Antioxidant and Neuroprotective Xenicane Diterpenes from the Brown Alga <i>Dictyota coriacea</i>

Yu, Qi; Liu, Ge; Chen, Fang; Jing, Chengcheng; Tang, Shuhua; Li, Ge; Wang, Chaojie; Zhu, Haoru; Zhao, Min; Sun, Zhan-Li; Wu, Jianzhang; Yan, Pengcheng

doi:10.1021/acsomega.2c07891

Cited by 6 publications

(8 citation statements)

References 37 publications

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“…The above data strongly suggested that 5 was an unusual nitrogen-containing xenicane-type diterpenoid. In general, the NMR data of 5 showed great similarities to those of dictyolactam A, which had been recently isolated from the same brown alga, D. coriacea . The only difference was at the C-18 position, where the ethoxy group in dictyolactam A was replaced by a hydroxy group in 5 , which was supported by the COSY cross-peak of 18-OH (δ H 2.09)/H-18 (δ H 5.51), together with the HMBC correlation from H-3 (δ H 2.67) to C-18 (δ C 79.3).…”

Section: Resultsmentioning

confidence: 68%

“…In general, the NMR data of 5 showed great similarities to those of dictyolactam A, which had been recently isolated from the same brown alga, D. coriacea. 22 The only difference was at the C-18 position, where the ethoxy group in dictyolactam A was replaced by a hydroxy group in 5, which was supported by the COSY cross-peak of 18-OH (δ H 2.09)/H-18 (δ H 5.51), together with the HMBC correlation from H-3 (δ H 2.67) to C-18 (δ C 79.3). On the basis of this replacement, a γ-hydroxyα,β-unsaturated lactam moiety was well recognized by the COSY cross-peak of NH/H-18 and the HMBC correlations from H-18 to the amide carbonyl carbon C-19 (δ C 171.5) and from NH/H-18 to C-1 (δ C 132.9) and C-2 (δ C 161.7).…”

Section: ■ Results and Discussionmentioning

confidence: 88%

“…34 and dictyolactams A and B and 9-demethoxy-9-ethoxyjoalin from D. coriacea. 22 The cytotoxicities of 1−7 against A549 and HL-60 cell lines were evaluated. However, none of them were active at the concentration of 20 μM.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…To date, only four metabolites belonging to this type have been previously reported from marine brown algae of the genus Dictyota (Dictyotacea), including joalin from Dictyota sp . and dictyolactams A and B and 9-demethoxy-9-ethoxyjoalin from D. coriacea …”

Section: Resultsmentioning

confidence: 99%

“…Previous phytochemical investigations of this alga have resulted in reports of a norsesquiterpenoid, epiloliolide, an 18-norxenicane norditerpenoid, pachyaldehyde, and 40 diterpenoids with various types of carbon frameworks, including crenulide (e . g., pachylactone), hydroazulene (pachydictyol A), decalin (methoxydictydiene), xenicane (acetyldictyolal), 7,18-cycloxenicane (acetylsanadaol), 18,19-cycloxenicane (acetylcoriacenone), and prenylated germacrane (acetoxypachydiol) skeletons, as well as a unique spirosuccinimide alkaloid and three rare nitrogenous xenicane diterpenoids, 9-demethoxy-9-ethoxyjoalin and dictyolactams A and B . In our ongoing search for more bioactive metabolites from Chinese marine alga, − D. coriacea collected off the coast of Nanji Island was chemically investigated, leading to the discovery of four new nitrogen-containing crenulide diterpenoids, namely, coriaceumins A–D ( 1 – 4 ), and two rare nitrogenous xenicane diterpenoids, dictyolactams C ( 5 ) and D ( 6 ), together with a known crenulide diterpenoid, 4-hydroxycrenulide ( 7 ).…”

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confidence: 99%

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Coriaceumins A–D, the First Nitrogen-Containing Crenulide Diterpenoids from the Brown Alga Dictyota coriacea Collected in the East China Sea

Wang,

Xu,

Tong

et al. 2023

J. Nat. Prod.

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A phytochemical investigation of an East China Sea collection of the brown alga Dictyota coriacea has led to the isolation of four novel nitrogen-containing crenulide diterpenoids, named coriaceumins A−D (1−4), two rare nitrogenous xenicane diterpenoids, dictyolactams C ( 5) and D (6), and one known crenulide diterpenoid, hydroxycrenulide (7). The structures of the new compounds were elucidated by detailed spectroscopic data analyses, including HRESIMS and 1D/2D NMR. The absolute configurations were determined by a comparison of the experimental ECD spectra with the spectra computed by DFT-based quantum chemical calculations. Coriaceumins A−D (1−4) represent the first examples of nitrogen-containing crenulide diterpenoids. In a bioassay, compounds 2, 3, 5, and 7 were found to exhibit different levels of inhibitory effects against protein tyrosine phosphatase 1B (PTP1B) with IC 50 values ranging from 7.3 to 19 μM. In addition, the primary structure−activity relationships of all the isolates were summarized.

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Section: Resultsmentioning

confidence: 68%

Section: ■ Results and Discussionmentioning

confidence: 88%

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

mentioning

confidence: 99%

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Coriaceumins A–D, the First Nitrogen-Containing Crenulide Diterpenoids from the Brown Alga Dictyota coriacea Collected in the East China Sea

Wang,

Xu,

Tong

et al. 2023

J. Nat. Prod.

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4-Hydroxydictyolactone alleviates cerebral ischemia injury by regulating neuroinflammation and autophagy via AMPK signaling pathway

Qi,

Zhu,

Chen

et al. 2024

Phytomedicine

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Anti-inflammatory diterpenoids from the brown alga Dictyota coriacea

Shiiba,

Kumagai,

Endo

et al. 2024

Bioscience, Biotechnology, and Biochemistry

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A new xenicane diterpene named 4α-acetoxyisodictyohemiacetal (1) was isolated from the brown alga Dictyota coriacea, along with 11 known diterpenoids. The structure of 1 was established by spectroscopic analyses, and its absolute configuration was determined by comparing the experimental and theoretical electronic circular dichroism (ECD) spectra. Two dictyodiacetal diastereomers (5 and 6) were isolated and the full NMR assignments were performed. The anti-inflammatory activities of the isolated compounds were evaluated using the lipopolysaccharide-stimulated mouse macrophage cell line, RAW264. The hemiacetal-containing xenicanes and dictyol-type diterpene inhibited not only the production of nitric oxide, but also the expression of inducible nitric oxide synthase, interleukin-6, and cyclooxygenase-2 mRNA in RAW264 cells. This study demonstrated that diterpenes from Dictyota coriacea may be useful as natural anti-inflammatory agents.

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Antioxidant and Neuroprotective Xenicane Diterpenes from the Brown Alga Dictyota coriacea

Cited by 6 publications

References 37 publications

Coriaceumins A–D, the First Nitrogen-Containing Crenulide Diterpenoids from the Brown Alga Dictyota coriacea Collected in the East China Sea

Coriaceumins A–D, the First Nitrogen-Containing Crenulide Diterpenoids from the Brown Alga Dictyota coriacea Collected in the East China Sea

4-Hydroxydictyolactone alleviates cerebral ischemia injury by regulating neuroinflammation and autophagy via AMPK signaling pathway

Anti-inflammatory diterpenoids from the brown alga Dictyota coriacea

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