Phytotoxic activity in Flourensia campestris and isolation of (−)-hamanasic acid A as its active principle compound

Silva, Mariana P.; Piazza, Leonardo A.; López, Daniela; Rivilli, Marisa Juana Lopez; Turco, Mauricio; Cantero, Juan José; Tourn, M.; Scopel, Ana L.

doi:10.1016/j.phytochem.2011.09.020

Cited by 32 publications

(58 citation statements)

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“…Surface Secreted Resins: Fresh organs were washed with gentle agitation in cold EtOAc during 20 s (short dips) [10] [13] [14]. Special care was taken for dipping intact organs in order to avoid contamination from endogenous sources.…”

Section: Tissue Extractionsmentioning

confidence: 99%

“…Resins were picked up using a micro syringe, weighed, and stored at −20˚C until analysis. ), and running the 2D-TLC as already described by Silva et al [10]. Means from triplicates were expressed as mg (-)HAA per g dry weight (mg•g −1 DW) in the case of whole tissue extractions, and as mg (-)HAA per 100 mg of total surface secreted or duct resins (mg % w/w).…”

Section: Tissue Extractionsmentioning

confidence: 99%

“…FC has been shown to produce a phytotoxic compound identified as (-)-hamanasic acid A {(-)HAA; 7-carboxy-8-hydroxy-1(2), 12(13)-dien-bisabolene} [10]. This bisabolanoid accumulates at exceptionally high concentrations in some FC organs (e.g., 1.6% of leaf dry weight).…”

Section: Introductionmentioning

confidence: 99%

“…There is growing evidence that metabolites that accumulate on plant surfaces are largely produced and secreted by glandular trichomes [11]- [14]. This might be the case of FC, since short dips of fresh and dry leaves and flowers in water or ethyl acetate (EtOAc) showed high concentrations of (-)HAA, accounting for almost 20% -30% of the total metabolites extracted [10]. In a recent paper, we have demonstrated that its natural occurrence is restricted only to some Flourensia species, strictly FC, FO and F. fiebrigii, being absent in F. hirta, F. riparia and F. niederleinii, and in 37 of the most representative co-occurring species of FC and FO [15].…”

Section: Introductionmentioning

confidence: 99%

“…Other resin components in Flourensia spp. have also been reported to have insect antifeedant [20]- [22], antifungal [23], antibacterial [24] [25], antialgal and antitermite properties [26], and herbicidal [10] [15] [20], and to act as tyrosinase inhibitors [27]. To our knowledge, the link between resins secretion and secretory structures in the genus Flourensia has never been addressed before.…”

Section: Introductionmentioning

confidence: 99%

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Secretory Structures in Flourensia campestris and F. oolepis: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Silva¹,

Tourn²,

López³

et al. 2015

AJPS

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In this work, the localization, density, morphology and ultrastructure of secretory structures in aerial organs of Flourensia campestris (FC) and F. oolepis (FO) (Asteraceae) by means of a combination of light, fluorescence, transmission (TEM) and scanning electron microscopy (SEM) were examined. The possible role of secretory structures in the production and secretion of the phytotoxic sesquiterpene (-)-hamanasic acid A ((-)HAA) in both species was also assessed. Capitate glandular trichomes were found in all reproductive organs of FC and FO, and were being reported for the first time. These glandular trichomes, typically associated to edges and veins, were of the same type as those already described for vegetative organs, and were abundant in involucral bracts and corolla of tubulose and ligulate flowers. Their density in reproductive organs of both species was similar (ca. 30/mm 2 ) and lower than that found in leaves (ca. 100/mm 2 ) and stems (ca. 160/mm 2 in FC, and up to 650/mm 2 in FO). Glandular trichomes in vegetative organs followed a species-* Corresponding authors. M. P. Silva et al. 926specific pattern of distribution. TEM and SEM observations suggest that each species differs in the way in which secretory materials are released to the outside: through cracks or pores in FC, or through a loose cuticle in FO. Similar inspections of the secretory ducts revealed lipophilic vacuoles localized in subepithelial and epithelial cells, in which secretions accumulated before being transferred to the duct. The presence of wall ingrowths in subepithelial cells suggests that granulocrine secretion operates in these species. Secretory ducts varied in density and diameter among the organs in both species, with the combination being maximal in woody stems. (-)HAA was only detected in surface secreted resins of both species, and its concentration (2D-TLC, GC-FID) was intimately associated with the distribution and density of glandular trichomes in each organ (capitula, leaves, and stems with primary or secondary growth). In addition, no (-)HAA was detected internally in the resins collected from secretory ducts. The composition of these resins showed distinctive profiles for FC and FO, and only four from ca. 30 compounds detected (GC/MS) were shared by both species. In addition to the elucidation of ultrastructural traits, distribution and density of secretory structures in aerial organs of FC and FO, present findings suggest a functional role for glandular trichomes in the secretion of the putative phytotoxic allelochemical (-)HAA.

