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Aspochalasin D

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Aspochalasin D
Category Enzyme inhibitors
Catalog number BBF-03968
CAS 71968-02-0
Molecular Weight 401.54
Molecular Formula C24H35NO4
Purity ≥95%

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Semi pilot, pilot and industrial plant 4 Manufacturing sites 7 Production lines at pilot scale 100+ Reactors of 30-4000 L; 170+ reactors of 20 KL-30 KL; 24+ reactors of >100 KL 2 Hydrogenation reactors (200 L, 4Mpa and 1000L, 4Mpa)

Product Description

Aspochalasin D is a potent inhibitor of mammalian tumor cell lines, first isolated from Aspergillus microcysticus. It has antibacterial activity against Gram-positive and Gram-negative bacteria at a concentration of 1 mg/ml. Aspochalasin D was found that it can strongly induce the formation of actin-containing rodlets in the cytoplasm of treated fibroblasts.

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Synonyms 1H-Cycloundec(d)isoindole-1,15(2H)-dione, 3,3a,4,6a,9,10,11,12-octahydro-11,12-dihydroxy-4,5,8-trimethyl-3-(2-methylpropyl)-, (3S,3aR,4S,6aS,7E,11R,12S,13E,15aS)-
Storage Store at -20°C
IUPAC Name (1S,3Z,5S,6R,9Z,11S,14S,15R,16S)-5,6-dihydroxy-9,13,14-trimethyl-16-(2-methylpropyl)-17-azatricyclo[9.7.0.01,15]octadeca-3,9,12-triene-2,18-dione
Canonical SMILES CC1C2C(NC(=O)C23C(C=C(CCC(C(C=CC3=O)O)O)C)C=C1C)CC(C)C
InChI InChI=1S/C24H35NO4/c1-13(2)10-18-22-16(5)15(4)12-17-11-14(3)6-7-19(26)20(27)8-9-21(28)24(17,22)23(29)25-18/h8-9,11-13,16-20,22,26-27H,6-7,10H2,1-5H3,(H,25,29)/b9-8+,14-11+/t16-,17+,18+,19-,20+,22+,24-/m1/s1
InChI Key GCIKKGSNXSCKCP-WBEGXGIOSA-N
Appearance Solid Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 607.6°C at 760 mmHg
Melting Point 148°C (dec.)
Density 1.15 g/cm3
1. Biomimetic Synthesis of (+)-Aspergillin PZ
Lukas Spessert, Nils Winter, Julius R Reyes, Dirk Trauner Angew Chem Int Ed Engl . 2018 Nov 19;57(47):15587-15591. doi: 10.1002/anie.201809703.
The cytochalasans are a large family of polyketide natural products with potent bioactivities. Amongst them, the aspochalasins show particularly intricate and fascinating structures. To gain insight into their structural diversity and innate reactivity, we have developed a rapid synthesis of aspochalasin D, the central member of the family. It proceeded in 13 steps starting from divinyl carbinol and utilized a high pressure Diels-Alder reaction that features high regio- and stereoselectivity. So far, our work has culminated in a biomimetic synthesis of aspergillin PZ, an intricate pentacyclic aspochalasan.
2. Trichodermone, a spiro-cytochalasan with a tetracyclic nucleus (7/5/6/5) skeleton from the plant endophytic fungus Trichoderma gamsii
Hailou Wang, Gang Ding, Hongwu Zhang, Xinzhong Liu, Zhongmei Zou, Li Li, Bo Song, Hong Chen J Nat Prod . 2014 Jan 24;77(1):164-7. doi: 10.1021/np4007487.
Trichodermone (1), the first spiro-cytochalasan with an unprecedented tetracyclic nucleus (7/5/6/5), together with its possible biosynthetic precursor aspochalasin D (2), was isolated from the endophytic fungus Trichoderma gamsii. Compound 2 displayed moderate inhibitory activity against HeLa cells with an IC50 value of 5.72 μM.
3. Aspochalamins A-D and aspochalasin Z produced by the endosymbiotic Fungus aspergillus niveus LU 9575. I. Taxonomy, fermentation, isolation and biological activities
Klaus Gebhardt, Winfried Beil, Siegfried Draeger, Judith Schimana, Alexandra Höltzel, Hans-Peter Fiedler, Konrad Dettner, Joachim Rheinheimer J Antibiot (Tokyo) . 2004 Nov;57(11):707-14. doi: 10.7164/antibiotics.57.707.
Aspochalamins A-D, a family of new cytochalasan antibiotics have been isolated from Aspergillus niveus, an endosymbiotic fungus isolated from the gut of a woodlouse belonging to the family Trichoniscidae. Besides aspochalamins, aspochalasin Z, a new member of the aspochalasin family, as well as the known mycotoxins aspochalasin D and citreoviridins A/C and B were isolated from the mycelium. Aspochalamins showed cytostatic effects towards various tumor cell lines and a weak antibacterial activity against Gram-positive bacteria.

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