Four new triterpenoid glycosides were isolated from the root bark of Mussaenda macrophylla. Their structures were determined as 3-O-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl-16α-hydroxy-23-deoxyprotobassic acid (1), 28-O-β-D-glucopyranosyl-16α-hydroxy-23-deoxyprotobassic acid (2), 3-O-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl-16α-hydroxyprotobassic acid (3), and 3-O-{[β-D-glucopyranosyl(1→6)-O-α-L-rhamnopyranosyl(1→2)-O-β-D-glucopyranosyl-(1→2)}-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-cycloarta-22,24-dien-27-oic acid (mussaendoside W, 4). Four known triterpenoids [3-O-acetyloleanolic acid (5), 3-O-acetyldaturadiol (6), rotundic acid (7), and 16α-hydroxyprotobassic acid (8)] were also isolated. The structures of 1-4 were determined by several spectroscopic techniques including 2D NMR methods. Compounds 1-6 showed inhibitory activity against a periodontopathic bacterium, Porphyromonas gingivalis, but were inactive against the cariogenic organism, Streptococcus mutans.

antimicrobial activity, triterpenoid glycoside, Mussaenda macrophylla

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28	C29	C30
3	bDGlcp	106.6	75.6	78.9	73.7	78.1	61.9
28	aLRhap	95.7	73.7	70.8	75.2	68.0	18.6
	Subst	47.5	70.8	89.6	42.7	56.4	67.2	40.6	39.1	48.5	39.4	23.7	126.5	143.5	42.6	36.6	75.1	47.1	41.7	46.9	30.7	34.0	33.5	28.0	14.2	18.6	26	26.2	176.8	33.2	23.6


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3	bDGlcp	4.90	4.20-4.41	4.16	4.20-4.41	?	4.20-4.41
28	aLRhap	6.18	4.20-4.41	4.20-4.41	4.08	?	1.61
	Subst


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3	bDGlcp	106.6/4.90	75.6/4.20-4.41	78.9/4.16	73.7/4.20-4.41	78.1/?	61.9/4.20-4.41
28	aLRhap	95.7/6.18	73.7/4.20-4.41	70.8/4.20-4.41	75.2/4.08	68.0/?	18.6/1.61
	Subst	NMR TSV error 2: unequal length of 13C and 1H datasets

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

C[C@@H]1O[C@@H](OC(=O)[C@]23CCC(C)(C)C[C@H]2C2=CC[C@@H]4[C@@]5(C)C[C@H](O)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)C(C)(C)[C@@H]5[C@H](O)C[C@@]4(C)[C@]2(C)C[C@H]3O)[C@H](O)[C@H](O)[C@H]1O

812.991 g/mol (C₄₂H₆₈O₁₅)

Four new triterpenoid glycosides were isolated from the root bark of Mussaenda macrophylla. Their structures were determined as 3-O-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl-16α-hydroxy-23-deoxyprotobassic acid (1), 28-O-β-D-glucopyranosyl-16α-hydroxy-23-deoxyprotobassic acid (2), 3-O-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl-16α-hydroxyprotobassic acid (3), and 3-O-{[β-D-glucopyranosyl(1→6)-O-α-L-rhamnopyranosyl(1→2)-O-β-D-glucopyranosyl-(1→2)}-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-cycloarta-22,24-dien-27-oic acid (mussaendoside W, 4). Four known triterpenoids [3-O-acetyloleanolic acid (5), 3-O-acetyldaturadiol (6), rotundic acid (7), and 16α-hydroxyprotobassic acid (8)] were also isolated. The structures of 1-4 were determined by several spectroscopic techniques including 2D NMR methods. Compounds 1-6 showed inhibitory activity against a periodontopathic bacterium, Porphyromonas gingivalis, but were inactive against the cariogenic organism, Streptococcus mutans.

antimicrobial activity, triterpenoid glycoside, Mussaenda macrophylla

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28	C29	C30
28	bDGlcp	95.8	75.3	78.5	73.8	72.7	62.2
	Subst	47.1	71.1	79.2	42.6	56.4	67.4	40.6	39.4	48.6	36.8	23.8	124.1	143.5	42.8	34.1	74.1	46.9	41.8	47.0	20	39.3	30.8	26.3	17.1	18.8	18.7	28.2	176.4	33.2	23.7


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
28	bDGlcp	6.31	4.22-4.37	4.22-4.37	4.22-4.37	4.22-4.37	4.22-4.37
	Subst


