- Antifungal activity of modified hederagenin glycosides from the leaves of Kalopanax pictum var. chinense
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Monodesmosides which were obtained from the partial degradation of hederagenin bisdesmosides exhibited significant antifungal effect against Microsporum canis, Coccidioides immitis, Trichophyton mentagrophytes, Cryptococcus neoformans, and Candida albican
- Lee, Min-Won,Kim, Sung Uk,Hahn, Dug-Ryoung
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- Antimicrobially active hederagenin glycosides from Cephalaria elmaliensis
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A phytochemical investigation of the aerial parts of Cephalaria elmaliensis resulted in the isolation of ten hederagenin-type triterpene saponins (1-10) including three new ones, elmalienoside A (1), elmalienoside B (2), elmalienoside C (3), and two known flavonoid glycosides (11-12). Their structures were identified by extensive spectroscopic techniques (1D and 2D NMR, HR ESIMS) and chemical evidence. The antimicrobial activity of the extracts and the pure compounds was evaluated by the MIC method. According to the results, all pure compounds including the new ones were found to be very active against both gram-positive and gram-negative bacteria. Georg Thieme Verlag KG Stuttgart · New York.
- Sarkahya, Nazlboeke,Krmzguel, Sueheyla
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- Bioactive oleanane-type saponins from the rhizomes of Anemone taipaiensis
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Investigation of the n-BuOH extract of the rhizomes of Anemone taipaiensis led to the isolation of five new oleanane-type triterpenoid saponins (1-5), together with seven known saponins (6-12). Their structures were determined by the extensive use of 1D and 2D NMR experiments along with ESIMS analyses and acid hydrolysis. The aglycone of 1, 2 and 4 was determined as siaresinolic acid, which was reported in this genus for the first time. The cytotoxicities of the saponins 1-12, prosapogenins 4a, 5a, 10a-12a and sapogenins siaresinolic acid (SA), oleanolic acid (OA), hederagenin (HE) were evaluated against five human cancer cell lines, including HepG2, HL-60, A549, HeLa and U87MG. The monodesmosidic saponins 6-8, 5a, 10a-12a and sapogenins SA, OA, HE exhibited cytotoxic activity toward all cancer cell lines, with IC 50 values ranging from 2.25 to 57.28 μM. Remarkably, the bisdesmosidic saponins 1-4 and 9 showed selective cytotoxicity against the U87MG cells.
- Wang, Xiao-Yang,Gao, Hui,Zhang, Wei,Li, Yuan,Cheng, Guang,Sun, Xiao-Li,Tang, Hai-Feng
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p. 5714 - 5720
(2013/10/01)
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- Triterpene glycosides from Kalopanax septemlobum. 1. Glycosides A, B, C, F, G1, G2, I2, H, and J from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea
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Eight known glycosides of hederagenin and the new triterpene glycoside 3-O-β-D-xylopyranosyl-(1→3)-O-α-L-rhamnopyranosyl-(1→2) -O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin were isolated by chromatographic methods from leaves of Kalopanax septemlobum var. maximowichii introduced to Crimea. The known 3-O-α-L-arabinopyranosyl-28-O-α-L-rhamnopyranosyl-(1→4) -O-6-O-acetyl-β-D-glucopyranosyl-(1→6)-O-β-D-glucopyranosyl ester of hederagenin was observed for the first time in Kalopanax septemlobum. 2005 Springer Science + Business Media, Inc.
- Grishkovets,Panov,Kachala,Shashkov
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p. 194 - 199
(2008/02/01)
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- Synthesis of α-hederin, δ-hederin, and related triterpenoid saponins
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The synthesis of α-hederin (3-O-[α-L-rhamnopyranosyl-(1→2) -α-L-arabinopyranosyl]hederagenin, 1), δ-hederin (3-O-(α-L-arabinopyranosyl)hederagenin, 3), and three related triterpenoid saponins is described as part of a study of the structure-activity relationships between triterpenoid saponins and hemolytic activity. 4-Methoxybenzyl α-L-arabinopyranoside (11) was synthesized first and then used to prepare the different arabinose acceptors. Glycosylation between the acceptors and 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (20) was performed in excellent yield to give the desired disaccharides. Coupling of the trichloroacetimidate derivatives of the disaccharides to allyl- or methyl-hederagenin gave the protected saponosides in high yields. The saponins and their corresponding methyl esters were then obtained in good to moderate yields after deprotection. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.
- Ple, Karen,Chwalek, Martin,Voutquenne-Nazabadioko, Laurence
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p. 1588 - 1603
(2007/10/03)
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- Metabolism of kalopanaxsaponin K by human intestinal bacteria and antirheumatoid arthritis activity of their metabolites.
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When kalopanaxsaponin K (KPK) from Kalopanax pictus was incubated for 24 h at 37 degrees C with human intestinal microflora, KPK was mainly metabolized to kalopanaxsaponin I (KPI) via kalopanaxsaponin H (KPH) rather than via kalopanaxsaponin J (KPJ), and then transformed to kalopanaxsaponin A (KPA) and hederagenin. Bacteroides sp., and Bifidobacterium sp. and Fusobacterium sp. transformed KPK to KPI and KPA and hederagenin via KPH or KPJ. However, Lactobacillus sp. and Streptococcus sp. transformed KPK to KPI, KPA, and hederagenin only via KPJ. The metabolite KPA of KPK showed potent antirheumatoid arthritis activity.
