Toxic rather than neuropharmacological effect of Ternstroemia sylvatica fruits and identification of 28-O-[β-l-6-rhamnopyranosyl]-R₁-barrigenol as a new compound with toxic effects in mice

Figures & data

Figure 1. Structure of compounds 1 and 1a.

Table 1. ¹H NMR and ¹³C NMR spectral data for compounds 1 and 1a.

	1		1a
Position	δ (^13C)^a	δ (^1H)^b	δ (^1H)^b
1	47.92	1.48 dd (J = 4, 12 Hz)
2	41.57	2.82 m
3	78.13	3.06 t (J = 12 Hz)	3.19 m
4	39.41	–	–
5	55.72	0.97 m
6	19.22	1.66 m
7	36.90	2.17 m
8	42.11	–	–
9	39.36	1.89 m
10	37.53	–	–
11	24.14	1.98 m
12	124.58	5.55 t (J = 4 Hz)	5.58 m
13	144.86	–	–
14	54.58	–	–
15	67.51	4.46 m	3.88 m
16	72.48	4.98 m	4.57 m
17	48.21	–	–
18	47.51	1.84 m
19	47.58
20	36.52	–	–
21	78.45	4.85 d (J = 12 Hz)	3.92 d (J = 6 Hz)
22	77.20	4.63 d (J = 12 Hz)	4.27 dd (J = 9, 6 Hz)
23	16.74	1.88 s	1.20 s
24	17.72	1.08 s	1.60 s
25	16.06	1.01 s	1.01 s
26	28.82	1.25 s	1.14 s
27	21.19	1.14 s	1.55 s
28	72.28	4.51 m	4.10 m
29	30.71	1.37 s	1.48 ws
30	19.54	1.41 s
1′	102.79	5.12 d (J = 4 Hz)	–
2′	72.87	4.44 dd (J = 4, 8 Hz)	–
3′	73.96	4.26 t (J = 8 Hz)	–
4′	67.78	4.13 m	–
5′	69.69	3.63 m	–
6′	18.71	1.64 d (J = 8 Hz)	–

^a100 MHz, Pyridine-d₅; ^b400 MHz, Pyridine-d₅.

Figure 2. Effect of methanol (A) and aqueous (B) extracts of Ternstroemia sylvatica on latency and duration of pentobarbital-induced hypnosis in mice. Bars represent mean ± S.E.M. n = 6. *p < 0.05 significantly different from vehicle; ANOVA followed by Dunnett’s test.

Table 2. Sedative effect in the exploratory cylinder test of Ternstroemia sylvatica extracts after intraperitoneal administration in mice.

Plant/Drug	Extract	ED50 ± S.E.M. (mg/kg)
Ternstroemia sylvatica (pericarp)	Methanol	61.9 ± 6.4
	Aqueous	41.5 ± 19.9
Ternstroemia sylvatica (seeds)	Methanol	13.8 ± 1.7
	Aqueous	4.9 ± 0.8
Diazepam	–	3.04 ± 1.14

Table 3. Sedative effect of Ternstroemia sylvatica aqueous extracts in the exploratory cylinder test by acute and repeated intragastric administration.

	Single dose		Repeat dose by 5 d
Dose (mg/kg)	Rearings/ 5 min ± S.E.M.	Mortality	Rearings/ 5 min ± S.E.M.	Mortality
Vehicle
–	55.2 ± 3.9	0/24	52.7 ± 3.7	0/17
Ternstroemia sylvatica (pericarp)
100	49.3 ± 3.6	0/6	55.7 ± 3.8	0/6
316	40.2 ± 5.2	0/6	53.3 ± 7.3	0/6
1000	50.5 ± 4.4	0/6	55.3 ± 6.5
Ternstroemia sylvatica (seeds)
5.6	32.0 ± 5.7*	0/6	63.0 ± 3.5	0/6
10	38.0 ± 2.9	0/6	60.2 ± 6.8	0/6
100	40.2 ± 6.3	0/6	55.5 ± 7.7	0/6
316	35.8 ± 7.8	0/6	39.7 ± 2.9	3/6
1000	37.3 ± 5.6	0/6	30 ± 0	5/6

Data represent mean ± S.E.M. n = 6. *p < 0.05 significantly different from vehicle; ANOVA followed by Dunnett’s test.

Figure 3. Effect of aqueous extract of Ternstroemia sylvatica seeds on motor coordination in the rota-rod test. Symbols represent mean ± S.E.M. n = 6.

Figure 4. Effect of 28-O-[β-l-6-rhamnopyranosyl]-R₁-barrigenol in Exploratory Cylinder test (A) and hole board test (B) in mice. Symbols represent mean ± S.E.M. n = 6. *p < 0.05 significantly different from vehicle; ANOVA followed by Dunnett’s test.

Figure 5. Effect of 28-O-[β-l-6-rhamnopyranosyl]-R₁-barrigenol (A) and aqueous extract of seeds from Ternstroemia sylvatica (B) in open field test in mice. Symbols represent mean ± S.E.M. n = 6. *p < 0.05 significantly different from vehicle; ANOVA followed by Dunnett’s test.

Figure 6. Selected key correlations in ¹H-¹H COSY, TOCSY and HMBC experiments of compound 1.

Figure 7. Selected key correlations in NOESY experiment of compound 1.