Heliopsis suffruticosa (Compositae, Heliantheae), a new species from western Zacatecas

Noya, David Ramírez; Elizondo, M. Socorro González; Torres, Jorge Molina

doi:10.21829/abm97.2011.248

Cited by 5 publications

(3 citation statements)

References 12 publications

(11 reference statements)

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“…By contrast, shortening at the methyl end possibly leads to the C 16 amides 135a in Echinacea angustifolia ), E. purpurea (Binns et al 2002) and in the four derivatives detected by GC/MS analysis in Heliopsis suffruticosa (Fig. 6) (Ramírez-Noya et al 2011). The elimination of the terminal propyl group results in the formation of acetylenic C 15 alkamides (136a,b,d) found in Achillea as well as in Echinacea species (Fig.…”

Section: Olefinic C 8 -C 4 Alkamidesmentioning

confidence: 99%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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Alkamides are natural products formed by connecting straight-chain, mostly unsaturated, aliphatic acids with various amines by an amide linkage. More than 300 derivatives are known from eight plant families consisting of various combinations of 200 acids with 23 amines. Apart from a few saturated derivatives alkamides with unsaturated acid parts are grouped into compounds with purely olefinic patterns and those with olefinic and acetylenic linkages. Derived from C 18 oleic acid the acid parts are modified either by chain elongations to C 28 or by oxidative shortenings to C 4 acid residues. Substrate and regiospecific desaturases and acetylenases are responsible for their characteristic patterns of unsaturation. Amine parts are derived from various amino acids by decarboxylation. Beside the widespread isobutylamines alkamides with six-and five-membered ring amines and those with phenylalanine derived amines are characteristic for the Asteraceae and Piperaceae while benzylamines are restricted to the Brassicaceae. Within the Asteraceae 2-methylbutylamine distinguishes the tribe Heliantheae from Anthemideae characterized by ring amines. Alkamides with elongated olefinic acid parts are mainly found in Piperaceae and Brassicaceae while acetylenic acid parts are typical for Asteraceae. A wide variety of biological activities ranges from the characteristic pungent/ tingling property and high insecticidal toxicity to significant antifungal, antibacterial, antiprotozoal, molluscicidal, cercaricidal, and acaricidal activity. They also act as plant growth-promoting substances. Position and stereochemistry of the double bonds are essential for the different qualities of the pungent taste. Medically alkamides possess anti-inflammatory and analgesic properties and are responsible for immunomodulatory and cannabinomimetic effects.

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Section: Olefinic C 8 -C 4 Alkamidesmentioning

confidence: 99%

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Greger

2015

Phytochem Rev

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“…Several species containing high levels of alkamides are found in the Asteraceae, Piperaceae and Rutaceae; being more frequent in the Asteraceae family ( Christensen & Lam, 1991 ; Parmar et al, 1997 ; Yang, 2008 ). The Heliopsis genus, which belongs to the Heliantheae tribe in the latter family, contains 16 species, most of them endemic to Mesoamerica ( García-Chávez, Ramírez-Chávez & Molina-Torres, 2004 ; Ramírez-Noya, González-Elizondo & Molina-Torres, 2011 ). Plants of this genus produce over 30 different alkamides.…”

Section: Introductionmentioning

confidence: 99%

Global gene expression analyses of the alkamide-producing plant Heliopsis longipes supports a polyketide synthase-mediated biosynthesis pathway

Buitimea-Cantúa

Marsch-Martínez

Ríos-Chávez

et al. 2020

PeerJ

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Background Alkamides are plant-specific bioactive molecules. They are low molecular weight N-substituted α-unsaturated acyl amides that display biological explicit activities in different organisms from bacteria, fungi, insects to mammals and plants. The acyl chain has been proposed to be biosynthesized from a fatty acid; however, this has not been demonstrated yet. Heliopsis longipes (Asteraceae) accumulates in root a C10 alkamide called affinin in its roots, but not in leaves. The closely related species Heliopsis annua does not produce alkamides. To elucidate the biosynthetic pathway of the alkamides acyl chain, a comparative global gene expression analysis contrasting roots and leaves of both species was performed. Methods Transcriptomics analysis allowed to identify genes highly expressed in H. longipes roots, but not in tissues and species that do not accumulate alkamides. The first domain searched was the Ketosynthase (KS) domain. The phylogenetic analysis using sequences of the KS domain of FAS and PKS from different organisms, revealed that KS domains of the differentially expressed transcripts in H. longipes roots and the KS domain found in transcripts of Echinacea purpurea, another alkamides producer species, were grouped together with a high bootstrap value of 100%, sharing great similarity. Among the annotated transcripts, we found some coding for the enzymatic domains KS, AT, ACP, DH, OR and TE, which presented higher expression in H. longipes roots than in leaves. The expression level of these genes was further evaluated by qRT-PCR. All unigenes tested showed higher expression in H. longipes roots than in any the other samples. Based on this and considering that the acyl chain of affinin presents unsaturated bonds at even C numbers, we propose a new putative biosynthesis pathway mediated by a four modules polyketide synthase (PKS). Results The global gene expression analysis led to the selection of a set of candidate genes involved in the biosynthesis of the acyl chain of affinin, suggesting that it may be performed by a non-iterative, partially reductive, four module type I PKS complex (PKS alk) previously thought to be absent from the plant kingdom.

