The macrolactins, a novel class of antiviral and cytotoxic macrolides from a deep-sea marine bacterium

Abstract

Celite and rinsed with 1.0 mL of dichloromethane, 1.0 mL of ethyl acetate, 12 mL of dichloromethane with 2% acetic acid, and 10 mL of ethyl acetate with 1% acetic acid. The filtrate was concentrated in vacuo to give a brown solid. The residue was chromatographed over 0.6 g of silica gel (eluted with ethyl acetate-hexane, 1:5 progressing to 1:1, and then with ethyl acetate-hexane-acetic acid, 66:31:2) to give 2.9 mg (32%) of pleurotin (1) as a pale yellow solid:

A New 24-membered Lactone and a New Polyene δ-Lactone from the Marine Bacterium Bacillus marinus

“…The UV bands at 236, 262 nm, and IR absorptions at 3378, 1693, 1638, and 1581 cm Ϫ1 suggested the presence of hydroxyl, carbonyl and olefinic groups. The 1 H-and 13 C-NMR data (Table 1) of 1 were closely related to those of macrolactin A [3], indicating a congener of macrolactins. The 13 C-NMR spectrum exhibited totally 24 carbon resonances including 12 vinyl carbons for six double bonds and a carbonyl carbon (Table 1), which accounted to seven sets of unsaturation.…”

“…Thus far nineteen macrolactins (macrolactins AϳS) have been reported, of which macrolactins AϳF were found from unidentified deep sea bacterium [3]. Macrolactins possess a wide range pharmacological activities, e.g.…”

Macrolactin S, a New Antibacterial Agent with Fab G-inhibitory Activity from Bacillus sp. AT28

“…Compound 1 is a derivative of macrolactin A [12] in which C-12 is hydroxylated. Macrolactin S was reported by another group earlier this year [13].…”

“…Macrolactins have been isolated from an unclassifiable deep-sea bacterium, Actinomadura sp., or Bacillus sp. Macrolactin A shows antibacterial activity, inhibits B16ϳF10 murine melanoma cancer cells in vitro, shows significant inhibition of mammalian herpes simplex viruses (types I and II) [12], and prevents glutamate neurotoxicity in N18-RE-105 cells [16]. In addition, macrolactins FϳR, 7-O-succinoylmacrolactin A, 7-Osuccinoylmacrolactin F, and 7-O-malonylmacrolactin A have been reported to exhibit antibacterial activity against S. aureus and B. subtilis [14, 17ϳ20].…”

“…In the course of our screening for FabG inhibitors from microbial metabolites, we have isolated a new 24-membered lactone compound named macrolactin S (1) together with the known compound, macrolactin B (2) [12], from Bacillus sp. AT28 (Fig.…”