{reflist}}


==See also==
* ]

⚫ == References ==
⚫ {{reflist}}


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