Abietane diterpenoids and their biological activities from Premna herbacea Roxb.

IF 3.4 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2026-03-01 Epub Date: 2025-11-24 DOI:10.1016/j.phytochem.2025.114722

Passakorn Teerapongpisan , Angkana Doungsanit , Wuttichai Jaidee , Waroton Paisuwan , Virayu Suthiphasilp , Sarawut Tontapha , Natcha Injan , Somkiat Nokbin , Pakit Kumboonma , Rawiwan Charoensup , Siau Hui Mah , Sarot Cheenpracha , Surat Laphookhieo , Tharakorn Maneerat

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Abstract

A phytochemical investigation of the roots of Premna herbacea Roxb. led to the isolation and characterization of ten abietane-type diterpenoids, including five previously undescribed compounds: premnaherbietones A and B (1 and 4), and premnaherbietanes A–C (5–7). Structural elucidation was achieved using comprehensive spectroscopic analysis (1D and 2D NMR, HRESIMS) and confirmed by electronic circular dichroism (ECD) calculations. The previously undescribed compounds possess diverse carbon skeletons, including quinonemethide abietane, 20(10 → 5)-abeo-abietane, and seco-4,5-abietane frameworks. Selected compounds (2, 3, 9, and 10) were evaluated for their α-glucosidase inhibitory and cytotoxic activities. Salvilenone (10) exhibited α-glucosidase inhibition with an IC₅₀ value of 34.6 μM, significantly outperforming the positive control, acarbose (IC₅₀ = 190.4 μM). In silico molecular docking revealed that compound 10 interacts with key active site residues of α-glucosidase through hydrogen bonding and π–π interactions, supporting its inhibitory potential. Bharangin (2) demonstrated notable cytotoxicity against A549 human lung adenocarcinoma cell lines with an IC₅₀ value of 19.4 μM. A plausible biosynthetic pathway for the isolated diterpenoids is also proposed.

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草甘膦Abietane二萜类化合物及其生物活性研究。

萱草根的植物化学研究。导致了10个abietane型二萜的分离和表征，包括5个以前未描述的化合物：premnaherbietones A和B(1和4),premnaherbietanes A- c（5-7）。通过综合光谱分析（1D和2D NMR， hresms）获得结构解析，并通过电子圆二色性（ECD）计算证实。先前描述的化合物具有不同的碳骨架，包括喹甲脒abietane， 20(10→5)- abietane和seco-4,5-abietane框架。选择化合物（2、3、9和10）进行α-葡萄糖苷酶抑制和细胞毒活性评价。salilenone（10）对α-葡萄糖苷酶的抑制作用IC50值为34.6 μM，显著优于阳性对照阿卡波糖（IC50 = 190.4 μM）。硅分子对接表明，化合物10通过氢键和π-π相互作用与α-葡萄糖苷酶的关键活性位点残基相互作用，支持其抑制潜力。Bharangin(2)对A549人肺腺癌细胞具有显著的细胞毒性，IC50值为19.4 μM。对分离的二萜化合物提出了一种可行的生物合成途径。

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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.