Eclalbasaponin II

Phytochemistry and neuroprotective effects of Eclipta alba (L.) Hassk.[Pubmed:31116703]

J Complement Integr Med. 2019 May 21;17(1). pii: /j/jcim.ahead-of-print/jcim-2019-0026/jcim-2019-0026.xml.

Eclipta alba (L.) Hassk. or Eclipta prostrata (Linn.) or Eclipta erecta (Linn.) is an herbaceous plant well known in Asian as African traditional medicines. These extracts are used in traditional medicine for treatment of microbial diseases and certain metabolic disorders. This review aimed to investigate phytochemical profile and neuroprotective effects of E. alba (L.) Hassk. Several compounds belonging to the families of phenolics, alkaloids, terpenoids and polysaccharides have been isolated, identified or characterized from E. alba extracts. This plant has a diverse neuropharmacological profile. Thus, its extract improves cognitive deficits and also attenuated epileptic seizures. Phytomolecules implicated in these potentials are Eclalbasaponin II and luteolin, respectively. This document updates isolated and identified organic compounds from the extracts of E. alba and reviews their neuropharmacological activities.

Antifungal Activity of Eclipta alba Metabolites against Sorghum Pathogens.[Pubmed:30909408]

Plants (Basel). 2019 Mar 22;8(3). pii: plants8030072.

Unscientific use of synthetic fungicides in plant disease management has environmental ramifications, such as disease resurgence and serious health problems due to their carcinogenicity. This has prompted the identification and development of eco-friendly greener alternatives. Eclipta alba extract was evaluated for its antifungal activity in in vitro and in vivo against sorghum fungal pathogens Fusarium thapsinum, Alternaria alternata, Epicoccum sorghinum, and Curvularia lunata. The column purified methanolic extract of E. alba exhibited good antifungal activity against the target pathogens. The MIC was observed at 80 mg/mL for all tested pathogenic fungi, whereas MFC was 80 mg/mL for E. sorghinum, 100 mg/mL for F. thapsinum, A. alternata, and C. lunata. In vitro germination percentage was significantly high in seeds treated with E. alba extract (98%) over untreated control (91%). Significant disease protection of 95% was observed in greenhouse and 66% disease protection was noticed in field experiments. The efficacy of E. alba extract in field conditions was improved with the use of E. alba extract formulation. The profile of phytochemicals in E. alba methanol fractions was obtained by ultra-performance liquid chromatography (UPLC) mass spectroscopy. The [M-H](-) at m/z 313.3, m/z 797.9, and m/z 269.0 revealed the presence of wedelolactone, Eclalbasaponin II, and apigenin, respectively. The H-nuclear magnetic resonance spectroscopy ((1)H-NMR) chemical shift value supported the findings of the mass spectrometry. The results highlighted the possible use of E. alba methanolic extract as alternative to chemical fungicide in sorghum disease management.

Eclalbasaponin II Ameliorates the Cognitive Impairment Induced by Cholinergic Blockade in Mice.[Pubmed:29164430]

Neurochem Res. 2018 Feb;43(2):351-362.

Eclalbasaponin II derived from Eclipta prostrata L. (Asteraceae) has been reported to have anti-fibrotic, anti-bacterial and autophagic activities, but its effect on cognitive function has not been investigated. We studied the effect of Eclalbasaponin II on cholinergic blockade-induced memory impairment in mice using the passive avoidance, Y-maze, and Morris water maze tasks. Eclalbasaponin II (10 or 20 mg/kg, p.o.) significantly ameliorated the cognitive dysfunction induced by scopolamine in the passive avoidance, Y-maze, and the Morris water maze tasks. To identify the mechanism of the memory-ameliorating effect of Eclalbasaponin II, acetylcholinesterase (AChE) activity assay, Western blot analysis and electrophysiology were conducted. Eclalbasaponin II inhibited the AChE activity in ex vivo study, and the administration of Eclalbasaponin II and its metabolite, echinocystic acid, increased the phosphorylation levels of memory-related signaling molecules, including protein kinase B (Akt) and glycogen synthase kinase-3beta (GSK-3beta), in the hippocampus. Although Eclalbasaponin II did not affect hippocampal long term potentiation (LTP), echinocystic acid significantly enhanced hippocampal LTP formation (30 muM). These results suggest that Eclalbasaponin II ameliorates cholinergic blockade-induced cognitive impairment via AChE inhibition, LTP formation and the activation of Akt-GSK-3beta signaling, and that Eclalbasaponin II may be a useful to treat cognitive impairment derived from cholinergic dysfunction.

