Onnamide A: Difference between revisions
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{{Chembox |
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| ImageFile = Onnamide-structure.png |
| ImageFile = Onnamide-structure.png |
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| OtherNames = (2''S'')-5-[(Diaminomethylene)amino]-2-({(2''E'',4''E'',6''E'',11''R'')-11-hydroxy-12-[(4''S'',4a''S'',6''R'',8''S'',8a''R'')-4-({(2''S'')-2-hydroxy-2-[(2''R'',5''R'',6''R'')-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2''H''-pyran-2-yl]acetyl}amino)-8-methox y-7,7-dimethylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]-2,4,6-dodecatrienoyl}amino)pentanoic acid |
| OtherNames = (2''S'')-5-[(Diaminomethylene)amino]-2-({(2''E'',4''E'',6''E'',11''R'')-11-hydroxy-12-[(4''S'',4a''S'',6''R'',8''S'',8a''R'')-4-({(2''S'')-2-hydroxy-2-[(2''R'',5''R'',6''R'')-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2''H''-pyran-2-yl]acetyl}amino)-8-methox y-7,7-dimethylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]-2,4,6-dodecatrienoyl}amino)pentanoic acid |
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|Section1 = {{Chembox Identifiers |
|Section1 = {{Chembox Identifiers |
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| CASNo = 115204-07-4 |
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| CASNo_Ref = {{Cascite|changed|CAS}} |
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| SMILES = C[C@H]1[C@H](O[C@](CC1=C)([C@@H](C(=O)N[C@@H]2[C@@H]3[C@@H]([C@H](C([C@H](O3)C[C@@H](CCC/C=C/C=C/C=C/C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)O)(C)C)OC)OCO2)O)OC)C |
| SMILES = C[C@H]1[C@H](O[C@](CC1=C)([C@@H](C(=O)N[C@@H]2[C@@H]3[C@@H]([C@H](C([C@H](O3)C[C@@H](CCC/C=C/C=C/C=C/C(=O)N[C@@H](CCCNC(=N)N)C(=O)O)O)(C)C)OC)OCO2)O)OC)C |
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| ChemSpiderID = 8548572 |
| ChemSpiderID = 8548572 |
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| PubChem = 101526809 |
| PubChem = 101526809 |
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| StdInChI=1S/C39H63N5O12/c1-23-21-39(52-7,56-25(3)24(23)2)32(47)34(48)44-35-31-30(53-22-54-35)33(51-6)38(4,5)28(55-31)20-26(45)16-13-11-9-8-10-12-14-18-29(46)43-27(36(49)50)17-15-19-42-37(40)41/h8-10,12,14,18,24-28,30-33,35,45,47H,1,11,13,15-17,19-22H2,2-7H3,(H,43,46)(H,44,48)(H,49,50)(H4,40,41,42)/b9-8+,12-10+,18-14+/t24-,25-,26-,27+,28-,30+,31+,32+,33-,35+,39-/m1/s1 |
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| StdInChIKey = YWUNVHXKGMPHDM-XTDHNIAMSA-N |
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|Section2 = {{Chembox Properties |
|Section2 = {{Chembox Properties |
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'''Onnamide A''' is a bioactive natural product found in ''Theonella swinhoei'', a species of marine sponge whose genus is well known for yielding a diverse set of biologically active natural products, including the swinholides<ref name="ref7">{{cite journal |author1=Isao Kitagawa |author2=Motomasa Kobayashi |author3=Taketo Katori |author4=Megumi Yamashita |author5=Junichi Tanaka |author6=Mitsunobu Doi |author7=Toshimasa Ishida |title=Absolute stereostructure of swinholide A; a potent cytotoxic macrolide from the Okinawan marine sponge Theonella swinhoei |journal=J. Am. Chem. Soc. |volume=112 |issue=9 |pages=3710–3712 |year=1990 |doi=10.1021/ja00165a094}}</ref> and polytheonamides.