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14α-Hydroxypaspalinine

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Category Others
Catalog number BBF-04735
CAS 151341-77-4
Molecular Weight 449.54
Molecular Formula C27H31NO5
Purity >95% by HPLC

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Product Description

14α-Hydroxypaspalinine is a secondary metabolite of indole isolated from Aspergillus niger. 14-α-hydroxypaspalinine is a member of the paspalinine-causing toxin family and is usually related to the toxicity of animals to pasture.

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Synonyms Hydroxypaspalinine, 14-alpha-
Storage Store at -20°C
IUPAC Name (1S,4R,5S,16R,18S,19S,23R)-18,19-dihydroxy-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=C3C(O2)(O1)CCC4(C3(C(CC5C4(C6=C(C5)C7=CC=CC=C7N6)C)O)O)C)C
InChI InChI=1S/C27H31NO5/c1-23(2)22-18(29)13-19-26(32-22,33-23)10-9-24(3)25(4)14(12-20(30)27(19,24)31)11-16-15-7-5-6-8-17(15)28-21(16)25/h5-8,13-14,20,22,28,30-31H,9-12H2,1-4H3/t14-,20+,22+,24-,25-,26+,27+/m1/s1
InChI Key JNHPMJVSUJKCKH-KCCNSQSLSA-N
Solubility Soluble in ethanol, methanol, DMF, DMSO
1. 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.

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