Halistanol sulfates I and J, new SIRT1–3 inhibitory steroid sulfates from a marine sponge of the genus Halichondria

Nakamura, Fumiaki; Kudo, Norio; Tomachi, Yuki; Nakata, Akiko; Takemoto, Misao; Ito, Akihiro; Tabei, Hodaka; Arai, Daisuke; Voogd, Nicole J. de; Yoshida, Minoru; Nakao, Yoichi; Fusetani, Nobuhiro

doi:10.1038/ja.2017.145

Cited by 18 publications

(10 citation statements)

References 27 publications

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“…Detailed analysis of the 1 H and 13 C NMR, COSY, HSQC, HMBC, and NOESY spectra of 10 (CD 3 OD, Table 1 and Table 2, Figure 2, substructures II and VIII, Figures S39–S44) and a comparison of its 1 H and 13 C chemical shift values with those reported in the literature for the previously described trisulfated steroids [1,2,3,4,5,6,7,8,9,10,11,12,13,14,15,16,17,18], indicated that 10 is a previously unreported 4 β -hydroxy derivative of halistanol sulfate C [3], which was named 4 β -hydroxyhalistanol sulfate C.…”

Section: Resultsmentioning

confidence: 99%

“…[3,4], Pseudoaxinissa digitata [5], and Halichondria sp. [6], ophirapsranol trisulfate from Topsentia ophiraphidites [7], four sterols isolated from the sponges Trachyopsis halichondroides and Cymbastela coralliophila [8], amaranzoles A-F from Phorbas amaranthus [9,10], and topsentinol K trisulfate from the sponge Topsentia sp. [11].…”

Section: Introductionmentioning

confidence: 99%

“…In fact, a broad range of activities has been described to trisulfate steroids such as antibacterial [1,15,20], antifungal [15,16,21], antiviral (including anti-HIV and anti-HSV effects) [5,12,13,22,23], antiparasitic [21], and antiplatelet activities [24]. In addition, the inhibition of different enzymes [6,11,18], promotion of angiogenesis [25], and antitumor activity against various tumor cell lines [7,15,17,26] have been described. Thus, the search for new trisulfated steroids from sponges, including the analyses of their chemical structures and physiological properties, continues to be a promising area of research.…”

Section: Introductionmentioning

confidence: 99%

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New Trisulfated Steroids from the Vietnamese Marine Sponge Halichondria vansoesti and Their PSA Expression and Glucose Uptake Inhibitory Activities

et al. 2019

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Seven new unusual polysulfated steroids—topsentiasterol sulfate G (1), topsentiasterol sulfate I (2), topsentiasterol sulfate H (3), bromotopsentiasterol sulfate D (4), dichlorotopsentiasterol sulfate D (8), bromochlorotopsentiasterol sulfate D (9), and 4β-hydroxyhalistanol sulfate C (10), as well as three previously described—topsentiasterol sulfate D (7), chlorotopsentiasterol sulfate D (5) and iodotopsentiasterol sulfate D (6) have been isolated from the marine sponge Halichondria vansoesti. Structures of these compounds were determined by detailed analysis of 1D- and 2D-NMR and HRESIMS data, as well as chemical transformations. The effects of the compounds on human prostate cancer cells PC-3 and 22Rv1 were investigated.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New Trisulfated Steroids from the Vietnamese Marine Sponge Halichondria vansoesti and Their PSA Expression and Glucose Uptake Inhibitory Activities

et al. 2019

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“…New analogues of the known trisulfate compound halistanol sulfate 155 bearing cyclopropyl rings on their side chains have been isolated from the marine sponge Halichondria sp. Halistanol sulfates I 156 and J 157 had IC 50 values for sirtuins 1–3 of 45.9, 18.9, and 32.6 µM and 67.9, 21.1, and 37.5 µM, respectively, compared to IC 50 s of the parent structure 105 of 49.1, 19.2, and 21.8 µM [ 103 ].…”

Section: Bioactive Steroidal Metabolitesmentioning

confidence: 99%

Microbial Sterolomics as a Chemical Biology Tool

Haubrich

2018

Molecules

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Metabolomics has become a powerful tool in chemical biology. Profiling the human sterolome has resulted in the discovery of noncanonical sterols, including oxysterols and meiosis-activating sterols. They are important to immune responses and development, and have been reviewed extensively. The triterpenoid metabolite fusidic acid has developed clinical relevance, and many steroidal metabolites from microbial sources possess varying bioactivities. Beyond the prospect of pharmacognostical agents, the profiling of minor metabolites can provide insight into an organism’s biosynthesis and phylogeny, as well as inform drug discovery about infectious diseases. This review aims to highlight recent discoveries from detailed sterolomic profiling in microorganisms and their phylogenic and pharmacological implications.

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“…Marine invertebrates are immensely diverse, well distributed in the world oceans [8], and widely known to contain medicinally relevant molecules [9,10,11]. While these metabolites play different roles in nature, e.g., they act as chemical defense, chemical communication or reproductive signaling molecules, they also find application as human medicines [12].…”

Section: Introductionmentioning

confidence: 99%

Antitumor Anthraquinones from an Easter Island Sea Anemone: Animal or Bacterial Origin?

et al. 2019

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The presence of two known anthraquinones, Lupinacidin A and Galvaquinone B, which have antitumor activity, has been identified in the sea anemone (Gyractis sesere) from Easter Island. So far, these anthraquinones have been characterized from terrestrial and marine Actinobacteria only. In order to identify the anthraquinones producer, we isolated Actinobacteria associated with the sea anemone and obtained representatives of seven actinobacterial genera. Studies of cultures of these bacteria by HPLC, NMR, and HRLCMS analyses showed that the producer of Lupinacidin A and Galvaquinone B indeed was one of the isolated Actinobacteria. The producer strain, SN26_14.1, was identified as a representative of the genus Verrucosispora. Genome analysis supported the biosynthetic potential to the production of these compounds by this strain. This study adds Verrucosispora as a new genus to the anthraquinone producers, in addition to well-known species of Streptomyces and Micromonospora. By a cultivation-based approach, the responsibility of symbionts of a marine invertebrate for the production of complex natural products found within the animal’s extracts could be demonstrated. This finding re-opens the debate about the producers of secondary metabolites in sea animals. Finally, it provides valuable information about the chemistry of bacteria harbored in the geographically-isolated and almost unstudied, Easter Island.

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Halistanol sulfates I and J, new SIRT1–3 inhibitory steroid sulfates from a marine sponge of the genus Halichondria

Cited by 18 publications

References 27 publications

New Trisulfated Steroids from the Vietnamese Marine Sponge Halichondria vansoesti and Their PSA Expression and Glucose Uptake Inhibitory Activities

New Trisulfated Steroids from the Vietnamese Marine Sponge Halichondria vansoesti and Their PSA Expression and Glucose Uptake Inhibitory Activities

Microbial Sterolomics as a Chemical Biology Tool

Antitumor Anthraquinones from an Easter Island Sea Anemone: Animal or Bacterial Origin?

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