<ref name="ref6">{{cite journal |author1=Micheal C. Wilson |author2=Tetsushi Mori |author3=Christian Rückert |author4=Agustinus R. Uria |author5=Maximilian J. Helf |author6=Kentaro Takada, Christine Gernert |author7=Ursula A. E. Steffens |author8=Nina Heycke |author9=Susanne Schmitt |author10=Christian Rinke |author11=Eric J. N. Helfrich |author12=Alexander O. Brachmann |author13=Cristian Gurgui |author14=Toshiyuki Wakimoto |author15=Matthias Kracht |author16=Max Crüsemann |author17=Ute Hentschel |author18=Ikuro Abe |author19=Shigeki Matsunaga |author20=Jörn Kalinowski |author21=Haruko Takeyama |author22=Jörn Pielic |title=An environmental bacterial taxon with a large and distinct metabolic repertoire |journal=Nature |volume=506 |issue=14 |pages=58–62 |year=2014 |doi=10.1038/nature12959 |pmid=24476823}}</ref> It bears structural similarities to the [[pederin]]s, a family of compounds known to inhibit protein synthesis in eukaryotic cells. Onnamide A and its analogues have attracted academic interest due to their cytotoxicity and potential for combating the growth and proliferation of cancer cells.<ref name="ref2">{{cite journal |author1=Kun-Hyung Lee |author2=Shinichi Nishimura |author3=Shigeki Matsunaga |author4=Nobuhiro Fusetani |author5=Sueharu Horinouchi |author6=Minoru Yoshida |title=Inhibition of protein synthesis and activation of stress-activated protein kinases by onnamide A and theopederin B, antitumor marine natural products. |journal=Cancer Sci. |volume=96 |issue=6 |pages=357–364 |year=2005 |doi=10.1111/j.1349-7006.2005.00055.x}}</ref> |
'''Onnamide A''' is a bioactive natural product found in ''Theonella swinhoei'', a species of marine sponge whose genus is well known for yielding a diverse set of biologically active natural products, including the swinholides<ref name="ref7">{{cite journal |author1=Isao Kitagawa |author2=Motomasa Kobayashi |author3=Taketo Katori |author4=Megumi Yamashita |author5=Junichi Tanaka |author6=Mitsunobu Doi |author7=Toshimasa Ishida |title=Absolute stereostructure of swinholide A; a potent cytotoxic macrolide from the Okinawan marine sponge Theonella swinhoei |journal=J. Am. Chem. Soc. |volume=112 |issue=9 |pages=3710–3712 |year=1990 |doi=10.1021/ja00165a094}}</ref> and polytheonamides.<ref name="ref6">{{cite journal |author1=Micheal C. Wilson |author2=Tetsushi Mori |author3=Christian Rückert |author4=Agustinus R. Uria |author5=Maximilian J. Helf |author6=Kentaro Takada, Christine Gernert |author7=Ursula A. E. Steffens |author8=Nina Heycke |author9=Susanne Schmitt |author10=Christian Rinke |author11=Eric J. N. Helfrich |author12=Alexander O. Brachmann |author13=Cristian Gurgui |author14=Toshiyuki Wakimoto |author15=Matthias Kracht |author16=Max Crüsemann |author17=Ute Hentschel |author18=Ikuro Abe |author19=Shigeki Matsunaga |author20=Jörn Kalinowski |author21=Haruko Takeyama |author22=Jörn Pielic |title=An environmental bacterial taxon with a large and distinct metabolic repertoire |journal=Nature |volume=506 |issue=14 |pages=58–62 |year=2014 |doi=10.1038/nature12959 |pmid=24476823|bibcode=2014Natur.506...58W |doi-access=free }}</ref> It bears structural similarities to the [[pederin]]s, a family of compounds known to inhibit protein synthesis in eukaryotic cells. Onnamide A and its analogues have attracted academic interest due to their cytotoxicity and potential for combating the growth and proliferation of cancer cells.<ref name="ref2">{{cite journal |author1=Kun-Hyung Lee |author2=Shinichi Nishimura |author3=Shigeki Matsunaga |author4=Nobuhiro Fusetani |author5=Sueharu Horinouchi |author6=Minoru Yoshida |title=Inhibition of protein synthesis and activation of stress-activated protein kinases by onnamide A and theopederin B, antitumor marine natural products. |journal=Cancer Sci. |volume=96 |issue=6 |pages=357–364 |year=2005 |doi=10.1111/j.1349-7006.2005.00055.x|pmid=15958059 |doi-access=free |pmc=11158271 }}</ref> |
