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

Abstract

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.

Chemical Constituents, Bioactivities, and Pharmacological Mechanisms of Dendrobium officinale: A Review of the Past Decade

“…Weighted gene coexpression network analysis also identified 66 transcription factors, mainly belonging to the AP2/ERF, MYB, bHLH, WRKY, bZIP, and Tify families, that were positively correlated with alkaloid content, as well as transcription factors involved in the regulation of TIAs and isoquinoline alkaloid biosynthesis, including DoFPS ( Dca007721 ), DoDHQS ( Dca008449 ), DoDHS ( Dca021396 and Dca004228 ), DoCS ( Dca015447 ), DoCM ( Dca012195 ), DoTYDC ( Dca021379 ), DoADH ( Dca025688 ), DoTR ( Dca027425 ), DoAOS ( Dca022684 and Dca000659 ), and DoOPR ( Dca023268 ) . Another study suggested that the alkaloid content in D. officinale samples treated with MeJA was highest at 32 days (343 μg/g), consistent with previous studies . Furthermore, based on solid-phase extraction coupled with high-performance liquid chromatography-tandem mass spectrometry (SPE-HPLC-LC-MS/MS), 49 compounds were identified from the MeJA-treated samples, including seven alkaloids .…”

“…29 Furthermore, based on solid-phase extraction coupled with high-performance liquid chromatographytandem mass spectrometry (SPE-HPLC-LC-MS/MS), 49 compounds were identified from the MeJA-treated samples, including seven alkaloids. 31 Despite the identification of many genes related to alkaloid synthesis through multiomics analysis, most genes have not yet been confirmed by functional studies, and their mechanisms remain incompletely understood.…”

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

“…122 Recently, 145 was identified in the perennial herb Dendrobium officinale , either. 123 144 and 145 have a 13-membered lactam ring 1,5,10-triazacyclo-tridecan-4-one, differing from that of the cyclic spermidine alkaloidal glycoside meehanine from M. urticifolia , which bears a 1,5,10-triazacyclotridecan-2-one. Besides, a substituent p -hydroxycinnamyl group instead of an acyl of meehanine is attached to the N 10 position of meefarnine.…”

Metabolomics-Based Analysis of the Effects of Different Cultivation Strategies on Metabolites of Dendrobium officinale Kimura et Migo

“…Dendrobium officinale Kimura et Migo is a famous plant with high medicinal value which has been recorded in Chinese Pharmacopoeia due to its various remarkable effects, such as cardiovascular protection [ 1 , 2 ], hypoglycemia [ 3 , 4 ], gastrointestinal protection [ 5 , 6 , 7 ], immune modulation [ 8 , 9 ], antitumor [ 10 , 11 , 12 ], anti-aging [ 13 , 14 ], and anti-osteoporosis [ 15 ]. Its main chemical constituents include polysaccharides [ 16 ], flavonoids [ 17 ], phenolic acids [ 18 ], amino acids [ 19 ], bibenzyl [ 20 ], alkaloids [ 21 ], coumarins, lignans [ 22 ], and organic acids [ 23 , 24 ], which are closely related to its pharmacological effects. (Specific information on some of the Dendrobium candidum compounds reported in the literature is shown in Table S2 ).…”