Cucumin S, a new phenylethyl chromone from <i>Cucumis melo</i> var. <i>reticulatus</i> seeds

Ibrahim, Sabrin R.M.; Mohamed, Gamal A.

doi:10.1016/j.bjp.2015.06.006

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Original Articles • Rev. bras. farmacogn. 25 (5) • Oct 2015 • https://doi.org/10.1016/j.bjp.2015.06.006 copy

Cucumin S, a new phenylethyl chromone from Cucumis melo var. reticulatus seeds

Authorship SCIMAGO INSTITUTIONS RANKINGS

ABSTRACT

A new phenylethyl chromenone, cucumin S [(R)-5,7-dihydroxy-2-[1-hydroxy-2-(4-hydroxy-3-methoxyphenyl)ethyl]chromone] (1), along with five known compounds: 5,7-dihydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (2), 5,7-dihydroxy-2-[2-(3,4-dihydroxyphenyl)ethyl]chromone (3), luteolin (4), quercetin (5), and 7-glucosyloxy-5-hydroxy-2-[2-(4-hydroxyphenyl)ethyl]chromone (6) were isolated from the EtOAc fraction of Cucumis melo var. reticulatus Ser., Cucurbitaceae, seeds. Their structures were determined by spectroscopic means (1D and 2D NMR), as well as HRESIMS, optical rotation measurement, and comparison with literature data. The isolated compounds 1–6 were assessed for their antioxidant activity using DPPH assay. Compounds 3, 4, and 5 showed potent activities compared to propyl gallate at concentration 100 µM.

Keywords:
Cucumis melo ; Cucurbitaceae; Chromone; Flavonoid; Antioxidant

No.	δ_H [mult., J (Hz)]^a a Measured at 500 and 125 MHz.	δ_C (mult.)^a a Measured at 500 and 125 MHz.	HMBC^b b Measured at 700 MHz.
2	-	168.6 (C)	-
3	6.47 s	110.6 (CH)	2, 4, 10, 8'
4	-	181.7 (C)	-
5	-	161.5 (C)	-
6	6.06 d (2.5)	98.2 (CH)	5, 7, 8, 10
7	-	164.2 (C)	-
8	6.24 d (2.5)	95.8 (CH)	7, 9, 10
9	-	158.6 (C)	-
10	-	102.3 (C)	-
1'	-	129.6 (C)	-
2'	7.28 d (2.5)	115.6 (CH)	1', 4', 6', 7'
3'	-	149.0 (C)	-
4'	-	145.9 (C)	-
5'	6.78 d (7.5)	117.8 (CH)	1', 3', 4', 6'
6'	7.23 dd (7.5, 2.5)	119.8 (CH)	1', 4', 7'
7'	3.26 dd (14.5, 6.0)	40.6 (CH₂)	2, 1', 2', 6', 8'
	2.73 dd (14.5, 3.5)
8'	5.91 dd (6.0, 3.5)	85.8 (CH)	2, 3, 1'
3'-OCH₃	3.87 s	57.3 (CH₃)	3'

Sample^* * Conc. (100 µM); Each value represents the mean ± S.D., n = 3.	Inhibition%
PG	97.39 ± 1.8
1	63.12 ± 1.6
2	67.09 ± 1.8
3	86.20 ± 0.9
4	87.16 ± 0.7
5	91.24 ± 0.8
6	56.07 ± 1.2

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E-mail: revista@sbfgnosia.org.br

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[1] * Corresponding author. E-mail: sribrahim@taibahu.edu.sa (S.R.M. Ibrahim).