Defensive Sesquiterpenes from <i>Senecio candidans</i> and <i>S. magellanicus</i>, and Their StructureActivity Relationships

Reina, Matı́as; Santana, Omar; Domínguez, Dulce M.; Villarroel, Luís; Fajardo, Víctor; Rodríguez, Matías L.; González-Coloma⊥, Azucena

doi:10.1002/cbdv.201100236

Cited by 13 publications

(15 citation statements)

References 36 publications

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“…The defensive chemistry of Senecio species from South America is being investigated . In Chile, the genus Senecio is represented by about 300 species, with a few ones, such as Senecio adenotrichius DC, having glandular trichomes on the surface of their leaves and stems .…”

Section: Introductionmentioning

confidence: 99%

Insect Antifeedant and Ixodicidal Compounds from Senecio adenotrichius

Ruiz-Vásquez

Olmeda

Zúñiga

et al. 2016

Chemistry & Biodiversity

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Nine eremophilane sesquiterpenes 1 - 9, two flavonoids 11 and 12, and two known pirrolizidine alkaloids 13 and 14, were isolated from Senecio adenotrichius DC. Their structures were elucidated on the basis of spectroscopic data and by comparison with previously reported spectroscopic data of similar compounds. Compounds 5, 7, and 9 have not been previously reported as natural products. The antifeedant activity of these compounds was tested against Spodoptera litoralis and Myzus persicae. Eremophilanes 1, 3, and 8 were strong antifeedants to M. persicae, and 1 and 8 to Spodoptera littoralis. Their ixodicidal activity was tested against the tick Hyalomma lusitanicum, with eremophilanes 1, 3, and 8, being strong ixodicidal agents.

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Section: Introductionmentioning

confidence: 99%

Insect Antifeedant and Ixodicidal Compounds from Senecio adenotrichius

Ruiz-Vásquez

Olmeda

Zúñiga

et al. 2016

Chemistry & Biodiversity

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“…Although most compounds delay root growth of the target species, the compounds 6β-hydroxy-8αmethoxyeremophila-1(10),7(11)-dien-12,8β-olide; Tolucanolide A and Tolucanolide C from S. candidans and S. magellanicus were able to stimulate the root development of L. sativa (Reina et al, 2012).…”

Section: Resultsmentioning

confidence: 99%

“…In addition to the S. candidans and S. magellanicus species, several sesquiterpenes were isolated, and the derivatives of these compounds were obtained, using an eremophilanolide derivative with a carbonyl at carbon 1 and another with a double bond between carbons 1 and 10, which inhibited the elongation of the L. sativa radicle (Reina et al, 2012). The secondary metabolite furanoeremophilane (6β-tigloyl-9-oxofuranoeremophilane) present in S. macrotis, S. asperulus (Portero et al, 2012) and S. magellanicus (Reina et al, 2012) were also able to delay the development of L. sativa radicle.…”

Section: Resultsmentioning

confidence: 99%

A study of the phytotoxic effects of the aerial parts of Senecio westermanii Dusén (Asteraceae) on Lactuca sativa L. and Allium cepa L. seeds

Merino

Ribas

Silva

et al. 2018

Braz. J. Pharm. Sci.

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The objective of this study was to evaluate the effects of the ethanolic crude extracts and fractions of the species Senecio westermanii Dusén on Lactuca sativa L. (lettuce) and Allium cepa L. (onion) seeds. We assessed the germination, growth, root respiration and photosynthesis of the target species in Petri dishes (9.0 cm diameter) containing filter paper n°6. The study was conducted using 50 seeds per plate and held in 4 replicates per concentration of each sample. In the germination there was an inhibitory effect of fractions hexane (FH) and chloroform (FCl) at concentrations of 500 and 1000 µg/mL. There was a reduction in the radicle growth of lettuce by 14 to 24% and a reduction of hypocotilum by 14 to 28%. As for the radicle of the onion was up 74% reduction to the FCl and the coleoptile was 24 and 45% reduction for FH and FCl, respectively. Inhibitory effects in the root respiration of lettuce were detected in all the samples analyzed, with results ranging from 16 to 83%. For the seeds of A. cepa, there was an encouragement for the FCl and ethyl acetate fractions (FAE), with results ranging from 94 to 142% and 76 to 150%, respectively. With regard to the photosynthesis of L. sativa, there was no significant difference between the control, and as for the A. cepa, there was a strain in inhibition concentrations of 250 and 500 µg/mL, which ranged from 27 to 68%. The samples of S. westermanii caused changes in the target species and thus can be used as a natural herbicide.

