Clerodane and 5 10-Seco-Clerodane-type diterpenoids from Salvia involucrata

Bustos-Brito, Celia; Pérez-Juanchi, Diana; Rivera‐Chávez, José; Hernández-Herrera, Alejandro David; Bedolla-García, Brenda Y.; Zamudio, Sergio; Ramírez‐Ápan, Teresa; Quijano, Leovigildo; Esquivel, Baldomero

doi:10.1016/j.molstruc.2021.130367

Cited by 4 publications

(1 citation statement)

References 30 publications

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“…ECD calculations in MeOH solution were carried out by employing a TD-SCF force field at the B3LYP/6-31G(d) theory level, with the default solvent model. The calculated excitation energy (nm) and rotatory strength (R) in dipole velocity (Rvel) form were simulated into an ECD curve using Equation (1), as implemented in the SpecDis software (Version 1.71), where E 0k and R 0k are the transition energy and rotatory strength of kth electronic transition, respectively, and σ is the exponential half width [ 43 , 44 ].

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Section: Methodsmentioning

confidence: 99%

Structure, Absolute Configuration, Antiproliferative and Phytotoxic Activities of Icetexane and Abietane Diterpenoids from Salvia carranzae and Chemotaxonomic Implications

Bustos-Brito,

Torres-Medicis,

Bedolla-García

et al. 2024

Molecules

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From the aerial parts of Salvia carranzae Zamudio and Bedolla, three new icetexane-type diterpenoids were isolated. Their structures were established through spectroscopic methods and named the following: salvicarranzanolide (1), 19-deoxo-salvicarranzanolide (2) and 19-deoxo-20-deoxy-salvicarranzanolide (3). In addition, the known icetexane-type diterpenoids, 6,7,11,14-tetrahydro-7-oxo-icetexone (4), iso-icetexone (5), 19-deoxo-iso-icetexone (6), icetexone (7), 19-deoxo-icetexone (8) and 7α-acetoxy-6,7-dihydroicetexone (9), were also isolated, along with the abietanes sessein (10) and ferruginol (11). α-Tocopherol was also identified. Compounds 5, 6 and 8 were tested for their antiproliferative activity using the sulforhodamine B assay on six cancer and one normal human cell lines. Diterpenoids 5 and 6 showed noteworthy antiproliferative activity, exhibiting an IC50 (μM) = 0.43 ± 0.01 and 1.34 ± 0.04, respectively, for U251 (glioblastoma), an IC50 (μM) = 0.45 ± 0.01 and 1.29 ± 0.06 for K5621 (myelogenous leukemia), 0.84 ± 0.07 and 1.03 ± 0.10 for HCT-15 (colon cancer), and 0.73 ± 0.06 and 0.95 ± 0.09 for SKLU-1 (lung adenocarcinoma) cell lines. On the other hand, the phytotoxicity of compounds 5–7 and 9–10 was evaluated on seed germination and root growth in some weeds such as Medicago sativa, Panicum miliaceum, Amaranthus hypochondriacus and Trifolium pratense as models. While compounds 5 and 10 exhibited a moderate inhibitory effect on the root growth of A. hypochondriacus and T. pratense at 100 ppm, the diterpenoids 6, 7 and 9 were ineffective in all the plant models. Taxonomic positions based on the chemical profiles found are also discussed.

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Section: Methodsmentioning

confidence: 99%