Abstract
Three new multiflorane-type triterpene esters, i.e. 7α-hydroxymultiflor-8-ene-3α,29-diol 3-acetate-29-benzoate (1), 7α-methoxymultiflor-8-ene-3α,29-diol 3,29-dibenzoate (2), and 7β-methoxymultiflor-8-ene-3α,29-diol 3,29-dibenzoate (3), were isolated from seeds of Cucurbita maxima, along with the known compound, multiflora-7,9(11)-diene-3α,29-diol 3,29-dibenzoate (4). Compound 1 exhibited melanogenesis inhibitory activities comparable with those of arbutin. In cytotoxicity assays, compounds 1 and 3 exhibited weak cytotoxicity, with IC50 values of 34.5–93.7 μM against HL-60 and P388 cells.
Highlights
Pumpkins, including Cucurbita moschata, C. pepo, and C. maxima, are gourd squashes of the genusCucurbita and the family Cucurbitaceae
We have reported the isolation of six multiflorane-type triterpenes including three new triterpenes: 7α-methoxymultiflor-8-ene-3α,29-diol 3-acetate-29-benzoate, 7-oxomultiflor-8ene-3α,29-diol 3-acetate-29-benzoate, and multiflora-7,9(11)-diene-3α,29-diol 3-p-hydroxybenzoate29-benzoate, from seeds of C. maxima produced in Japan, and the melanogenesis inhibitory and cytotoxic activities of these compounds [9]
In a continuing study to explore new compounds possessing potent biological activities from C. maxima seeds, we have isolated four multiflorane-type triterpenes from seeds of C. maxima produced in India, and determined the structures of three new compounds: 7α-hydroxymultiflor-8-ene-3α,29-diol 3-acetate-29-benzoate (1) 7α-methoxymultiflor-8ene-3α,29-diol 3,29-dibenzoate (2), and 7β-methoxymultiflor-8-ene-3α,29-diol 3,29-dibenzoate (3)
Summary
Pumpkins, including Cucurbita moschata, C. pepo, and C. maxima, are gourd squashes of the genus. Molecules 2014, 19 flowers, and seeds have been eaten as vegetables containing vitamins A, C, and E. Several triterpenes, such as cucurbita-5,24-dienol [5] and α- and β-amyrin [6], are present in the seeds of Cucurbita maxima. We have reported the isolation of six multiflorane-type triterpenes including three new triterpenes: 7α-methoxymultiflor-8-ene-3α,29-diol 3-acetate-29-benzoate, 7-oxomultiflor-8ene-3α,29-diol 3-acetate-29-benzoate, and multiflora-7,9(11)-diene-3α,29-diol 3-p-hydroxybenzoate29-benzoate, from seeds of C. maxima produced in Japan, and the melanogenesis inhibitory and cytotoxic activities of these compounds [9]. 1–3, were evaluated for inhibitory effects on α-MSH-induced melanogenesis in B16 melanomas, and cytotoxic activities against the HL-60 and P388 leukemia cell lines
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