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

Author:

Chen Shu-Rong1,Chen Yih-Fung23,Lin Jue-Jun2,Ke Tzu-Yi2,Lin Yun-Sheng4,Cheng Yuan-Bin1

Affiliation:

1. Department of Marine Biotechnology and Resources, National Sun Yat-sen University, Kaohsiung, Taiwan

2. Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical University, Kaohsiung, Taiwan

3. Department of Medical Research, Kaohsiung Medical University Hospital, Kaohsiung, Taiwan

4. Department of Biological Science and Technology, Meiho University, Pingtung, Taiwan

Abstract

AbstractThree 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.

Funder

Ministry of Science and Technology, Taiwan

Publisher

Georg Thieme Verlag KG

Subject

Organic Chemistry,Complementary and alternative medicine,Drug Discovery,Pharmaceutical Science,Pharmacology,Molecular Medicine,Analytical Chemistry

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