Antartin, a Cytotoxic Zizaane-Type Sesquiterpenoid from a Streptomyces sp. Isolated from an Antarctic Marine Sediment

Kim, Dayoung; Lee, Eun Ju; Lee, Jihye; Leutou, Alain Simplice; Shin, Yern Hyerk; Choi, Bomi; Hwang, Ji Sun; Hahn, Dongyup; Choi, Hyukjae; Chin, Jungwook; Cho, Sung Jin; Hong, Yong Deog; Ko, Jaeyoung; Seong, Chi Nam; Maloney, Katherine N.; Oh, Dong Chan; Yang, Inho; Hwang, Hayoung; Nam, Sang Jip

doi:10.3390/md16040130

Cited by 17 publications

(8 citation statements)

References 24 publications

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“…Members of the Streptomycetales, specifically the Streptomyces genus are responsible for the synthesis of most of the antibiotics currently in use [63]. However, there are few reports of compounds isolated from Antarctic Streptomyces strains [64][65][66]. AD domain sequences associated with the non-Streptomyces actinobacteria, showed a prevalent distribution (>50% of relative abundance) in some samples: e.g., Mycobacterium in sample 87 and Nocardia in sample 72 (Table S5).…”

Section: Taxonomic Identity Of Nrps Genesmentioning

confidence: 99%

Diversity of Bacterial Biosynthetic Genes in Maritime Antarctica

et al. 2020

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Bacterial natural products (NPs) are still a major source of new drug leads. Polyketides (PKs) and non-ribosomal peptides (NRP) are two pharmaceutically important families of NPs and recent studies have revealed Antarctica to harbor endemic polyketide synthase (PKS) and non-ribosomal peptide synthetase (NRPS) genes, likely to be involved in the production of novel metabolites. Despite this, the diversity of secondary metabolites genes in Antarctica is still poorly explored. In this study, a computational bioprospection approach was employed to study the diversity and identity of PKS and NRPS genes to one of the most biodiverse areas in maritime Antarctica-Maxwell Bay. Amplicon sequencing of soil samples targeting ketosynthase (KS) and adenylation (AD) domains of PKS and NRPS genes, respectively, revealed abundant and unexplored chemical diversity in this peninsula. About 20% of AD domain sequences were only distantly related to characterized biosynthetic genes. Several PKS and NRPS genes were found to be closely associated to recently described metabolites including those from uncultured and candidate phyla. The combination of new approaches in computational biology and new culture-dependent and -independent strategies is thus critical for the recovery of the potential novel chemistry encoded in Antarctica microorganisms. target the highly conserved ketosynthase (KS) and adenylation (AD) domains of PKS and NRPS genes, respectively. A growing number of studies have employed the PCR-based sequence tag approach to uncover PKS and NRPS gene diversity across different environmental microbiomes [7][8][9].Extreme environments, such as Antarctica, have the potential to reveal novel molecules since they are still a poorly explored source of chemical scaffolds and novel chemical diversity [10,11]. As such, metabarcoding approaches to study PKS and NRPS diversity in Antarctic ecosystems represent a simple and effective strategy to understand the biosynthetic potential of a large number of sampling sites [7]. A couple of such studies have been carried out very recently in Antarctica [12,13] revealing that soils at different Antarctica locations harbor multiple endemic PKS and NRPS genes, likely to be involved in the synthesis of new chemical diversity. In Antarctic soils, the percentage of yet-uncultured genera is expected to be much higher [14] than the 82% described for general soils [15]. A considerable fraction of such uncultured bacteria corresponds to members of the NP-rich Actinobacteria [16,17] and Cyanobacteria [18,19] phyla.King George Island is one of the largest ice-free and biodiverse areas in maritime Antarctica [20]. It harbors a high density of scientific stations, particularly in Maxwell Bay [21], where most of terrestrial biology research takes place. Although bacterial diversity studies have been conducted in this area [22,23], the diversity of bacterial biosynthetic genes has not been a target of study. Here, we perform a detailed study on soil samples from Maxwell Bay, with the main goal of assessing the...

