Penicidones A-C, three cytotoxic alkaloidal metabolites of an endophytic Penicillium sp.

Phytochemistry

Volumn 69, Issue 2, 2008, Pages 571-576

  Ge, Hui Ming ^a   Shen, Yao ^a   Zhu, Chun Hua ^a   Tan, Shu Hua ^a   Ding, Hui ^a   Song, Yong Chun ^a   Tan, Ren Xiang ^a  

^a NANJING UNIVERSITY   (China)

Author keywords

Alkaloid; Cytotoxicity; Endophyte; Fagaceae; Penicidone A; Penicidone B; Penicidone C; Penicillium sp.; Quercus variabilis

Indexed keywords

PENICIDONE A; PENICIDONE B; PENICIDONE C; PYRIDONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CELL SURVIVAL; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PENICILLIUM; TUMOR CELL LINE;

CELL LINE, TUMOR; CELL SURVIVAL; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PENICILLIUM; PYRIDONES;

FAGACEAE; PENICILLIUM; PENICILLIUM SP.; QUERCUS VARIABILIS;

EID: 37549039422     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.07.014     Document Type: Article

References (24)

1. Chen H., Yeung S.-M., Que N.L.S., Müller T., Schmidt R.R., and Liu H.-W. Expression, purification, and characterization of TylB, an aminotransferase involved in the biosynthesis of mycaminose. J. Am. Chem. Soc. 121 (1999) 7166-7167
2. De Stefano S., Nicoletti R., Zambardino S., and Milone A. Structure elucidation of a novel funicone-like compound produced by Penicillium pinophilum. Nat. Prod. Lett. 16 (2002) 207-211
3. Fuska J., Uhrin D., Proksa B., Voticky Z., and Ruppeldt J. The structure of vermistatin, a new metabolite from Penicillium vermiculatum. J. Antibiot. 39 (1986) 1605-1608
4. Ge H.M., Song Y.C., Chen J.R., Hua S., Wu J.Y., and Tan R.X. Paranolin: a new xanthene-based metabolite from Paraphaeosphaeria nolinae. Helv. Chim. Acta 89 (2006) 502-506
5. Jiao R.H., Xu S., Liu J.Y., Ge H.M., Ding H., Xu C., Zhu H.L., and Tan R.X. Chaetominine, a cytotoxic alkaloid produced by endophytic Chaetomium sp. IFB-E015. Org. Lett. 8 (2006) 5709-5712
6. Kimura Y., Yoshinari T., Shimada A., and Hamasaki T. Isofunicone, a pollen growth inhibitor produced by the fungus Penicillium sp. Phytochemistry 40 (1995) 629-631
7. Komai S.-i., Hosoe T., Itabashi T., Nozawa K., Okada K., De Campos T., Galba M., Chikamori M., Yaguchi T., Fukushima K., Miyaji M., and Kawai K.-i. A new funicone derivative isolated from Talaromyces flavus IFM52668. Mycotoxins 54 (2004) 15-19
8. Komai S.-i., Hosoe T., Itabashi T., Nozawa K., Yaguchi T., Fukushima K., and Kawai K.-i. New vermistatin derivatives isolated from Penicillium simplicissimum. Heterocycles 65 (2005) 2771-2776
9. Lee D.Y.-W., and Liu Y. Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, isolated from Silybum marianum (milk thistle). J. Nat. Prod. 66 (2003) 1171-1174
10. Menicagli R., Samaritani S., Signore G., Vaglini F., and Via L.D. In vitro cytotoxic activities of 2-alkyl-4,6-diheteroalkyl-1,3,5-triazines: new molecules in anticancer research. J. Med. Chem. 47 (2004) 4649-4652
11. Merlini L., Nasini G., and Selva A. The structure of funicone a new metabolite from Penicillium funiculosum. Tetrahedron 26 (1970) 2739-2749
12. Müller E.L., and Faulkner D.N. Absolute configuration of halisulfate 3 from the sponge Ircinia sp. Tetrahedron 53 (1997) 5373-5378
13. Murtaza N., Husain S.A., Sarfaraz T.B., Sultana N., and Faizi S. Isolation and identification of vermistatin, ergosterol, stearic acid, and mannitol, metabolic products of Penicillium verruculosum. Planta Med. 63 (1997) 191-194
14. Nozawa K., Nakajima S., and Kawai K. A γ-pyrone derivative, rapicone, from Ramichloridium apiculatum. Phytochemistry 31 (1992) 4177-4179
15. Okabe H., Matsuo K., and Nishioka I. Rhubarb (Rhei rhizoma). II. Anthraquinone glycosides. Chem. Pharm. Bull. 21 (1973) 1254-1260
16. Shen L., Ye Y.H., Wang X.T., Zhu H.L., Xu C., Song Y.C., Li H., and Tan R.X. Structure and total synthesis of aspernigerin: a novel cytotoxic endophyte metabolite. Chem. Eur. J. 12 (2006) 4393-4396
17. Strobel G.A. Endophytes as sources of bioactive products. Microbes Infect. 5 (2003) 535-544
18. Tabata N., Tomoda H., and Omura S. Erabulenols, inhibitors of cholesteryl ester transfer protein produced by Penicillium sp. FO-5637 II. Structure elucidation of erabulenols A and B. J. Antibiot. 51 (1998) 624-628
19. Tan R.X., and Zou W.X. Endophytes: a rich source of functional metabolites. Nat. Prod. Rep. 18 (2001) 448-459
20. Upadhyay R.K., Strobel G.A., Coval S.J., and Clardy J. Fijiensin, the first phytotoxin from Mycosphaerella fijiensis, the causative agent of Black Sigatoka disease. Experientia 46 (1990) 982-984
21. Wei J.C. Manual of Fungi Determination (Chinese) (1979), Science and Technology Press, Shanghai pp. 132-134
22. Yang X.W., Gu Z.M., Ma C.M., Hattori M., and Namba T. A new indole derivative isolated from the root of tuber fleeceflower (Polygonum multiforum). Chin. Tradit. Herb. Drugs 29 (1998) 5-11
23. Yu N.J., and Guo S.X. Studies on the chemical constituents from culture filtrate of a fungus isolated from Ganoderma lucidum. Nat. Prod. R&D 14 (2002) 24-26
24. Zhang H.W., Song Y.C., and Tan R.X. Biology and chemistry of enodphytes. Nat. Prod. Rep. 23 (2006) 753-771