Ent-trachyloban-19-oic acid isolated from Iostephane heterophylla as a promising antibacterial agent against Streptococcus mutans biofilms

Hernández, Dulce Milagros Razo-Blanco; Díaz-Ruiz, Gloria; Rivero-Cruz, Blanca; Bye, Robert; Aguilar, María Isabel; Rivero-Cruz, J. Fausto

doi:10.1016/j.fitote.2011.12.022

Cited by 15 publications

(22 citation statements)

References 18 publications

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“…It has been confirmed in other compounds such as hydroquinones that antioxidant activity greatly changes when an OH group is present on the side chain [20]. Xanthorrhizol ( 1 ) has drawn attention from drug discovery researchers [21] because it has numerous beneficial physiological activities such as neuroprotective ability [22], lipid peroxidation inhibitory ability (antioxidant ability [22,23]), and antibacterial ability [24,25]. Acetylation of the phenolic OH in xanthorrhizol ( 1 ) reduces its physiological activity, strongly suggesting that the phenolic OH group is involved in the physiological activity mechanism [22,23,24].…”

Section: Introductionmentioning

confidence: 99%

“…Evaluation of the antioxidant activity of compounds such as xanthorrhizol ( 1 ) has been carried out using DPPH assays and lipid peroxide suppression reactions [21,22,23,24]. Analytical evaluation of compounds with different side chain functional groups in the same skeleton showed a difference in antioxidant activity, but the influence of the side chain on a compound’s antioxidant activity has rarely been discussed.…”

Section: Introductionmentioning

confidence: 99%

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Effect of Side Chain Functional Groups on the DPPH Radical Scavenging Activity of Bisabolane-Type Phenols

et al. 2019

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Methods for improving the antioxidant activity of phenolic compounds have been widely investigated; however, most studies have focused on the structure–activity correlations of substituents on the aromatic rings of catechols or flavonoids. We investigated the influence of side chain functional groups on the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity of xanthorrhizol and curcuphenol analogues. These compounds were synthesised by the side chain functional group conversion of curcumene, followed by direct oxidation of the aromatic ring. We determined the DPPH radical scavenging activity from the half-maximal effective concentration (EC50) obtained from a DPPH assay in methanol. The positional relationships of the side chain with the aromatic ring and phenolic OH group were determined using density functional theory calculations, and the stability of different conformations was compared. Electron transfer-proton transfer was determined to be the dominant mechanism in the DPPH reaction with xanthorrhizol analogues, based on the correlation between the EC50 and ionisation potential. The radical cation was greatly stabilised in the structure where the side chain functional group was close to the aromatic ring. Stabilisation also depended on the phenolic OH group position. In future antioxidant design, aromatic ring substituent conversion and the use of functional groups far from the OH group or ring should be explored.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Effect of Side Chain Functional Groups on the DPPH Radical Scavenging Activity of Bisabolane-Type Phenols

et al. 2019

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“…Presence of the 19-O-(β-D-glucopyranosyl) group in trachylobanoic acid skeleton increased acetylocholinesterase inhibitory activity, while starting material trachyloban-19-oic acid (1) was moderately active. The report of AChE inhibitory activity for this class of compounds is very relevant since trachylobane diterpenes can be isolated in high amounts from nature (Hernández et al 2012) being a straightforward source of starting material for industrial new drugs development. Therefore, drugs from this class arise as potential greener and cheaper alternatives for the development of anti-Alzheimer medicines to replace available medicines currently used in therapeutics.…”

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confidence: 99%

A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by Mucor plumbeus

Santos

Takahashi

2017

An. Acad. Bras. Ciênc.

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The in vitro metabolism of a widespread natural product, trachyloban-19-oic acid (1), by the fungal species Mucor plumbeus was studied in a sucrose-yeast liquid medium. Two products were isolated, and their structures were determined by spectroscopic means as 7β-hydroxytrachyloban-19-oic acid (5) and trachyloban-19-O-β-D-glucopyranosyl ester (6). To the best of our knowledge, compound 6 is herein reported by the first time in the literature. These compounds were assayed for acetylcholinesterase inhibition along with some related compounds. Compound 6 showed the highest acetylcholinesterase inhibitory activity at 10000 µg/mL among the tested compounds, a result (92.89%) comparable to the activity of the positive control, galanthamine (94.21%). Therefore, biotransformation of the natural product 1 by M. plumbeus produced a novel compound with potential as a new lead to develop anti-Alzheimer medicines.

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“…The main pharmacological activity in the reviewed studies is antimicrobial. The ent-trachyloban-19-oic acid, isolated from the roots of Iostephane heterophylla (Figure 3C), is a potent antibacterial agent in the treatment of oral pathogens as Streptococcus mutans (Hernández et al 2012). Two SQLs identified in Ambrosia confertiflora, santamarine and reynosin have bactericidal activity against Mycobacterium tuberculosis (Coronado-Aceves et al 2016).…”

Section: Discussionmentioning

confidence: 99%

Ethnopharmacology of the Asteraceae family in Mexico

Cilia-López¹,

Cariño-Cortés

Zurita-Salinas

2021

Bot. Sci.

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Background: In Mexico, the Asteraceae are part of traditional knowledge where its members have several uses, but they are particularly remarkable in traditional medicine and are used for different purposes. Questions: What pharmacologically studies have been carried out with Asteraceae species used in Mexican traditional medicine? What pharmacological activities have been tested? What compounds are responsible for the tested activities? Species studied: Asteraceae species used in Mexican traditional medicine pharmacologically tested. Methods: A database including scientific studies on Asteraceae species which studies on pharmacological activity or phytochemical characterization was compiled and analyzed. Results: From 249 reviewed studies only 202 fulfilled the criteria for our analysis. A total of 101 species distributed in 65 genera and 16 tribes were registered. The tribes Heliantheae and Senecioneae were the most studied. Ageratina pichinchensis, Artemisia ludoviciana, Heliopsis longipes, and Heterotheca inuloides were the most studied species. In Mexico, the Asteraceae family is mainly used in the treatment of diseases or symptoms related to the digestive and respiratory systems. In 48 % of the studies some biocidal activity was evaluated but only 21.8 % included phytochemical characterizations. Conclusions: The antimicrobial activity and phytochemical characterizations are the main kind of ethnopharmacological studies for Asteraceae in Mexico. Most of the compounds responsible for the activities have not been identified yet. The uses of Asteraceae in Mexico are similar to other countries emphasizing its cultural importance in the world. Mexican Asteraceae should be prioritized in conservation and bioscreening schemes.

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Ent-trachyloban-19-oic acid isolated from Iostephane heterophylla as a promising antibacterial agent against Streptococcus mutans biofilms

Cited by 15 publications

References 18 publications

Effect of Side Chain Functional Groups on the DPPH Radical Scavenging Activity of Bisabolane-Type Phenols

Effect of Side Chain Functional Groups on the DPPH Radical Scavenging Activity of Bisabolane-Type Phenols

A New Acetylcholinesterase Inhibitor from Green Glycosylation of Trachyloban-19-oic Acid by Mucor plumbeus

Ethnopharmacology of the Asteraceae family in Mexico

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