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Siliquapyranone: a tannic acid Tetrahydropyran-2-one isolated from the leaves of carob (Ceratonia siliqua) by pressurised hot water extraction

Citation

Deans, BJ and Skierka, BE and Karagiannakis, BW and Vuong, D and Lacey, E and Smith, JA and Bissember, AC, Siliquapyranone: a tannic acid Tetrahydropyran-2-one isolated from the leaves of carob (Ceratonia siliqua) by pressurised hot water extraction, Australian Journal of Chemistry, 71, (9) pp. 702-707. ISSN 0004-9425 (2018) [Refereed Article]

Copyright Statement

Journal compilation copyright CSIRO 2018

DOI: doi:10.1071/CH18265

Abstract

Studies 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.

Item Details

Item Type:Refereed Article
Keywords:natural products, carob, glycosides
Research Division:Chemical Sciences
Research Group:Organic Chemistry
Research Field:Organic Chemical Synthesis
Objective Division:Expanding Knowledge
Objective Group:Expanding Knowledge
Objective Field:Expanding Knowledge in the Chemical Sciences
UTAS Author:Deans, BJ (Miss Bianca Deans)
UTAS Author:Skierka, BE (Mrs Brianna Skierka)
UTAS Author:Karagiannakis, BW (Mr Benjamin Karagiannakis)
UTAS Author:Smith, JA (Associate Professor Jason Smith)
UTAS Author:Bissember, AC (Associate Professor Alex Bissember)
ID Code:128492
Year Published:2018
Web of Science® Times Cited:4
Deposited By:Chemistry
Deposited On:2018-09-25
Last Modified:2019-03-07
Downloads:0

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