Dysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa

Abstract Four unusual meroterpenoids, dysivillosins A–D (1–4), were isolated from an organic extract of the marine sponge Dysidea villosa collected from the South China Sea. Their planar structures were determined by 1D and 2D NMR and HRESIMS techniques, while the relative and absolute configuration...

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Autores principales:	Wei-Hua Jiao, Bao-Hui Cheng, Guo-Hua Shi, Guo-Dong Chen, Bin-Bin Gu, Yong-Jun Zhou, Li-Li Hong, Fan Yang, Zhi-Qiang Liu, Shu-Qi Qiu, Zhi-Gang Liu, Ping-Chang Yang, Hou-Wen Lin
Formato:	article
Lenguaje:	EN
Publicado:	Nature Portfolio 2017
Materias:	Medicine R Science Q
Acceso en línea:	https://doaj.org/article/bad279f65d6f41ea8f99206438725142
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spelling	oai:doaj.org-article:bad279f65d6f41ea8f992064387251422021-12-02T11:40:15ZDysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa10.1038/s41598-017-04021-z2045-2322https://doaj.org/article/bad279f65d6f41ea8f992064387251422017-08-01T00:00:00Zhttps://doi.org/10.1038/s41598-017-04021-zhttps://doaj.org/toc/2045-2322Abstract Four unusual meroterpenoids, dysivillosins A–D (1–4), were isolated from an organic extract of the marine sponge Dysidea villosa collected from the South China Sea. Their planar structures were determined by 1D and 2D NMR and HRESIMS techniques, while the relative and absolute configurations were elucidated by NOESY experiments and comparison between the calculated and experimental ECD spectra. To the best of our knowledge, dysivillosins A–D are the first examples of terpene-polyketide-pyridine hybrid metabolites from the nature. Anti-allergic activity evaluation showed that compounds 1–4 potently inhibited the release of β-hexosaminidase, a marker of degranulation, in a dose-dependent manner with IC50 values of 8.2–19.9 μM. Additionally, the four meroterpenoids could downregulate the production of lipid mediator leukotrienes B4 (LTB4) and pro-inflammatory cytokine interleukin-4 (IL-4) in the antigen-stimulated RBL-2H3 mast cells. Further biological investigations revealed that dysivillosin A (1) could suppress the phosphorylation of Syk and PLCγ1 in IgE/FcɛRI/Syk signaling pathway, which resulted in the inhibition of degranulation and the downregulation of LTB4 and IL-4 production in mast cells.Wei-Hua JiaoBao-Hui ChengGuo-Hua ShiGuo-Dong ChenBin-Bin GuYong-Jun ZhouLi-Li HongFan YangZhi-Qiang LiuShu-Qi QiuZhi-Gang LiuPing-Chang YangHou-Wen LinNature PortfolioarticleMedicineRScienceQENScientific Reports, Vol 7, Iss 1, Pp 1-10 (2017)
institution	DOAJ
collection	DOAJ
language	EN
topic	Medicine R Science Q
spellingShingle	Medicine R Science Q Wei-Hua Jiao Bao-Hui Cheng Guo-Hua Shi Guo-Dong Chen Bin-Bin Gu Yong-Jun Zhou Li-Li Hong Fan Yang Zhi-Qiang Liu Shu-Qi Qiu Zhi-Gang Liu Ping-Chang Yang Hou-Wen Lin Dysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa
description	Abstract Four unusual meroterpenoids, dysivillosins A–D (1–4), were isolated from an organic extract of the marine sponge Dysidea villosa collected from the South China Sea. Their planar structures were determined by 1D and 2D NMR and HRESIMS techniques, while the relative and absolute configurations were elucidated by NOESY experiments and comparison between the calculated and experimental ECD spectra. To the best of our knowledge, dysivillosins A–D are the first examples of terpene-polyketide-pyridine hybrid metabolites from the nature. Anti-allergic activity evaluation showed that compounds 1–4 potently inhibited the release of β-hexosaminidase, a marker of degranulation, in a dose-dependent manner with IC50 values of 8.2–19.9 μM. Additionally, the four meroterpenoids could downregulate the production of lipid mediator leukotrienes B4 (LTB4) and pro-inflammatory cytokine interleukin-4 (IL-4) in the antigen-stimulated RBL-2H3 mast cells. Further biological investigations revealed that dysivillosin A (1) could suppress the phosphorylation of Syk and PLCγ1 in IgE/FcɛRI/Syk signaling pathway, which resulted in the inhibition of degranulation and the downregulation of LTB4 and IL-4 production in mast cells.
format	article
author	Wei-Hua Jiao Bao-Hui Cheng Guo-Hua Shi Guo-Dong Chen Bin-Bin Gu Yong-Jun Zhou Li-Li Hong Fan Yang Zhi-Qiang Liu Shu-Qi Qiu Zhi-Gang Liu Ping-Chang Yang Hou-Wen Lin
author_facet	Wei-Hua Jiao Bao-Hui Cheng Guo-Hua Shi Guo-Dong Chen Bin-Bin Gu Yong-Jun Zhou Li-Li Hong Fan Yang Zhi-Qiang Liu Shu-Qi Qiu Zhi-Gang Liu Ping-Chang Yang Hou-Wen Lin
author_sort	Wei-Hua Jiao
title	Dysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa
title_short	Dysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa
title_full	Dysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa
title_fullStr	Dysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa
title_full_unstemmed	Dysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa
title_sort	dysivillosins a–d, unusual anti-allergic meroterpenoids from the marine sponge dysidea villosa
publisher	Nature Portfolio
publishDate	2017
url	https://doaj.org/article/bad279f65d6f41ea8f99206438725142
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Dysivillosins A–D, Unusual Anti-allergic Meroterpenoids from the Marine Sponge Dysidea villosa

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