- Kim, Dong-Hyun,Bae, Eun-Ah,Han, Myung Joo,Park, Hee-Juhn,Choi, Jong-Won
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- Metabolism of kalopanaxsaponin B and H by human intestinal bacteria and antidiabetic activity of their metabolites
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To investigate the relationship between the intestinal bacterial metabolism of kalopanaxsaponin B and H from Kalopanax pictus (Araliaceae), and their antidiabetic effect, kalopanaxsaponin B and H were metabolized by human intestinal microflora and the antidiabetic activity of their metabolites was measured. Human intestinal microflora metabolized kalopanaxsaponin B to kalopanaxsaponin A, hederagenin 3-O-α-L- arabinopyranoside and hederagenin. The main metabolites of kalopanaxsaponin B were kalopanaxsaponin A and hederagenin. Kalopanaxsaponin H was metabolized to kalopanaxsaponin A and I, hederagenin 3-O-α-L-arabinopyranoside and hederagenin. The main metabolites of kalopanaxsaponin H were kalopanaxsaponin I and hederagenin. Among kalopanaxsaponin B, H and their metabolites, kalopanaxsaponin A showed the most potent antidiabetic activity, followed by hederagenin. However, the main components, kalopanaxsaponin B and H, in K. pictus were inactive.
- Kim, Dong-Hyun,Yu, Ki-Woong,Bae, Eun-Ah,Park, Hee-Juhn,Choi, Jong-Won
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p. 360 - 365
(2007/10/03)
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- On the Structure of Saponins from Astrantia major L. Part 38: On the Knowledge of the Constituents of Some Saniculoideae
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From fresh plant material of Astrantia major L. a complex of saponins was isolated and separated into its main components.The complex comtains mono- and bisdesmosides with triterpene acids as aglycon.The dominating part of glycosides at C-3 of the aglyca is the 3-O-α-L-rhamnopyranosyl-(1->2)-α-L-arabinopyranoside linked with hederagenin (α-hederin) or oleanolic acid (β-hederin) and bisdesmosidically as hederagenin-28-O-L-rhamnopyranosylester (hederasaponin C) and as hederagenin-28-O-D-glucopyranosyl-(1->6)-D-glucopyranosylester (diipsacosid B).Furthermore a gypsogenic acid-3-O-D-glucopyranosyl-(1->2)-glucopyranosid was identified.
- Hiller, K.,Adler, Claudia,Galetzka, G.,Franke, P.,Gruendemann, E.,Hille, J.
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p. 343 - 345
(2007/10/02)
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- Studies on the constituents of Hedera rhombea Bean. IV. On the hederagenin glycosides
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On the basis of chemical and physicochemical evidence, the structures of two new hederagenin bisdesmosides, named Kizuta saponins K8 (X) and K11 (I), which were isolated from the stem and bark of Hedera rhombea Bean (Araliaceae), were established to be as follows: X, 3-O-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamnopyranosyl-(1 →4)-6-O-acetyl-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester; I,3-O-α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranosyl-hederagenin 28-O-α-L-rhamnopyranosyl(1→4)-6-O-acetyl-β-D-glucopyranosyl-(1→6)-β-D -glucopyranosyl ester. A glucoside mixture (XIII) was considered to be a mixture of the β-D glucopyranosides of campesterol (trace), stigmasterol and β-sitosterol based on chemical and physicochemical evidence.
- Kizu,Hirabayashi,Suzuki,Tomimori
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p. 3473 - 3478
(2007/10/02)
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- Saponins of Pericarps of Sapindus mukurossi GAERTN. and Solubilization of Monodesmosides by Bisdesmosides
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From pericarps of Sapindus mukurossi (Japanese name: Enmei-hi), saponins of hederagenin (1), 2-7, 9, 11 and 12 were isolated along with sapindosides A (10) and B (8), both of which have already been isolated from this crude drug.Saponins 7 and 9 were identified as α-L-arabinopyranosyl(1->3)-α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranoside and α-L-arabinofuranosyl(1->3)-α-L-rhamnopyranosyl(1->2)-α-L-arabinopyranoside of 1, respectively, both of which were recently isolated from Lecaniodiscus cupanoides by Sandberg et al.New saponins named mukurozi-saponins E1 (11) and G (12) were proved to be the mono-acetate of 8 and the di-acetate of 7, respectively.By means of mass and 13C nuclear magnetic resonance (NMR) spectroscopy, the locations of the acetyl groups of 11 and 12 were established to be at the 4-hydroxyl group of the xylosyl unit of 8 and at the 3,4-hydroxyl groups of the terminal arabinosyl unit of 7, respectively.The other new saponins, named mukurozi-saponins X (6), Y1 (5) and Y2 (4), were revealed to be β-sophorosyl esters of 10, 8 and 7, respectively, by comparison of the mass and 13C NMR spectra with those of the β-sophorosyl ester of 1 (13), which was synthesized from 1 as a reference compound for the study of the anomalous glycosylation shifts.Studies on the structures of the remaining saponins, 2 and 3, are in progress.The water solubilities of the monodesmosides, 7-9, which cause remarkable enhancement of the absorption of sodium ampicillin from rat intestine and rectum, were greatly increased by the bisdesmosides, 4-6.
- Kimata, Hiroko,Nakashima, Taeko,Kokubin, Setsuko,Nakayama, Keiso,Mitoma, Yohko,,et al.
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p. 1998 - 2005
(2007/10/02)
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