Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

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Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect

https://gifu-pu.repo.nii.ac.jp/records/2000025

Item type			研究室原著論文(1)
公開日			2023-10-19
タイトル
	タイトル		Sulfur-containing spiroketals from Breynia disticha and evaluations of their anti-inflammatory effect
	言語		en
言語
	言語		eng
資源タイプ
	資源タイプ識別子		http://purl.org/coar/resource_type/c_6501
	資源タイプ		journal article
著者
		姓名	Nakashima Ken-ichi
		言語	en
		姓名	Abe Naohito
		言語	en
		姓名	Oyama Masayoshi
		言語	en
		姓名	Murata Hiroko
		言語	en
		姓名	Inoue Makoto
		言語	en
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	言語		en
	値		Breynia spp. are a key source of sulfur-containing spiroketal glycosides with potential anti-inflammatory activity. In this study, three new sulfur-containing spiroketals - breynin J (1), epibreynin J (2), and probreynogenin (3) - along with four known compounds - probreynin I (4), phyllaemblic acid (5), breynin B (6), and epibreynin B (7) - were isolated from the roots of Breynia disticha. The structures of compounds 1-7 were elucidated by extensive 1D and 2D NMR spectroscopic analyses, including 1D total correlation spectroscopy (TOCSY), HSQC, HMBC, double quantum-filtered (DQF)-COSY, heteronuclear two-bond correlation (H2BC), and HSQC-TOCSY experiments, as well as high-resolution electrospray ionization HRESIMS anal., and quantum chem. electronic CD calculations Furthermore, the absolute configurations of sugar residues were determined by derivatization of the hydrolyzates with l-cysteine Me ester and o-tolyl isothiocyanate followed by HPLC anal. The anti-inflammatory effects of the isolated compounds were evaluated based on the mRNA levels of proinflammatory cytokines in lipopolysaccharide (LPS)-stimulated RAW 264.7 murine macrophage cells. Compounds 1, 2, 6, and 7 inhibited the increase in interleukin (IL)-1β and IL-6 mRNA levels stimulated by LPS. Moreover, the most potent compound 7 was found to significantly inhibit the production of IL-1β and IL-6 proteins, as revealed by the anal. of culture supernatants.
bibliographic_information			en : Beilstein Journal of Organic Chemistry 巻 19, 号 1, p. 1604-1614, ページ数 11, 発行日 2023-10-19
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	値		10.3762/bjoc.19.117