Golmaenone, a new diketopiperazine alkaloid from the marine-derived fungus Aspergillus sp.

Chemical and Pharmaceutical Bulletin

Volumn 52, Issue 3, 2004, Pages 375-376

  Li, Yong ^a   Li, Xifeng ^a   Kim, Se Kwon ^a   Kang, Jung Sook ^b   Choi, Hong Dae ^c   Rho, Jung Rae ^d   Son, Byeng Wha ^a  

^a Pukyong National University   (South Korea)

^b Pusan National University   (South Korea)

^c Dong Eui University   (South Korea)

^d Kunsan National University   (South Korea)

Author keywords

Aspergillus sp.; Diketopiperazine alkaloid; Golmaenone; L alanyl L tryptophan anhydride; Marine derived fungus; Neoechinulin A

Indexed keywords

1,1 DIPHENYL 2 PICRYLHYDRAZYL; ALANYLTRYPTOPHAN ANHYDRIDE; ALKALOID DERIVATIVE; ASCORBIC ACID; GOLMAENONE; NEOECHINULIN A; OXYBENZONE; PIPERAZINEDIONE; SUNSCREEN; UNCLASSIFIED DRUG; 2,2-DIPHENYL-1-PICRYLHYDRAZYL; ALANYL TRYPTOPHAN ANHYDRIDE; ALANYL-TRYPTOPHAN ANHYDRIDE; BENZOPHENONE DERIVATIVE; CYCLOPEPTIDE; DIPEPTIDE; INDOLE ALKALOID; PICRIC ACID; PIPERAZINE DERIVATIVE; SCAVENGER;

ARTICLE; ASPERGILLUS; CONTROLLED STUDY; DRUG ACTIVITY; DRUG ISOLATION; DRUG POTENCY; FUNGUS CULTURE; IC 50; NONHUMAN; RADIATION PROTECTION; SPECTROSCOPY; STEREOCHEMISTRY; ULTRAVIOLET A RADIATION; CHEMICAL STRUCTURE; CHEMISTRY; COMPARATIVE STUDY; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET RADIATION;

ASCORBIC ACID; ASPERGILLUS; BENZOPHENONES; DIPEPTIDES; FREE RADICAL SCAVENGERS; INDOLE ALKALOIDS; INHIBITORY CONCENTRATION 50; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTIDES, CYCLIC; PICRATES; PIPERAZINES; SUNSCREENING AGENTS; ULTRAVIOLET RAYS;

EID: 3042684086     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.52.375     Document Type: Article

References (14)

1. Sorensen D., Larsen T. O., Christophersen C., Nielsen P. H., Anthoni, U., Phytochemistry, 51, 1181-1183 (1999).
2. Jiang Z., Boyd K. G., Mearns-Spragg A., Adams D. R., Wright P. C., Burgess J. G., Nat. Prod. Lett., 14, 435-440 (2000).
3. Kozlovsky A. G., Vinokurova N. G., Adanin V. M., Burkhardt G., Dahse H., Gräfe U., J. Nat. Prod., 64, 553 (2001).
4. Kozlovsky A. G., Marfenina O. G., Vinokurova N. G., Zhelifonova V. P., Adanin V. M., Mycotoxins, 48, 37-43 (1998).
5. Lee S. M., Li X. F., Jiang H., Cheng J. G., Seong S., Choi H. D., Son B. W., Tetrahedron Lett., 44, 7707-7710 (2003).
6. The fungal strain was identified as a Aspergillus sp. based on fatty acid methyl ester analysis and growth characteristics (Korean Culture Center of Microorganisms, Seoul, Korea). Their analysis showed a similarity index of 0.62.
7. The fungus was cultured (20 l) for 30 d (static) at 29°C in SWS medium: soytone (0.1%), soluble starch (1.0%), and seawater (100%).
8. 4Na: 378.1430). See Table 1 for NMR spectral data.
9. Marchelli R., Dossena A., Pochini A., Dradi E., J. Chem. Soc. Perkin Trans. 1, 1977, 713-717 (1977).
10. Fujii K., Ikai Y., Mayumi T., Oka H., Suzuki M., Harada K.-I., Anal. Chem., 69, 3346-3352 (1997).
11. 2O (100 μl), and derivatized with L-FDAA. The L-FDAA derivatives, from the hydrolyzates, were compared with similarly derivatized standard amino acids (L-alanine and D-alanine) by HPLC [YMC ODS-A (10x250 mm), 10 μm, flow rate 1 ml/min, UV detection at 340 nm] using an isocratic elution of MeCN-0.1% (v/v) aqueous TFA (1:1). The retention times of L-FDAA derivatives of standard amino acids, L-alanine and D-alanine, were 9.6 and 10.6 min, respectively, and the retention times of L-FDAA derivatives of hydrolyzates were 9.6 min, respectively.
12. 3) δ: 143.8 (C-2), 102.9 (C-3), 126.0 (C-3a), 118.9 (C-4), 121.0 (C-5), 122.3 (C-6), 111.2 (C-7), 134.3 (C-7a), 111.9 (C-8), 124.5 (C-9), 159.8 (C-10), 51.7 (C-12), 165.7 (C-13), 39.2 (C-15), 144.3 (C-16), 113.3 (C-17), 27.3 (C-18), 27.4 (C-19), 20.9 (C-20).
13. Yagi R., Doi M., Biosci. Biotechnol. Biochem., 63, 932-933 (1999).
14. Hamasaki T., Nagayama K., Hatsuda Y., Agric. Biol. Chem., 40, 2487 (1976).