Antibacterial activities of chemical constituents from the aerial parts of Hedyotis pilulifera

Figures & data

Table 1. ¹H (500 MHz) and ¹³C (125 MHz) NMR data of compounds 1, 4, and 5 [δ (ppm), J (Hz)].

Position	1^a		4^a		5^b
	δC	δH	δC	δH	δC	δH
	1	39.0		39.2	0.96^c, 1.53^c	39.1^c	1.66^c, 1.77^c
2	28.2		28.9	1.89^c, 2.05^c	27.1	1.28^c, 1.58^c
3	78.2	3.48 dd (9.5, 6.0)	80.7	3.64 dd (11.5, 3.5)	74.1	3.64 dd (11.5, 4.5)
4	39.5	−	43.6	–	43.3^d	–
5	55.9		56.9	1.00^c	48.7^c	1.20^c
6	18.9		19.7	1.38^c, 1.71^c	19.3	1.47^c
7	33.4		34.4	1.38^c, 1.62^c	33.7	1.32^c, 1.68^c
8	39.9	−	40.8	–	41.0	–
9	48.2		48.3	1.84^c	48.5^c	1.77^c
10	37.5	−	37.6	–	37.9	–
11	23.8		24.7	1.96^c, 2.08^c	24.7	2.01^c, 1.21^c
12	122.7	5.53 br.s	128.4	5.62 brs	129.4	5.30 m
13	144.9	−	140.4	–	140.1	–
14	42.3	−	42.5	–	42.7	–
15	28.4		29.8	1.30^c, 2.33m	29.6	1.01^c, 1.84^c
16	23.9		26.9	2.07^c, 3.15 m	26.7	1.58^c, 2.58 m
17	46.8	−	48.8	–	49.0^c	–
18	42.1	3.33 dd (13.0, 2.5)	55.1	3.07 s	55.1	2.53 s
19	46.6		73.2	–	73.6	–
20	31.1	−	42.9	1.52^c	43.1	1.37^c
21	34.3		27.4	1.36^c, 1.55^c	27.4	1.37^c, 1.77^c
22	33.3		39.0	2.08^c, 2.19^c	39.5	1.03^c, 1.62^c
23	28.9	1.27 s	24.1	1.56 s	67.5	3.57 d (12.0) 3.31^c
24	16.7	1.05 s	65.1	4.51 d (10.5); 3.68 d (10.5)	12.7	0.73 s
25	15.6	0.92 s	16.5^d	0.90 s	16.2^d	1.00 s
26	17.5	1.03 s	17.5^d	1.09 s	17.6^d	0.83 s
27	26.3	1.31 s	25.1	1.74 s	24.9	1.36 s
28	180.3	−	181.2	–	182.9	–
29	33.4	0.98 s	27.6	1.47 s	27.3	1.21 s
30	23.9	1.05 s	17.3^d	1.14 d (6.5)	16.6^d	0.95 d (6.0)

^a Measured in pyridine-d₅.

^b Measured in CD₃OD.

^c Overlapped signals.

^d Reassigned using 2D-NMR.

Figure 1. Chemical structures of isolated compounds (1–20): oleanolic acid (1), betulinic acid (2), pomolic acid 3β-acetate (3), rotungenic acid (4), rotundic acid (5), stigmast-4-ene-3,6-dione (6), daucosterol (7), benzyl hydroperoxide (8), 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-propan-1-one (9), octadeca-9Z,12Z-dienoic acid (10), 9,12,13-trihydroxyoctadeca-10E-enoic acid (11), 9,12,13-trihydroxyoctadeca-10E,15Z-dienoic acid (12), α-tocopherolquinone (13), (7S*,8R*,7′R*,8′S*)-icariol A2-9-O-β-xylopyranoside (14), (2S,3S,4R,2′R)-2-(2′-hydroxytetracosanoylamino)octadecane-1,3,4-triol (15), (2S)-1-O-linolenoyl-2-O-linolenoyl-3-O-β-d-galactopyranosyl-sn-glycerol (16), (2S)-1-O-linolenoyl-2-O-linoleoyl-3-O-β-d-galactopyranosyl-sn-glycerol (17), (2S)-1-O-linoleoyl-2-O-linoleoyl-3-O-β-d-galactopyranosyl-sn-glycerol (18), (2S)-1-O-linolenoyl-2-O-palmitoyl-3-O-β-d-galactopyranosyl-sn-glycerol (19), and (2S)-1-O-linoleoyl-2-O-palmitoyl-3-O-β-d-galactopyranosyl-sn-glycerol (20).

Table 2. Antibacterial activities of compounds 1, 2, 4–6, and 15.

Compounds	MIC (μg/mL)
	S. aureus	B. subtilis	M. smegmatis
	1	10	>20	2.5
2	20	20	>20
4	2.5	2.5	1.25
5	10	5	>20
6	>20	20	>20
15	20	> 20	>20
Ampicillin	5	10	10