Diketopiperazines and phthalides from a marine derived fungus of the order pleosporales

Planta Medica

Volumn 74, Issue 1, 2008, Pages 69-72

  Prachyawarakorn, Vilailak ^a,b   Mahidol, Chulabhorn ^a,b,d   Sureram, Sanya ^a   Sangpetsiripan, Suwannee ^a   Wiyakrutta, Suthep ^c   Ruchirawat, Somsak ^a,b,d   Kittakoop, Prasat ^a,b  

^a CHULABHORN RESEARCH INSTITUTE   (Thailand)

^b Research and Innovation   (Thailand)

^c MAHIDOL UNIVERSITY   (Thailand)

^d MAHIDOL UNIVERSITY   (Thailand)

Author keywords

Cytotoxicity; Diketopiperazines; Marine derived fungi; Phthalides; Pleosporales

Indexed keywords

3 (3' HYDROXYBUTYL) 7 METHOXYPHTHALIDE; 3 BUTYL 7 METHOXYPHTHALIDE; 6 BENZYLIDINE 3 HYDROXYMETHYL 1,4 DIMETHYL 3 METHYLSULFANYLPIPERAZINE 2,5 DIONE; BIS N NORGLIOVICTIN; BISDETHIODI(METHYLTHIO)HYALODENDRIN; ETOPOSIDE; NATURAL PRODUCT; PHTHALIDE DERIVATIVE; PIPERAZINEDIONE; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; FUNGAL STRAIN; FUNGUS; HUMAN; HUMAN CELL; MARINE SPECIES; NUCLEOTIDE SEQUENCE; PLEOSPORALES;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; BENZOFURANS; CELL LINE, TUMOR; DIKETOPIPERAZINES; FUNGI; HUMANS; PHYTOTHERAPY; SEAWATER;

FUNGI; PLEOSPORALES;

EID: 39149083695     PISSN: 00320943     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-993783     Document Type: Article

References (17)

1. Chin YW, Balunas MJ, Chai HB, Kinghorn AD. Drug discovery from natural sources. AAPS J 2006; 8: E239-53
2. Cragg GM, Newman DJ, Yang SS. Natural product extracts of plant and marine origin having antileukemia potential. The NCI experience. J Nat Prod 2006; 69: 488-98
3. Kralj A, Kehraus S, Krick A, van Echten-Deckert G, König GM. Two new depsipeptides from the marine fungus Spicellum roseum. Planta Med 2007; 73: 366-71
4. Wright AD, Lang-Unnasch N. Potential antimalarial lead structures from fungi of marine origin. Planta Med 2005; 71: 964-6
5. White TJ, Bruns T, Lee S, Taylor J. Amplification and direct sequencing of fungal ribosomal RNA genes for phylogenetics. In: Innes MA, Gelfand DH, Sninky JJ, White TJ, editors. PCR protocols: a guide to methods and applications. San Diego: Academic Press; 1990: 315-22
6. Altschul SF, Madden TL, Schäffer AA, Zhang J, Zhang Z, Miller W et al. Gapped BLAST and PSI-BLAST: a new generation of protein database search programs. Nucleic Acids Res 1997; 25: 3389-402
7. Thompson JD, Higgins DG, Gibson TJ. CLUSTAL W: improving the sensitivity of progressive multiple sequence alignment through sequence weighting, position-specific gap penalties and weight matrix choice. Nucleic Acids Res 1994; 22: 4673-80
8. Swofford DL. PAUP*. Phylogenetic Analysis Using Parsimony (*and Other Methods), Version 4. Sunderland, MA: Sinauer Associates; 2003
9. Eriksson OE. Myconet. 2006; 12: 1-82. Available at http://www.umu.se/myconet/M_outline.html. Accessed March 24, 2006
10. Tengchaisri T, Chawengkirttikul R, Rachaphaew N, Reutrakul V, Sangsuwan R, Sirisinha S. Antitumor activity of triptolide against cholangiocarcinoma growth in vitro and in hamsters. Cancer Lett 1998; 133: 169-75
11. Michel KH, Chaney MO, Jones ND, Hoehn MM, Nagarajan R. Epipolythiopiperazinedione antibiotics from Penicillium turbatum. J Antibiot 1974; 27: 57-64
12. Isaka M, Palasarn S, Rachtawee P, Vimuttipong S, Kongsaeree P. Unique diketopiperazine dimers from the insect pathogenic fungus Verticillium hemipterigenum BCC 1449. Org Lett 2005; 7: 2257-60
13. Kirby GW, Rao GV, Robins DJ. New co-metabolites of gliotoxin in Gliocladium virens. J Chem Soc [Perkin I]; 1998: 301-4
14. Ohzeki T, Mori K. Synthesis and absolute configuration of (-)-3-butyl-7-hydroxyphthalide, a cytotoxic metabolite of Penicillium vulpinum. Biosci Biotechnol Biochem 2003; 67: 2240-4
15. Dale JA, Mosher HS. Nuclear magnetic resonance enantiomer reagents. Configurational correlations via nuclear magnetic resonance chemical shifts of diastereomeric mandelate, O-methylmandelate, and α-methoxy-α-trifluoromethylphenylacetate (MTPA) esters. J Am Chem Soc 1973; 95: 512-9
16. Nishikawa A, Hashimoto Y, Shirai R. Synthesis of 6-amylsalicyclic acid from 3-anisaldehyde: conversion of phthalide to thiophthalide by aluminum halide-butanethiol. Tetrahedron Lett 1998; 39: 7307-8
17. Anstiss M, Clayden J, Grube A, Youssef LH. Lithiation and stereoselective transformations of 3-aroyl-2,2,4,4-tetramethyloxazolidines (TMO amides), a new class of acid-labile atropisomeric amides. Synlett; 2002: 290-4