Phytochemical study of Fissistigma fulgens (Hook.f. & Thomson) Merr. leaves: Previously undescribed dihydrochalcone derivatives and their biological activities

IF 3.4 2区生物学 Q2 BIOCHEMISTRY & MOLECULAR BIOLOGY

Phytochemistry Pub Date : 2026-03-01 Epub Date: 2025-12-02 DOI:10.1016/j.phytochem.2025.114735

Passakorn Teerapongpisan , Wuttichai Jaidee , Theanchai Wiwasuku , Sarot Cheenpracha , Natcha Injan , Somkiat Nokbin , Kittirat Saharat , Atthapan Morchang , Phateep Hankittichai , Rawiwan Charoensup , Raymond J. Andersen , Surat Laphookhieo

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Abstract

The first phytochemical investigation of the leaves of Fissistigma fulgens (Hook.f. & Thomson) Merr. led to the isolation and identification of five previously undescribed dihydrochalcone derivatives, including two dimeric dihydrochalcones, fissisfulgenones A and B (1 and 2), and three monomeric dihydrochalcones, fissisfulgenones C–E (3–5), along with three known compounds. Their structures were elucidated by spectroscopic analysis. The dimeric structure of fissisfulgenone A (1) was confirmed by single-crystal X-ray diffraction analysis using Cu–Kα radiation. The pure enantiomers of the scalemic mixtures of 1–3 were successfully resolved using chiral-phase HPLC, and their absolute configurations were determined by comparing experimental and calculated ECD spectra. Fissisfulgenones A (1), C (3), and D (4) were evaluated for biological activities, including cytotoxicity against human breast adenocarcinoma (MDA-MB231), human lung carcinoma (A549), human hepatocellular carcinoma (Huh7), and human colorectal adenocarcinoma (SW480 and HT29), antiviral activity against dengue virus (DENV), and nitric oxide production inhibitory activity in LPS-stimulated RAW 264.7 macrophages. Among them, fissisfulgenone C (3) exhibited the highest cytotoxicity against SW480 and HT29 cells with IC₅₀ values of 40.6 and 68.0 μM, respectively, whereas fissisfulgenone D (4) showed cytotoxicity against MDA-MB231, A549, and Huh7 cell lines with IC₅₀ values of 48.7, 38.3, and 21.2 μM, respectively. Notably, fissisfulgenone A (1) significantly reduced virus production in DENV-infected Huh7 cells at a sub-toxic dose of 50.0 μM. Regarding anti-inflammatory activity, fissisfulgenone C (3) exhibited strong nitric oxide inhibition, markedly reducing LPS-induced levels with an IC₅₀ value of 5.27 μM and preserving normal macrophage morphology. Fissisfulgenone A (1) also showed similar effects at lower, non-toxic concentrations.

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富氏裂柱属植物化学研究。& Thomson)。叶：先前未描述的二氢查尔酮衍生物及其生物活性。

富尔根（fisistigma fulgens, Hook.f.）叶片的首次植物化学研究。& Thomson)。导致分离和鉴定了五种以前未描述的二氢查尔酮衍生物，包括两种二聚体二氢查尔酮，fisisfulgenones A和B(1和2)，三种单体二氢查尔酮，fisisfulgenones C-E(3-5)，以及三种已知化合物。通过光谱分析对其结构进行了鉴定。用cu - k - α辐射单晶x射线衍射分析证实了fisisfulgenone A(1)的二聚体结构。用手相高效液相色谱法成功地分离了1-3标度混合物的纯对映体，并通过比较实验和计算ECD谱确定了它们的绝对构型。对Fissisfulgenones A(1)、C(3)和D(4)的生物活性进行了评估，包括对人乳腺腺癌（MDA-MB231）、人肺癌（A549）、人肝细胞癌（Huh7）和人结直肠腺癌（SW480和HT29）的细胞毒性、对登革热病毒（DENV）的抗病毒活性，以及对lps刺激的RAW 264.7巨噬细胞一氧化氮产生的抑制活性。其中，fissisfulgenone C(3)对SW480和HT29细胞的IC50值最高，分别为40.6和68.0 μM; fissisfulgenone D(4)对MDA-MB231、A549和Huh7细胞系的IC50值分别为48.7、38.3和21.2 μM。值得注意的是，fisisfulgenone A(1)在50.0 μM的亚毒性剂量下显著降低了denv感染的Huh7细胞的病毒产量。在抗炎活性方面，fisisfulgenone C(3)表现出强烈的一氧化氮抑制作用，显著降低lps诱导的水平，IC50值为5.27 μM，并保持正常的巨噬细胞形态。fisisfulgenone A(1)在较低的无毒浓度下也表现出类似的效果。

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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.