1988Chemical and Pharmaceutical BulletinOpen access

Studies on the saponins of Lonicera japonica THUNB.

HIDEAKI KAWAI, Masanori Kuroyanagi, Kaoru Umehara, Akira Ueno, Motoyoshi Satake

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Abstract

From the aerial parts of Lonicera japonica THUNB.(Caprifoliaceae), twelve triterpenoidalsaponins having oleanolic acid and hederagenin as aglycones, were isolated.The stnuctures of fournew saponins, 6, 9, 11 and 12, were established to be 3-O-α-L-arabinopyranosyl-28-O-[β-Dglucopyramosyl (1→6)-β-D-glucopyranosyl] oleanolic acid, 3-O-[α-L-rahmnopyranosyl (1→2)-α-L-arabinopyranosyl]-28-O-β-D-glucopyramosyl hederagenin, 3-O-[α-L-rhamnopyramosyl (1→2)-α-L-arabinopyramosyl]-28-O-[β-D-glucopyramosyl (1→6)-β-D-glucopyranosyl] oieanolic acid and 3-O-[α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoyl]-28-O-[6-acetyl-β-D-giucopyranosyl (1→6)-β-D-glucopyranosyl] hederagenin, respectively, by means of carbon-13 nuclear magneticresonance spectroscopy and chemical evidence.The present studies revealed that the saponin compositionsof the materials collected at different places were significantly different from each other.Among these sapomins, monodesmosides showed strong hemolytic activity, but bisdesmosidesshowed weak hemolytic activity.

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From the aerial parts of Lonicera japonica THUNB.(Caprifoliaceae), twelve triterpenoidalsaponins having oleanolic acid and hederagenin as aglycones, were isolated.The stnuctures of fournew saponins, 6, 9, 11 and 12, were established to be 3-O-α-L-arabinopyranosyl-28-O-[β-Dglucopyramosyl (1→6)-β-D-glucopyranosyl] oleanolic acid, 3-O-[α-L-rahmnopyranosyl (1→2)-α-L-arabinopyranosyl]-28-O-β-D-glucopyramosyl hederagenin, 3-O-[α-L-rhamnopyramosyl (1→2)-α-L-arabinopyramosyl]-28-O-[β-D-glucopyramosyl (1→6)-β-D-glucopyranosyl] oieanolic acid and 3-O-[α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoyl]-28-O-[6-acetyl-β-D-giucopyranosyl (1→6)-β-D-glucopyranosyl] hederagenin, respectively, by means of carbon-13 nuclear magneticresonance spectroscopy and chemical evidence.The present studies revealed that the saponin compositionsof the materials collected at different places were significantly different from each other.Among these sapomins, monodesmosides showed strong hemolytic activity, but bisdesmosidesshowed weak hemolytic activity.

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Available abstract

From the aerial parts of Lonicera japonica THUNB.(Caprifoliaceae), twelve triterpenoidalsaponins having oleanolic acid and hederagenin as aglycones, were isolated.The stnuctures of fournew saponins, 6, 9, 11 and 12, were established to be 3-O-α-L-arabinopyranosyl-28-O-[β-Dglucopyramosyl (1→6)-β-D-glucopyranosyl] oleanolic acid, 3-O-[α-L-rahmnopyranosyl (1→2)-α-L-arabinopyranosyl]-28-O-β-D-glucopyramosyl hederagenin, 3-O-[α-L-rhamnopyramosyl (1→2)-α-L-arabinopyramosyl]-28-O-[β-D-glucopyramosyl (1→6)-β-D-glucopyranosyl] oieanolic acid and 3-O-[α-L-rhamnopyranosyl (1→2)-α-L-arabinopyranoyl]-28-O-[6-acetyl-β-D-giucopyranosyl (1→6)-β-D-glucopyranosyl] hederagenin, respectively, by means of carbon-13 nuclear magneticresonance spectroscopy and chemical evidence.The present studies revealed that the saponin compositionsof the materials collected at different places were significantly different from each other.Among these sapomins, monodesmosides showed strong hemolytic activity, but bisdesmosidesshowed weak hemolytic activity.

Key concepts: Hederagenin, Caprifoliaceae, Oleanolic acid, Chemistry, Saponin, Triterpene, Stereochemistry, Traditional medicine

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