Spicochalasin A and New Aspochalasins from the Marine‐Derived Fungus Spicaria elegans

• Published in: European Journal of Organic Chemistry Vol. 2009; no. 18; pp. 3045 - 3051
• Main Authors: Lin, Zhenjian, Zhu, Tianjiao, Wei, Hongjuan, Zhang, Guojian, Wang, Hui, Gu, Qianqun
• Format: Book Review Journal Article
• Language: English
• Published: Weinheim WILEY‐VCH Verlag 01.06.2009; Wiley; Wiley-VCH
• Subjects: Alicyclic compounds; Alicyclic compounds, terpenoids, prostaglandins, steroids; Antibiotics; Antibiotics. Antiinfectious agents. Antiparasitic agents; Antineoplastic agents; Antitumor agents; Biological and medical sciences; Chemistry; Chemistry, Organic; Cytochalasans; Exact sciences and technology; General aspects; Marine fungi; Medical sciences; Natural products; Organic chemistry; Pharmacology. Drug treatments; Physical Sciences; Preparations and properties; Science & Technology; Spicochalasin A; PATHWAYS; Marine fungi; METABOLITES; Cytochalasans; Antitumor agents; Antibiotics; Natural products; BIOSYNTHESIS; ASPERGILLUS-FLAVIPES; Spicochalasin A; A-D; Antineoplastic agent; Pentacyclic compound; Molecular structure; Metabolite; Cytotoxicity; NMR spectrometry; Fungi; Marine environment; Ester; Alkaloid; Fungi Imperfecti; Human; Natural compound; X ray diffraction; HL60 cell line; Antibiotic; Cyclic compound; Absolute configuration; Mass spectrometry; Structural analysis
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.200801085

Different culture conditions directed by the OSMAC (one strain‐many compounds) approach drastically modified the metabolites of the fungus Spicaria elegans, which yielded the novel spicochalasin A (1), five new aspochalasins M–Q (2–6), and two known aspochalasins (7 and 8). The gross structures of 1–6 were elucidated by 1D and 2D NMR and MS methods, and their absolute configurations were determined by X‐ray diffraction and the Mosher ester method. Spicochalasin A (1) has a unique pentacyclic system and was found to be moderately cytotoxic towards human leukemic HL‐60 cells with an IC50 value of 19.9 μM.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009) Different culture conditions directed by the OSMAC (one strain‐many compounds) approach yielded a novel spicochalasin A (1) and five new aspochalasins M–Q (2–6). Their absolute configurations were determined by X‐ray diffraction and the Mosherester method. Spicochalasin A (1) has a unique pentacyclic system and was found to be moderately cytotoxic towards human leukemic HL‐60 cells with an IC50 value of 19.9 μM.