Diphenethylpiperidine alkaloids with tracheal smooth muscle relaxation activity from Hippobroma longiflora (L.) G. Don

Chan, Zi-Yang; Govindaraju, Kayatri; Krishnan, Premanand; Low, Yun‐Yee; Chong, Kam-Weng; Yong, Kien-Thai; Ting, Kang Nee; Lim, Kuan‐Hon

doi:10.1016/j.phytol.2019.01.035

Cited by 8 publications

(12 citation statements)

References 13 publications

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“…The EtOAc phase extract was further subjected to solvent partitioning to obtain a hexanesoluble extract and a 75 % MeOH (aq) -soluble extract, which was then further subjected to repeated column chromatography (CC) and purified by reverse-phase HPLC to yield new alkaloids (1-3) (▶ Fig. 1), along with five known compounds (4)(5)(6)(7)(8). Compared with data from the literature, the known secondary metabolites were identified as (−)-cis-2′,2″-diphenyllobelidiol N-oxide (4) [7], norlobeline (5) [8], (−)-lobeline (6) [9], nor-(−)-cis-2′,2″-diphenyllobelidiol (7) (PubChem CID: 92 245 343), and (−)-cis-2′,2″-diphenyllobelidiol (8) [9].…”

Section: Resultsmentioning

confidence: 99%

“…1), along with five known compounds (4)(5)(6)(7)(8). Compared with data from the literature, the known secondary metabolites were identified as (−)-cis-2′,2″-diphenyllobelidiol N-oxide (4) [7], norlobeline (5) [8], (−)-lobeline (6) [9], nor-(−)-cis-2′,2″-diphenyllobelidiol (7) (PubChem CID: 92 245 343), and (−)-cis-2′,2″-diphenyllobelidiol (8) [9].…”

Section: Resultsmentioning

confidence: 99%

“…As shown in ▶ Fig. 4, the higher R 2 between calculated (2″S-3) and experimental data was used to determine the configuration of 2″ to be S. The absolute configuration of 3 was thus identified as 2R,6S,2″S by the similar NOESY correlations between 3 and 6 (the structure was determined by X-ray single crystallographic analysis) [7] and the quantum chemistry calculations. Consequently, the structure of 3 was defined as (−)-lobeline N-oxide.…”

Section: Structure Elucidation Of Compounds 1-3mentioning

confidence: 99%

“…Three compounds (6)(7)(8) in sufficient amounts were further investigated for neuroprotective potential against PIPN by using the previously established image-based high-content platform of paclitaxel-induced neurite damage on primary cultured dorsal root ganglion (DRG) neurons [12,13]. 5-Hydroxydecanoate (5-HD), a previously identified potential lead for alleviating paclitaxel-induced neurotoxicity [12], was used as a reference control at a concentration of 1.0 µM (▶ Fig.…”

Section: The Neuroprotective Potentials Of Compounds 6-8 Against Pacl...mentioning

confidence: 99%

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2,6-Disubstituted Piperidine Alkaloids with Neuroprotective Activity from Hippobroma longiflora

Chen

Lin

et al. 2022

Planta Med

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Three new alkaloids, hipporidine A (1), hipporidine B (2), and (−)-lobeline N-oxide (3), were discovered from the whole plant of Hippobroma longiflora together with five known compounds (4–8). Their 2,6-disubstituted piperidine structures were established based on the HRESIMS, NMR (COSY, HMBC, HSQC, NOESY), and UV spectroscopic data. Hipporidines A (1) and B (2) possess a rare 1,3-oxazinane moiety. Compound 3 is the N-oxide derivative of (−)-lobeline (6). Moreover, the absolute configuration of norlobeline (5) was established by single-crystal X-ray diffraction analysis. Three major secondary metabolites (6–8) were evaluated for their neuroprotective effect against paclitaxel-induced neurotoxicity. Consequently, pretreatment with compound 8 at a concentration of 1.0 µM displayed significant attenuation on paclitaxel-damaged neurite outgrowth of dorsal root ganglion neurons without interfering with the cytotoxicity of paclitaxel on cervical cancer SiHa cells.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Structure Elucidation Of Compounds 1-3mentioning

confidence: 99%

Section: The Neuroprotective Potentials Of Compounds 6-8 Against Pacl...mentioning

confidence: 99%

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2,6-Disubstituted Piperidine Alkaloids with Neuroprotective Activity from Hippobroma longiflora

Chen

Lin

et al. 2022

Planta Med

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“…Three diphenethylpiperidine alkaloids named hippofoline A, hippofoline B, and (À)-cis-2 0 ,2 00 -diphenyllobelidiol N-oxide were reported alongside (À)-lobeline and (À)-cis-2 0 ,2 00 -diphenyllobelidiol. In carbachol treated rats, hippofoline B and (À)-cis-2 0 ,2 00 -diphenyllobelidiol are responsible for inducing relaxation effects (Chan et al 2019). The ethanol extracts of leaves, stems, and flowers contain alkaloids, saponins, flavonoids that act as antibacterial agents.…”

Section: Phytochemistrymentioning

confidence: 99%