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Section: Tissue Extractionsmentioning

confidence: 99%

Section: Tissue Extractionsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Secretory Structures in Flourensia campestris and F. oolepis: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Silva¹,

Tourn²,

López³

et al. 2015

AJPS

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Chemistry and Biology of the GenusFlourensia(Asteraceae)

Rios

2015

Chemistry & Biodiversity

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Flourensia species are dominant plants that are adapted to semidesertic and desertic regions. It is believed that they are successful plants because they employ several protection mechanisms, including the formation of a waxy film on their aerial parts to protect them from dehydration. This waxy film contains chemical compounds that are capable of inhibiting the growth of other plants and of acting as allelopathic and herbicidal agents and as germination inhibitors. These plants also limit herbivory, and they exhibit insecticidal, insect antifeedant, antibacterial, antifungal, antialgal, and antitermite activities. Sesquiterpenes, flavonoids, benzofurans, chromenes, coumarins, lupan triterpenes, aliphatic lactones, and aromatic and acetilenic compounds have all been isolated from the organic extracts of Flourensia species. Monoterpenes, sesquiterpenes, and aliphatic hydrocarbons are the main constituents found in their essential oils. This review is an overview of the chemical constituents and of the biological activities of Flourensia species.

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Volatiles and Nonvolatiles in Flourensia campestris Griseb. (Asteraceae), How Much Do Capitate Glandular Trichomes Matter?

Piazza

López

Silva

et al. 2018

Chemistry & Biodiversity

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The distribution and ultrastructure of capitate glandular trichomes (GTs) in Flourensia species (Asteraceae) have been recently elucidated, but their metabolic activity and potential biological function remain unexplored. Selective nonvolatile metabolites from isolated GTs were strikingly similar to those found on leaf surfaces. The phytotoxic allelochemical sesquiterpene (-)-hamanasic acid A ((-)-HAA) was the major constituent (ca. 40%) in GTs. Although GTs are quaternary ammonium compounds (QACs)-accumulating species, glycine betaine was not found in GTs; it was only present in the leaf mesophyll. Two (-)-HAA accompanying surface secreted products: compounds 4-hydroxyacetophenone (piceol; 1) and 2-hydroxy-5-methoxyacetophenone (2), which were isolated and fully characterized (GC/MS, NMR), were present in the volatiles found in GTs. The essential oils of fresh leaves revealed ca. 33% monoterpenes, 26% hydrocarbon- and 30% oxygenated sesquiterpenes, most of them related to cadinene and bisabolene derivatives. Present results suggest a main role of GTs in determining the volatile and nonvolatile composition of F. campestris leaves. Based on the known activities of the compounds identified, it can be suggested that GTs in F. campestris would play key ecological functions in plant-pathogen and plant-plant interactions. In addition, the strikingly high contribution of compounds derived from cadinene and bisabolene pathways, highlights the potential of this species as a source of high-valued bioproducts.

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Phytotoxic activity in Flourensia campestris and isolation of (−)-hamanasic acid A as its active principle compound

Cited by 32 publications

References 53 publications

Secretory Structures in <i>Flourensia campestris</i> and <i>F. oolepis</i>: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Secretory Structures in <i>Flourensia campestris</i> and <i>F. oolepis</i>: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Chemistry and Biology of the GenusFlourensia(Asteraceae)

Volatiles and Nonvolatiles in Flourensia campestris Griseb. (Asteraceae), How Much Do Capitate Glandular Trichomes Matter?

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Phytotoxic activity in Flourensia campestris and isolation of (−)-hamanasic acid A as its active principle compound

Cited by 32 publications

References 53 publications

Secretory Structures in &lt;i&gt;Flourensia campestris&lt;/i&gt; and &lt;i&gt;F. oolepis&lt;/i&gt;: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Secretory Structures in &lt;i&gt;Flourensia campestris&lt;/i&gt; and &lt;i&gt;F. oolepis&lt;/i&gt;: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Chemistry and Biology of the GenusFlourensia(Asteraceae)

Volatiles and Nonvolatiles in Flourensia campestris Griseb. (Asteraceae), How Much Do Capitate Glandular Trichomes Matter?

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Secretory Structures in <i>Flourensia campestris</i> and <i>F. oolepis</i>: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion

Secretory Structures in <i>Flourensia campestris</i> and <i>F. oolepis</i>: Ultrastructure, Distribution, and (-)-Hamanasic Acid A Secretion