Eclalbasaponin II induces autophagic and apoptotic cell death in human ovarian cancer cells.[Pubmed:27032907]

J Pharmacol Sci. 2016 Sep;132(1):6-14.

Triterpenoids echinocystic acid and its glycosides, isolated from several Eclipta prostrata, have been reported to possess various biological activities such as anti-inflammatory, anti-bacterial, and anti-diabetic activity. However, the cytotoxicity of the triterpenoids in human cancer cells and their molecular mechanism of action are poorly understood. In the present study, we found that Eclalbasaponin II with one glucose moiety has potent cytotoxicity in three ovarian cancer cells and two endometrial cancer cells compared to an aglycone echinocystic acid and eclalbasaponin I with two glucose moiety. Eclalbasaponin II treatment dose-dependently increased sub G1 population. Annexin V staining revealed that Eclalbasaponin II induced apoptosis in SKOV3 and A2780 ovarian cancer cells. In addition, Eclalbasaponin II-induced cell death was associated with characteristics of autophagy; an increase in acidic vesicular organelle content and elevation of the levels of LC3-II. Interestingly, autophagy inhibitor BaF1 suppressed the Eclalbasaponin II-induced apoptosis. Moreover, Eclalbasaponin II activated JNK and p38 signaling and inhibited the mTOR signaling. We further demonstrated that pre-treatment with a JNK and p38 inhibitor and mTOR activator attenuated the Eclalbasaponin II-induced autophagy. This suggests that Eclalbasaponin II induces apoptotic and autophagic cell death through the regulation of JNK, p38, and mTOR signaling in human ovarian cancer cells.

Echinocystic acid isolated from Eclipta prostrata suppresses lipopolysaccharide-induced iNOS, TNF-alpha, and IL-6 expressions via NF-kappaB inactivation in RAW 264.7 macrophages.[Pubmed:23877917]

Planta Med. 2013 Aug;79(12):1031-7.

In this study, we aimed to identify the compounds in Eclipta prostrata responsible for its anti-inflammatory effects using an in vitro bioassay. Three triterpenoids, eclalbasaponin I, Eclalbasaponin II, and echinocystic acid, were isolated from an EtOAc fraction of the 70 % EtOH extract of E. prostrata by activity-guided fractionation based on the inhibition of nitric oxide release from lipopolysaccharide-induced RAW 264.7 macrophages. Of these three triterpenoids, echinocystic acid inhibited lipopolysaccharide-induced production of nitric oxide and cytokines such as tumor necrosis factor-alpha and interleukin-6. Consistent with these observations, echinocystic acid concentration-dependently inhibited lipopolysaccharide-induced inducible nitric oxide synthase expression at the protein level and inducible nitric oxide synthase, tumor necrosis factor-alpha, and interleukin-6 expression at the mRNA level, and inhibited lipopolysaccharide-induced iNOS promoter binding activity. In addition, echinocystic acid suppressed the lipopolysaccharide-induced transcriptional activity of nuclear factor-kappaB by blocking the nuclear translocation of p65.

Antiproliferative activity of triterpenoids from Eclipta prostrata on hepatic stellate cells.[Pubmed:18061418]

Phytomedicine. 2008 Sep;15(9):775-80.

Hepatic stellate cells (HSCs) have been known to play a key role in the pathogenesis of liver fibrosis. In the course of screening antifibrotic activity of natural products employing HSC-T6, a rat hepatic stellate cell line as an in vitro assay system, the methanolic extract of aerial parts of Eclipta prostrata L. showed significant inhibitory activity on HSCs proliferation. Activity-guided fractionation led to the isolation of five oleanane-type triterpenoids, echinocystic acid (1), Eclalbasaponin II (2), eclalbasaponin V (3), eclalbasaponin I (4) and Eclalbasaponin III (5), which are all echinocystic acid derivatives. Among the five echinocystic acid derivatives isolated, echinocystic acid (1) and Eclalbasaponin II (2) significantly inhibited the proliferation of HSCs in dose- and time-dependent manners. Our present study also suggests the importance of free carboxylic acid at C-28 position in echinocystic acid derivatives for the antifibrotic activity. Taken together, antifibrotic activity of E. prostrata and its triterpenoids might suggest the therapeutic potentials against liver fibrosis.