A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf

Silva, Gustavo da; Martinho, Ana; Soengas, Raquel G.; Duarte, Ana Paula; Serrano, R; Gomes, Eduardo; Silva, Olga

doi:10.1016/j.fitote.2015.07.020

Cited by 7 publications

(8 citation statements)

References 15 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Meefarnine B was a spermidine alkaloid containing a polyamine heterocyclic ring. These alkaloids are generally considered to be synthesized by putrescine, which is produced by the degradation of L -arginine or L -ornithine ( da Silva et al, 2015 ). The MS 2 and MS 3 spectra of meefarnine B indicated that the NH 3 group on N-5 was cleaved to produce the m/z 421 due to the collision dissociation effect ( Figures 4B,C ).…”

Section: Resultsmentioning

confidence: 99%

Identification of alkaloids and related intermediates of Dendrobium officinale by solid-phase extraction coupled with high-performance liquid chromatography tandem mass spectrometry

Song

Zhang²,

Manzoor³

et al. 2022

Front. Plant Sci.

View full text Add to dashboard Cite

Jasmonate (JA) signaling plays a pivotal role in plant stress responses and secondary metabolism. Many studies have demonstrated that JA effectively induce the expressions of alkaloid biosynthetic genes in various plants, which rendered to the accumulation of alkaloid to counteract stresses. Despite the multiple roles of JA in the regulation of plant growth and different stresses, less studied involved in the regulatory role of JA in Dendrobium officinale alkaloids. A strategy for the rapid identification of alkaloid and the intermediates of D. officinale was established based on a solid-phase extraction coupled with high-performance liquid chromatography tandem mass spectrometry method. By using SPE-LC-MS/MS method, the potential compounds were tentatively identified by aligning the accurate molecular weight with the METLIN and Dictionary of Natural Products databases. The chemical structures and main characteristic fragments of the potential compounds were further confirmed by retrieving the multistage mass spectra from the MassBank and METLIN databases. The Mass Frontier software was used to speculate the fragmentation pathway of the identified compounds. Seven alkaloids were separated and identified from D. officinale, which were mainly classified into five types (tropane alkaloids, tetrahydroisoquinoline alkaloids, quinolizidine alkaloids, piperidine alkaloids, and spermidine alkaloids). Besides the alkaloids, forty-nine chemical substances, including guanidines, nucleotides, dipeptides, sphingolipids and nitrogen-containing glucosides, were concurrently identified. These findings gives the composition of chemicals currently found in D. officinale, which could provide the scientific method for the identification of alkaloids in other Dendrobium plants.

show abstract

Section: Resultsmentioning

confidence: 99%

Identification of alkaloids and related intermediates of Dendrobium officinale by solid-phase extraction coupled with high-performance liquid chromatography tandem mass spectrometry

Song

Zhang²,

Manzoor³

et al. 2022

Front. Plant Sci.

View full text Add to dashboard Cite

show abstract

“…Meefarnine B was a spermidine alkaloid containing a polyamine heterocyclic ring. These alkaloids are generally considered to be synthesized by putrescine, which is produced by the degradation of L-arginine or L-ornithine (da Silva et al, 2015). The MS 2 and MS 3 spectra of meefarnine B indicate that the NH 3 group on N-5 was cleaved to produce the fragment m/z 421 under the collision dissociation effect ( Figure 4b and 4c ).…”

Section: Resultsmentioning

confidence: 99%

Identification of Alkaloids and Related Intermediates of Dendrobium officinale by Solid-Phase Extraction Coupled with High-Performance Liquid Chromatography Tandem Mass Spectrometry

Song

Zhang

Manzoor

et al. 2022

Preprint

View full text Add to dashboard Cite

JA signaling plays a pivotal role in plant stress responses and secondary metabolism. Many studies have demonstrated that jasmonates effectively induce the expressions of alkaloid biosynthesis genes in various plants, which rendered to the accumulation of alkaloid to counteract stresses. Despite the multiple roles of JAs in the regulation of plant growth and different stresses, less studied involved in the regulatory role of JA in Dendrobium officinale. Here, a strategy for the rapid identification of alkaloid and precursors of D. officinale was established based on a solid-phase extraction-high performance liquid chromatography-linear ion trap- Orbitrap tandem mass spectrometry (SPE-HPLC-LTQ-Orbitrap) method. The potential compounds were tentatively identified by aligning the accurate molecular weight with the METLIN and Dictionary of Natural Products databases. The chemical structures and main characteristic fragments of the potential compounds were further confirmed by retrieving the multistage mass spectra from the MassBank and METLIN databases.The Mass Frontier software was used to speculate the fragmentation pathway of the identified compounds. As a result, seven alkaloids were separated and identified from D. officinale, which were mainly classified into five types (tropane alkaloids, tetrahydroisoquinoline alkaloids, quinolizidine alkaloids, piperidine alkaloids and spermidine alkaloids). Besides the alkaloids, forty-nine chemical substances, including guanidines, nucleotides, dipeptides, sphingolipids and nitrogen-containing glucosides, were concurrently identified in the experiment. Taken together, this study revealed the composition of chemicals currently found in D. officinale, which could provide the scientific method for the identification of alkaloids in other Dendrobium plants.

show abstract

“…A similar cyclic spermidine alkaloid, (2 S )-9-benzoyl-1-methyl-2-phenyl-1,5,9-triazacyclo-tridecan-4-one ( 147 , designated as gymnarine), which was isolated from the leaves of the Gymnosporia arenicola , possesses a 13-membered macrocycle and a substituent benzoyl at C 9 . 125 Like meefarnine and androderine, 147 has one 2 S configuration at C 2 and one amide carbonyl at C 4 , except for one methyl at C 1 . Noticeably, the substituent group at C 9 of 147 is a benzoyl rather than that of a furoyl in 146 .…”

Section: Structure and Bioactivity Of Polyamine-containing Natural Pr...mentioning

confidence: 99%

Polyamine-containing natural products: structure, bioactivity, and biosynthesis

Long,

Zhou,

Zhou

et al. 2024

Nat. Prod. Rep.

View full text Add to dashboard Cite

show abstract

A new spermidine macrocyclic alkaloid isolated from Gymnosporia arenicola leaf

Cited by 7 publications

References 15 publications

Identification of alkaloids and related intermediates of Dendrobium officinale by solid-phase extraction coupled with high-performance liquid chromatography tandem mass spectrometry

Identification of alkaloids and related intermediates of Dendrobium officinale by solid-phase extraction coupled with high-performance liquid chromatography tandem mass spectrometry

Identification of Alkaloids and Related Intermediates of Dendrobium officinale by Solid-Phase Extraction Coupled with High-Performance Liquid Chromatography Tandem Mass Spectrometry

Polyamine-containing natural products: structure, bioactivity, and biosynthesis

Contact Info

Product

Resources

About