Studies on Leguminous Plants. Part XL. Two New Triterpenoidal Glycosides from Medicago polymorpha L.

Kinjo, Junei; Uemura, Hadzuki; Nakamura, Motoyuki; Nohara, Toshihiro

doi:10.1248/cpb.42.1339

Cited by 30 publications

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“…A limited number of caulophyllogenin glycosides have been isolated from Caulophyllum robustum (Berberidaceae), 13) Chrysanthellum procumbens (Compositae), 14) Medicago polymorpha (Leguminosae), 15) Leontice kiangnanensis (Berberidaceae), 16) and Aralia elata (Araliaceae). 17) Compound 3 was obtained as colorless powder, mp 218- …”

Section: Resultsmentioning

confidence: 99%

Activity-Guided Isolation of Saponins from Kalopanax pictus with Anti-inflammatory Activity.

Lee

Kang

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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Kalopanax pictus NAKAI (Araliaceae) is a deciduous tree found in countries of the Orient. The stem bark of Kalopanax pictus has been used in traditional medicine to treat neuralgia, rheumatic arthritis, lumbago, 1) furuncle, carbuncle, wound,2) diarrhea and scabies.3) Phytochemical studies demonstrated the presence of saponins, 4) polyacetylenes, 5) phenylpropanoid glycosides, 5) lignans, 5) as well as simple phenolic glycosides.5) During an ongoing collaborative search for novel anti-inflammatory agents originating from plants, an ethyl acetate fraction of the stem bark of Kalopanax pictus exhibited significant anti-inflammatory activity in a vascular permeability test.6) Anti-rheumatic activity on adjuvant-induced arthritis in rats 7) and antinociceptive 8) and antioxidative activities 9) of EtOAc fraction and kalopanaxsaponins A and I were reported. However, this plant has not been investigated previously for systematic isolation of its anti-inflammatory components. We report herein the bioassay-guided chromatographic fractionation of an ethyl acetate soluble extract of K. pictus, which has led to the isolation of two anti-inflammatory saponins together with a novel inactive saponin. Results and DiscussionResults of the activity-guided isolation from K. pictus extract are summarized in Chart 1. From the ethyl acetate soluble fraction (Fr.) which showed potent activity in the vascular permeability test, eleven subfractions (Frs. 1-11) were obtained and the activity was tested using doses proportional to the yields obtained in the isolation procedure. As shown in Table 1, only Fr. 8 showed significant inhibition of vascular permeability at 250 mg/kg. This fraction was further divided into 5 subfractions (Frs. 8-A-8-E) by column chromatography. Fractions 8-B and 8-D elicited inhibition of vascular permeability at doses of 120 and 100 mg/kg, respectively, while Frs. 8-A and 8-E were negative (Fig. 1). Fraction 8-C was a mixture of Frs. 8-B and 8-D. Fraction 8-B was crystallized from MeOH to give compound 1. Repeated column chromatography of Fr. 8-D followed by recrystallization yielded compounds 2 and 3. Compounds 1 and 2 at doses of 50 mg/kg showed potent inhibition of vascular permeability (Fig. 2), while compound 3 exhibited no activity. ϩ peak at m/z 789.4405. The IR spectrum of 2 showed absorption bands at 1700 cm Ϫ1 for carboxylic acid and strong absorption bands at 3436 and 1053 cm Ϫ1 suggestive of an oligoglycosidic structure. On acid hydrolysis of 2 with 5% aqueous hydrochloric acid (HCl)-60% dioxane solution, 2 yielded L-arabinose and Lrhamnose, which were identified by GLC analysis of the trimethylsilyl thiazolidine derivatives as the sugars 11) and an aglycon, caulophyllogenin.12) It showed signals for six angular methyl groups at d 0.98, 1.04, 1.05, 1.08, 1.17 and 1.79 (all singlets for C-25, 29, 26, 24, 30 and 27 CH 3 groups), as well as signals for two anomeric protons at d 5.13 (d, Jϭ6.2 Hz) and 6.26 (br s) in the 1 H-NMR spectrum. Comparison of the 1 H-and 13 C-NMR spectra of 2 with those of 1 sh...

