Phytotoxic neo-clerodane and rearranged neo-clerodane type diterpenoids from Salvia albiflora

IF 2.1 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-01-25 DOI:10.1016/j.tet.2025.134490

Celia Bustos-Brito , Pablo Yair Montaño-Hernández , Omar Salas-Huerta , Daniela Itziguari Ramírez-González , Diana Pérez-Juanchi , Juan Pablo Torres-Medicis , Martha Lydia Macías-Rubalcava , Brenda Y. Bedolla-García , Sergio Zamudio , Leovigildo Quijano , Baldomero Esquivel

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引用次数: 0

Abstract

Three previously undescribed diterpenoids (1–3) were isolated from the leaves of Salvia albiflora Martens & Galeotti and named salbiflorin A (1), salbiflorin B (2), and deoxysalvisousolide (3). Furthermore, six known compounds, including salvixalapadiene (4), salvihispin H (5), salvisousolide (6), tilifodiolide (7), salvigenolide (8), and 2α-hydroxy-7α-acetoxy-12-oxo-15:16-epoxy-neoclerodan-3,13(16),14-trien-18:19-olide (9) were also isolated. The structure and absolute configuration of the new compounds were established primarily through the application of 1D and 2D ¹H and ¹³C NMR experiments, HR-DART-MS, and a combination of experimental and theoretical ECD data. Salbiflorin A (1) and B (2), constitute the first examples of a 9,10-seco-salvileucalane-derived diterpenoids. The phytotoxic activity of compounds 1−3, 6 and 8 was evaluated on the germination and root growth of four weed model species, Amaranthus hypochondriacus L., Panicum miliaceum L., Medicago sativa L., and Trifolium pratense L. Salbiflorin B (2) exhibited the highest activity in A. hypocondriacus and T. pratense, with IC₅₀ values of 115.1 ± 3.14 and 122 ± 2.02 μM, respectively.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.