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“…The biological activity of Istanbulin A has been explored in the recent literature but, in general, the information provided regarding the enantiomeric identity of the compound is not complete (Mir-Babayev & Houghton, 2002;Reina et al, 2012;Fu et al, 2015;Xu et al, 2018). Therefore, unfortunately, it is not possible to clearly associate the reported activity with a corresponding enantiomeric and/or crystalline form.…”

Section: Antimicrobial Activitymentioning

confidence: 99%

“…These compounds were first discovered from a phytochemical investigation of the Smyrnium genus (Umbelliferae) (Ulubelen et al, 1971(Ulubelen et al, , 1979(Ulubelen et al, , 1982Budě šínský et al, 1984;Gö ren & Ulubelen 1987;Cox et al, 1980). More recently, several studies explored the use of Istanbulins as insect antifeedants and fungicidal, cytotoxic, phytotoxic, antioxidant, anti-inflammatory and antimicrobial agents, among other applications (see, for example, Reina et al, 2012;Fu et al, 2015). Although most of the reported compounds were obtained from the Smyrnium genus, there are some examples which were isolated from others, such as Sarcandra (Zen & Luo, 1983;Wang et al, 1988;Zhu et al, 2008), Chloranthus (Fu et al, 2015;Xu et al, 2010), Salvia (Aydog muş et al, 2006) and Senecio (Glauco et al, 1986;Ló pez-Rodríguez et al, 2009;Reina et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

Revisiting the absolute chirality and polymorphism of (–)-Istanbulin A

et al. 2020

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The terpenoid (−)-Istanbulin A is a natural product isolated from Senecio filaginoides DC, one of the 270 species of Senecio (Asteraceae) which occurs in Argentina. The structure and absolute configuration of this compound [9a-hydroxy-3,4a,5-trimethyl-4a,6,7,8a,9,9a-hexahydro-4H,5H-naphtho[2,3-b]-furan-2,8-dione or (4S,5R,8R,10S)-1-oxo-8β-hydroxy-10βH-eremophil-7(11)-en-12,8β-olide, C15H20O4] were determined by single-crystal X-ray diffraction studies. It proved to be a sesquiterpene lactone showing an eremophilanolide skeleton whose chirality is described as 4S,5R,8R,10S. Structural results were also in agreement with the one- and two-dimensional (1D and 2D) NMR and HR–ESI–MS data, and other complementary spectroscopic information. In addition, (−)-Istanbulin A is a polymorph of the previously reported form of (−)-Istanbulin A, form I; thus, the title compound is denoted form II or polymorph II. Structural data and a literature search allowed the chirality of Istanbulin A to be revisited. The antimicrobial and antifungal activities of (−)-Istanbulin A, form II, were evaluated in order to establish a reference for future comparisons and applications related to specific crystal forms of Istanbulins.

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Defensive Sesquiterpenes from Senecio candidans and S. magellanicus, and Their StructureActivity Relationships

Cited by 13 publications

References 36 publications

Insect Antifeedant and Ixodicidal Compounds from Senecio adenotrichius

Insect Antifeedant and Ixodicidal Compounds from Senecio adenotrichius

A study of the phytotoxic effects of the aerial parts of Senecio westermanii Dusén (Asteraceae) on Lactuca sativa L. and Allium cepa L. seeds

Revisiting the absolute chirality and polymorphism of (–)-Istanbulin A

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