Benzofuran and Bithiophenes from Root Cultures of Tagetes patula

Parodi, Felix J.; Fischer, Nikolaus H.; Flores, Hector E.

doi:10.1021/np50057a028

Cited by 27 publications

(5 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…To date, the chemical analyses of different extracts of T. patula reported in the literature have confirmed the presence of important classes of secondary metabolites, such as flavonoids, alkaloids, thiophenes, and benzofurans . The latter two classes are important indicators of the anthelmintic potential of the extract and have been proven to be involved in the control of nematodes.…”

Section: Resultsmentioning

confidence: 84%

Chemical Composition andIn vitroAnthelmintic Activity of Extracts ofTagetes patulaAgainst a Multidrug‐Resistant Isolate ofHaemonchus contortus

Politi

Júnior

Fantatto

et al. 2018

Chemistry & Biodiversity

View full text Add to dashboard Cite

Sheep breeding has suffered economic losses due to parasitism by gastrointestinal nematodes, particularly Haemonchus contortus. The use of natural products, specifically Tagetes patula, has been suggested as an alternative method of combatting this issue. Chemical analyses of the extracts of this species described in the literature report the presence of important classes of secondary metabolites such as thiophenes, flavonoids, alkaloids, and benzofurans, some of which were identified and isolated in this study. The aim of this work was to test the effect of the essential oil (EO) and the ethanolic extract of the aerial parts (Tp ) of T. patula on eggs and larvae of H. contortus, through an egg hatch test (EHT) and a larval development test (LDT). In the EHT, the EO showed 100% inhibition at 0.75 mg mL (LC = 0.0780 mg mL ), and the Tp showed 100% inhibition at 100 mg mL (LC = 12.8 mg mL ). In the LDT, the EO showed 100% inhibition at 0.375 mg mL (LC = 0.0400 mg mL ), and the Tp showed 100% inhibition at 1.56 mg mL (LC = 0.340 mg mL ). Compared to available literature data, the results presented here suggest that the crude extracts of T. patula have substantial potential for controlling this nematode by interrupting its life cycle and/or preventing it from reaching the infective stage.

show abstract

Section: Resultsmentioning

confidence: 84%

Chemical Composition andIn vitroAnthelmintic Activity of Extracts ofTagetes patulaAgainst a Multidrug‐Resistant Isolate ofHaemonchus contortus

Politi

Júnior

Fantatto

et al. 2018

Chemistry & Biodiversity

View full text Add to dashboard Cite

show abstract

“…The phytochemical study of D. pinnata allowed the isolation of seven thiophene derivatives: 2,2′:5′,2′′-terthiophene (1), 19 5-methyl-2,2′:5′,2′′-terthiophene (2), 14 3′-methoxy-2,2′:5′,2′′-terthiophene (3), 19 5-(3-buten-1-ynyl)-2,2′-bithiophene (4), 14 5-(4-hydroxybut-1ynyl)-2,2′-bithiophene (5), 14 5-(4-acetoxy-1-butynyl)-2,2′-bithiophene (6), 20 and 5-(4-hydroxybut-1-one)-2,2′-bithiophene (7). 21 Together with hyperin (8), 22 catechin (9), 23 patuletin (10), 24 quercetagetin-7-O-β-glucoside (11), 25 quercitrin (12), 22 and phloracetophenone 4′glucoside (13) 26 (Figure 1).…”

Section: Chemical Composition Of D Pinnatamentioning

confidence: 99%

Recognition of antioxidants and photosensitizers in Dyssodia pinnata by EPR spectroscopy

Arciniegas

Gómez‐Vidales

Pérez‐Castorena

et al. 2019

Phytochemical Analysis

View full text Add to dashboard Cite

Introduction Previous studies report the isolation mainly of terthiophene derivatives and flavonoids from Dyssodia species. Terthiophenes are known as photosensitizers by their capacity to generate singlet oxygen (1O2), and flavonoid antioxidant activity is recognized. These opposite properties could represent interesting options in photodynamic therapy. Objective To determine the antioxidant and photosensitizer activities of extracts and isolates of Dyssodia pinnata by electron paramagnetic resonance (EPR). Methodology Extracts and isolates were evaluated as antioxidants by the interactions with copper ion (Cu2+) observed in EPR, and by the 2,2‐diphenyl‐1‐picrylhydrazyl radical (DPPH) and the thiobarbituric reactive substances (TBARS) methods. Their abilities as 1O2 producers were also estimated by EPR. Results Terthiophenes were obtained from hexane (DPH) and acetone (DPA) extracts, and flavonoids from DPA and methanol (DPM) extracts. The interaction with Cu2+ of extracts and isolated compounds of Dyssodia pinnata showed two effects in EPR: reduction and chelation; flavonoids exhibited both effects, while terthiophenes showed only reduction. DPA, DPM, and flavonoids were active in DPPH and TBARS assays. Quercetagetin‐7‐O‐β‐glucoside showed the highest antioxidant and chelating activities, 3‐glycosidated flavonoids were less active. Upon irradiation extracts and terthiophenes induced 1O2 formation. Conclusion Flavonoid reducing activity on Cu2+ and free radical scavenging capacity were related to the number of hydroxy groups and to the conjugation between the B and C rings. All tested flavonols showed a major complex with Cu2+, with the most probable site of chelation between the 5‐hydroxy and 4‐oxo groups. Extracts and terthiophene derivatives showed photosensitizer activity. Thus, EPR is useful to evaluate free radical scavenging and pro‐oxidant properties.

show abstract

“…Bithiophenes 5-(4-acetoxy-1-butenyl)-2,2′-bithiophene and 5-(buten-1-nyl)-2,2′-bithiophene and a benzofuran isoeuparin (5-acetyl-4-hydroxy-2-isopropenylbenzofuran) were isolated from root cultures (Parodi et al 1988 ). The benzofurans, isoeuparin and (−)-4-hydroxytremetone were isolated from T. patula root cultures (Margl et al 2005 ).…”

Section: Root Phytochemicalsmentioning

confidence: 99%

Tagetes patula

Lim¹

2013

Edible Medicinal and Non-Medicinal Plants

View full text Add to dashboard Cite

Benzofuran and Bithiophenes from Root Cultures of Tagetes patula

Cited by 27 publications

References 4 publications

Chemical Composition andIn vitroAnthelmintic Activity of Extracts ofTagetes patulaAgainst a Multidrug‐Resistant Isolate ofHaemonchus contortus

Chemical Composition andIn vitroAnthelmintic Activity of Extracts ofTagetes patulaAgainst a Multidrug‐Resistant Isolate ofHaemonchus contortus

Recognition of antioxidants and photosensitizers in Dyssodia pinnata by EPR spectroscopy

Tagetes patula

Contact Info

Product

Resources

About