Anominine
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| Category | Others |
| Catalog number | BBF-04669 |
| CAS | 120991-21-1 |
| Molecular Weight | 405.6 |
| Molecular Formula | C28H39NO |
| Purity | >95% by HPLC |
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Description
Anominine is an indole diterpenoid isolated from new Aspergillus species, which has insecticidal activity.
Specification
| Synonyms | Nominine; (+)-Nominine |
| Storage | Store at -20°C |
| IUPAC Name | (1R,4S,4aR,8S,8aR)-8-(1H-indol-3-ylmethyl)-4,4a-dimethyl-7-methylidene-8a-(4-methylpent-3-enyl)-2,3,4,5,6,8-hexahydro-1H-naphthalen-1-ol |
| Canonical SMILES | CC1CCC(C2(C1(CCC(=C)C2CC3=CNC4=CC=CC=C43)C)CCC=C(C)C)O |
| InChI | InChI=1S/C28H39NO/c1-19(2)9-8-15-28-24(17-22-18-29-25-11-7-6-10-23(22)25)20(3)14-16-27(28,5)21(4)12-13-26(28)30/h6-7,9-11,18,21,24,26,29-30H,3,8,12-17H2,1-2,4-5H3/t21-,24-,26+,27+,28-/m0/s1 |
| InChI Key | BSSPRCKKWJRAJZ-HBDSXALQSA-N |
Properties
| Solubility | Soluble in methanol, DMSO |
Reference Reading
1. Comprehensive chemotaxonomic and genomic profiling of a biosynthetically talented Australian fungus, Aspergillus burnettii sp. nov
Lene Lange, Cameron L M Gilchrist, John I Pitt, Yit-Heng Chooi, Heather J Lacey, Ernest Lacey, Bo Pilgaard, Andrew M Piggott, Daniel Vuong Fungal Genet Biol . 2020 Oct;143:103435. doi: 10.1016/j.fgb.2020.103435.
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.
2. Total synthesis of (-)-anominine
Josep Bonjoch, Ben Bradshaw, Gorka Etxebarria-Jardí J Am Chem Soc . 2010 May 5;132(17):5966-7. doi: 10.1021/ja101994q.
The first total synthesis of anominine has been achieved, and the absolute configuration of the product has been determined. The key features include the development of a new, highly efficient organocatalyzed method for the asymmetric synthesis of Wieland-Miescher ketone building blocks, an unusual selenoxide [2,3]-sigmatropic rearrangement, and a ZrCl(4)-catalyzed indole coupling as well as several chemoselective transformations controlled by the structurally congested nature of the bicyclic core.
3. Polycyclic framework synthesis of anominine and tubingensin A indole diterpenoids
Josep Bonjoch, Ben Bradshaw, Gorka Etxebarria-Jardí Org Biomol Chem . 2008 Feb 21;6(4):772-8. doi: 10.1039/b718280e.
A highly congested decalin embodying an alpha-methylene ketone is synthesized in 11 steps from the Wieland-Miescher ketone and efficiently converted to the polycyclic frameworks of anominine and tubingensin A, which constitutes the first approach to the skeleton of these indole diterpenoids.
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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 ╳