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Section: Resultsmentioning

confidence: 99%

Activity-Guided Isolation of Saponins from Kalopanax pictus with Anti-inflammatory Activity.

Lee

Kang

et al. 2002

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…A most favourable position from a mechanistic point of view is the 2b, giving the 2b-OH derivatives, bayogenin, medicagenic and zanhic acids, representing the most abundant structural types of sapogenins isolated until now from the analyzed Medicago species (Tava and Avato 2006). The 16a derivatives were detected as caulophyllogenin in M. polymorpha (Kinjo et al 1994) and as zanhic acid in M. arborea (Tava et al 2005), M. sativa (Oleszek et al 1992;Bialy et al 1999) and M. truncatula Kapusta et al 2005). More recently, two 30-OH substituted sapogenins, named queretaroic acid and 2b-hydroxy queretaroic acid, were characterized in M. arabica ).…”

Section: Aglyconesmentioning

confidence: 99%

“…Saponins from M. hybrida roots are characterized by the presence of short sugar chain bidesmosides of hederagenin and medicagenic acid (Bialy et al 2006). M. lupulina leaves contain mono and disaccharide saponins of hederagenin and medicagenic acid (Oleszek et al 1988), while saponins from the leaves of M. polymorpha predominantly consist of short sugar chain bidesmosides of hederagenin and caulophyllogenin (Kinjo et al 1994).…”

Section: Sugar Chainsmentioning

confidence: 99%

“…Alternatively a b-D-glucopyranose, or the corresponding uronic derivative, are present as, for example, in root saponins isolated from M. hybrida (Bialy et al 2006). The second monosaccharide unit linked at the C-2 position of a-L-arabinopyranose can be a-L-rhamnopyranose, as in M. polymorpha (Kinjo et al 1994), or b-D-glucopyranose as in M. arabica ) and M. sativa (Massiot et al 1988;Timbekova et al 1996).…”

Section: Sugar Chainsmentioning

confidence: 99%

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Biosynthesis of saponins in the genus Medicago

2010

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Saponins from Medicago species are glycosidic compounds with an aglycone moiety formed through the enzymatic cyclization of 2,3-oxidosqualene by the beta-amyrin cyclase. All the saponins from Medicago genus possess the triterpenic pentacyclic nucleus belonging to the class of beta-amyrin. The so formed beta-amyrin skeleton can be further modified by oxidative reactions, mediated by cytochromes belonging to the class of cytochrome P450, to give different saponin compounds, characterized by the presence of hydroxyl or carboxyl groups located in specific positions of the triterpenic skeleton. Based on the position and the oxidation degree of the substituents, it is possible to distinguish two groups of saponins (sapogenins) in Medicago spp: (1) sapogenins possessing an OH group on C-24 (soyasapogenols A, B and E) without any substituent at the C-28 atom, and (2) sapogenins possessing the COOH group at C-28 that are associated with different oxidation degrees (zero, OH, CHO, COOH) at C-23. These results seem to indicate that the oxidation at C-24 and the presence of the COOH group at C-28 are mutually exclusive. The subdivision in the aglycone moiety is reflected also in the sugar moiety, operated by glycosyltranferases, as the saponins of the two groups differ for the position and the nature of the sugar chains. Based on these findings, new considerations on the biosynthesis of saponins in the genus Medicago can be drawn and a biosynthetic scheme is proposed

