In vitro antileishmanial, antiplasmodial and cytotoxic activities of a new ventiloquinone and five known triterpenes from Parinari excelsa

Figures & data

Table 1.  In vitro antileishmanial and antiplasmodial activities and cytotoxicity of crude extracts and isolated compounds (1–7) from P. excelsa.

Crude extracts	L. don. axen.		P. falc. k1		Cytotox. L6
	IC50 (µg/mL)	SI	IC50 (µg/mL)	SI	IC50 (µg/mL)
PeLMc	19.33	nd	4.1	nd	>90
PeLMe	32.37	nd	>5	nd	>90
PeBMc	5.19	7.1	3.41	10.8	36.88
PeBMe	12.32	4.2	4.42	11.8	52.07
Miltefosine	0.199
Chloroquine			0.085
Podophyllotoxin					0.008
Compounds	IC50 (µM)	SI	IC50 (µM)	SI	IC50 (µg/mL)
1	23.5	7.1	28.3	5.9	73.5
2	8.2	10.7	69.9	1.3	40.1
3	7.7	7.8	77.9	0.8	27.3
4	–	nd	–	nd	>100
5	171.5	nd	145.0	nd	>100
6	–	nd	74.1	nd	>100
7	152.7	nd	90.5	nd	>100

PeLMc, P. excelsa leave methylene chloride crude extract; PeLMe, P. excelsa leave methanol crude extract; PeBMc, P. excelsa stem bark methylene chloride crude extract; PeBMe, P. excelsa stem bark methanol crude extract; nd, not determined; SI (selectivity index) = IC₅₀ Cytotoxcity/IC₅₀ Parasites.

Table 2.  ¹H, ¹³C, COSY and HMBC NMR spectral data of 7.

No	δC (ppm)	δH (ppm), multiplicity, J (Hz)	COSY correlation ^1JH-H	HMBC correlation ^2Jc-H and ^3Jc-H
1	119.1	–	–	–
2	127.2	7.56 (1H, d, J = 8.0 Hz)	H3	H2(C1, C11, C9, C3, C4)
3	101.1	6.62 (1H, J = 8.0 Hz)	H2	H3(C1, C2, C4, C10)
4	153.5	–	–	–
5	131.9	–	–	–
6	136.1	–	–	–
7	107.6	–	–	–
8	143.2	–	–	–
9	119.0	–	–	–
10	117.4	–	–	–
11	199.8	–	–	–
12	28.7	2.57 (3H, br s)	–	H12(C1, C11)
13	96.1	6.02 (4H, br s)	–	H13(C13),
14	55.7	3.21 (2H, br s)	–	H14(C15, C17)
15	94.1	6.02 (2H, br s)	–	H15(C5, C16)
16	63.5	3.40 (2H, q, J = 7.0	H17	H16(C15, C17)
17	15.7	1.15 (3H, t, J = 7.0)	H16	H17(C16,)
18	95.6	6.32 (2H, br s)	–	H18(C6, C19)
19	55.7	3.21 (2H, br s)	–	H19(C19)
20	30.1	3.35 (2H, d, J = 6.0)	H21	H20(C7, C8, C6, C21, C22)
21	137.1	6.10 (1H, m)	H20, H22	H21(C7, C20, C22)
22	117.4	4.93 (1H, dd, J =  2.1; 14.6) & 4.96 (1H, dd, J = 2.1; 14.6)	H21	H22(C21, C20)
23	56.6	3.70 (3H, br s)	–	H23(C8)

Figure 1.  16β-Hydroxylupane-1,20(29)-dien-3-one (1), (3-β)-3-hydroxyolean-12-en-28-oic acid (2), 3β-hydroxy-olean-5,12-dien-28-oic acid (3), Daucosterol (4), 3-O-β-d-glucopyranosyl-stigmasta-5,11(12)-diene (5), chlorogenic acid (6) and 1-(7-allyl-5-(ethoxymethoxy)-8-methoxy-4,6-bis(methoxymethoxy)naphthalen-1-yl)ethanone (7). Black arrow: HMB correlation (²J_C-H and ³J_C-H).