Sesquiterpene enantiomers from Alismatis Rhizoma

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2024-12-12 DOI:10.1016/j.phytochem.2024.114359

Shan-Shan Liu , Yun Li , Yun-He An , Jing-Jing Zhu , Mei Zhang , Wei Wang , Li-Hua Yan , Zhi-Min Wang

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引用次数: 0

Abstract

A pair of dinor-sesquiterpene enantiomers (1a/1b), eight pairs of guaiane-type sesquiterpenes enantiomers (2a/2b, 3a/3b, 4a/4b, 5a/5b, 6a/6b, 7a/7b, 8a/8b, 9a/9b) and two guaiane-type sesquiterpenes (10, 11), including eleven undescribed ones (1a, 1b, 2a, 2b, 3a, 3b, 4a, 5b, 6a, 10, and 11), were isolated from the aqueous extract of Alismatis Rhizoma. The structures were elucidated by combining 1D and 2D NMR and HRESIMS spectroscopic data. The absolute configurations were determined by experimental and calculated ECD spectra, [Mo₂(OAc)₄]-induced ECD spectral analysis, and comparison of the experimental ECD spectra with those of similar analogs. Compound 5b (NO inhibition rate, 52.63%) and 8b (36.49%) showed comparable activity to indomethacin (46.36%) against LPS-induced NO production in RAW 264.7 murine macrophages at 100 μM with obvious stereoselectivity, whereas compounds 1–10 exerted no or extremely low cytotoxicities against MCF-7 and MDA-MB-231 cells (IC₅₀ ＞ 100 μM).

Abstract Image

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泽泻的倍半萜对映体。

从泽泻水提物中分离得到1对二倍半萜对映体（1a/1b）， 8对愈蓝烷型倍半萜对映体（2a/2b、3a/3b、4a/4b、5a/5b、6a/6b、7a/7b、8a/8b、9a/9b）和2对愈蓝烷型倍半萜对映体（10,11），包括11个未描述的愈蓝烷型倍半萜对映体（1a、1b、2a、2b、3a、3b、4a、5b、6a、10和11）。结合一维、二维核磁共振和HRESIMS光谱数据对其结构进行了分析。通过实验和计算ECD谱，[Mo2(OAc)4]诱导ECD谱分析，并与相似类似物的实验ECD谱进行比较，确定了绝对构型。化合物5b （NO抑制率为52.63%）和8b（36.49%）对lps诱导的RAW 264.7小鼠巨噬细胞（100 μM） NO产生的抑制活性与吲哚美辛（46.36%）相当，具有明显的立体选择性，而化合物1-10对MCF-7和MDA-MB-231细胞（IC50 bb0 100 μM）没有或极低的细胞毒性。

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来源期刊

Phytochemistry 生物-植物科学

CiteScore

6.40

自引率

7.90%

发文量

443

审稿时长

39 days

期刊介绍： Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.