Tandem Solid-Phase Extraction Followed by HPLC-ESI/QTOF/MS/MS for Rapid Screening and Structural Identification of Trace Diterpenoids in Flowers of <i>Rhododendron molle</i>

Hongyan, Zou; Luo, Jun; Xu, Defeng; Kong, Ling–Yi

doi:10.1002/pca.2501

Cited by 18 publications

(10 citation statements)

References 15 publications

(18 reference statements)

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“…Thus, the structure of 17 was elucidated as 3β-[(β- d -glucopyranosyl)oxy]-2α,5β,6β,10α,14β,16α-hexahydroxygrayanane. This structure was reported recently by Kong’s group in a rapid screening of R. molle and was identified tentatively based on MS fragmentation analysis …”

Section: Resultsmentioning

confidence: 54%

Antinociceptive Grayanoids from the Roots of Rhododendron molle

Liu

Zhang

et al. 2015

J. Nat. Prod.

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Nine new grayanoids (1-9), together with 11 known compounds, were isolated from the roots of Rhododendron molle. The structures of the new compounds (1-9) were determined on the basis of spectroscopic analysis, including HRESIMS, and 1D and 2D NMR data. Compounds 4, 6, 12, and 14-20 showed significant antinociceptive activities in an acetic acid-induced writhing test. In particular, 14 and 15 were found to be more potent than morphine for both acute and inflammatory pain models and 100-fold more potent than gabapentin in a diabetic neuropathic pain model.

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Section: Resultsmentioning

confidence: 54%

Antinociceptive Grayanoids from the Roots of Rhododendron molle

Liu

Zhang

et al. 2015

J. Nat. Prod.

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“…Limonoids have moderate polarity and are concentrated in the crude extract for possible separation using an ODS‐SPE column according to polarity. This process has often been used in sample pretreatment methodologies 22–24 …”

Section: Resultsmentioning

confidence: 99%

MS diagnostic model and rapid distinguishing of bioactive limonoids in fruits of Melia toosendan using solid‐phase extraction coupled with LC–MS/MS

Cui

Zhao

et al. 2020

Phytochemical Analysis

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Introduction Melia toosendan Sieb. et Zucc. has been used as a Chinese folk medicine for roundworm treatment since ancient times. Many diverse limonoids have been isolated from Meliaceae plants, but it remains difficult to isolate and identify other limonoids because of their small natural concentrations. Objective This study was performed to overcome the difficulties associated with fast and accurate identification of limonoids and establish a reliable and sensitive method for the analysis of minor limonoids in M. toosendan fruits. Methods An efficient strategy for enrichment, detection, and identification of minor limonoids from M. toosendan fruits using solid‐phase extraction with high‐performance liquid chromatography–quadrupole time‐of‐flight tandem mass spectrometry (SPE‐HPLC‐Q‐TOF‐MS/MS) was developed herein. Results Characteristic fragmentations and fragmentation ions containing trichilin‐, nimbin‐, and vilasinin‐class limonoid skeletons were initially studied, and characteristic diagnostic ions involved retro Diels‐Alder (RDA) reactions or homolytic cleavages, which were used to identify minor limonoids. In total, 13 limonoids, including four new ones, were identified. Conclusion This is the first report on the analysis of M. toosendan fruits to identify limonoids. This novel analysis method may stimulate further research regarding the identification of limonoids in other plant species.

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“…Comparison of their NMR data (Tables 2 and 3) revealed that micranthanoside H (13) differed from the known rhodomoside A (16) 7 by the presence of a tetrasubstituted double bond (δ C 125.5, C-10; 138.1, C-9) in 13, instead of the exocyclic double bond (δ H 5.03, s; 5.01, s, H 2 -20; δ C 113.8, C-20; 152.4, C-10) in 16. The HMBC correlations from H 3 -20 (δ H 1.69, s) to C-9 (δ C 138.1), C-10 (δ C 125.5), and C-1 (δ C 44.9) revealed the position of the tetrasubstituted Δ 9 (10) double bond. Thus, the structure of compound 13 was defined as 3β-(β-D-glucopyranosyloxy)-5β,6β,14β,16α-tetrahydroxygrayan-9(10)-ene.…”

Section: Journal Of Natural Productsmentioning

confidence: 98%

“…To date, more than 100 grayanane diterpenoids have been reported from nature; however, grayanane diterpenoid glucosides are relatively rare. Since the first grayanane diterpenoid glucoside, grayanoside A, was isolated from Leucothoe grayana in 1978, only a total of 23 grayanane diterpenoid glucosides have been reported from the Ericaceae plants, namely, grayanosides A–D, − craiobiosides A and B, rhodomosides A–F, , 1β-rhodomoside B, rhojaponin VI-3-glucoside, , pierosides A and C, pierisformosides A–C, , pierisformosides H and I, 3β-(β- d -glucopyranosyloxy)-5β,6β,10α,16β-tetrahydroxygrayan-9(11)-ene, and rhododeoside I . Among them, craiobioside A and rhojaponin VI-3-glucoside were reported to show significant antinociceptive activity …”

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confidence: 99%

Grayanane Diterpenoid Glucosides from the Leaves of Rhododendron micranthum and Their Bioactivities Evaluation

et al. 2018

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Thirteen new grayanane diterpenoid glucosides, 3-epi-grayanoside B (1), micranthanosides A−E (2−6), 7αhydroxygrayanoside C (7), micranthanoside F (8), 14β-acetyoxymicranthanoside F (9), micranthanoside G (10), 14-Oacetylmicranthanoside G (11), 14β-hydroxypieroside A (12), and micranthanoside H (13), and six known analogues (14−19) were isolated from the leaves of Rhododendron micranthum. The structures of 1−19 were elucidated based on spectroscopic analysis, comparison with literature, and chemical methods. The absolute configurations of 3-epi-grayanoside B (1) and micranthanosides A (2) and C (4) were defined by single-crystal X-ray diffraction analysis. This is the first report of the crystal structures of grayanane diterpenoid glucosides. 3-epi-Grayanoside B (1) represents the first example of a 3α-oxygrayanane diterpenoid glucoside, and micranthanosides A−D (2−5) are the first examples of 5α-hydroxy-1-βH-grayanane diterpenoids. In addition, micranthanosides C−F (4−6 and 8) and 14β-acetyoxymicranthanoside F (9) represent the first examples of grayanane glucosides with the glucosylation at C-16.All the grayanane diterpenoid glucosides 1−19 were assayed for their antiinflammatory, antitumor, and PTP1B inhibitory activities, but did not show significant activities at 40 μM. Grayanane diterpenoid glucosides 1−18 were evaluated for their antinociceptive activity, and compounds 2, 3, 7−10, 12, 13, and 16 showed significant antinociceptive effects with percentage inhibitions in excess of 50%.

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Tandem Solid-Phase Extraction Followed by HPLC-ESI/QTOF/MS/MS for Rapid Screening and Structural Identification of Trace Diterpenoids in Flowers of Rhododendron molle

Abstract: By qualitative research of diterpenoids in this plant by HPLC-ESI/QTOF/MS/MS, a reliable methodology for the analysis of these active constituents of R. molle was established for the first time.

Cited by 18 publications

References 15 publications

Antinociceptive Grayanoids from the Roots of Rhododendron molle

Antinociceptive Grayanoids from the Roots of Rhododendron molle

MS diagnostic model and rapid distinguishing of bioactive limonoids in fruits of Melia toosendan using solid‐phase extraction coupled with LC–MS/MS

Grayanane Diterpenoid Glucosides from the Leaves of Rhododendron micranthum and Their Bioactivities Evaluation

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