(±)-Pestalachloride D, an Antibacterial Racemate of Chlorinated Benzophenone Derivative from a Soft Coral-Derived Fungus Pestalotiopsis sp.

Abstract

A new antibacterial chlorinated benzophenone derivative, (±)-pestalachloride D (1), along with a related analog, (±)-pestalachloride C (2), was recently isolated from the marine-derived fungus Pestalotiopsis sp. isolated from a soft coral Sarcophyton sp. collected from Yongxing Island in the South China Sea. Both chiral HPLC analysis and single-crystal X-ray data indicated that 1 is a racemic mixture. Interestingly, 1 did not exhibit any effect in the zebrafish embryo teratogenicity assay, while 2 led to abnormal growth. The potential impact on zebrafish embryo growth is discussed based on their crystal structures. The main difference of crystal structures between 1 and 2 is that the six-member non-aromatic ring (O4, C10, C9, C8, C2′, and C3′) in 1 exhibits a distorted chair conformation, while 2 shows a distorted boat conformation. Moreover, compounds 1 and 2 both exhibited moderate antibacterial activity.

Marine Pharmacology in 2012–2013: Marine Compounds with Antibacterial, Antidiabetic, Antifungal, Anti-Inflammatory, Antiprotozoal, Antituberculosis, and Antiviral Activities; Affecting the Immune and Nervous Systems, and Other Miscellaneous Mechanisms of Action

“…[69]; a new anthraquinone-citrin derivative (MIC = 16 μg/mL), isolated from the sea fan-derived fungus Penicillium citrinum PSU-F51 [114]; and a new chlorinated benzophenone derivative, (±)-pestalachloride C (MIC = 5–20 μM) from a South China Sea soft coral-derived fungus Pestalotiopsis sp. [115]. Finally, during 2012–2013, the novel marine lipopeptides, peptidolipins B–F (MIC = 64 μg/mL), were isolated from an ascidian-derived Gram positive Nocardia sp.…”

Antimicrobial discovery from natural and unusual sources

“…Pestalone is a chlorinated benzophenone antibiotic compound, isolated from the combined cultivation of the marine fungi of Pestalotia species (isolated from the surface of the Bahamian brown alga Rosenvingea species) and showed antibacterial activities against methicillin‐resistant S. aureus and vancomycin‐resistant Enterococcus faecium . Similarly, pestalachloride D, which is an antibacterial chlorinated benzophenone derivative from the marine fungi Pestalotiopsis species, isolated from a soft coral Sarcophyton species is known to possess antibacterial activities against E. coli , Vibrio anguillarum and Vibrio parahaemolyticus . The marine Trichoderma species, isolated from sponges, is known to produce aminolipopeptides trichoderins A, A1 and B which exhibit antibacterial activity against Mycobacterium smegmatis , Mycobacterium bovis BCG and M. tuberculosis H37Rv .…”

“…[42] Similarly, pestalachloride D, which is an antibacterial chlorinated benzophenone derivative from the marine fungi Pestalotiopsis species, isolated from a soft coral Sarcophyton species is known to possess antibacterial activities against E. coli, Vibrio anguillarum and Vibrio parahaemolyticus. [43] The marine Trichoderma species, isolated from sponges, is known to produce aminolipopeptides trichoderins A, A1 and B which exhibit antibacterial activity against Mycobacterium smegmatis, Mycobacterium bovis BCG and M. tuberculosis H37Rv. [44] (Table 1).…”

New Metabolites and Bioactive Chlorinated Benzophenone Derivatives Produced by a Marine-Derived Fungus Pestalotiopsis heterocornis

“…However, only a few fungi of the genus Pestalotiopsis have been reported from marine fauna [14]. Therefore, marine fungi of the genus Pestalotiopsis associated with the sponges could be expected to metabolize biologically interesting and chemically diverse compounds.…”