Paspalinine
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| Category | Mycotoxins |
| Catalog number | BBF-04466 |
| CAS | 63722-91-8 |
| Molecular Weight | 433.54 |
| Molecular Formula | C27H31NO4 |
| Purity | ≥98% |
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Description
Paspalinine is a tremorgenic mycotoxin extracted from the fermentation broth of Aspergillus flavus OUCMDZ-2205. It can inhibit the combination of [125I]charybdotoxin (ChTX) to maxi-K channels in bovine aortic smooth muscle sarcolemmal membranes. It displays tremorgenic action due in part to their inhibition of GABAA receptor function. It shows insecticidal properties.
Specification
| Synonyms | 4H-3,15a-Epoxy-1-benzoxepino(6',7':6,7)indeno(1,2-b)indol-4-one, 2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-5b-hydroxy-2,2,13b,13c-tetramethyl-, (3R-(3alpha,5balpha,7abeta,13balpha,13cbeta,15aalpha))-; 4H-3,15a-Epoxy-1-benzoxepino[6',7':6,7]indeno[1,2-b]indol-4-one, 2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-5b-hydroxy-2,2,13b,13c-tetramethyl-, (3R,5bS,7aS,13bS,13cR,15aS)- |
| Storage | Store at -20°C |
| IUPAC Name | (1S,4R,5S,16S,19S,23R)-19-hydroxy-4,5,24,24-tetramethyl-25,26-dioxa-7-azaheptacyclo[21.2.1.01,20.04,19.05,16.06,14.08,13]hexacosa-6(14),8,10,12,20-pentaen-22-one |
| Canonical SMILES | CC1(C2C(=O)C=C3C4(CCC5CC6=C(C5(C4(CCC3(O2)O1)C)C)NC7=CC=CC=C67)O)C |
| InChI | InChI=1S/C27H31NO4/c1-23(2)22-19(29)14-20-26(30)10-9-15-13-17-16-7-5-6-8-18(16)28-21(17)25(15,4)24(26,3)11-12-27(20,31-22)32-23/h5-8,14-15,22,28,30H,9-13H2,1-4H3/t15-,22-,24+,25+,26+,27-/m0/s1 |
| InChI Key | BPTIXFRJAOKMRK-SAMRHTEJSA-N |
| Source | Paspalinine is a tremorgenic mycotoxin that has been found in fungi of the genera Penicillium and Aspergillus. |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Parasites |
| Boiling Point | 631.8±55.0°C (Predicted) |
| Density | 1.34±0.1 g/cm3 (Predicted) |
| Solubility | Soluble in Chloroform, Methanol |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. They are thought to inhibit gamma-aminobutyric acid (GABA) receptors, both pre- and postsynaptic, as well as inhibit transmitter breakdown at the GABA-T receptors. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. In addition, paspalinine inhibits presynaptic high-conductance Ca+2 activated maxi-K+ channels in the smooth muscle. |
Reference Reading
1. Asymmetric Total Synthesis of Indole Diterpenes Paspalicine, Paspalinine, and Paspalinine-13-ene
Lian-Dong Guo, Zejun Xu, Rongbiao Tong Angew Chem Int Ed Engl. 2022 Jan 17;61(3):e202115384. doi: 10.1002/anie.202115384. Epub 2021 Nov 27.
Paspaline-derived indole diterpenes (IDTs) are structurally complex mycotoxins with unique tremorgenic activity. Reported are asymmetric total syntheses of three paspaline-derived IDTs paspalicine, paspalinine and paspalinine-13-ene. Our synthesis features a green Achmatowicz rearrangement/bicycloketalization for the efficient construction of FG rings (75 % yield) and a cascade ring-closing metathesis of dienyne for highly regioselective formation of CD rings (72 % yield). Other highlights include four palladium-mediated reactions (Stille, aza-Wacker, Suzuki, and Heck) to forge the BE rings and the installation of two continuous all-carbon quaternary stereocenters via reductive ring-opening of cyclopropane and α-methylation of the conjugate ester. Our new synthetic strategy is expected to be applicable to the chemical synthesis of other paspaline-derived IDTs and will facilitate the bioactivity studies of these agriculturally and pharmacologically important IDTs.
2. Recent advances in the total syntheses of indole diterpenoids
Masaru Enomoto Biosci Biotechnol Biochem. 2021 Jan 7;85(1):13-23. doi: 10.1093/bbb/zbaa061.
Indole diterpenoids constitute a large family of natural products that are characterized by a hybrid molecular architecture consisting of an indole nucleus and diterpenoid moiety. Their pharmacologically and agriculturally important biological properties as well as intriguing molecular architectures have attracted much attention from many synthetic organic chemists. In 2012, we succeeded in the concise total synthesis of a paspalane-type indole diterpenoid, namely paspalinine, by developing a highly efficient indole ring formation protocol. After the report of this total synthesis, 4 research groups achieved the total syntheses of other paspalane- and nodulisporane-type indole diterpenoids using current state-of-the-art methods. This review summarizes the total syntheses of the paspalane- and nodulisporane-type indole diterpenoids that were described in the last 10 years.
3. Comprehensive chemotaxonomic and genomic profiling of a biosynthetically talented Australian fungus, Aspergillus burnettii sp. nov
Cameron L M Gilchrist, Heather J Lacey, Daniel Vuong, John I Pitt, Lene Lange, Ernest Lacey, Bo Pilgaard, Yit-Heng Chooi, Andrew M Piggott Fungal Genet Biol. 2020 Oct;143:103435. doi: 10.1016/j.fgb.2020.103435. Epub 2020 Jul 20.
Aspergillus burnettii is a new species belonging to the A. alliaceus clade in Aspergillus subgenus Circumdati section Flavi isolated from peanut-growing properties in southern Queensland, Australia. A. burnettii is a fast-growing, floccose fungus with distinctive brown conidia and is a talented producer of biomass-degrading enzymes and secondary metabolites. Chemical profiling of A. burnettii revealed the metabolites ochratoxin A, kotanins, isokotanins, asperlicin E, anominine and paspalinine, which are common to subgenus Circumdati, together with burnettiene A, burnettramic acids, burnettides, and high levels of 14α-hydroxypaspalinine and hirsutide. The genome of A. burnettii was sequenced and an annotated draft genome is presented. A. burnettii is rich in secondary metabolite biosynthetic gene clusters, containing 51 polyketide synthases, 28 non-ribosomal peptide synthetases and 19 genes related to terpene biosynthesis. Functional annotation of digestive enzymes of A. burnettii and A. alliaceus revealed overlapping carbon utilisation profiles, consistent with a close phylogenetic relationship.
Spectrum
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C27H31NO4
Molecular Weight (Monoisotopic Mass): 433.2253 Da
Molecular Weight (Avergae Mass): 433.5393 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C27H31NO4
Molecular Weight (Monoisotopic Mass): 433.2253 Da
Molecular Weight (Avergae Mass): 433.5393 Da
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
