Biodiversity of Convolvulaceous species that contain ergot alkaloids, indole diterpene alkaloids, and swainsonine

Cook, Daniel; Lee, Stephen T.; Panaccione, Daniel G.; Leadmon, Caroline E.; Clay, Keith; Gardner, Dale R.

doi:10.1016/j.bse.2019.103921

Cited by 11 publications

(15 citation statements)

References 28 publications

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“…4 ). A distinct heritable fungal symbiont that produces the toxic indolizidine alkaloid swainsonine occurs in I. carnea , I. costata and other species in the Jalapae and related clades 29 , 30 , potentially reflecting selection against redundant functions of multiple symbionts or their increased physiological costs such that only one endosymbiont can persist within a single host species 31 , 32 . In other clades, most species are EA- with occasional EA+ taxa (e.g., I. batatoides, I. mauritiana ).…”

Section: Resultsmentioning

confidence: 99%

Diversification of ergot alkaloids and heritable fungal symbionts in morning glories

et al. 2021

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Heritable microorganisms play critical roles in life cycles of many macro-organisms but their prevalence and functional roles are unknown for most plants. Bioactive ergot alkaloids produced by heritable Periglandula fungi occur in some morning glories (Convolvulaceae), similar to ergot alkaloids in grasses infected with related fungi. Ergot alkaloids have been of longstanding interest given their toxic effects, psychoactive properties, and medical applications. Here we show that ergot alkaloids are concentrated in four morning glory clades exhibiting differences in alkaloid profiles and are more prevalent in species with larger seeds than those with smaller seeds. Further, we found a phylogenetically-independent, positive correlation between seed mass and alkaloid concentrations in symbiotic species. Our findings suggest that heritable symbiosis has diversified among particular clades by vertical transmission through seeds combined with host speciation, and that ergot alkaloids are particularly beneficial to species with larger seeds. Our results are consistent with the defensive symbiosis hypothesis where bioactive ergot alkaloids from Periglandula symbionts protect seeds and seedlings from natural enemies, and provide a framework for exploring microbial chemistry in other plant-microbe interactions.

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Section: Resultsmentioning

confidence: 99%

Diversification of ergot alkaloids and heritable fungal symbionts in morning glories

et al. 2021

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“…& Schult. is a herbaceous perennial plant growing in South and Central America, as well as in West Africa and South Asia. , The aerial parts have been well studied because of the acute toxicity in cattle due to the presence of ergot alkaloids. ,− Despite its toxicity, the plant is still used in traditional medicine, particularly the roots, against dracunculiasis, postpartum bleeding, and stomachache . The roots have shown antioxidant and diuretic activities, − but no phytochemical investigation has been reported so far.…”

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confidence: 99%

Phytochemical Investigation of the Roots of Ipomoea asarifolia and Antiproliferative Activity of the Isolated Compounds against Multiple Myeloma Cells

et al. 2021

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Ipomoea asarifolia is a herbaceous plant belonging to the family Convolvulaceae and is native to tropical regions of Africa, America, and Asia. A dichloromethane root extract showed antiproliferative activity against multiple myeloma cells (RPMI 8226). The phytochemical investigation led to the isolation of 15 compounds. Compounds 1–4, named (4S,8S)-1-(furan-3-yl)-9-hydroxy-4,8-dimethylnonane-1,6-dione, isoferulic acid hexadecyl ester, caffeic acid hexadecyl ester, and asarifolin I, respectively, are described for the first time. The structures of these molecules were established from their NMR, UV, IR spectroscopic, and MS data. 4-Hydroxycinnamic acid hexadecyl ester (5), 4-hydroxycinnamic acid octadecyl ester (6), 4-hydroxycinnamic acid eicosyl ester (7), caffeic acid octadecyl ester (8), pescapreins III, IV, XXI, XXIII, XXV, and XXVI (9–14), and stoloniferin III (15) were also isolated. All compounds were tested against a multiple myeloma cell line (RPMI 8226). When their IC50 value was lower than 10 μM, the compounds were also tested against two other multiple myeloma cell lines, MM.1S and MM.1R. Compound 3 was the most potent, with an IC50 value of 3.0 μM against RPMI 8226 cells.

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“…muelleri . The use of herbarium specimens facilitated the characterization of several indole diterpene alkaloids. , Subsequently, 30 convolvulaceous species (Argyreia, Ipomoea, and Stictocardia) were screened for the ergot alkaloids, indole diterpene alkaloids, and swainsonine, using herbarium specimens . Indole diterpene alkaloids were detected using HPLC–MS in several taxa previously not reported to contain them.…”

Section: Indole-diterpene-alkaloid-containing Plantsmentioning

confidence: 99%

“…96,97 Subsequently, 30 convolvulaceous species (Argyreia, Ipomoea, and Stictocardia) were screened for the ergot alkaloids, indole diterpene alkaloids, and swainsonine, using herbarium specimens. 98 Indole diterpene alkaloids were detected using HPLC−MS in several taxa previously not reported to contain them. The degradation of some indole diterpene alkaloids, terpendole K and 6,7dehydroterpendole A, was found to be influenced by the age of the herbarium specimen.…”

Section: ■ Monofluoroacetate-containing Plantsmentioning

confidence: 99%

Use of Herbarium Voucher Specimens To Investigate Phytochemical Composition in Poisonous Plant Research

Cook

Lee

Gardner

et al. 2021

J. Agric. Food Chem.

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Poisonous plants cause large losses to the livestock industry through death, reduced production efficiency, reproductive dysfunction, and compromised harvesting of rangeland and pasture forages. Research investigating poisonous plants is complex because there are hundreds of genera of toxic plants representing thousands of species. To investigate the effects of poisonous plants on livestock, a clear understanding of the taxonomic identity of the plant and the ability to collect the plant in sufficient quantities for scientific studies is required. Subsequently, the active principles must be defined and investigated in the taxa of interest to better predict risk and make recommendations to reduce losses. Herbaria are collections of preserved plant specimens and are an important resource in poisonous plant research. Voucher specimens have often been used in the identification of the plant for the experimental reproduction of suspected livestock poisoning associated with a spontaneous case. More recently, herbarium specimens have been used to investigate the chemical composition of toxic plants as well as the distribution of different chemotypes over the landscape. The primary purpose of this review is to highlight the chemical analysis of herbarium specimens in poisonous plant research.

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Biodiversity of Convolvulaceous species that contain ergot alkaloids, indole diterpene alkaloids, and swainsonine

Cited by 11 publications

References 28 publications

Diversification of ergot alkaloids and heritable fungal symbionts in morning glories

Diversification of ergot alkaloids and heritable fungal symbionts in morning glories

Phytochemical Investigation of the Roots of Ipomoea asarifolia and Antiproliferative Activity of the Isolated Compounds against Multiple Myeloma Cells

Use of Herbarium Voucher Specimens To Investigate Phytochemical Composition in Poisonous Plant Research

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