New glycosides of the fungus Acremonium striatisporum isolated from a sea cucumber

• Published in: Journal of natural products (Washington, D.C.) Vol. 67; no. 6; pp. 1047 - 1051
• Main Authors: Afiyatullov, S.S, Kalinovsky, A.I, Kuznetsova, T.A, Pivkin, M.V, Prokof'eva, N.G, Dmitrenok, P.S, Elyakov, G.B
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.06.2004; Amer Chemical Soc
• Subjects: Acremonium - chemistry; Acremonium striatisporum; Animals; Antineoplastic Agents - chemistry; Antineoplastic Agents - isolation & purification; Antineoplastic Agents - pharmacology; Chemistry, Medicinal; Diterpenes - chemistry; Diterpenes - isolation & purification; Diterpenes - pharmacology; Drug Screening Assays, Antitumor; Eupentacta fraudatrix; Glycosides - chemistry; Glycosides - isolation & purification; Glycosides - pharmacology; Holothurioidea; Inhibitory Concentration 50; Life Sciences & Biomedicine; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Pharmacology & Pharmacy; Plant Sciences; Science & Technology; Sea Cucumbers - chemistry; Stereoisomerism; ACIDS; CONFIGURATION; NATURALLY-OCCURRING SUBSTANCES; B METABOLITES; VIRESCENS LINK WALLR; MAGNETIC-RESONANCE SPECTROSCOPY; C-13 CHEMICAL-SHIFTS
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np0305324

Four new diterpene glycosides, virescenosides R (1), S (2), T (3), and U (4), have been isolated from a marine strain of Acremonium striatisporum KMM 4401 associated with the holothurian Eupentacta fraudatrix. Their structures have been elucidated on the basis of HRFABMS, 1D and 2D NMR (H-1, C-13, DEPT, COSY-45, COSY-RCT, HSQC, HMBC, and NOESY spectra), and the results of acidic hydrolysis as 19-O-{beta-D-glucopyranosyl(1-->6)-beta-D-altropyranosyl}-isopimara-7,15-diene-2alpha,3beta-diol (1), 19-O-beta-D-altropyranosyl-3-oxo-isopimara-8(14),15-diene-7alpha-ol (2), 19-O-beta-D-altropyranosyl-3,7-dioxo-isopimara-8,15-diene (3), and 19-O-beta-D-altropyranosyl-3,7-dioxo-isopimara-8(14),15-diene (4). The cytotoxic activity of the virescenosides was examined.