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
28	bDGlcp	95.8/6.31	75.3/4.22-4.37	78.5/4.22-4.37	73.8/4.22-4.37	72.7/4.22-4.37	62.2/4.22-4.37
	Subst	NMR TSV error 2: unequal length of 13C and 1H datasets

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC1(C)CC[C@@]2(C(=O)O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)[C@@H](C1)C1=CC[C@@H]3[C@@]4(C)C[C@H](O)[C@H](O)C(C)(C)[C@@H]4[C@H](O)C[C@@]3(C)[C@]1(C)C[C@H]2O

666.849 g/mol (C₃₆H₅₈O₁₁)

Four new triterpenoid glycosides were isolated from the root bark of Mussaenda macrophylla. Their structures were determined as 3-O-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl-16α-hydroxy-23-deoxyprotobassic acid (1), 28-O-β-D-glucopyranosyl-16α-hydroxy-23-deoxyprotobassic acid (2), 3-O-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl-16α-hydroxyprotobassic acid (3), and 3-O-{[β-D-glucopyranosyl(1→6)-O-α-L-rhamnopyranosyl(1→2)-O-β-D-glucopyranosyl-(1→2)}-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-cycloarta-22,24-dien-27-oic acid (mussaendoside W, 4). Four known triterpenoids [3-O-acetyloleanolic acid (5), 3-O-acetyldaturadiol (6), rotundic acid (7), and 16α-hydroxyprotobassic acid (8)] were also isolated. The structures of 1-4 were determined by several spectroscopic techniques including 2D NMR methods. Compounds 1-6 showed inhibitory activity against a periodontopathic bacterium, Porphyromonas gingivalis, but were inactive against the cariogenic organism, Streptococcus mutans.

antimicrobial activity, triterpenoid glycoside, Mussaenda macrophylla

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28	C29	C30
3	bDGlcp	106.2	74.7	78.5	73.4	77.8	61.5
28	aLRhap	95.2	73.2	70.5	74.9	67.8	18.1
	Subst	46.6	70.1	88.9	42.2	55.9	66.8	40.1	38.7	48.0	36.2	24.1	129.0	143.1	42.2	36.2	74.8	46.6	41.2	46.8	30.3	33.8	30.6	68.6	16.6	20.8	18.1	25.7	176.2	32.7	23.1


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6
3	bDGlcp	4.94	4.10-4.34	?	4.10-4.34	?	4.10-4.34
28	aLRhap	6.22	4.10-4.34	4.10-4.34	?	?	1.71
	Subst


1H/13C HSQC data:
Linkage	Residue	C1/H1	C2/H2	C3/H3	C4/H4	C5/H5	C6/H6
3	bDGlcp	106.2/4.94	74.7/4.10-4.34	78.5/?	73.4/4.10-4.34	77.8/?	61.5/4.10-4.34
28	aLRhap	95.2/6.22	73.2/4.10-4.34	70.5/4.10-4.34	74.9/?	67.8/?	18.1/1.71
	Subst	NMR TSV error 2: unequal length of 13C and 1H datasets

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

C[C@@H]1O[C@@H](OC(=O)[C@]23CCC(C)(C)C[C@H]2C2=CC[C@@H]4[C@@]5(C)C[C@H](O)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@](C)(CO)[C@@H]5[C@H](O)C[C@@]4(C)[C@]2(C)C[C@H]3O)[C@H](O)[C@H](O)[C@H]1O

828.99 g/mol (C₄₂H₆₈O₁₆)

Four new triterpenoid glycosides were isolated from the root bark of Mussaenda macrophylla. Their structures were determined as 3-O-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl-16α-hydroxy-23-deoxyprotobassic acid (1), 28-O-β-D-glucopyranosyl-16α-hydroxy-23-deoxyprotobassic acid (2), 3-O-β-D-glucopyranosyl-28-O-α-L-rhamnopyranosyl-16α-hydroxyprotobassic acid (3), and 3-O-{[β-D-glucopyranosyl(1→6)-O-α-L-rhamnopyranosyl(1→2)-O-β-D-glucopyranosyl-(1→2)}-O-β-D-glucopyranosyl-(1→3)-O-β-D-glucopyranosyl-cycloarta-22,24-dien-27-oic acid (mussaendoside W, 4). Four known triterpenoids [3-O-acetyloleanolic acid (5), 3-O-acetyldaturadiol (6), rotundic acid (7), and 16α-hydroxyprotobassic acid (8)] were also isolated. The structures of 1-4 were determined by several spectroscopic techniques including 2D NMR methods. Compounds 1-6 showed inhibitory activity against a periodontopathic bacterium, Porphyromonas gingivalis, but were inactive against the cariogenic organism, Streptococcus mutans.

