Cereusitin A, a cyclic tetrapeptide from a Bacillus cereus strain isolated from the soft coral Antillogorgia (syn. Pseudopterogorgia) elisabethae. Issue 7 (15th February 2017)

• Record Type: Journal Article
• Authors: Pinzón-Espinosa, Angela; Martinez-Matamoros, Diana; Castellanos, Leonardo; Duque, Carmenza; Rodríguez, Jaime; Jiménez, Carlos; Ramos, Freddy A.
• Is Part Of: Tetrahedron letters. Volume 58:Issue 7(2017)
• Page Start: 634
• Page End: 637
• Publication Date: 2017-02-15
• Subjects: Bacillus cereus -- Cyclopeptide -- 4-Hydroxyproline -- Marfey's method -- Marine natural products; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2017.01.002
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: A cyclic tetrapeptide (1 ) was isolated from a marine strain Bacillus cereus . 4-( R )-hydroxysattabacin (2 ), and three parabens were also isolated and identified. Absolute configuration of cereusitin A (1 ) was established by Marfey method. The compounds were tested against human pathogens and phytopathogenic. fungi. Abstract: Two new compounds, cereusitin A (1), the tetrapeptide cyclo-(L-phenylalanyl- trans -4-hydroxy-L-prolyl-L-leucyl- trans -4-hydroxy-L-proline and 4-( R )-hydroxysattabacin (2 ), along with the methyl, isopropyl, and propyl esters of p-hydroxybenzoic acid (3 –5 ) were isolated from the organic extracts of the culture of the B. cereus RKHC-09 strain in two culture media (MOLP and B1), recovered from the sea fan Antillogorgia elisabethae (syn. Pseudopterogorgia elisabethae ). Cereusitin A (1) showed mild antifungal activity against Colletotrichum gloeosporoides C26 (yam pathogen) but was inactive against Fusarium oxysporum f.sp. dianthi (carnation pathogen). The methyl and propyl esters of p -hydroxybenzoic acid (4 and5 ) showed antimicrobial activity against S. aureus ATCC 33591 and S. cerevisiae, with an MIC of 2 μM.