From the air-dried roots of Glycyrrhiza uralensis FISCHER collected in Xinjiang province, China ("Shinkyo-Kanzo" in Japanese), a new oleanene-type triterpene oligoglycoside named licorice-saponin L3 and a new chalcone oligoglycoside named isoliquiritin apioside were isolated together with glycyrrhizin, 18α-glycyrrhizin, apioglycyrrhizin, arabo-glycyrrhizin, licorice-saponins A3,E2,G2,and H2,and six known flavonoid glycosides. On the basis of chemical and physicochemical evidence, the structures of licorice-saponin L3 and isoliquiritin apioside were elucidated as 3β-[α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-22β-acetoxy-24-hydroxyolean-12-en-30-oic acid (1) and 4-O-[β-D-apiofuranosyl(1→2)-β-D-glucopyranosyl]isoliquiritigenin (6), respectively.

Glycyrrhiza uralensis, oleanene-type triterpene oligoglycoside, licorice-saponin L3, isoliquiritin apioside, licorice root, chalcone oligoglycoside

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
3,2,2	aLRhap	101.8	72.3	73.9	74.4	69.4	18.5
3,2	aLArap	102.2	78.1	76.7	70.7	66.8
3	bDGlcpA	105.4	78.1	75.8	72.6	77.6	172.2
22	Ac	170.3	21.4
	Subst

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)O[C@@H]1C[C@](C)(C(=O)O)C[C@H]2[C@H]3C=C[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6OC[C@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O)[C@](C)(CO)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@]21C

985.127 g/mol (C₄₉H₇₆O₂₀)

From the air-dried roots of Glycyrrhiza uralensis FISCHER collected in Xinjiang province, China ("Shinkyo-Kanzo" in Japanese), a new oleanene-type triterpene oligoglycoside named licorice-saponin L3 and a new chalcone oligoglycoside named isoliquiritin apioside were isolated together with glycyrrhizin, 18α-glycyrrhizin, apioglycyrrhizin, arabo-glycyrrhizin, licorice-saponins A3,E2,G2,and H2,and six known flavonoid glycosides. On the basis of chemical and physicochemical evidence, the structures of licorice-saponin L3 and isoliquiritin apioside were elucidated as 3β-[α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-22β-acetoxy-24-hydroxyolean-12-en-30-oic acid (1) and 4-O-[β-D-apiofuranosyl(1→2)-β-D-glucopyranosyl]isoliquiritigenin (6), respectively.

Glycyrrhiza uralensis, oleanene-type triterpene oligoglycoside, licorice-saponin L3, isoliquiritin apioside, licorice root, chalcone oligoglycoside

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

CC(=O)O[C@@H]1C[C@](C)(C(=O)O)C[C@H]2[C@H]3C=C[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@H](C(=O)O)[C@@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O)C(C)(C)[C@@H]5CC[C@@]4(C)[C@]3(C)CC[C@]21C

1013.137 g/mol (C₅₀H₇₆O₂₁)

From the air-dried roots of Glycyrrhiza uralensis FISCHER collected in Xinjiang province, China ("Shinkyo-Kanzo" in Japanese), a new oleanene-type triterpene oligoglycoside named licorice-saponin L3 and a new chalcone oligoglycoside named isoliquiritin apioside were isolated together with glycyrrhizin, 18α-glycyrrhizin, apioglycyrrhizin, arabo-glycyrrhizin, licorice-saponins A3,E2,G2,and H2,and six known flavonoid glycosides. On the basis of chemical and physicochemical evidence, the structures of licorice-saponin L3 and isoliquiritin apioside were elucidated as 3β-[α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-22β-acetoxy-24-hydroxyolean-12-en-30-oic acid (1) and 4-O-[β-D-apiofuranosyl(1→2)-β-D-glucopyranosyl]isoliquiritigenin (6), respectively.

Glycyrrhiza uralensis, oleanene-type triterpene oligoglycoside, licorice-saponin L3, isoliquiritin apioside, licorice root, chalcone oligoglycoside

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4,2	bDApif	108.6	77.1	79.4	74.1	64.5
4	bDGlcp	98.7	77.1	76.3	70.2	76.3	59.7
	Subst

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=C(/C=C/c1ccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2OC[C@](O)(CO)[C@H]2O)cc1)c1ccc(O)cc1O

550.513 g/mol (C₂₆H₃₀O₁₃)

From the air-dried roots of Glycyrrhiza uralensis FISCHER collected in Xinjiang province, China ("Shinkyo-Kanzo" in Japanese), a new oleanene-type triterpene oligoglycoside named licorice-saponin L3 and a new chalcone oligoglycoside named isoliquiritin apioside were isolated together with glycyrrhizin, 18α-glycyrrhizin, apioglycyrrhizin, arabo-glycyrrhizin, licorice-saponins A3,E2,G2,and H2,and six known flavonoid glycosides. On the basis of chemical and physicochemical evidence, the structures of licorice-saponin L3 and isoliquiritin apioside were elucidated as 3β-[α-L-rhamnopyranosyl(1→2)-α-L-arabinopyranosyl(1→2)-β-D-glucuronopyranosyloxy]-22β-acetoxy-24-hydroxyolean-12-en-30-oic acid (1) and 4-O-[β-D-apiofuranosyl(1→2)-β-D-glucopyranosyl]isoliquiritigenin (6), respectively.

Glycyrrhiza uralensis, oleanene-type triterpene oligoglycoside, licorice-saponin L3, isoliquiritin apioside, licorice root, chalcone oligoglycoside

13C NMR data:
Linkage	Residue	C1	C2	C3	C4	C5	C6
4',2	bDApif	109.1	76.9	79.4	74.1	64.4
4'	bDGlcp	98.2	76.9	76.3	69.7	76.3	60.1
	Subst


1H NMR data:
missing...

There is only one chemically distinct structure:

SVGMWSMILES3D molIonize

 

O=C(/C=C/c1ccc(O)cc1)c1ccc(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O[C@@H]2OC[C@](O)(CO)[C@H]2O)cc1O

550.513 g/mol (C₂₆H₃₀O₁₃)