Abstract
Nine new gingerols, including three 6-oxo-shogaol derivatives [(Z)-6-oxo-[6]-shogaol (1), (Z)-6-oxo-[8]-shogaol (2), (Z)-6-oxo-[10]-shogaol (3)], one 6-oxoparadol derivative [6-oxo-[6]-paradol (4)], one isoshogaol derivative [(E)-[4]-isoshogaol (5)], and four paradoldiene derivatives [(4E,6Z)-[4]-paradoldiene (8), (4E,6E)-[6]-paradoldiene (9), (4E,6E)-[8]-paradoldiene (10), (4E,6Z)-[8]-paradoldiene (11)], together with eight known analogues, were isolated from the rhizoma of Zingiber officinale. Their structures were elucidated on the basis of spectroscopic data. It was noted that the isolation of 6-oxo-shogaol derivatives represents the first report of gingerols containing one 1,4-enedione motif. Their structures were elucidated on the basis of spectroscopic and HRESIMS data. All the new compounds were evaluated for their cytotoxic activities against human cancer cells (MCF-7, HepG-2, KYSE-150).
Highlights
Ginger, known as white ginger, is the dry rhizoma of Zingiber officinale, which has been a popular spice world-wide
Chemical investigations have revealed the presence of volatile oils, gingerols, and diarylheptanoids, responsible for its pungency and other pharmacological properties [13]
Our efforts resulted in the isolation of nine new gingerols and eight known analogues (Figure 1), whose cytotoxic activities against human cancer cells (MCF-7, HepG-2, KYSE-150) were subsequently evaluated
Summary
Known as white ginger, is the dry rhizoma of Zingiber officinale, which has been a popular spice world-wide. As a Chinese medicine, it has been used in the treatment of nausea and vomiting, coughs, cold and so forth, for more than 2000 years [1,2,3]. In the traditional Chinese medicine theory system, Z. officinale is a warm medicine which can warm the spleen and stomach to dispel cold and warm the lungs, to reduce or eliminate dampness and phlegm (Huiyang Tongmai). Pharmacological studies on Z. officinale showed its effects on oxidative stress [4,5], tumor [6,7], degenerative diseases [8], vomiting [9], the cardiovascular system [10], and indigestion [11,12]. Our efforts resulted in the isolation of nine new gingerols and eight known analogues (Figure 1), whose cytotoxic activities against human cancer cells (MCF-7, HepG-2, KYSE-150) were subsequently evaluated.
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