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“…Further isolation of this fraction by combination of silica gel column chromatography (CC), ODS CC and preparative HPLC afforded sixteen triterpenoid saponins, including a new compound, acanthopanaxoside E (1). The known saponins were identified as silphioside F (2), 11) copteroside B (3), 11) 13) silphioside G (6), 14) ilexoside XLVIII (7), 15) 18) hemsgiganoside B (11), 19) anhuienside C (12), 20) ciwujianoside C 3 (13), 21) hederasaponin B (14), 22) eleutheroside L (15) 23) and ciwujianoside A 1 (16) C-NMR spectrum showed an ester carbonyl signal at d C 176.0 (C-28). In the 1 H-NMR spectrum, signals assignable to carbinylic protons of the aglycon were observed at d 3.42 (dd, Jϭ11.7, 3.9 Hz) and 5.30 (br s), suggesting the carbinylic protons could be placed at 3a and 16b, respectively.…”

Section: Resultsmentioning

confidence: 99%

Pancreatic Lipase-Inhibiting Triterpenoid Saponins from Fruits of Acanthopanax senticosus

et al. 2007

Chem. Pharm. Bull.

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A increasing number of people are suffering from obesity, which is often associated with the development of type II diabetes, coronary heart diseases, hyperlipidemia, hypertension, and metabolic syndrome.1,2) It is well known that pancreatic lipase plays an important role in lipid digestion. The inhibition of pancreatic lipase reduces the efficiency of dietary fat absorption in the small intestine and thereby promotes modest long-term reduction in body weight. 3)Acanthopanax senticosus (RUPR. et MAXIM.) HARMS. is a shrub, belonging to the family Araliaceae, which is commonly distributed in the northeast of Asia. Different parts of the plant have been widely used as traditional Chinese medicines for the treatment of a variety of human diseases, such as ischemic heart diseases, neurasthenia, hypertension, arthritis, and tumors.4) Recently, we have reported fifteen triterpenoid saponins from the leaves of A. senticosus, among which ciwujianoside C 1 , tauroside H 1 , 3-O-a-L-rhamnopyranosyl-(1→2)-a -L-arabinopyranosyl mesembryanthemoidigenic acid, acanthopanaxoside C, sessiloside, and chiisanoside exhibited pancreatic lipase inhibitory activity in vitro.5) The occurrence of triterpenoid saponins has also been demonstrated in a previous chemical investigation of the fruits of A. senticosus.6) As our continuous investigation on bioactive triterpenoid saponins 5,7-9) and our current interest in the natural lipase inhibitors, 5,9,10) we initiated a chemical investigation of the fruits of A. senticosus. The total saponin fraction exhibited inhibitory activity on pancreatic lipase with the IC 50 value of 3.63 mg/ml. Further isolation of this fraction resulted in the isolation of sixteen triterpenoid saponins (1-16), including a new compound, acanthopanaxoside E (1). The biological activities of 1-16 against pancreatic lipase were examined. Silphioside F (2), 11) copteroside B (3), Results and DiscussionThe air-dried fruits of A. senticosus were extracted with 70% EtOH. The 70% EtOH extract was suspended in H 2 O and then partitioned successively with EtOAc and n-BuOH. The n-BuOH soluble fraction was subjected to a Diaion HP-20 column, followed by washing with H 2 O and 50% MeOH to remove phenolic compounds, and then with MeOH to result in a crude saponin fraction, which inhibited pancreatic lipase (IC 50 value: 3.63 mg/ml). Further isolation of this fraction by combination of silica gel column chromatography (CC), ODS CC and preparative HPLC afforded sixteen triterpenoid saponins, including a new compound, acanthopanaxoside E (1). The known saponins were identified as silphioside F (2), China. Received February 7, 2007; accepted April 19, 2007; published

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Studies on Leguminous Plants. Part XL. Two New Triterpenoidal Glycosides from Medicago polymorpha L.

Cited by 30 publications

References 0 publications

Activity-Guided Isolation of Saponins from Kalopanax pictus with Anti-inflammatory Activity.

Activity-Guided Isolation of Saponins from Kalopanax pictus with Anti-inflammatory Activity.

Biosynthesis of saponins in the genus Medicago

Pancreatic Lipase-Inhibiting Triterpenoid Saponins from Fruits of Acanthopanax senticosus

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