Academic Journal
LC/MS guided discovery of new kavalactone derivatives in the pericarps of Alpinia zerumbet.
| Title: | LC/MS guided discovery of new kavalactone derivatives in the pericarps of Alpinia zerumbet. |
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| Authors: | Nishidono Y; Pharmaceutical Research and Technology Institute, Kindai University, Higashi-osaka, Osaka 577-8502, Japan; College of Pharmaceutical Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan. Electronic address: nisidono@phar.kindai.ac.jp., Okuyama T; Department of Pancreatobiliary Surgery, Kansai Medical University, Hirakata, Osaka 573-1010, Japan., Nakatake R; Department of Pancreatobiliary Surgery, Kansai Medical University, Hirakata, Osaka 573-1010, Japan., Tanaka K; College of Pharmaceutical Sciences, Ritsumeikan University, Kusatsu, Shiga 525-8577, Japan., Morikawa T; Pharmaceutical Research and Technology Institute, Kindai University, Higashi-osaka, Osaka 577-8502, Japan; Antiaging Center, Kindai University, Higashi-osaka, Osaka 577-8502, Japan. |
| Source: | Fitoterapia [Fitoterapia] 2026 Oct; Vol. 194, pp. 107450. Date of Electronic Publication: 2026 Sep 04. |
| Publication Type: | Journal Article |
| Language: | English |
| Journal Info: | Publisher: Elsevier Country of Publication: Netherlands NLM ID: 16930290R Publication Model: Print-Electronic Cited Medium: Internet ISSN: 1873-6971 (Electronic) Linking ISSN: 0367326X NLM ISO Abbreviation: Fitoterapia Subsets: MEDLINE |
| Imprint Name(s): | Publication: 1999- : [Amsterdam] : Elsevier Original Publication: Milano : Inverni & Della Beffa S.p.A. |
| MeSH Terms: | Alpinia*/chemistry , Pyrones*/chemistry , Pyrones*/isolation & purification , Lactones*/chemistry , Lactones*/isolation & purification, Fruit/chemistry ; Chromatography, Liquid/methods ; Monoterpenes/chemistry ; Monoterpenes/isolation & purification ; Plant Extracts/chemistry ; Magnetic Resonance Spectroscopy ; Mass Spectrometry |
| Abstract: | An LC/MS guided phytochemical investigation of the pericarps of Alpinia zerumbet yielded five new kavalactone derivatives (1, 4, 5, 21, and 22) along with some known compounds. These comprised two new kavalactone-monoterpene conjugates possessing tricyclic α-pyrone or bicyclic α-pyrone scaffolds and three new hydroxylated kavalactones. Their structures were elucidated by comprehensive spectroscopic analyses (HRESIMS and 1D/2D NMR) and TD-DFT ECD calculations. Moreover, the absolute configuration of the previously described zerumin E4 (18) was revised. Plausible biosynthetic pathways are proposed to rationalize the oxidative derivatization of kavalactone scaffolds and the limited diastereomeric outcomes observed in the kavalactone-monoterpene conjugates. The present findings expand the current knowledge of chemical diversity of the pericarps and provide insights into the phytochemical basis underlying the medicinal use of A. zerumbet fruits. (Copyright © 2026 Elsevier B.V. All rights reserved.) |
| Competing Interests: | Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper. |
| Contributed Indexing: | Keywords: Alpinia zerumbet; Kavalactone derivatives; Shell ginger; Zingiberaceae; α-Pyrones |
| Substance Nomenclature: | 0 (Pyrones) 0 (Lactones) 0 (Monoterpenes) 0 (Plant Extracts) |
| Entry Date(s): | Date Created: 20260828 Date Completed: 20260928 Latest Revision: 20260928 |
| Update Code: | 20260929 |
| DOI: | 10.1016/j.fitote.2026.107450 |
| PMID: | 42665056 |
| Database: | MEDLINE |
| ISSN: | 1873-6971 |
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| DOI: | 10.1016/j.fitote.2026.107450 |