A new stilbene from Oeceoclades maculata and chemophenetic significance

IF 1.4 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology Pub Date : 2025-04-13 DOI:10.1016/j.bse.2025.105023

Paula C. Perin , Silas H. de Carvalho , Gredson K. de Souza , Silvana M. de Oliveira , Denise M.B. Ghiraldi , Beatriz V. Diniz , Melyssa F.N. Negri , Eduardo J. Pilau , Paula D. Macruz , Maria A. Milaneze-Gutierre , Antonio G. Ferreira , Taicia P. Fill , Roberto G.S. Berlinck , Armando M. Pomini

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Abstract

Oeceoclades maculata Lindl. (Orchidaceae) is a terrestrial orchid species native to the African continent but widely distributed across the Americas, representing a rare example of an invasive orchid. A chemical investigation of specimens collected in Brazil led to the isolation and structural characterization of a previously unreported natural product, 2,3,2′,5′-tetramethoxy-4,3′-dihydroxy-stilbene (1), which has been named ingasine. Its structure was elucidated through 1D and 2D NMR spectroscopy, as well as HR-ESI-MS analysis. In addition to this novel compound, several previously described metabolites were identified, including cycloartane triterpenes and a phenanthrenoid. Dereplication studies allowed for the putative identification of flavonoids, stilbene, and alkaloids as the major compound classes. The antiproliferative activity of the crude extract and its fractions was evaluated against VERO cells and human cervical cancer HeLa cells. Furthermore, the chemophenetic relationships of the identified compounds within the Eulophiinae subtribe were analyzed and discussed.

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一种新的黄斑枝二苯乙烯及其化学化学意义

Oeceoclades maculata Lindl.（兰科）是一种陆生兰花物种，原产于非洲大陆，但广泛分布于美洲各地，是入侵兰花的一个罕见例子。通过对在巴西采集的标本进行化学研究，我们分离出一种以前未报道过的天然产物 2,3,2′,5′-四甲氧基-4,3′-二羟基二苯乙烯 (1)，并确定了其结构特征。通过一维和二维核磁共振光谱以及 HR-ESI-MS 分析，阐明了它的结构。除了这种新型化合物外，还发现了几种以前描述过的代谢物，包括环木菠萝烷三萜类化合物和一种菲类化合物。通过去复制研究，可以确定黄酮类、二苯乙烯类和生物碱类是主要的化合物类别。评估了粗提取物及其馏分对 VERO 细胞和人类宫颈癌 HeLa 细胞的抗增殖活性。此外，还分析和讨论了所鉴定的化合物在 Eulophiinae 亚族中的化学遗传学关系。

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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.