Three New Phenolic Compounds from Salacia cochinchinensis Lour and Their α-Glucosidase Inhibitory Activities†

doi:10.7503/cjcu20180622

Abstract

Abstract:

Five compounds were isolated from the stems and leaves of Salacia cochinchinensis Lour. By comprehensive spectroscopic analyses including mass spectroscopy(MS), infrared radiation(IR), 1D and 2D nuclear magnetic resonance(NMR) [heteronuclear single quantum coherence(HSQC), heteronuclear multiple bond correlation(HMBC), ¹H-¹H chemical-shift correlation spectroscopy(¹H-¹H COSY) and rotating frame overhauser effect spectroscopy(ROESY)], their structures were elucidated as Salaciacochinoside A(1), 5'-O-3,4,5-trimethoxybenzoyl-β-D-apiofuranoside(2), 5-methoxy-anticerol A(3), 21α,30-dihydroxy-D∶A-friedooleanan-3-one(4) and 21α,26-dihydroxyfriedelan-3-one(5), respectively. Compounds 1—3 were new compounds. All the compounds were assayed for the anti-diabetic activities. Compounds 1 and 3 exhibited remarkable bioactivity, inhibiting α-glucosidase with IC₅₀ values of 0.32 and 0.59 μmol/L, respectively. Compounds 2, 4 and 5 showed none anti-diabetic activity in current experiment.

Key words: Salacia cochinchinensis, Phenolic compound, α-Glucosidase inhibitory activity;

CLC Number:

O629

TrendMD:

ZHANG Juanrong,YOU Huimei,JING Yuxing,ZHAO Jiaowen,WANG Wei,LIU Wenxing,ZHOU Min,JIANG Zhiyong. Three New Phenolic Compounds from Salacia cochinchinensis Lour and Their α-Glucosidase Inhibitory Activities^†[J]. Chem. J. Chinese Universities, 2019, 40(3): 456.

Figures/Tables 5

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No.	Compound 1		Compound 2		Compound 3
No.	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H
1	129.7, s		121.2, s		140.1, s
2	106.3, d	6.85, s	108.6, d	7.35, s	105.3, d	6.76, s
3	149.3, s		149.1, s		154.6, s
4	137.0, s		142.4, s		136.4, s
5	149.3, s		149.1, s		154.6, s
6	106.3, d	6.85, s	108.6, d	7.35, s	105.3, d	6.76, s
7	85.8, d	4.30, d(9.1)	168.0, s		75.3, d	4.62, d(5.4)
8	78.1, d	4.06, m			77.5, d	3.68, m
9	17.4, q	1.19, d(6.3)			64.4, t	3.42, dd(11.2, 6.2)
						3.56, dd(11.2, 4.4)
3-MeO	56.9, q	4.02, s	57.0, q	3.89, s	56.8, q	3.86, s
4-MeO			56.0, q	3.38, s
5-MeO	56.9, q	4.02, s	57.0, q	3.89, s	56.8, q	3.86, s
1'	99.7, d	4.76, d(7.7)	111.6, d	4.87, d(2.6)	62.3, d	3.75, d(5.0)
2'	81.1, d	3.31, dd(9.4, 7.9)	78.9, d	3.97, d(2.5)	85.0, d	4.00, dd(9.9, 5.0)
3'	75.2, d	3.77, t(9.1)	79.1, s		62.3, d	3.75, d(5.0)
4'	72.0, d	3.59, d(8.8)	75.0, t	3.89, d(9.8)
				4.04, d(9.8)
5'	79.9, d	3.64, m	67.7, t	4.32, s
6'	62.7, t	3.90, dd(12.0, 5.4)
		4.07, m

No.	Compound 1		Compound 2		Compound 3
No.	δ_C	δ_H	δ_C	δ_H	δ_C	δ_H
1	129.7, s		121.2, s		140.1, s
2	106.3, d	6.85, s	108.6, d	7.35, s	105.3, d	6.76, s
3	149.3, s		149.1, s		154.6, s
4	137.0, s		142.4, s		136.4, s
5	149.3, s		149.1, s		154.6, s
6	106.3, d	6.85, s	108.6, d	7.35, s	105.3, d	6.76, s
7	85.8, d	4.30, d(9.1)	168.0, s		75.3, d	4.62, d(5.4)
8	78.1, d	4.06, m			77.5, d	3.68, m
9	17.4, q	1.19, d(6.3)			64.4, t	3.42, dd(11.2, 6.2)
						3.56, dd(11.2, 4.4)
3-MeO	56.9, q	4.02, s	57.0, q	3.89, s	56.8, q	3.86, s
4-MeO			56.0, q	3.38, s
5-MeO	56.9, q	4.02, s	57.0, q	3.89, s	56.8, q	3.86, s
1'	99.7, d	4.76, d(7.7)	111.6, d	4.87, d(2.6)	62.3, d	3.75, d(5.0)
2'	81.1, d	3.31, dd(9.4, 7.9)	78.9, d	3.97, d(2.5)	85.0, d	4.00, dd(9.9, 5.0)
3'	75.2, d	3.77, t(9.1)	79.1, s		62.3, d	3.75, d(5.0)
4'	72.0, d	3.59, d(8.8)	75.0, t	3.89, d(9.8)
				4.04, d(9.8)
5'	79.9, d	3.64, m	67.7, t	4.32, s
6'	62.7, t	3.90, dd(12.0, 5.4)
		4.07, m

Compd.	IC₅₀±SD/(μmol·L^-1)(n=3)	Compd.	IC₅₀±SD/(μmol·L^-1)(n=3)
1	0.32±0.01	4	>20
2	>20	5	>20
3	0.59±0.03	Acarbose	0.13±0.003

Compd.	IC₅₀±SD/(μmol·L^-1)(n=3)	Compd.	IC₅₀±SD/(μmol·L^-1)(n=3)
1	0.32±0.01	4	>20
2	>20	5	>20
3	0.59±0.03	Acarbose	0.13±0.003