Chemical constituents from the seeds of Khaya grandifoliola C.DC; their chemophenetic significance and antibacterial activities

IF 2 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology Pub Date : 2025-07-29 DOI:10.1016/j.bse.2025.105104

Akafack Lyliane Sorelle , Appolinaire Kene Dongmo , Billy Toussie Tchegnitegni , Blandine Kampa-kuemkon Nkenfou , Jean Francois Zeutsop , Raymond Ngansop Nono , Pépin Nkeng-Efouet Alango , Bruno Ndjakou Lenta , Norbert Sewald , Jean Rodolphe Chouna

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Abstract

Chemical exploration of the CH₂Cl₂/MeOH extract of the seeds of Khaya grandifoliola C.DC led to the isolation of one previously unreported limonoid (7), together with 19 known compounds. The structures of all the isolated compounds were established by interpretation of their spectroscopic and spectrometric data, including 1D and 2D NMR and HRESIMS analysis. The full NMR assignment of 2α,3β-dihydroxymexicanolide (2) and that of the new compound 7 were reported together with the chemophenetic significance of the isolated compounds. The crude extract, fractions, and some isolates were screened for their antibacterial properties against five pathogenic strains: three Gram negative, Escherichia coli ATCC25922, Klebsiella pneumoniae NR41BB, Salmonella typhimurium (clinical isolate), and two Gram positive, Staphylococcus aureus ATCC12600 and Enterococcus faecalis ATCC51299. Fraction D displayed a significant activity against Escherichia. coli ATCC25922 with an MIC value of 31.25 μg/mL. Among the pure compounds, the best MIC (31.25 μg/mL) was obtained with proceranolide (1) against E. coli ATCC25922. The isolates were also screened for their cytotoxic activity against the human cervix carcinoma KB-3-1 cell line, and no significant activity was observed.

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大叶茶籽化学成分的研究它们的化学化学意义和抗菌活性

对Khaya grandfoliola C.DC种子的CH2Cl2/MeOH提取物进行化学探索，分离出一种以前未报道的类柠檬素(7)，以及19种已知化合物。所有分离化合物的结构都是通过光谱和光谱数据的解释来确定的，包括1D和2D NMR和HRESIMS分析。报道了2α，3β-二羟基墨西哥烷内酯(2)和新化合物7的完整核磁共振配位以及分离化合物的化学亲缘意义。筛选粗提物、馏分及部分分离物对革兰氏阴性3株、大肠埃希菌ATCC25922、肺炎克雷伯菌NR41BB、鼠伤寒沙门菌（临床分离株）、革兰氏阳性2株、金黄色葡萄球菌ATCC12600、粪肠球菌ATCC51299等5种病原菌的抑菌性能。片段D对埃希氏菌具有显著的抑菌活性。大肠杆菌ATCC25922的MIC值为31.25 μg/mL。纯化合物中，原麻内酯(1)对大肠杆菌ATCC25922的MIC最高，为31.25 μg/mL。分离物对人宫颈癌KB-3-1细胞株的细胞毒活性也进行了筛选，未观察到明显的细胞毒活性。

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来源期刊

Biochemical Systematics and Ecology 生物-进化生物学

CiteScore

3.00

自引率

12.50%

发文量

147

审稿时长

43 days

期刊介绍： Biochemical Systematics and Ecology is devoted to the publication of original papers and reviews, both submitted and invited, in two subject areas: I) the application of biochemistry to problems relating to systematic biology of organisms (biochemical systematics); II) the role of biochemistry in interactions between organisms or between an organism and its environment (biochemical ecology). In the Biochemical Systematics subject area, comparative studies of the distribution of (secondary) metabolites within a wider taxon (e.g. genus or family) are welcome. Comparative studies, encompassing multiple accessions of each of the taxa within their distribution are particularly encouraged. Welcome are also studies combining classical chemosystematic studies (such as comparative HPLC-MS or GC-MS investigations) with (macro-) molecular phylogenetic studies. Studies that involve the comparative use of compounds to help differentiate among species such as adulterants or substitutes that illustrate the applied use of chemosystematics are welcome. In contrast, studies solely employing macromolecular phylogenetic techniques (gene sequences, RAPD studies etc.) will be considered out of scope. Discouraged are manuscripts that report known or new compounds from a single source taxon without addressing a systematic hypothesis. Also considered out of scope are studies using outdated and hard to reproduce macromolecular techniques such as RAPDs in combination with standard chemosystematic techniques such as GC-FID and GC-MS.