A new Butenolide Derivative from the Brown Alga <i>Sargassum micracanthum</i>

Kim, Ji-Yul; Lee, Jeong Min; Kim, Hyunsoo; Ki, Dae‐Won; Yim, Mi‐Jin; Ko, Seok‐Chun; Shin, Jung Min; Lee, Myeong Seok; Park, Yun Gyeong; Lee, Dae-Sung

doi:10.1177/1934578x211068606

Cited by 3 publications

(3 citation statements)

References 23 publications

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“…Compound 1 was similar in structure to sargassumin A except for the presence of a hydroxyl group (C-11) in 1 , which replaced the ketone moiety in sargassumin A. 12 The E -configuration at C-13 in 1 was elucidated by comparing the carbon chemical shift ( Z -form: above δ C 20.0). The stereochemistry at C-4 in 1 was determined to be R on the basis of a positive Cotton effect at 210 nm.…”

Section: Resultsmentioning

confidence: 99%

Sargassumin C, a Novel Butenolide from Sargassum micracanthum

Kim

Lee

et al. 2022

Natural Product Communications

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Objective: In our ongoing effort to search for the novel secondary metabolites from the marine algae, chemical investigation of a methanolic extract of Sargassum micracanthum led to the isolation of a novel butenolide (1) and a known compound (2). Methods: The methanolic extract of S. micracanthum was partitioned and subjected to medium pressure column chromatography and preparative-HPLC to yield two compounds (1 and 2). Their structures were established based on comprehensive spectroscopic data (1D NMR, 2D NMR, and HRESIMS). These compounds (1 and 2) were evaluated for the production of the NO in lipopolysaccharide (LPS)-induced RAW264.7 cells and pro-inflammatory cytokines such as IL-6, IL-1 β, TNF- α, and IL-10. Results: A new compound (1) was determined to be a new butenolide derivative, and a known compound (2) were identified as 2-hydroxy-(5 E,9 E)-6,10,14-trimethylpentadeca-5,9-dien-12-one. Compounds 1 and 2 showed inhibitory activities in a dose-dependent manner on LPS-induced NO production in RAW264.7 cells and pro-inflammatory cytokines. Conclusion: A new butenolide, sargassumin C (1), and 2-hydroxy-(5 E,9 E)-6,10,14-trimethylpentadeca-5,9-dien-12-one (2) were isolated from the brown alga, S. micracanthum. Compound 2 was more effective than 1 on NO production and pro-inflammatory cytokines.

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Section: Resultsmentioning

confidence: 99%

Sargassumin C, a Novel Butenolide from Sargassum micracanthum

Kim

Lee

et al. 2022

Natural Product Communications

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“…A butenolide 877, named sargassumin A, was reported from a South Korean (Jeju Island) Sargassum micracanthum; this manuscript was submitted in mid-2021 and accepted for publication in December of that year. 334 The name sargassumin A was then used for a different lactone 878 along with sargassumin B 879, from a Jeju Island Sargassum macrocarpum, published by a different group with their manuscript submitted and accepted well aer the former paper was published. 335 Butenolide sargassumin C 880 was subsequently reported from S. micracanthum and is related to 877, 336 although this publication shows the authors were obviously aware of the others publication and therefore they did not use the name sargassumin B.…”

Section: Brown Algaementioning

confidence: 99%

Marine natural products

Carroll,

Copp,

Grkovic

et al. 2024

Nat. Prod. Rep.

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“…ABTS and DPPH radical scavenging assays were conducted according to a previously reported protocol. 21,22 Briefly, ABTS was dissolved in H 2 O (7 mM) and incubated with potassium persulfate (2.45 mM) in the dark. The absorbances of the samples and mixed solutions were measured at 734 nm.…”

Section: Measurement Of Anti-oxidant Activitiesmentioning

confidence: 99%

Two New Meroterpenoid Derivatives From Sargassum macrocarpum With Their Anti-Oxidant Activities

Kim

Choi

Lee

et al. 2023

Natural Product Communications

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Objective: The purpose of this study was to search for novel secondary metabolites present in the marine brown alga, Sargassum macrocarpum C. Agardh. Methods: The methanolic extract of S. macrocarpum was partitioned and fractionated using a silica gel column, medium pressure liquid chromatography, and preparative-high performance liquid chromatography to obtain four compounds (1-4). These structures were elucidated using nuclear magnetic resonance spectroscopic and high resolution-electrospray ionization-mass spectroscopy methods. The isolated compounds were evaluated for their anti-oxidant activities using 2,2′-azinobis (3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals. Result: Two undescribed meroterpenoid derivatives (1 and 2), together with two known racemic meroterpenoids (3 and 4) were isolated from the methanolic extract of S. macrocarpum. All compounds were confirmed to be meroterpenoid derivatives. All these compounds exhibited ABTS and DPPH radical scavenging activities. Conclusions: The four meroterpenoids (1-4) were isolated from S. macrocarpum. Compound 3 showed the most anti-oxidant effect with IC50 values of 9.9 (ABTS radical) and 22.4 μM (DPPH radical), respectively.

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A new Butenolide Derivative from the Brown Alga Sargassum micracanthum

Cited by 3 publications

References 23 publications

Sargassumin C, a Novel Butenolide from Sargassum micracanthum

Sargassumin C, a Novel Butenolide from Sargassum micracanthum

Marine natural products

Two New Meroterpenoid Derivatives From Sargassum macrocarpum With Their Anti-Oxidant Activities

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