High impact information on NSC87530

• Since glycyrrhetinic acid was proved to suppress tumor promoter effects, several oleanane-type triterpenes which were chemically derived from oleanolic acid and hederagenin were tested in vitro and in vivo against the action of tumor promoter, 12-O-tetradecanoylphorbol 13-acetate [1].
• The model legume Medicago truncatula synthesizes more than 30 different saponins based on at least five triterpene aglycones; soyasapogenols B and E, medicagenic acid, hederagenin and bayogenin [2].
• Moreover, hederagenin and its 3-O-glycosides were found to be cytotoxic on various tumor cell lines, P-388, L-1210, U-937, HL-60, SNU-5 and HepG2, while 3,28-di-O-glycosides of hederagenin were not cytotoxic [3].
• This suggested that hederagenin glycosides might effectively prevent the metabolic activation of AFB1 or scavenge the electrophilic intermediate capable of inducing mutation [3].
• The antifungal activity of triterpenoid saponins, with hederagenin or oleanolic acid as aglycone, was investigated in vitro by the agar dilution method [4].

Biological context of NSC87530

• Its structure was established as hederagenin 3-O-beta-D-galactopyranosyl-(1-->2)-beta-D- glucopyranoside on the basis of hydrolysis and spectral evidence including 1D and 2D NMR techniques [5].
• Glycosylation of hederagenin with the trichloroacetimidate derivatives of six commercial disaccharides (D-cellobiose, D-lactose, D-maltose, D-melibiose, D-gentiobiose, D-isomaltose) was performed giving the protected saponins in high yields [6].
• A detailed chromatographic study using centrifugal partition chromatography revealed that a pentacyclic triterpenoid, i.e., hederagenin, is the antitrichomonas constituent of the plant with a IC50 of 2.8 microM [7].
• To further complete our study of the structure-activity relationships of triterpenoid saponins, alpha-hederin and related hederagenin diglycosides were synthesized to better understand the influence of the second sugar (alpha-l-rhamnose, beta-d-xylose or beta-d-glucose) and the substitution of this sugar on alpha-l-arabinose (position 2, 3 or 4) [8].
• In the rheumatoidal rat, induced by Freund's complete adjuvant (FCA) reagent, we investigated the effects of hederagenin monodesmosides of K. pictus on oxidative stress and hepatic drug-metabolizing enzymes [9].

Anatomical context of NSC87530

• Hederagenin saponins are largely represented in nature and possess many biological activities such as haemolytic, antiviral, fungicidal, molluscicidal or cytotoxic, partially due to their interaction with the cell membrane [8].

Associations of NSC87530 with other chemical compounds

• Monodesmosidic hederagenin derivatives were shown to exhibit a broad spectrum of activity against yeast as well as dermatophyte species. alpha-Hederin was the most active compound, and Candida glabrata was the most susceptible strain [4].
• From the aerial part of Clematis tibetana, two new hederagenin 3,28-O-bisdesmosides called clematibetosides A and C, and a new gypsogenin 3,28-O-bisdesmoside called clematibetoside B, have been isolated together with ten known saponins [10].
• Comparison of cytoprotective effects of saponins isolated from leaves of Aralia elata Seem. (Araliaceae) with synthesized bisdesmosides of oleanoic acid and hederagenin on carbon tetrachloride-induced hepatic injury [11].
• The same behaviour is observed for serine protease porcine pancreatic elastase: the glycosides are devoid of inhibitory action, while genins are potent competitive inhibitors (oleanolic acid IC50 = 5.1 microM; hederagenin IC50 = 40.6 microM) [12].
• 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 [13].

References