Lipoxygenase inhibition by novel fatty acid ester from Annona squamosa seeds

Figures & data

Table I.  ¹H (500 MHz) and ¹³C NMR (75 MHz) chemical shift assignments for compound 1.

Carbon Nos.	^1H NMR (δ ppm) ^b	Multiplicity ^a J (Hz)	^13C NMR (δ ppm) ^b	Multiplicity^a
1	4.21	dd, J1a,2 = 8 J1b,2 = 6	69.18	CH2
2	1.66	dd, J2,1a = 8 J2,1b = 6	40.22	–CH–
3	0.82	D, J3,2 = 7.0	11.39	CH3
4	0.85	D, J4,2 = 7.0	14.37	CH3
2′	–	–	169.36	–C–
3′	1.60	T	31.64	–CH2–
4′	1.24	M	30.70	CH2
5′	1.31	M	22.90	CH2
6′	1.35	M	24.98	CH2
7′	1.35	M	30.14	CH2
8′	–	–	133.59	–C–
9′	7.68	dd, J9′,10′ = 6 Hz J9′,13′ = 3 Hz	132.38	–CH–
10′	7.51	dd, J10′,9′ = 6 Hz J10′,12′ = 4 Hz	129.86	–CH–
11′	–	–	133.59	–C–
12′	7.51	dd, J12′,13′ = 6 Hz J12′,10′ = 4 Hz	129.86	–CH–
13′	7.68	dd, J13′,12′ = 6 Hz J13′,9′ = 3 Hz	132.38	–CH–

^aMultiplicity assignments based on DEPT experiment; ^bOne-bond heteronuclear correlations determined by HMQC experiment.

Figure 1.  All diagnostic EMS fragment ions of 1.

Figure 2.  HMBC interactions for compound 1.

Table II.  In vitro inhibition of Lipoxygenase by compound 1 and extracts of Annona squamosa.

No.	Sample	Conc. of extracts 40μg/200 ml	% Inhibition	IC50(μM)
	Compound 1	–	–	IC50 69.05 ± 5.06 μM
1.	Pet. ether extract of seeds of Annona squamosa	40	52.7	–
2.	Alcoholic extract of seeds of Annona squamosa	40	26.7	–
3.	Fruit pulp of Annona squamosa	40	22.2
4.	Baicalein	–	–	IC50 22.6 ± 0.5 μM