InChI=1S/C16H21NO6/c1-9(11-6-17-12-5-3-2-4-10(11)12)16(22)23-8-14(20)15(21)13(19)7-18/h2-6,9,13-15,17-21H,7-8H2,1H3/t9-,13-,14-,15-/m1/s1 |
YBXVDDODTFXOHM-SEWBAHNZSA-N |
C[C@@H](C(=O)OC[C@@H](O)[C@H](O)[C@H](O)CO)c1c[nH]c2ccccc12 |
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Paecilomyces sp.
(NCBI:txid40383)
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Isolated from cultures
of strain
CAFT156
See:
PubMed
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plant growth regulator
A chemical, natural or artificial, that can affect the rate of growth of a plant.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
fungal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
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View more via ChEBI Ontology
(2R,3R,4R)-2,3,4,5-tetrahydroxypentyl (2R)-2-(1H-indol-3-yl)propanoate
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2-(3-Indolyl)propanoylmannitol
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KEGG COMPOUND
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Acremoauxin A
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KEGG COMPOUND
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125537-93-1
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CAS Registry Number
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KEGG COMPOUND
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22790054
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Reaxys Registry Number
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Reaxys
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Talontsi FM, Nwemeguela Kenla TJ, Dittrich B, Douanla-Meli C, Laatsch H (2012) Paeciloside A, a new antimicrobial and cytotoxic polyketide from Paecilomyces sp. strain CAFT156. Planta medica 78, 1020-1023 [PubMed:22692953] [show Abstract] Paeciloside A (1) and eight known compounds, acremoauxin A (2), farinosones A (3) and B (4), 1,5-dideoxy-3-C-methyl-arabitol (5), ergosterol, ergosterol peroxide, cerebroside C, and adenosine, were isolated from cultures of Paecilomyces sp. CAFT156, an endophytic fungus occurring in Enantia chlorantha Oliv (Annonaceae) leaves. The structure of the new compound 1 was elucidated using MS, UV, 1D and 2D NMR experiments, while its absolute configuration was established by subsequent single-crystal X-ray diffraction analysis using copper Kα radiation and invariom nonspherical scattering factors. Paeciloside A (1) and compounds 2, 4, and 5 displayed inhibitory effects on two gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus at a concentration of 40 µg per paper disk and moderate cytotoxicity towards brine shrimp larvae (Artemia salina). This study presents the first report on an endophytic fungus isolated from E. chlorantha Oliv and its natural products. | Richter JM, Whitefield BW, Maimone TJ, Lin DW, Castroviejo MP, Baran PS (2007) Scope and mechanism of direct indole and pyrrole couplings adjacent to carbonyl compounds: total synthesis of acremoauxin A and oxazinin 3. Journal of the American Chemical Society 129, 12857-12869 [PubMed:17900115] [show Abstract] Full details are provided for a recently invented method to couple indoles and pyrroles to carbonyl compounds. The reaction is ideally suited for structurally complex substrates and exhibits high levels of chemoselectivity (functional group tolerability), regioselectivity (coupling occurs exclusively at C-3 of indole or C-2 of pyrrole), stereoselectivity (substrate control), and practicality (amenable to scaleup). In addition, quaternary stereocenters are easily and predictably generated. The reaction has been applied to a number of synthetic problems including total syntheses of members of the hapalindole family of natural products, ketorolac, acremoauxin A, and oxazinin 3. Mechanistically, this coupling protocol appears to operate by a single electron-transfer process requiring generation of an electron-deficient radical adjacent to a carbonyl which is then intercepted by an indole or pyrrole anion. |
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