antimicrobial activity, triterpenoid glycoside, Mussaenda macrophylla

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6	C7	C8	C9	C10	C11	C12	C13	C14	C15	C16	C17	C18	C19	C20	C21	C22	C23	C24	C25	C26	C27	C28	C29	C30
3,2,2	aLRhap	101.9	72.2	72.3	74.0	69.4	18.9
3,2,6	bDGlcp	104.3	76.9	78.1	?	77.6	62.5
3,2	bDGlcp	101.4	80.5	77.9	?	74.8	72.0
3,3	bDGlcp	104.6	75.9	77.7	71.2	78.6	62.3
3	bDGlcp	105.1	77.7	79.0	71.1	75.0	62.0
	Subst	32.3	29.7	90.4	41.4	48.0	21.2	26.3	47.7	19.9	26.2	26.6	33.0	45.6	49.2	35.0	28.8	52.0	18.5	29.9	41.3	20.0	147.9	123.4	134.6	128.9	13.1	168.7	19.5	26.0	15.5


1H NMR data:
Linkage	Residue	H1	H2	H3	H4	H5	H6	H7	H8	H9	H10	H11	H12	H13	H14	H15	H16	H17	H18	H19	H20	H21	H22	H23	H24	H25	H26	H27	H28	H29	H30
3,2,2	aLRhap	6.16	4.77	4.72	4.35	4.78	1.84
3,2,6	bDGlcp	5.14	4.00	4.22	4.32	4.03	4.25
3,2	bDGlcp	5.58	4.38	4.30	4.25	3.99	4.62-4.73
3,3	bDGlcp	5.27	4.03	4.51	4.15	4.04	4.39
3	bDGlcp	4.91	4.62	4.14	3.75	4.01	4.55
	Subst	1.20-1.54	2.37	3.43	-	1.53	1.55	-	1.31	-	-	-	1.60	-	-	-	-	1.70	1.04	0.31-0.53	2.19	1.08	5.93	6.39	7.46	-	2.19	-	0.96	1.31	1.20


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	C11/H11	C12/H12	C13/H13	C14/H14	C15/H15	C16/H16	C17/H17	C18/H18	C19/H19	C20/H20	C21/H21	C22/H22	C23/H23	C24/H24	C25/H25	C26/H26	C27/H27	C28/H28	C29/H29	C30/H30
3,2,2	aLRhap	101.9/6.16	72.2/4.77	72.3/4.72	74.0/4.35	69.4/4.78	18.9/1.84
3,2,6	bDGlcp	104.3/5.14	76.9/4.00	78.1/4.22	?/4.32	77.6/4.03	62.5/4.25
3,2	bDGlcp	101.4/5.58	80.5/4.38	77.9/4.30	?/4.25	74.8/3.99	72.0/4.62-4.73
3,3	bDGlcp	104.6/5.27	75.9/4.03	77.7/4.51	71.2/4.15	78.6/4.04	62.3/4.39
3	bDGlcp	105.1/4.91	77.7/4.62	79.0/4.14	71.1/3.75	75.0/4.01	62.0/4.55
	Subst	32.3/1.20-1.54	29.7/2.37	90.4/3.43		48.0/1.53	21.2/1.55		47.7/1.31				33.0/1.60					52.0/1.70	18.5/1.04	29.9/0.31-0.53	41.3/2.19	20.0/1.08	147.9/5.93	123.4/6.39	134.6/7.46		13.1/2.19		19.5/0.96	26.0/1.31	15.5/1.20

The spectrum also has 2 signals at unknown positions (not plotted).

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

C/C(=C\C=C\[C@@H](C)C1CC[C@@]2(C)[C@@H]3CC[C@H]4C(C)(C)[C@@H](O[C@@H]5O[C@H](CO)[C@@H](O)[C@H](O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@H]5O[C@@H]5O[C@H](CO[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H](O)[C@H](O)[C@H]5O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)CC[C@@]45C[C@@]35CC[C@]12C)C(=O)O

1249.401 g/mol (C₆₀H₉₆O₂₇)