Puupehenol, a Potent Antioxidant Antimicrobial Meroterpenoid from a Hawaiian Deep-Water <i>Dactylospongia</i> sp. Sponge

Hagiwara, Kehau A.; Hernandez, Jaaziel E. Garcia; Harper, Mary Kay; Carroll, Anthony Richard; Motti, Cherie A.; Awaya, Jonathan D.; Nguyen, Hoang-Yen X.; Wright, Anthony D.

doi:10.1021/np500793g

Cited by 37 publications

(52 citation statements)

References 23 publications

(41 reference statements)

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“…20). 191 The authors suggested that the well-known puupehenone may be a work-up artefact of the natural precursor puupehenol. Two epimeric sesquiterpene chromenols, named cyclorenierin A and B (158), were found in Haliclona sp., an Indo-Pacic sponge from Vanuatu.…”

Section: Spongesmentioning

confidence: 99%

“…26). 227 Several low molecular weight chromenes, such as pterochromenes L1 (190), L2 (191) and L4 (192), were isolated from Taiwanese Pteris lingipinna 228 . 6-Hydroxyeupatoriochromene B (193) was obtained from Ageratina riparia (Asteraceae) 229 and nally, one of the rst insect anti-juvenile hormones, precocene 2 (194) (6,7-dimethoxy-2,2-dimethylchromene) was found in Ageratum houstonianum (Asteraceae).…”

Section: Plantsmentioning

confidence: 99%

See 1 more Smart Citation

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Birringer

Siems²,

Maxones

et al. 2018

RSC Adv.

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Section: Spongesmentioning

confidence: 99%

Section: Plantsmentioning

confidence: 99%

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Birringer

Siems²,

Maxones

et al. 2018

RSC Adv.

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“…Terpene quinones, including puupehenone metabolites, have been extensively studied for their antimicrobial and cytotoxic properties (32,(48)(49)(50)(51)(52). Nonetheless, this is the first report demonstrating that they selectively inhibit dormant drug-tolerant M. tuberculosis.…”

Section: Discussionmentioning

confidence: 99%

Selective Killing of Dormant Mycobacterium tuberculosis by Marine Natural Products

Felix

Gupta

Geden

et al. 2017

Antimicrob Agents Chemother

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The dormant phenotype acquired by Mycobacterium tuberculosis during infection poses a major challenge in disease treatment, since these bacilli show tolerance to front-line drugs. Therefore, it is imperative to find novel compounds that effectively kill dormant bacteria. By screening 4,400 marine natural product samples against dual-fluorescent M. tuberculosis under both replicating and nonreplicating conditions, we have identified compounds that are selectively active against dormant M. tuberculosis. This validates our strategy of screening all compounds in both assays as opposed to using the dormancy model as a secondary screen. Bioassayguided deconvolution enabled the identification of unique pharmacophores active in each screening model. To confirm the activity of samples against dormant M. tuberculosis, we used a luciferase reporter assay and enumerated CFU. The structures of five purified active compounds were defined by nuclear magnetic resonance (NMR) and mass spectrometry. We identified two lipid compounds with potent activity toward dormant and actively growing M. tuberculosis strains. One of these was commercially obtained and showed similar activity against M. tuberculosis in both screening models. Furthermore, puupehenone-like molecules were purified with potent and selective activity against dormant M. tuberculosis. In conclusion, we have identified and characterized antimycobacterial compounds from marine organisms with novel activity profiles which appear to target M. tuberculosis pathways that are conditionally essential for dormancy survival.

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“…The FRAP assay performed was slight modified according to the previous reported literature252627. The FRAP reagent was freshly prepared by adding 3 M CH 3 COOH buffer (pH 3.6), 0.1 M 2,4,6-Tris(2-pyridyl)-s-triazine and 0.2 M FeCl3 at 10:1:1 volume ratio in 0.4 M HCl.…”

Section: Methodsmentioning

confidence: 99%

Antioxidative Polyketones from the Mangrove-Derived Fungus Ascomycota sp. SK2YWS-L

Tan

Liu

Chen

et al. 2016

Sci Rep

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Three novel 2,3-diaryl indone derivatives, ascomindones A−C (1−3), and two new isobenzofuran derivatives, ascomfurans A (4) and B (5), together with four know compounds (6−9) were isolated from the culture of a mangrove-derived fungus Ascomycota sp. SK2YWS-L. Their structures were elucidated on the interpretation of spectroscopic data. 1 and 4 were further constructed by analysis of X-ray diffraction. Antioxidant properties based on 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl radical scavenging activities and the ferric reducing ability power (FRAP) of the new compounds were assayed. All of them exhibited significant effects, of which 1 showed more potent activity than ascorbic acid in scavenging DPPH radical with IC50 value of 18.1 μM.

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Puupehenol, a Potent Antioxidant Antimicrobial Meroterpenoid from a Hawaiian Deep-Water Dactylospongia sp. Sponge

Cited by 37 publications

References 23 publications

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Natural 6-hydroxy-chromanols and -chromenols: structural diversity, biosynthetic pathways and health implications

Selective Killing of Dormant Mycobacterium tuberculosis by Marine Natural Products

Antioxidative Polyketones from the Mangrove-Derived Fungus Ascomycota sp. SK2YWS-L

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