Biochemometrics-Based Identification of Gallic Acid and Gallic Acid Galloylglucosides From Kalanchoe fedtschenkoi With Cytotoxic Effects on Cultured Melanoma Cells.

IF 3 3区生物学 Q2 BIOCHEMICAL RESEARCH METHODS

Phytochemical Analysis Pub Date : 2024-11-25 DOI:10.1002/pca.3480

Livia Marques Casanova, José Xavier do Nascimento Júnior, Jacqueline Elis de Souza, Raul do Couto Rodrigues, Amanda Bandeira Araújo, Emmanuel Arrais, Luiz Claudio de Oliveira Silva, Yasmim M Bessa Menezes, Raíssa Mara Kao Yien, Luzineide Wanderley Tinoco, Sônia Soares Costa, Mauro Sola-Penna, Patrícia Zancan

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引用次数: 0

Abstract

Introduction: Kalanchoe Adans. (Crassulaceae) is a genus of widespread succulent plants extensively studied for their biological activities. Plants of the genus are considered a potential source of antitumor agents.

Objective: This study aimed to investigate the effect of an aqueous extract and fractions of leaves of Kalanchoe fedtschenkoi R. Hamet & H. Perrier on the proliferation of melanoma cell lines employing an NMR-based biochemometric approach complemented with HPLC-DAD and UHPLC-MS/MS analyses.

Material and methods: The n-butanol fraction (KFBuOH) from K. fedtschenkoi aqueous leaf extract, which decreased B16F10 murine melanoma cells viability by 65% at 100 μg/mL, was fractionated with RP-18 SPE and Sephadex LH-20 column chromatography. The fractions were analyzed by ¹H-NMR spectroscopy and submitted to MTT cytotoxicity assays against cultured melanoma cells. Orthogonal projection to latent structures discriminant analysis (OPLS-DA) was used to correlate their ¹H-NMR profile and cytotoxic activity.

Results: This strategy enabled the identification of gallic acid (1) and two gallic acid glucosides-gallic acid 4-O-(6'-O-galloyl)-glucopyranoside) (2) and gallic acid 3-O-(6'-O-galloyl)-glucopyranoside) (3)-as putative bioactive substances, which was further corroborated by subsequent assays with enriched fractions and a gallic acid standard. The fractions enriched in gallic acid (KFA) and gallic acid galloylglucosides (KFB) evidenced selective cytotoxicity towards B16F10 cells (IC₅₀ 43.0 and 56.6 μg/mL, respectively) and MV3 human melanoma cells (IC₅₀ 93.6 and 66.1 μg/mL, respectively).

Conclusion: These results suggest a potential therapeutic use for K. fedtschenkoi in melanoma treatment. This is the first study to evidence a potential antitumor activity for gallic acid galloylglucosides.

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基于生物化学计量学鉴定对培养黑色素瘤细胞具有细胞毒性作用的Kalanchoe fedtschenkoi中的没食子酸和没食子酸五倍子酰葡萄糖苷。

介绍：Kalanchoe Adans.(Crassulaceae)是一种广泛分布的肉质植物属，因其生物活性而被广泛研究。该属植物被认为是抗肿瘤药物的潜在来源：本研究旨在研究 Kalanchoe fedtschenkoi R. Hamet & H. Perrier 的水提取物和叶片馏分对黑色素瘤细胞系增殖的影响：用 RP-18 SPE 和 Sephadex LH-20 柱色谱法对从 K. fedtschenkoi 水叶提取物中提取的正丁醇馏分 (KFBuOH) 进行分馏。对馏分进行了 1H-NMR 光谱分析，并对培养的黑色素瘤细胞进行了 MTT 细胞毒性试验。利用正交投影潜结构判别分析（OPLS-DA）将它们的 1H-NMR 图谱与细胞毒性活性联系起来：结果：这一方法鉴定出没食子酸（1）和两种没食子酸葡萄糖苷-没食子酸 4-O-(6'-O-吡咯酰基)-吡喃葡萄糖苷（2）和没食子酸 3-O-(6'-O-吡咯酰基)-吡喃葡萄糖苷（3）--为假定的生物活性物质。富含没食子酸（KFA）和没食子酸没食子酰葡萄糖苷（KFB）的馏分对 B16F10 细胞（IC50 分别为 43.0 和 56.6 μg/mL）和 MV3 人类黑色素瘤细胞（IC50 分别为 93.6 和 66.1 μg/mL）具有选择性细胞毒性：这些结果表明了 K. fedtschenkoi 在黑色素瘤治疗中的潜在疗效。这是首次证明没食子酸五倍子酰葡萄糖苷具有潜在抗肿瘤活性的研究。

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来源期刊

Phytochemical Analysis 生物-分析化学

CiteScore

6.00

自引率

6.10%

发文量

审稿时长

1.7 months

期刊介绍： Phytochemical Analysis is devoted to the publication of original articles concerning the development, improvement, validation and/or extension of application of analytical methodology in the plant sciences. The spectrum of coverage is broad, encompassing methods and techniques relevant to the detection (including bio-screening), extraction, separation, purification, identification and quantification of compounds in plant biochemistry, plant cellular and molecular biology, plant biotechnology, the food sciences, agriculture and horticulture. The Journal publishes papers describing significant novelty in the analysis of whole plants (including algae), plant cells, tissues and organs, plant-derived extracts and plant products (including those which have been partially or completely refined for use in the food, agrochemical, pharmaceutical and related industries). All forms of physical, chemical, biochemical, spectroscopic, radiometric, electrometric, chromatographic, metabolomic and chemometric investigations of plant products (monomeric species as well as polymeric molecules such as nucleic acids, proteins, lipids and carbohydrates) are included within the remit of the Journal. Papers dealing with novel methods relating to areas such as data handling/ data mining in plant sciences will also be welcomed.