Secondary metabolites from marine-derived Streptomyces antibioticus strain H74-21

Abstract

A new secondary metabolite, (2S,3R)-l-threonine, N-[3-(formylamino)-2-hydroxybenzoyl]-ethyl ester (streptomyceamide C, 1), together with four known compounds 1, 4-dimethyl-3-isopropyl-2,5-piperidinedione (2), cyclo-((S)-Pro-8- hydroxy-(R)-Ile (3), cyclo-((S)-Pro-(R)-Leu (4), and seco-((S)-Pro-(R)-Val) (5), were isolated from the EtOH extract of the fermented mycelium of the marine-derived streptomycete strain H74-21, which was isolated from sea sediment in a mangrove site. The structure of the new compound was established on the basis of its spectroscopic data, including 1D and 2D NMR, HR-TOF-MS. Their antifungal activities against Candida albicans and cytotoxicities against human breast adenocarcinoma cell line MCF-7, human glioblastoma cell line SF-268 and human lung cancer cell line NCI-H460 were tested. Compounds 1 only displayed cytotoxicity against human breast adenocarcinoma cell line MCF-7 with the IC50 value of 27.0 μg/mL. However, compounds 1-5 do not show antifungal activities at the test concentration of 1 mg/mL, and 2-5 have no cytotoxicities at the test concentration of 50 μg/mL.

Diversity, Novelty, and Antimicrobial Activity of Endophytic Actinobacteria From Mangrove Plants in Beilun Estuary National Nature Reserve of Guangxi, China

“…Furthermore, at least 84 new compounds including some “hot molecules,” such as salinosporamides, xiamycins and novel indolocarbazoles, were discovered from mangrove actinobacteria. ( Kyeremeh et al, 2014 ; Xu et al, 2014 ; Ding et al, 2015 ; Fu et al, 2016 ; Han et al, 2016 ; Mangamuri et al, 2016a , b ; Chen et al, 2017 ; Ye et al, 2017 ).…”

A New Lignanamide from the Root of Lycium yunnanense Kuang and Its Antioxidant Activity

“…Finally, we calculated the configurations between C-7/C-7′, C-8/C-8′ with the lowest energy of compound 1 in ChemDraw [ 16 ]. All of these results suggested that the substitution of the THF ring of 1 should possess a 7, 8- trans /8, 8′- trans /7′, 8′- trans relative configuration [ 17 , 18 , 19 ].…”

Cytotoxic compounds from marine actinomycetes: sources, structures and bioactivity

“…A polycyclic tetramate macrolactam, 16-hydroxymaltophilin (57), isolated from Actinoalloteichus cyanogriseus WH1-2216-6, shows cytotoxicity toward BXPC-3, HCT-116, Jurkat, PANC-1, A549, MCF-7 and L-02 cell lines, with IC 50 values of 4.5, 5.7, 7.5, 7.9, 9.5, 9.7 and 235.9 μM, respectively [38].…”

“…Compound 91 exhibits inhibitory activity toward HCC366, A549 and HCC44 cells, with IC 50 values of 2.8, 4.1 and 8.4 μM, respectively, and compound 92 inhibits HCC366 and A549 cells, with IC 50 values of 2.2 and 3.7 μM, respectively. The compound (2S,3R)-L-threonine, N-[3-(formylamino)-2-hydroxybenzoyl]-ethyl ester (streptomyceamide C, 93) has been isolated from EtOH extract of the fermented mycelium of the marinederived streptomycete strain H74-21 isolated from a sea sediment in a mangrove site [57]. Compound 93 shows cytotoxicity toward MCF-7, with an IC 50 of 27.0 μg/mL.…”