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==History== |
==History== |
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Onnamide A was first isolated in 1988 from ''Theonella spp.,'' a genus of marine sponges residing off the coast of [[Okinawa]], [[Japan]],<ref name="ref1">{{cite journal |author1=Shinichi Sakemi |author2=Toshio Ichiba |author3=Shigeo Kohmoto |author4=Gabriel Saucy |author5=Tatsuo Higa |title=Isolation and structure elucidation of onnamide A, a new bioactive metabolite of a marine sponge, Theonella sp. |journal=J. Am. Chem. Soc. |volume=110 |issue=14 |pages=4851–4853 |year=1988 |doi=10.1111/j.1349-7006.2005.00055.x}}</ref> as part of a bioassay aimed at discovering novel marine natural products possessing antiviral activity. Eight analogues possessing similar structure, as well as cytotoxicity were reported in 1992. |
Onnamide A was first isolated in 1988 from ''Theonella spp.,'' a genus of marine sponges residing off the coast of [[Okinawa Island|Okinawa]], [[Japan]],<ref name="ref1">{{cite journal |author1=Shinichi Sakemi |author2=Toshio Ichiba |author3=Shigeo Kohmoto |author4=Gabriel Saucy |author5=Tatsuo Higa |title=Isolation and structure elucidation of onnamide A, a new bioactive metabolite of a marine sponge, Theonella sp. |journal=J. Am. Chem. Soc. |volume=110 |issue=14 |pages=4851–4853 |year=1988 |doi=10.1111/j.1349-7006.2005.00055.x|pmid=15958059 |s2cid=30688113 |doi-access=free |pmc=11158271 }}</ref> as part of a bioassay aimed at discovering novel marine natural products possessing antiviral activity. Eight analogues possessing similar structure, as well as cytotoxicity were reported in 1992. |
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==Structure== |
==Structure== |
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Onnamide A is a complex biomolecule with a 39 unique carbon atoms and 11 degrees of unsaturation. Its core contains three rings, two of which comprise a dimeric [[lactone]] structure. It contains a long side chain that has a three conjugated ''trans-'' olefins that connects to an amide bond, terminating in an [[arginine]] residue. The stereochemical assignments of onnamide A have been extensively characterized by experimental and advanced [[Nuclear magnetic resonance|NMR]] studies.<ref name="ref1" /><ref name="ref3">{{cite journal |author1=Yoshinari Miyata |author2=Shigeki Matsunaga |title=Structure elucidation of 21,22-dihydroxyonnamides A1–A4 from the marine sponge Theonella swinhoei: an empirical rule to assign the relative stereochemistry of linear 1,5-diols. |journal=Tetrahedron Lett. |volume=49 |pages=6334–6336 |year=2008 |doi=10.1016/j.tetlet.2008.08.057}}</ref> |
Onnamide A is a complex biomolecule with a 39 unique carbon atoms and 11 degrees of unsaturation. Its core contains three rings, two of which comprise a dimeric [[lactone]] structure. It contains a long side chain that has a three conjugated ''trans-'' olefins that connects to an amide bond, terminating in an [[arginine]] residue. The stereochemical assignments of onnamide A have been extensively characterized by experimental and advanced [[Nuclear magnetic resonance|NMR]] studies.<ref name="ref1" /><ref name="ref3">{{cite journal |author1=Yoshinari Miyata |author2=Shigeki Matsunaga |title=Structure elucidation of 21,22-dihydroxyonnamides A1–A4 from the marine sponge Theonella swinhoei: an empirical rule to assign the relative stereochemistry of linear 1,5-diols. |journal=Tetrahedron Lett. |volume=49 |issue=44 |pages=6334–6336 |year=2008 |doi=10.1016/j.tetlet.2008.08.057}}</ref> |
