Four new aaptamine alkaloids from marine sponge <i>Aaptos aaptos</i>

Trang, Đỗ Thị; Tài, Bùi Hữu; Hằng, Đan Thị Thúy; Yến, Phạm Hải; Nhiệm, Nguyễn Xuân; Kiệm, Phan Văn

doi:10.1080/14786419.2021.1917572

Cited by 11 publications

(7 citation statements)

References 22 publications

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“…The cytotoxic assay protocol are the same as described in our previous work. [10,11] 10) [1] by the coincidence between their NMR spectra with those of the corresponding compounds reported data and further confirmed by HRESIMS, HSQC, HMBC spectra. The CD spectra of compounds 3, 8-10 showed no Cotton effects suggesting that they were enantiomers, which have been separated by the chiral column.…”

Section: Cytotoxic Assaysupporting

confidence: 65%

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Xestospongiene VN1, a new brominated polyunsaturated lipid from marine sponge Xestospongia testudinaria (Lamark, 1815)

Tai,

Hang,

Thung

et al. 2022

Vietnam Journal of Chemistry

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Phytochemical study on the methanol extract of the marine sponge Xestospongia testudinaria (Lamark, 1815) led to the isolation of one new ((6Z,8E,13E,15Z)‐6,14,16‐tribromo‐5,10‐dihydroxyhexadeca‐6,8,13,15‐tetraenoic acid named xestospongiene VN1, 1) and nine known brominated polyunsaturated compounds, xestospongiene z5 & z6 (2), xestospongiene z9 & z10 (3), xestospongiene S (4), xestospongic acid (5), xestospongic acid methyl ester (6), (13E,17E)‐18‐bromo‐octadeca‐13,17‐diene‐5,7,15‐triymoic acid (7), xestospongiene I & J (8), xestospongiene K & L (9), and xestospongiene C & D (10). The chemical structures of these compounds were elucidated by extensive spectroscopic analyses including HR‐ESI‐MS, 1D and 2D NMR, circular dichroism, and by comparison of the spectral data with those of previously reported data. This is the first report of these compounds from Vietnamese marine sponge X. testudinaria.

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Section: Cytotoxic Assaysupporting

confidence: 65%

“…The equipment used for characterization are the same as described in our previous work. [10,11] in ultrasonic bath for 3 times (each, 50 L, room temperature, 60 mins). After filtration, the filtrate was evaporated under reduced pressure to give MeOH extract (52 g).…”

Section: General Experimental Proceduresmentioning

confidence: 99%

Xestospongiene VN1, a new brominated polyunsaturated lipid from marine sponge Xestospongia testudinaria (Lamark, 1815)

Tai,

Hang,

Thung

et al. 2022

Vietnam Journal of Chemistry

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“…These results indicated that the chemical structure of compound 1 was similar to that of 3,5-dimethoxycarbonyl-1,6-naphthyridine, with the only difference being the replacement of the methoxycarbonyl group at C-5 ketone. [13] Structure of compound 1 was further confirmed using single-crystal X-ray diffraction analysis (Figure 3). Finally, compound 1 was unambiguously identified as 4-methoxycarbonyl-5-oxo-1,6-naphthyridine.…”

Section: Structure Elucidationmentioning

confidence: 86%

“…General experimental procedures 1 H-, 13 C-NMR, and 2D-NMR spectra were recorded on NMR spectra were measured on a Bruker 500 spectrometer (500 MHz for 1 H and 125 MHz for 13 C) (Bruker Daltonics Inc., Billerica, MA, USA), with δ in ppm with solvent residual signals as internal standards (DMSO: δ H 2.50 ppm, δ C 39.5 ppm), and J in Hz. Melting point were measured by a JH-WRS-2 microcomputer melting point instrument (Shanghai Jiahang Instrument Co., Ltd, Shanghai, China).…”

Section: Methodsmentioning

confidence: 99%

Anti‐Inflammatory Effects of New Naphthyridine from Sponge Aaptos suberitoides in LPS‐Stimulated RAW 264.7 Macrophages via Regulation of MAPK and Nrf2 Signaling Pathways

Liu

Zhang

et al. 2023

Chemistry & Biodiversity

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Two new naphthyridine compounds, 4‐methoxycarbonyl‐5‐oxo‐1,6‐naphthyridine (1) and 5‐methoxycarbonyl‐4‐oxo‐1,6‐naphthyridine (2) were obtained from the MeOH extracts of sponge Aaptos suberitoides. Their structures were determined by spectroscopic methods, including HR‐ESI‐MS, 1D‐NMR (1H‐NMR, 13C‐NMR), 2D‐NMR (COSY, HSQC, HMBC). The structure of compound 1 was further confirmed via single crystal X‐ray diffraction analysis. Compound 1 was found to reduce NO production in LPS‐induced RAW 264.7 macrophages with IC50 value of 0.15 mM. In addition, it decreased the mRNA expression levels of pro‐inflammatory mediators, such as the tumor necrosis factor‐α (TNF‐α), interleukin‐6 (IL‐6), interleukin‐1β (IL‐1β), inducible nitric oxide synthase (iNOS) and cyclooxygenase‐2 (COX2) in LPS‐induced macrophages. It also decreased the protein expression of iNOS and COX‐2 in LPS‐induced macrophages. Mechanistic studies further revealed that compound 1 inhibited the mitogen‐activated protein kinase (MAPK), and activated the nuclear factor erythroid 2‐related factor 2/heme oxygenase‐1 (Nrf2/HO‐1) signaling pathways in LPS‐induced RAW 264.7 macrophages.

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“…The cytotoxic assay protocols are the same as described in our previous works. [16,17] 3. RESULTS AND DISCUSSION Compounds 2-6 were identified as holothurin A2 (2), [18,19] desulfoechinoside A (3), [20] echinoside B (4), [20] holothurin A (5), [18,21] holothurin B (6) [18] by the coincidence between their NMR spectra with those of the corresponding compounds reported data and further confirmed by HRESIMS, HSQC, HMBC spectra.…”

Section: Cytotoxic Assaymentioning

confidence: 99%

Chemical constituents of marine sponge Ianthella basta (Pallas, 1766)

Hang,

Thung,

Trang

et al. 2022

Vietnam Journal of Chemistry

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Phytochemical study on the methanol extract of the elephant ear sponge Ianthella basta (Pallas, 1766) led to the isolation of one new (named lanthebastanoside A, 1) and nine known compounds, holothurin A2 (2), desulfoechinoside A (3), echinoside B (4), holothurin A (5), holothurin B (6), adenine (7), adenosine (8), thymidine (9), and thymine (10). The chemical structures of compounds 1‐6 were elucidated by extensive spectroscopic analyses including HR‐ESI‐MS, 1D and 2D NMR, and by comparison of the spectral data with those of previously reported data. Compounds 7‐10 were identified by 1H NMR data and comparing their retention times with authentic samples by HPLC analysis. This is the first report of compounds 2‐6 from marine sponge.

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Four new aaptamine alkaloids from marine sponge Aaptos aaptos

Cited by 11 publications

References 22 publications

Xestospongiene VN1, a new brominated polyunsaturated lipid from marine sponge Xestospongia testudinaria (Lamark, 1815)

Xestospongiene VN1, a new brominated polyunsaturated lipid from marine sponge Xestospongia testudinaria (Lamark, 1815)

Anti‐Inflammatory Effects of New Naphthyridine from Sponge Aaptos suberitoides in LPS‐Stimulated RAW 264.7 Macrophages via Regulation of MAPK and Nrf2 Signaling Pathways

Chemical constituents of marine sponge Ianthella basta (Pallas, 1766)

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