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Siliquapyranone: a tannic acid Tetrahydropyran-2-one isolated from the leaves of carob (Ceratonia siliqua) by pressurised hot water extraction
journal contribution
posted on 2023-05-19, 21:30 authored by Bianca DeansBianca Deans, Skierka, BE, Karagiannakis, BW, Vuong, D, Lacey, E, Jason SmithJason Smith, Alexander BissemberAlexander BissemberStudies of the phytochemistry of carob (Ceratonia siliqua) leaf material are extremely limited. This report features the second natural product isolation study of carob leaves and the first such investigation of C. siliqua grown in Australia. Investigation of leaf material from seven carob cultivars using pressurised hot water extraction (PHWE) revealed the presence of high levels of myricitrin, D-pinitol, and sucrose in addition to the previously unreported natural product siliquapyranone {(2R,3R,4S,5R,6R)-5-hydroxy-6-(hydroxymethyl)-2-(((2S,4S)-2-methyl-6-oxotetrahydro-2H-pyran-4-yl)oxy)tetrahydro-2H-pyran-3,4-diyl bis(3,4,5-trihydroxybenzoate)}. Siliquapyranone represents a biosynthetic fusion of conventional 2,3-gallate esters on a b-glucose tannin with a hydroxytetrahydro-2H-pyran-2-one-related non-tannin tetrahydropyran-2-one, parasorboside. Preliminary biological testing indicates that siliquapyranone exhibits weak activity against both tumour and normal cell lines. This suggests that, like most tannins and parasorboside, siliquapyranone may act as an antifeedant.
History
Publication title
Australian Journal of ChemistryVolume
71Issue
9Pagination
702-707ISSN
0004-9425Department/School
School of Natural SciencesPublisher
CSIRO PublishingPlace of publication
150 Oxford St, Po Box 1139, Collingwood, Australia, Victoria, 3066Rights statement
Journal compilation copyright CSIRO 2018Repository Status
- Restricted