Two new sacrolide-class oxylipins from the edible cyanobacterium Aphanothece sacrum

Oku, Naohiko; Hana, Sayaka; Matsumoto, Michito; Yonejima, Kohsuke; Tansei, Keijiroh; Isogai, Yasuhiro; Igarashi, Yasuhiro

doi:10.1038/ja.2017.32

Cited by 11 publications

(16 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Some cyanobacterial species are consumed as food, nutritional supplements, or folk medicines in many parts of the world [2], and have offered attractive opportunities for drug discovery. Results from the limited number of attempts include an antifungal lipopeptide nostofungicidine [3] and an antioxidant nostocionone [4] from Nostoc commune, an unusual antibacterial n-1 fatty acid from N. verrucosum [2], and the sacrolides, antimicrobial oxylipin macrolactones from Aphanothece sacrum [5,6].…”

Section: Resultsmentioning

confidence: 99%

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

Oku¹,

Hayashi²,

Yamaguchi³

et al. 2022

Preprint

View full text Add to dashboard Cite

A new antibacterial 3-monoacyl-sn-glycerol, nostochopcerol (1), was isolated from a cultured algal mass of edible cyanobacterium Nostochopsis lobatus MAC0804NAN. The structure of 1 was established by the analysis of NMR and MS data while its chirality was established by comparison of optical rotation with synthetically prepared authentics. Compound 1 inhibited the growth of Bacillus subtilis and Staphylococcus aureus at MIC 50 μg/mL and 100 μg/mL, respectively.

show abstract

Section: Resultsmentioning

confidence: 99%

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

Oku¹,

Hayashi²,

Yamaguchi³

et al. 2022

Preprint

View full text Add to dashboard Cite

show abstract

“…Indeed, wound‐activated compounds, commonly produced as anti‐grazer defences in diatoms (Pohnert, 2000), are poorly studied in cyanobacteria (Fink et al, 2006). However, in freshwater, a phylogenetically distant, edible cyanobacterium, Aphanothece sacrum , was demonstrated to produce wound‐activated compounds identified as oxylipin metabolites (Oku et al, 2017) (i.e., molecules enzymatically or chemically derived from fatty acid peroxidation, with antibiotic and infochemical activities). Oxylipins are produced by lipoxygenases, a family of non‐heme iron‐containing fatty acid dioxygenases, which have been first described in Oscillatoriales (Beneytout et al, 1989).…”

Section: Discussionmentioning

confidence: 99%

Constitutive and activated toxigenic activity ofHalomicronema metazoicum(Cyanoprokaryota, Cyanophyta)

et al. 2022

View full text Add to dashboard Cite

Phormidium-like cyanobacteria produce a variety of biologically active molecules. We isolated a free-living strain of Halomicronema metazoicum, previously known uniquely as a symbiont of marine sponges, and demonstrated that its spent medium was toxic for various protozoans and fish parasites. However, we still ignore if its mats contain constitutive or activated defences influencing the physiology of other organisms, with potential influences on organisms that share the same environment. The goal of this study is to clarify if Phormidium-like cyanobacteria accumulate toxic bioactive molecules in the colony tissues, for example for anti-grazing purposes, or if they constitutively secrete them in the medium, with a potential allelopathic function. To address this hypothesis, the toxigenic power of cyanobacterial spent medium and of disintegrated cells (to simulate lysis) was assayed using standard toxicity-tests on nauplii of the brine shrimp Artemia salina. Toxigenic effects were triggered by the spent culture medium, but the homogenates (disintegrated cyanobacteria cells) did not show any acute toxicity. In addition, chronic toxicity tests of the spent medium demonstrated a reduced but still present toxigenic effect, with an inverse correlation between toxicity and medium dilution. The present research contributes to the understanding of cyanobacteria chemical-ecology and shows that they may play fundamental ecological roles, influencing the survival and the blooms of various co-habiting species by constitutively releasing toxic exudates. Since the bioactive compounds produced by H. metazoicum are stable in water, and considering the bioactivity of exudates on invertebrates' physiology, our results might be exploited for the development of novel biotechnologies in the fields of aquaculture, ecological conservation and medicine, due to the potential antitumoral and anti-parasitic activity demonstrated in strictly related species.

show abstract

“…It should be noted that sacrolide A had a minimum inhibitory concentration of 0.5 μg/mL against S. aureus. 17 Photoisomerization Reaction between Saclipin A and Saclipin B. It was found that photoisomerization occurred between purified saclipin A and B.…”

Section: Identification Of Uva-/uvb-absorbing Compounds Inmentioning

confidence: 99%

“…The saclipins were barely present in fresh A. sacrum but were abundant in dried commercial products (Figure 3), while sacrolide A has been detected in fresh A. sacrum but not in dried samples. 17 As oxylipins are known to be substances that respond to various environmental and biotic stresses, 23,24 saclipins may contribute to a defense mechanism against drought and associated stresses in A. sacrum. Moreover, although sacrolide A has been reported to have antibacterial activity against microorganisms such as S. aureus, 17 the saclipins showed no antibacterial activity, at least up to concentrations of 1.53 μg/mL (Figure S2).…”

Section: Identification Of Uva-/uvb-absorbing Compounds Inmentioning

confidence: 99%

Identification of Desiccation Stress-Inducible Antioxidative and Antiglycative Ultraviolet-Absorbing Oxylipins, Saclipin A and Saclipin B, in an Edible Cyanobacterium Aphanothece sacrum

Uchida,

Maoka,

Palaga

et al. 2023

J. Agric. Food Chem.

View full text Add to dashboard Cite

Aphanothece sacrum, a freshwater cyanobacterium, is an edible cyanobacterial strain. We identified two compounds belonging to the oxylipin family that possess UV-absorbing abilities and accumulate in the dried sample of A. sacrum. The compounds, named saclipin A and saclipin B, exhibited strong UV-absorption properties with the absorption maxima at 316 and 319 nm, respectively, and the molar extinction coefficients of 26,454 and 30,555 M–1 cm–1, respectively. The chemical structures of saclipins A and B have been elucidated, revealing that they have an all-E and a 12Z isomeric relationship within the triene structure. The saclipins could be isomerized by photoirradiation, with the cis-form saclipin B proving to be more stable in methanol, ethanol, or acetonitrile. Under drought stress conditions, the accumulation of saclipins A and B in A. sacrum was found to be increased 20- and 10-fold, respectively. Purified saclipins from A. sacrum showed biocompatibility and valuable bioactivities. Specifically, saclipins exhibited radical scavenging activity, maintaining their activity even 40 min after the reaction began. Additionally, they demonstrated inhibitory activity against glycation of elastin and collagen, which are constituents of dermal tissue. Notably, saclipins showed higher activity than the well-known glycation inhibitor aminoguanidine against collagen glycation.

show abstract

Two new sacrolide-class oxylipins from the edible cyanobacterium Aphanothece sacrum

Cited by 11 publications

References 12 publications

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

Nostochopcerol, a new antibacterial monoacylglycerol from the edible cyanobacterium Nostochopsis lobatus

Constitutive and activated toxigenic activity ofHalomicronema metazoicum(Cyanoprokaryota, Cyanophyta)

Identification of Desiccation Stress-Inducible Antioxidative and Antiglycative Ultraviolet-Absorbing Oxylipins, Saclipin A and Saclipin B, in an Edible Cyanobacterium Aphanothece sacrum

Contact Info

Product

Resources

About