New terpenoids from Callicarpa nudiflora and their chemotaxonomic significance

IF 1.4 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Biochemical Systematics and Ecology Pub Date : 2024-07-20 DOI:10.1016/j.bse.2024.104872

Xue-Ying Lin , Gui-Fei Chen , Zi-Xiao Jiang , Yi-Tao Xing , Yang-Yang Liu

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Abstract

The comprehensive phytochemical investigation of the Callicarpa nudiflora resulted in the isolation of a new labdane diterpenoid 16(R/S)-3,4-seco-11E,13E-labdien-15,16-olide-3-al (2), together with sixteen known compounds: two sesquiterpenoids (1R,3S,4R,5S,9S)-3,4-epoxy-5-hydroxy-8(13)-caryophyllen (1), and 4β,10α-aromadendranediol (3), eight labdane analogues (4–11), a pimarane-type diterpenoid (12), three flavonoids (13–15), and two lignans (16, and 17). The structures were elucidated by extensive NMR and HRESIMS analysis. This marks the first comprehensive report of the NMR data of compound 1, as well as the absolute configurations of compounds 1 and 3. The chemotaxonomic significance of the isolated compounds was also discussed. Compounds 1, 3, 14, 16, and 17 were being reported from the genus Callicarpa for the first time, while 3,4-seco-labdane diterpenoids 4–11 were previously obtained only from C. nudiflora.

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来自裸花胼胝树的新萜类化合物及其化学分类学意义

通过对裸花马缨丹进行全面的植物化学研究，分离出了一种新的唇烷二萜类化合物 16(R/S)-3,4-seco-11E,13E-labdien-15,16-olide-3-al (2)，以及十六种已知化合物：两种倍半萜类化合物（1R,3S,4R,5S,9S）-3,4-环氧-5-羟基-8(13)-加里叶烯（1）和 4β,10α-阿罗门二醇（3）、八种拉布二烯类似物（4-11）、一种吡马烷类二萜（12）、三种黄酮类化合物（13-15）和两种木脂素（16 和 17）。通过广泛的核磁共振和 HRESIMS 分析阐明了这些化合物的结构。这是首次全面报道化合物 1 的核磁共振数据以及化合物 1 和 3 的绝对构型。此外，还讨论了分离化合物的化学分类学意义。化合物 1、3、14、16 和 17 是首次从 Callicarpa 属中分离出来，而 3,4-seco-labdane二萜类化合物 4-11 以前仅从 C. nudiflora 中获得。

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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.