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==Biosynthesis== |
==Biosynthesis== |
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[[File:Onnamide.png|1200px|proposed biosynthetic pathway for onnamide A via PKS-NRPS, showing polyketide and non-ribosomal polypeptide features]] |
[[File:Onnamide.png|1200px|proposed biosynthetic pathway for onnamide A via PKS-NRPS, showing polyketide and non-ribosomal polypeptide features]] |
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Genomic studies suggest strong homology with ''Ped'' genes, which encode the production of [[pederin]]s, structurally similar compounds synthesized by bacterial endosymbionts of ''[[Paederus]]'' beetles. This suggests that onnamide A is actually the product of bacterial [[endosymbiont]]s of the marine sponges from which the compound was first isolated. |
Genomic studies suggest strong homology with ''Ped'' genes, which encode the production of [[pederin]]s, structurally similar compounds synthesized by bacterial endosymbionts of ''[[Paederus]]'' beetles. This suggests that onnamide A is actually the product of bacterial [[endosymbiont]]s of the marine sponges from which the compound was first isolated. Thus, the biosynthetic pathway of onnamide A is envisioned to undertake analogous steps as those that lead to pederin, utilizing a prokaryotic PKS-NRPS system.<ref name="ref4">{{cite journal |author1=Jörn Piel |author2=Dequan Hui |author3=Gaiping Wen |author4=Daniel Butzke |author5=Matthias Platzer |author6=Nobuhiro Fusetani |author7=Shigeki Matsunaga |title=Antitumor polyketide biosynthesis by an uncultivated bacterial symbiont of the marine sponge Theonella swinhoei |journal=Proc. Natl. Acad. Sci. |volume=101 |issue=46 |pages=16222–16227 |year=2004 |doi=10.1073/pnas.0405976101|pmid=15520376 |pmc=528957 |bibcode=2004PNAS..10116222P |doi-access=free }}</ref> |
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== Cytotoxicity == |
== Cytotoxicity == |
Latest revision as of 15:00, 14 September 2024
Names | |
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Other names
(2S)-5-[(Diaminomethylene)amino]-2-({(2E,4E,6E,11R)-11-hydroxy-12-[(4S,4aS,6R,8S,8aR)-4-({(2S)-2-hydroxy-2-[(2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylenetetrahydro-2H-pyran-2-yl]acetyl}amino)-8-methox y-7,7-dimethylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]-2,4,6-dodecatrienoyl}amino)pentanoic acid
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Identifiers | |
3D model (JSmol)
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ChemSpider | |
PubChem CID
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Properties | |
C39H63N5O12 | |
Molar mass | 793.956 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Onnamide A is a bioactive natural product found in Theonella swinhoei, a species of marine sponge whose genus is well known for yielding a diverse set of biologically active natural products, including the swinholides[1] and polytheonamides.[2] It bears structural similarities to the pederins, a family of compounds known to inhibit protein synthesis in eukaryotic cells. Onnamide A and its analogues have attracted academic interest due to their cytotoxicity and potential for combating the growth and proliferation of cancer cells.[3]
History
[edit]Onnamide A was first isolated in 1988 from Theonella spp., a genus of marine sponges residing off the coast of Okinawa, Japan,[4] as part of a bioassay aimed at discovering novel marine natural products possessing antiviral activity. Eight analogues possessing similar structure, as well as cytotoxicity were reported in 1992.
