Chemical constituents with their alpha-glucosidase inhibitory activity from the whole plant of Ceratophyllum demersum

IF 3.2 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2024-09-25 DOI:10.1016/j.phytochem.2024.114290

Thuc-Huy Duong , Thammarat Aree , Thi-Kim-Dung Le , Van-Son Dang , Ngoc-Hong Nguyen , Jirapast Sichaem

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引用次数: 0

Abstract

From Ceratophyllum demersum growing in Vietnam, twelve compounds were isolated and structurally elucidated, including six previously undescribed compounds, demersones A-D (1–4), acetylvelutins A and B (8 and 9), together with six known compounds, (+)-cyclocolorenone (5), 1-hydroxycyclocolorenone (6), 10-hydroxycyclocolorenone (7), retusin (10), betulinic acid (11), and lupeol (12). The chemical structures and stereochemistry of 1–12 were identified through analysis of spectroscopic data (1D and 2D NMR and HRESIMS), ECD data, and DFT calculation. Notably, this is the first time that humulene-type (1 and 2), guaiane-type (3), and aromadendrane-type (4–7) sesquiterpenoids have been reported in this genus. Compounds 8 and 9 are the first examples of 8-acetoxyflavones found in nature. Upon evaluation of the alpha-glucosidase of 1–3 and 5–12, it was found that 12 exhibited the highest potential with an IC₅₀ value of 15.4 ± 1.1 μM. The molecular docking of 3 and 8 was further studied.

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叶枯素全草中的化学成分及其α-葡萄糖苷酶抑制活性

从生长在越南的 Ceratophyllum demersum 中分离并阐明了 12 种化合物的结构，其中包括 6 种以前未曾描述过的化合物 demersones A-D (1-4)、乙酰绒毛素 A 和 B (8 和 9)，以及 6 种已知化合物 (+)-cyclocolorenone (5)、1-hydroxycyclocolorenone (6)、10-hydroxycyclocolorenone (7)、retusin (10)、betulinic acid (11) 和 lupeol (12)。通过分析光谱数据（1D 和 2D NMR 以及 HRESIMS）、ECD 数据和 DFT 计算，确定了 1-12 的化学结构和立体化学性质。值得注意的是，这是该属首次报道胡芦巴烯型（1 和 2）、愈创木烯型（3）和芳香丹烯型（4-7）倍半萜化合物。化合物 8 和 9 是自然界中首次发现的 8-乙酰氧基黄酮类化合物。在对 1-3 和 5-12 的α-葡萄糖苷酶进行评估后发现，12 表现出最高的潜力，其 IC50 值为 15.4 ± 1.1 μM。对 3 和 8 的分子对接进行了进一步研究。

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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.