Two new iridoid glycosides (1 and 2), together with the known compounds barlerin (3) and verbascoside (4), were isolated from Barleria prionitis. The new iridoid glycosides were determined to be 6-O-trans-p-coumaroyl-8-O-acetylshanzhiside methyl ester (1) and its cis isomer (2) by using spectroscopic, especially 2D NMR, data, A 3:1 mixture of 1 and 2 was shown to have potent in vitro activity against respiratory syncytial virus (EC50 2.46 mu g/mL, IC50 42.2 mu g/mL).

glycosides, Iridoids, Barleria prionitis, respiratory virus

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10
1	bDGlcp	100.38	74.72	78.00	71.70	78.42	63.01
6	xXpCoum	127.12	131.16	116.89	161.35	116.89	131.16	115.42	146.63	168.44
8	Ac	172.85	22.22
11	Me	51.86
	Subst	95.46	154.48	108.62	40.04	78.86	45.19	89.63	50.44	21.84	168.44


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10
1	bDGlcp	4.68	3.20	3.38	3.27	3.35	3.67-3.92
6	xXpCoum	-	7.47	6.81	-	6.81	7.47	6.34	7.62	-
8	Ac	-	1.98
11	Me	3.70
	Subst	5.91	7.53	-	3.34	5.39	2.13-2.42	-	3.05	1.58	-


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10
1	bDGlcp	100.38/4.68	74.72/3.20	78.00/3.38	71.70/3.27	78.42/3.35	63.01/3.67-3.92
6	xXpCoum		131.16/7.47	116.89/6.81		116.89/6.81	131.16/7.47	115.42/6.34	146.63/7.62	
8	Ac		22.22/1.98
11	Me	51.86/3.70
	Subst	95.46/5.91	154.48/7.53		40.04/3.34	78.86/5.39	45.19/2.13-2.42		50.44/3.05	21.84/1.58	

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2C1[C@H](OC(=O)/C=C/c1ccc(O)cc1)C[C@]2(C)OC(C)=O

594.566 g/mol (C₂₈H₃₄O₁₄)

Two new iridoid glycosides (1 and 2), together with the known compounds barlerin (3) and verbascoside (4), were isolated from Barleria prionitis. The new iridoid glycosides were determined to be 6-O-trans-p-coumaroyl-8-O-acetylshanzhiside methyl ester (1) and its cis isomer (2) by using spectroscopic, especially 2D NMR, data, A 3:1 mixture of 1 and 2 was shown to have potent in vitro activity against respiratory syncytial virus (EC50 2.46 mu g/mL, IC50 42.2 mu g/mL).

glycosides, Iridoids, Barleria prionitis, respiratory virus

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10
1	bDGlcp	100.38	74.64	77.94	71.57	78.35	62.92
6	Subst2	127.60	133.59	115.91	160.08	115.91	133.59	116.92	144.94	167.63
8	Ac	172.88	22.14
11	Me	51.88
	Subst1	95.43	154.55	18.62	39.93	78.69	45.06	89.55	50.33	21.88	168.46


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10
1	bDGlcp	4.66	3.21	3.37	3.28	3.34	3.67-3.91
6	Subst2	-	7.63	6.76	-	6.76	7.63	5.78	6.90	-
8	Ac	-	1.89
11	Me	3.70
	Subst1	5.87	7.52	-	3.26	5.37	2.10-2.40	-	2.92	1.55	-


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6	C7/H7	C8/H8	C9/H9	C10/H10
1	bDGlcp	100.38/4.66	74.64/3.21	77.94/3.37	71.57/3.28	78.35/3.34	62.92/3.67-3.91
6	Subst2		133.59/7.63	115.91/6.76		115.91/6.76	133.59/7.63	116.92/5.78	144.94/6.90	
8	Ac		22.14/1.89
11	Me	51.88/3.70
	Subst1	95.43/5.87	154.55/7.52		39.93/3.26	78.69/5.37	45.06/2.10-2.40		50.33/2.92	21.88/1.55	

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2C1[C@H](OC(=O)/C=C\c1ccc(O)cc1)C[C@]2(C)OC(C)=O

594.566 g/mol (C₂₈H₃₄O₁₄)

Two new iridoid glycosides (1 and 2), together with the known compounds barlerin (3) and verbascoside (4), were isolated from Barleria prionitis. The new iridoid glycosides were determined to be 6-O-trans-p-coumaroyl-8-O-acetylshanzhiside methyl ester (1) and its cis isomer (2) by using spectroscopic, especially 2D NMR, data, A 3:1 mixture of 1 and 2 was shown to have potent in vitro activity against respiratory syncytial virus (EC50 2.46 mu g/mL, IC50 42.2 mu g/mL).

glycosides, Iridoids, Barleria prionitis, respiratory virus

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

COC(=O)C1=CO[C@@H](O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C2C1[C@H](O)C[C@]2(C)OC(C)=O

448.421 g/mol (C₁₉H₂₈O₁₂)

Two new iridoid glycosides (1 and 2), together with the known compounds barlerin (3) and verbascoside (4), were isolated from Barleria prionitis. The new iridoid glycosides were determined to be 6-O-trans-p-coumaroyl-8-O-acetylshanzhiside methyl ester (1) and its cis isomer (2) by using spectroscopic, especially 2D NMR, data, A 3:1 mixture of 1 and 2 was shown to have potent in vitro activity against respiratory syncytial virus (EC50 2.46 mu g/mL, IC50 42.2 mu g/mL).

glycosides, Iridoids, Barleria prionitis, respiratory virus

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

C[C@@H]1O[C@@H](O[C@@H]2[C@@H](O)[C@H](OCCc3ccc(O)c(O)c3)O[C@H](CO)[C@H]2OC(=O)/C=C/c2ccc(O)c(O)c2)[C@H](O)[C@H](O)[C@H]1O

624.592 g/mol (C₂₉H₃₆O₁₅)