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“…Este sesgo puede deberse en parte a una tradición botánica mucho más antigua y arraigada en el centro y sur del país, así como al área de influencia histórica y distribución de las instituciones que desarrollan el mayor porcentaje de investigación en biodiversidad. Por otra parte, se han descubierto 64 especies nuevas de plantas vasculares en la SMO de 2010 a la fecha (Henrickson & Van Devender 2010, Henrickson et al 2011, Mayfield & Steinmann 2010, González-Tamayo & Hernández-Hernández 2010, Jimeno-Sevilla & Carrillo-Reyes 2010, Nesom 2010, Saarela et al 2010, Sánchez-Ken 2010, Estrada-C et al 2011, Ramírez-Noya et al 2011, Turner 2011, 2012, 2013a, 2013b, 2013c, González-Elizondo et al 2012a, Reyes-Santiago et al 2012a, Van Devender & Nesom 2012, Borhidi et al 2013, Cruz-Durán & Sousa 2013, González-Gallegos 2013, González-Gallegos & López-Enríquez 2016, Rodríguez & Ortiz-Catedral 2013, Anderson 2014, Costea et al 2014, Folk & Freudenstein 2014, Spellenberg 2014, Steinmann 2014, Castro-Castro et al 2015, Wallnofer 2015, Mcdonnell & Fishbein 2016, Pérez-Cálix 2016, Ruiz-Sánchez & Castro-Castro 2016, Ruiz-Sánchez et al 2017…”

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Inventario de las plantas vasculares y tipos de vegetación del Santuario El Palmito, Sinaloa, México

et al. 2019

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Antecedentes: El Santuario El Palmito es parte de una de las regiones terrestres prioritarias de México. Destaca por su diversidad de aves y alberga a uno de los bosques mesófilos más norteños en la vertiente del Pacífico. Sin embargo, carece de un inventario sistemático de su flora. Preguntas: ¿Cuáles son los tipos de vegetación y sus elementos característicos en el Santuario? ¿Cuántas y cuáles familias, géneros y especies de plantas vasculares alberga? ¿Cuáles son las formas biológicas presentes en el área? ¿Existen especies bajo alguna categoría de protección? Especies de estudio: Plantas vasculares. Sitio de estudio y años de estudio: Santuario El Palmito, Sinaloa, México; octubre 2017 a octubre 2018. Métodos: Se realizaron muestreos de la flora cada mes durante un año. Los ejemplares se identificaron con ayuda de literatura especializada, taxónomos especialistas y cotejo con ejemplares de herbario. El inventario se complementó con algunas bases de datos en línea y especímenes de herbario. Resultados: Se registraron 492 especies, 285 géneros y 103 familias. Asteraceae, Fabaceae, Orchidaceae, Poaceae, Fagaceae y Lamiaceae fueron las familias con mayor riqueza. Se obtuvieron 53 registros nuevos de plantas vasculares para Sinaloa. Las formas biológicas predominantes fueron las hierbas (370 spp.), luego los arbustos (73) y los árboles (60). Por otra parte se registraron 14 especies (2.8 %) en alguna de las categorías de riesgo de la NOM-059-SEMARNAT-2010 y la UICN. Conclusiones: El alto porcentaje de registros nuevos para la flora sinaloense pone de manifiesto la necesidad de continuar con las exploraciones en la entidad.

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Heliopsis suffruticosa (Compositae, Heliantheae), a new species from western Zacatecas

Cited by 5 publications

References 12 publications

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Alkamides: a critical reconsideration of a multifunctional class of unsaturated fatty acid amides

Global gene expression analyses of the alkamide-producing plant Heliopsis longipes supports a polyketide synthase-mediated biosynthesis pathway

Inventario de las plantas vasculares y tipos de vegetación del Santuario El Palmito, Sinaloa, México

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