Cytotoxic activity of the chloroform extract and four diterpenes isolated from Salvia ballotiflora

Campos-Xolalpa, Nimsi; Alonso-Castro, Ángel Josabad; Sánchez-Mendoza, Ernesto; Zavala-Sánchez, Miguel Ángel; Pérez-Gutiérrez, Salúd

doi:10.1016/j.bjp.2017.01.007

Cited by 20 publications

(18 citation statements)

References 15 publications

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“…The same biological activity was also recently described for icetexane-derivatives isolated from Premna and Amentotaxus species [ 48 , 49 , 50 ]. Furthermore, 19-deoxyisoicetexone isolated from S. ballotiflora exhibited similar activity when compared to cisplatin on HeLa cells with IC 50 (μM) = 9.36 [ 21 ]. These facts prompted us to assay diterpenoids 3 , 4 , 6 – 8 and 10 for antiproliferative activity using six human cancer cell lines (U251, PC-3, K562, HCT-15, MCF-7, and SKLU-1), and a primary culture of healthy gingival human fibroblasts (FGH) at 1.0 or 50.0 μM (when cytotoxicity at 50.0 μM results were too high).…”

Section: Resultsmentioning

confidence: 99%

“…Previous work on several populations of Salvia ballotiflora indicated that this species produced an interesting array of icetexane and abietane diterpenoids. Several members of this type of diterpenoids have been targeted for synthetic work due to their structural features and the biological activity exhibited by some icetexanes [ 16 , 17 , 18 , 19 , 20 ] as anti-proliferative activity, in vitro, against some human cancer cell lines [ 9 , 11 , 21 ]. On this issue, while the aqueous-methanolic extract of S. ballotiflora displayed cytotoxicity to Vero cells [ 22 ], the icetexane derivatives isolated from the chloroform extract of the same species showed cytotoxic activity, with 19-deoxyicetexone [ 23 ] being the most active compound against the HeLa cervical cancer cell line [ 21 ].…”

Section: Introductionmentioning

confidence: 99%

“…Several members of this type of diterpenoids have been targeted for synthetic work due to their structural features and the biological activity exhibited by some icetexanes [ 16 , 17 , 18 , 19 , 20 ] as anti-proliferative activity, in vitro, against some human cancer cell lines [ 9 , 11 , 21 ]. On this issue, while the aqueous-methanolic extract of S. ballotiflora displayed cytotoxicity to Vero cells [ 22 ], the icetexane derivatives isolated from the chloroform extract of the same species showed cytotoxic activity, with 19-deoxyicetexone [ 23 ] being the most active compound against the HeLa cervical cancer cell line [ 21 ]. In turn, 19-deoxyicetexone showed anti-diarrheal activity in a rodent model [ 24 ], the essential oil of the aerial parts of the plant exhibited insecticide activity against Spodoptera frugiperda Walker (Lepidoptera, Noctuidae) [ 25 ], and the chloroform extract of the aerial parts showed insecticide and insectistatic activities against the same insect [ 26 ].…”

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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From the aerial parts of Salvia ballotiflora, eleven diterpenoids were isolated; among them, four icetexanes and one abietane (1–5) 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.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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

et al. 2017

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“…The diterpenes were isolated from ECL by open column chromatography using a mixture of hexane-ethyl acetate as described earlier [ 6 ].…”

Section: Methodsmentioning

confidence: 99%

“…Additional, some studies have found that different diterpenes exhibited an important anti-inflammatory effect [ 10 ]. Recently, DEOX, DIC, and DAM were obtained from the hexane-washed chloroform extract of S. ballotiflora (ECL), and the cytotoxic activity of ECL was determined against the cancer cell lines A549, CT26, HeLa, and MCF7 [ 6 ]. These results show that S. ballotiflora and some of its metabolites have cytotoxic activity, and anti-inflammatory activity.…”

Section: Introductionmentioning

confidence: 99%

Anti-inflammatory and antitumor activities of the chloroform extract and anti-inflammatory effect of the three diterpenes isolated from Salvia ballotiflora Benth

Campos-Xolalpa

Alonso-Castro

Ortíz‐Sánchez

et al. 2021

BMC Complement Med Ther

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Background Drugs used for the treatment of diseases associated with chronic inflammation, such as cancer and rheumatoid arthritis have the potential to cause undesirable side-effects, which might result in patients ending treatment prematurely. However, plants are a viable option for the treatment of inflammatory diseases. In this study, we assessed the in vivo and in vitro anti-inflammatory activity, and the antitumor effects of the chloroform extract of Salvia ballotiflora (ECL). The pro-apoptotic effects of ECL in CT26 cells were also determined. Methods The chloroform extract of Salvia ballotiflora (ECL) was standardized using 19-deoxyicetexone (DEOX) as a phytochemical marker. The anti-inflammatory activity of ECL was determined on acute and chronic inflammatory models using the TPA-induced mouse ear edema assay. The antitumor activity of ECL was evaluated by the subcutaneous inoculation of CT26 cells on the back of Balb/c mice. In vitro CT26 cell death induced by ECL was determined by Annexin V/propidium iodide staining assay using flow cytometry. ECL and the diterpenes isolated from the chloroform extract included 19-deoxyicetexone (DEOX), icetexone (ICT), and 7,20-dihydroanastomosine (DAM), which were tested in LPS-stimulated J774A.1 macrophages to quantify pro-inflammatory cytokine levels. The in vitro anti-arthritic activity of ECL was determined using the bovine serum protein (BSP) denaturation assay. Results ECL exerted anti-inflammatory activities in acute (84% of inhibition, 2 mg/ear) and chronic models (62.71%, at 100 mg/kg). ECL showed antitumor activity at 200 mg/kg and 300 mg/kg, reducing tumor volume by 30 and 40%, respectively. ECL (9.5 μg/mL) induced in vitro apoptosis in CT26 cells by 29.1% (48 h of treatment) and 93.9% (72 h of treatment). ECL (10 μg/ml) decreased levels of NO (53.7%), pro-inflammatory cytokines IL-6 (44.9%), IL-1β (71.9%), and TNF-α (40.1%), but increased the production of the anti-inflammatory cytokine IL-10 (44%). The diterpenes DEOX, ICT, and DAM decreased levels of NO (38.34, 47.63, 67.15%), IL-6 (57.84, 60.45, 44.26%), and TNF-α (38.90, 31.30, 32.83%), respectively. ECL showed in vitro antiarthritic activity (IC50 = 482.65 μg/mL). Conclusions ECL exhibited anti-inflammatory and anti-tumor activities. Furthermore, the diterpenes DEOX, DAM, and ICT showed anti-inflammatory activity by reducing levels of NO, TNF-α, and IL-6.

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Terpenes of the Genus Salvia: Cytotoxicity and Antitumoral Effects

Campos-Xolalpa

Pérez-Gutiérrez

Pérez-González

et al. 2018

Anticancer Plants: Natural Products and Biotechnological Implements

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Cytotoxic activity of the chloroform extract and four diterpenes isolated from Salvia ballotiflora

Cited by 20 publications

References 15 publications

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

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

Anti-inflammatory and antitumor activities of the chloroform extract and anti-inflammatory effect of the three diterpenes isolated from Salvia ballotiflora Benth

Terpenes of the Genus Salvia: Cytotoxicity and Antitumoral Effects

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