Structure
[edit]Onnamide A is a complex biomolecule with a 39 unique carbon atoms and 11 degrees of unsaturation. Its core contains three rings, two of which comprise a dimeric lactone structure. It contains a long side chain that has a three conjugated trans- olefins that connects to an amide bond, terminating in an arginine residue. The stereochemical assignments of onnamide A have been extensively characterized by experimental and advanced NMR studies.[4][5]
Biosynthesis
[edit]Genomic studies suggest strong homology with Ped genes, which encode the production of pederins, structurally similar compounds synthesized by bacterial endosymbionts of Paederus beetles. This suggests that onnamide A is actually the product of bacterial endosymbionts of the marine sponges from which the compound was first isolated. Thus, the biosynthetic pathway of onnamide A is envisioned to undertake analogous steps as those that lead to pederin, utilizing a prokaryotic PKS-NRPS system.[6]
Cytotoxicity
[edit]Onnamide A inhibits protein synthesis in cell lines, leading to induction of stress-activated protein kinases apoptosis in the affected cell.[3] Its derivatives have been found to be highly toxic towards leukemic cells of the P388 cell line.[7]
See also
[edit]References
[edit]- ^ Isao Kitagawa; Motomasa Kobayashi; Taketo Katori; Megumi Yamashita; Junichi Tanaka; Mitsunobu Doi; Toshimasa Ishida (1990). "Absolute stereostructure of swinholide A; a potent cytotoxic macrolide from the Okinawan marine sponge Theonella swinhoei". J. Am. Chem. Soc. 112 (9): 3710–3712. doi:10.1021/ja00165a094.
- ^ Micheal C. Wilson; Tetsushi Mori; Christian Rückert; Agustinus R. Uria; Maximilian J. Helf; Kentaro Takada, Christine Gernert; Ursula A. E. Steffens; Nina Heycke; Susanne Schmitt; Christian Rinke; Eric J. N. Helfrich; Alexander O. Brachmann; Cristian Gurgui; Toshiyuki Wakimoto; Matthias Kracht; Max Crüsemann; Ute Hentschel; Ikuro Abe; Shigeki Matsunaga; Jörn Kalinowski; Haruko Takeyama; Jörn Pielic (2014). "An environmental bacterial taxon with a large and distinct metabolic repertoire". Nature. 506 (14): 58–62. Bibcode:2014Natur.506...58W. doi:10.1038/nature12959. PMID 24476823.
- ^ a b Kun-Hyung Lee; Shinichi Nishimura; Shigeki Matsunaga; Nobuhiro Fusetani; Sueharu Horinouchi; Minoru Yoshida (2005). "Inhibition of protein synthesis and activation of stress-activated protein kinases by onnamide A and theopederin B, antitumor marine natural products". Cancer Sci. 96 (6): 357–364. doi:10.1111/j.1349-7006.2005.00055.x. PMC 11158271. PMID 15958059.
- ^ a b Shinichi Sakemi; Toshio Ichiba; Shigeo Kohmoto; Gabriel Saucy; Tatsuo Higa (1988). "Isolation and structure elucidation of onnamide A, a new bioactive metabolite of a marine sponge, Theonella sp". J. Am. Chem. Soc. 110 (14): 4851–4853. doi:10.1111/j.1349-7006.2005.00055.x. PMC 11158271. PMID 15958059. S2CID 30688113.
- ^ Yoshinari Miyata; Shigeki Matsunaga (2008). "Structure elucidation of 21,22-dihydroxyonnamides A1–A4 from the marine sponge Theonella swinhoei: an empirical rule to assign the relative stereochemistry of linear 1,5-diols". Tetrahedron Lett. 49 (44): 6334–6336. doi:10.1016/j.tetlet.2008.08.057.
- ^ Jörn Piel; Dequan Hui; Gaiping Wen; Daniel Butzke; Matthias Platzer; Nobuhiro Fusetani; Shigeki Matsunaga (2004). "Antitumor polyketide biosynthesis by an uncultivated bacterial symbiont of the marine sponge Theonella swinhoei". Proc. Natl. Acad. Sci. 101 (46): 16222–16227. Bibcode:2004PNAS..10116222P. doi:10.1073/pnas.0405976101. PMC 528957. PMID 15520376.
- ^ Shigeki Matsunaga; Nobuhiro Fusetani; Youichi Nakao (1992). "Eight New Cytotoxic Metabolites Closely Related to Onnamide A from Two Marine Sponges of the Genus Theonella". Tetrahedron. 48 (39): 8369–8376. doi:10.1016/S0040-4020(01)86585-6.