Three new sesquiterpene aminoquinones from a Vietnamese Spongia sp. and their biological activities

Abstract

Sesquiterpenoid quinones with remarkable properties, such as anti-inflammatory, antibacterial, antiviral, antitumor, antiangiogenic, and differentiation-inducing activities, have reportedly been isolated from the marine sponge genera Dysidea, Spongia, and Dactylospongia. In our continuing search for bioactive compounds from marine sponges, three new sesquiterpenoid quinones, langcoquinones D-F (1-3), were isolated from the ethyl acetate extract of Spongia sp. collected from Vietnam. Their chemical structures were elucidated on the basis of extensive spectroscopic analyses. The newly isolated compounds 1-3 were assessed for their antibacterial activities against Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus, and Gram-negative bacteria, Klebsiella pneumoniae and Escherichia coli, as well as their cytotoxic activities against three human cancer cell lines (A549, lung cancer; MCF7, breast cancer; HeLa, cervical cancer) and a human normal cell line (WI-38 fibroblast). All compounds were inactive against the Gram-negative bacteria. Furthermore, langcoquinones E (2) and F (3) lacked antibacterial activities against the Gram-positive bacteria and cytotoxic activities against the tested cell lines. However, langcoquinone D (1) exhibited good antibacterial activities against Bacillus subtilis and Staphylococcus aureus, with MIC values of 12.5 and 25.0 µM, respectively. Furthermore, 1 exhibited significant cytotoxic activities against three human cancer cell lines (A549, lung cancer; MCF7, breast cancer; HeLa, cervical cancer) and a human normal cell line (WI-38 fibroblast).

A New Sesquiterpenoid Aminoquinone from an Indonesian Marine Sponge

“…Sponges are a prolific source of bioactive compounds [1,2,3,4,5,6,7]; in particular, the genera Dysidea , Spongia , and Dactylospongia (family Spongidae) represent a rich source of bioactive sesquiterpenoid quinones and hydroquinones [8]. Merosesquiterpenes contain a sesquiterpene unit joined to a phenolic or quinone moiety and arise from a mixed polyketide-terpenoid biosynthetic pathway.…”

“…Merosesquiterpenes contain a sesquiterpene unit joined to a phenolic or quinone moiety and arise from a mixed polyketide-terpenoid biosynthetic pathway. [9,10] These merosesquiterpenoids continue to attract considerable attention due to their structural diversity and intrinsic biological activities [11] including, but not limited to, antimicrobial [8,12], anti-HIV [13,14], Golgi disruptor agents [15], potent hypoxic inducers in prostate cancer cell lines [16,17], and apoptotic inducers in leukemic cells [18]. Over the years, more than 70 sesquiterpene quinones/hydroquinones have been described in the literature, mainly featuring drimane or rearranged drimane skeletons [19].…”

Bioactive Prenyl- and Terpenyl-Quinones/Hydroquinones of Marine Origin †

“…From a marine sponge Spongia sp., collected off Son Cha, Vietnam, many sesquiterpene aminoquinones/HQs were isolated by Morita et al [ 91 , 92 , 93 ]. The aminoquinones were called langcoquinones A-F ( 177 , 185 , 175 , 186 , 187 , 182 ) ( Table 3 ), and the HQs were called langconols A–C ( 211 – 213 ) ( Table 6 ).…”

An Anti-Inflammatory 2,4-Cyclized-3,4-Secospongian Diterpenoid and Furanoterpene-Related Metabolites of a Marine Sponge Spongia sp. from the Red Sea

“…Many natural products from sponges have been shown to exhibit a variety of biological activities, such as antimicrobial [ 2 , 3 , 4 , 5 ], antiviral [ 6 , 7 , 8 ], antiprotozoal [ 8 , 9 , 10 ], cytotoxic [ 6 , 11 , 12 , 13 ], anti-inflammatory [ 14 , 15 , 16 ], antioxidant [ 4 , 17 , 18 ], immunosuppressive [ 1 , 19 , 20 ], and antifeedant [ 21 , 22 , 23 ]. The genus Spongia (Spongidae) has been chemically investigated since 1971 [ 24 ] and the studies have led to the discovery of a series of furanoterpenes [ 24 , 25 , 26 ], spongian diterpenoids [ 27 , 28 , 29 , 30 , 31 , 32 ], scalarane sesterterpenoids [ 33 , 34 , 35 ], sesquiterpene quinones [ 36 , 37 ], along with other kinds of metabolites, for example, sterols [ 38 , 39 , 40 ] and macrolides [ 41 ].…”