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Article

Structure, Absolute Configuration, and Antiproliferative Activity of Abietane and Icetexane Diterpenoids from Salvia ballotiflora

1
Instituto de Química, Universidad Nacional Autónoma de México (UNAM), Circuito Exterior, Ciudad Universitaria, Mexico City 04510, Mexico
2
Facultad de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, Mexico City 04510, Mexico
3
Departamento de Química, Centro de Investigación y de Estudios Avanzados del Instituto Politécnico Nacional, Apartado 14-740, Mexico City 07000, Mexico
*
Authors to whom correspondence should be addressed.
Molecules 2017, 22(10), 1690; https://doi.org/10.3390/molecules22101690
Received: 31 August 2017 / Accepted: 29 September 2017 / Published: 18 October 2017
(This article belongs to the Collection Bioactive Compounds)
From the aerial parts of Salvia ballotiflora, eleven diterpenoids were isolated; among them, four icetexanes and one abietane (15) are reported for the first time. Their structures were established by spectroscopic means, mainly 1H- and 13C-NMR, including 1D and 2D homo- and hetero-nuclear experiments. Most of the isolated diterpenoids were tested for their antiproliferative, anti-inflammatory, and radical scavenging activities using the sulforhodamine B assay on six cancer cell lines, the TPA-induced ear edema test in mice, and the reduction of the DPPH assay, respectively. Some diterpenoids showed anti-proliferative activity, these being icetexanes 6 and 3, which were the most active with IC50 (μM) = 0.27 ± 0.08 and 1.40 ± 0.03, respectively, for U251 (human glioblastoma) and IC50 (μM) = 0.0.46 ± 0.05 and 0.82 ± 0.06 for SKLU-1 (human lung adenocarcinoma), when compared with adriamycin (IC50 (μM) = 0.08 ± 0.003 and 0.05 ± 0.003, as the positive control), respectively. Compounds 3 and 10 showed significant reduction of the induced ear edema of 37.4 ± 2.8 and 25.4 ± 3.0% (at 1.0 μmol/ear), respectively. Compound 4 was the sole active diterpenoid in the antioxidant assay (IC50 = 98. 4 ± 3.3), using α-tocopherol as the positive control (IC50 (μM) = 31.7 ± 1.04). The diterpenoid profile found is of chemotaxonomic relevance and reinforces the evolutionary link of S. ballotiflora with other members of the section Tomentellae. View Full-Text
Keywords: Salvia ballotiflora; icetexane diterpenoids; abietane diterpenoids; antiproliferative activity; anti-inflammatory activity; radical scavenger capacity; VCD analyses Salvia ballotiflora; icetexane diterpenoids; abietane diterpenoids; antiproliferative activity; anti-inflammatory activity; radical scavenger capacity; VCD analyses
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MDPI and ACS Style

Esquivel, B.; Bustos-Brito, C.; Sánchez-Castellanos, M.; Nieto-Camacho, A.; Ramírez-Apan, T.; Joseph-Nathan, P.; Quijano, L. Structure, Absolute Configuration, and Antiproliferative Activity of Abietane and Icetexane Diterpenoids from Salvia ballotiflora. Molecules 2017, 22, 1690. https://doi.org/10.3390/molecules22101690

AMA Style

Esquivel B, Bustos-Brito C, Sánchez-Castellanos M, Nieto-Camacho A, Ramírez-Apan T, Joseph-Nathan P, Quijano L. Structure, Absolute Configuration, and Antiproliferative Activity of Abietane and Icetexane Diterpenoids from Salvia ballotiflora. Molecules. 2017; 22(10):1690. https://doi.org/10.3390/molecules22101690

Chicago/Turabian Style

Esquivel, Baldomero, Celia Bustos-Brito, Mariano Sánchez-Castellanos, Antonio Nieto-Camacho, Teresa Ramírez-Apan, Pedro Joseph-Nathan, and Leovigildo Quijano. 2017. "Structure, Absolute Configuration, and Antiproliferative Activity of Abietane and Icetexane Diterpenoids from Salvia ballotiflora" Molecules 22, no. 10: 1690. https://doi.org/10.3390/molecules22101690

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