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Section: Taxonomic Identity Of Nrps Genesmentioning

confidence: 99%

Diversity of Bacterial Biosynthetic Genes in Maritime Antarctica

et al. 2020

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“…Streptomyces sp. SCO-736, isolated from an Antarctic marine sediment, was found to produce antartin ( 10 ) a tricyclic zizaane-type sesquiterpene with an unusual phenyl group ( Figure 3 ) [ 79 ]. Tricyclic sesquiterpenes are an important class of marine natural products characterized by structural diversity often unprecedented when compared to terrestrial metabolites.…”

Section: Marine Compounds From Polar Regionsmentioning

confidence: 99%

“…They often display interesting biological activity, such as antifouling, cytotoxic, antibiotic, antifungal, antiparasitic and anti-inflammatory activities [ 182 ]. Antartin displays moderate cytotoxicity against a wide range of cancer cell lines, A549, H1299 and U87 cell lines, by causing cell cycle arrest at the G1 phase [ 79 ].…”

Section: Marine Compounds From Polar Regionsmentioning

confidence: 99%

Marine Terpenoids from Polar Latitudes and Their Potential Applications in Biotechnology

et al. 2020

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Polar marine biota have adapted to thrive under one of the ocean’s most inhospitable scenarios, where extremes of temperature, light photoperiod and ice disturbance, along with ecological interactions, have selected species with a unique suite of secondary metabolites. Organisms of Arctic and Antarctic oceans are prolific sources of natural products, exhibiting wide structural diversity and remarkable bioactivities for human applications. Chemical skeletons belonging to terpene families are the most commonly found compounds, whereas cytotoxic antimicrobial properties, the capacity to prevent infections, are the most widely reported activities from these environments. This review firstly summarizes the regulations on access and benefit sharing requirements for research in polar environments. Then it provides an overview of the natural product arsenal from Antarctic and Arctic marine organisms that displays promising uses for fighting human disease. Microbes, such as bacteria and fungi, and macroorganisms, such as sponges, macroalgae, ascidians, corals, bryozoans, echinoderms and mollusks, are the main focus of this review. The biological origin, the structure of terpenes and terpenoids, derivatives and their biotechnological potential are described. This survey aims to highlight the chemical diversity of marine polar life and the versatility of this group of biomolecules, in an effort to encourage further research in drug discovery.

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“…SCO-736 has been isolated from marine sediments of the Antarctica coast. This bacterium produced antartin, a tricyclic zizaene-type sesquiterpene with a phenyl group that is cytotoxic to A549, H1299, and U87 cancer cells by inducing cell cycle arrest ( Kim et al ., 2018 ). Further HPLC-UV guided isolation of the culture broth of this strain has yielded a novel bioactive compound, antaroide ( 1 , Fig.…”

Section: Introductionmentioning

confidence: 99%

Antaroide, a Novel Natural Nine-Membered Macrolide, Inhibits Melanin Biosynthesis in B16F10 Murine Melanoma Cells

Ryu

Baek

Kim

et al. 2021

Biomolecules & Therapeutics

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The demand for natural substances with anti-melanogenic activity is increasing due to the recent interest in skin whitening. Intensive investigation on the culture broth of Streptomyces sp. SCO-736, a marine bacterium from the Antarctica coast, has led to the isolation of a new natural product named antaroide (1). The chemical structure was established through the interpretation of MS, UV, and NMR spectroscopic data. Antaroide is a nine-membered macrolide with lactone and lactam moieties. To investigate its applicability in skin whitening cosmetics, its anti-melanogenic activity in B16F10 murine melanoma cells was examined. As a result, antaroide displayed strong inhibitory activities against melanin synthesis and also attenuated the dendrite formation induced by the α-melanocyte stimulating hormone (α-MSH). Antaroide suppressed the mRNA expression of the melanogenic enzymes such as tyrosinase, TRP-1 and TRP-2. This suggests that it may serve as a transcriptional regulator of melanogenesis. Collectively, the discovery of this novel natural nine-membered macrolide and its anti-melanogenic activity could give new insights for the development of skin whitening agents.

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Antartin, a Cytotoxic Zizaane-Type Sesquiterpenoid from a Streptomyces sp. Isolated from an Antarctic Marine Sediment

Cited by 17 publications

References 24 publications

Diversity of Bacterial Biosynthetic Genes in Maritime Antarctica

Diversity of Bacterial Biosynthetic Genes in Maritime Antarctica

Marine Terpenoids from Polar Latitudes and Their Potential Applications in Biotechnology

Antaroide, a Novel Natural Nine-Membered Macrolide, Inhibits Melanin Biosynthesis in B16F10 Murine Melanoma Cells

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