Moroidin
Overview
Description
(8R,9S,12S,15S,18S,21S,27S)-21-[3-(diaminomethylideneamino)propyl]-12-(2-methylpropyl)-10,13,16,19,22,25-hexaoxo-9-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]-8,15-di(propan-2-yl)-2,11,14,17,20,23,26,30,32-nonazapentacyclo[16.14.2.13,7.129,32.04,33]hexatriaconta-1(33),3,5,7(36),29(35),30-hexaene-27-carboxylic acid is a natural product found in Dendrocnide moroides and Celosia argentea with data available.
Scientific Research Applications
Chemical Structure and Mechanism of Action
Moroidin consists of eight amino acids with unique structural features, including tryptophan side-chain cross-links. Its primary mechanism involves the inhibition of tubulin polymerization, which is crucial for cell division. By binding to tubulin, this compound disrupts the cytoskeletal structure of cancer cells, leading to cell cycle arrest and apoptosis. This mechanism is similar to that of established chemotherapeutic agents like vincristine and paclitaxel .
Cancer Treatment
This compound and its analogs, such as celogentin C, have shown promise as anti-cancer agents. Research indicates that these compounds exhibit cytotoxic effects against various cancer cell lines, including lung adenocarcinoma .
- Case Study: Lung Cancer
Pain Management
Interestingly, this compound's pain-inducing properties may also be leveraged for therapeutic purposes. Researchers propose that compounds causing pain can sometimes be used to modulate pain pathways effectively. By altering this compound's structure, it may be possible to develop a pain reliever that exhausts pain receptors or acts as an antagonist .
Inhibition of Vasculogenic Mimicry
This compound has been identified as a potential agent against vasculogenic mimicry (VM), a process utilized by glioblastoma cells to promote tumor growth and metastasis. Studies indicate that this compound inhibits VM formation in glioblastoma cells by affecting key signaling pathways (ERK/β-catenin) involved in epithelial-mesenchymal transition (EMT) .
Biosynthesis and Production Challenges
The natural extraction of this compound from Dendrocnide moroides poses significant challenges due to low yields. Recent advancements in biosynthesis have enabled researchers to produce this compound analogs in transgenic plants like tobacco and Nicotiana benthamiana. This method allows for scalable production while facilitating further research into this compound's pharmacological properties .
| Biosynthesis Method | Source Plant | Yield | Notes |
|---|---|---|---|
| Transgenic Expression | Nicotiana benthamiana | Increased yield | Enables large-scale production of this compound analogs |
| Natural Extraction | Dendrocnide moroides | Low yield (0.002% w/w) | Limited by availability and extraction difficulties |
Properties
Molecular Formula |
C47H66N14O10 |
|---|---|
Molecular Weight |
987.1 g/mol |
IUPAC Name |
(8R,9S,12S,15S,18S,21S,27S)-21-[3-(diaminomethylideneamino)propyl]-12-(2-methylpropyl)-10,13,16,19,22,25-hexaoxo-9-[[(2S)-5-oxopyrrolidine-2-carbonyl]amino]-8,15-di(propan-2-yl)-2,11,14,17,20,23,26,30,32-nonazapentacyclo[16.14.2.13,7.129,32.04,33]hexatriaconta-1(33),3,5,7(36),29(35),30-hexaene-27-carboxylic acid |
InChI |
InChI=1S/C47H66N14O10/c1-21(2)14-31-43(67)59-37(23(5)6)44(68)58-32-17-27-26-10-9-24(36(22(3)4)38(45(69)57-31)60-41(65)29-11-12-34(62)53-29)15-30(26)55-39(27)61-19-25(52-20-61)16-33(46(70)71)54-35(63)18-51-40(64)28(56-42(32)66)8-7-13-50-47(48)49/h9-10,15,19-23,28-29,31-33,36-38,55H,7-8,11-14,16-18H2,1-6H3,(H,51,64)(H,53,62)(H,54,63)(H,56,66)(H,57,69)(H,58,68)(H,59,67)(H,60,65)(H,70,71)(H4,48,49,50)/t28-,29-,31-,32-,33-,36+,37-,38-/m0/s1 |
InChI Key |
UCSHFBQCLZMAJY-QFMFBHDYSA-N |
SMILES |
CC(C)CC1C(=O)NC(C(=O)NC2CC3=C(NC4=C3C=CC(=C4)C(C(C(=O)N1)NC(=O)C5CCC(=O)N5)C(C)C)N6C=C(CC(NC(=O)CNC(=O)C(NC2=O)CCCN=C(N)N)C(=O)O)N=C6)C(C)C |
Isomeric SMILES |
CC(C)C[C@H]1C(=O)N[C@H](C(=O)N[C@H]2CC3=C(NC4=C3C=CC(=C4)[C@H]([C@@H](C(=O)N1)NC(=O)[C@@H]5CCC(=O)N5)C(C)C)N6C=C(C[C@H](NC(=O)CNC(=O)[C@@H](NC2=O)CCCN=C(N)N)C(=O)O)N=C6)C(C)C |
Canonical SMILES |
CC(C)CC1C(=O)NC(C(=O)NC2CC3=C(NC4=C3C=CC(=C4)C(C(C(=O)N1)NC(=O)C5CCC(=O)N5)C(C)C)N6C=C(CC(NC(=O)CNC(=O)C(NC2=O)CCCN=C(N)N)C(=O)O)N=C6)C(C)C |
Origin of Product |
United States |
Retrosynthesis Analysis
AI-Powered Synthesis Planning: Our tool employs the Template_relevance Pistachio, Template_relevance Bkms_metabolic, Template_relevance Pistachio_ringbreaker, Template_relevance Reaxys, Template_relevance Reaxys_biocatalysis model, leveraging a vast database of chemical reactions to predict feasible synthetic routes.
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Strategy Settings
| Precursor scoring | Relevance Heuristic |
|---|---|
| Min. plausibility | 0.01 |
| Model | Template_relevance |
| Template Set | Pistachio/Bkms_metabolic/Pistachio_ringbreaker/Reaxys/Reaxys_biocatalysis |
| Top-N result to add to graph | 6 |
Feasible Synthetic Routes
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