alpha-Hederin

1 Hedera sp.

Kalopanaxsaponin A is a triterpenoid saponin that is hederagenin attached to a 2-O-(6-deoxy-alpha-L-mannopyranosyl)-alpha-L-arabinopyranosyl residue at position 3 via a glycosidic linkage. It has been isolated from the stem bark of Kalopanax pictus. It has a role as an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid, a triterpenoid saponin, a disaccharide derivative and a hydroxy monocarboxylic acid. It derives from a hederagenin

The haploinsufficiency profile of alpha-hederin suggests a caspofungin-like antifungal mode of action.[Pubmed:24569176]

Phytochemistry. 2014 May;101:116-20.

The leaves of common ivy (Hedera helix) contain the cytotoxic saponin alpha-Hederin, which is inhibitory to Candida albicans at low concentrations. To investigate the mode of action of alpha-Hederin, a haploinsufficiency screen was carried out using a library of 1152 Saccharomyces cerevisiae deletion strains. An ethanol ivy extract containing alpha-Hederin was used in the initial screen to reduce the amount of compound required. Strains exhibiting disproportionately low growth were then examined in more detail by comparing growth curves in the presence and absence of alpha-Hederin. This approach identified three hypersensitive strains carrying gene deletions for components of the transcription related proteins SWI/SNF, RNA polymerase II and the RSC complex. Saponin cytotoxicity is often attributed to membrane damage, however alpha-Hederin did not induce hypersensitivity with an aminophospholipid translocase deletion strain that is frequently hypersensitive to membrane damaging agents. The haploinsufficiency profile of alpha-Hederin is most similar to that reported for drugs such as caspofungin that inhibit synthesis of the fungal cell wall. Screening with plant extracts rather than isolated compounds, provides a valuable shortcut in haploinsufficiency screening provided hypersensitive strains are then confirmed as such using purified active principles.

The anticancer effect and mechanism of alpha-hederin on breast cancer cells.[Pubmed:24842044]

Int J Oncol. 2014 Aug;45(2):757-63.

Natural plant products occupy a very important position in the area of cancer chemotherapy. Many triterpenoid saponins have been proved as potential agents for chemoprevention and therapy of breast cancer. alpha-Hederin, a monodesmosidic triterpenoid saponin distributed in Hedera or Nigella species, displays many biological activities. It is increasingly investigated for its promising anticancer potential since it has been shown to have cytotoxicity against several types of cancer cells. However, studies of alpha-Hederin on breast cancer are limited, most of which focus on biological activity, while the mechanisms have not been widely reported yet. Previously, we purified and identified alpha-Hederin from Clematis ganpiniana, a herb used in traditional Chinese medicine with antitumor action. In the present study, alpha-Hederin showed strong inhibitory activity on the growth of breast cancer cells and induced apoptosis in these cells. alpha-Hederin induced depolarization of mitochondrial membrane potential which released Apaf-1 and cytochrome c from the intermembrane space into the cytosol, where they promoted caspase-3 and caspase-9 activation. This is the first report on the growth inhibition and pro-apoptotic effects of alpha-Hederin on breast cancer cells and the relative apoptosis pathways. It implied that triterpenoid saponin alpha-Hederin could be a promising candidate for chemotherapy of breast cancer.

Alpha-hederin potentiates 5-FU antitumor activity in human colon adenocarcinoma cells.[Pubmed:18546204]

Phytother Res. 2008 Oct;22(10):1299-302.

The aim of this study was to investigate the ability of alpha-Hederin to improve the efficacy of widely prescribed 5-fluorouracil (5-FU) in a human colon adenocarcinoma model. Drug combinations of alpha-Hederin and 5-FU using both fixed-concentration and combination index methods were performed in vitro in HT-29 cells. The results showed that alpha-Hederin at sub-IC(50) cytotoxic concentrations enhanced 5-FU cytotoxicity about 3.3-fold (p < 0.001). Simultaneous combination of alpha-Hederin and 5-FU at their IC(50) ratio showed either a synergistic effect at a moderate cytotoxic range (25% of cell growth inhibition) or an antagonistic effect at a high level of growth inhibition. The data indicate therefore that it is possible to optimize colorectal cancer cell sensitivity to 5-FU with alpha-Hederin.

Acute anti-inflammatory activity of four saponins isolated from ivy: alpha-hederin, hederasaponin-C, hederacolchiside-E and hederacolchiside-F in carrageenan-induced rat paw edema.[Pubmed:16008120]

Phytomedicine. 2005 Jun;12(6-7):440-4.

The anti-inflammatory potential of alpha-Hederin (monodesmoside) and hederasaponin-C from Hedera helix, and hederacolchisides-E and -F (bidesmosides) from H. colchica was investigated in carrageenan-induced acute paw edema in rats. Saponins and indomethacin were given orally in concentrations of 0.02 and 20mg/kg body wt. For the first phase of acute inflammation, indomethacin was found as the most potent drug. alpha-Hederin and hederasaponin-C were found ineffective, while hederacolchisides-E and -F showed slight anti-inflammatory effects on the first phase. For the second phase of acute inflammation, indomethacin and hederacolchiside-F were determined as very potent compounds. alpha-Hederin was found ineffective for the second phase, either. Despite hederasaponin-C and -E were found effective in the second phase of inflammation, they were not found as effective as indomethacin and hederacolchiside-F. As a conclusion, hederasaponin-C, -E and -F, may exert their anti-inflammatory effects by blocking bradykinin or other inflammation mediators. The latter affect may occur via affecting prostaglandin pathways. Regarding the structure activity relationship, it is likely that sugars at C3 position and Rha7-Glcl-6Glc moiety at C28 position are essential for the acute anti-inflammatory effect.

Protective effects of alpha-hederin, chlorophyllin and ascorbic acid towards the induction of micronuclei by doxorubicin in cultured human lymphocytes.[Pubmed:8671733]

Mutagenesis. 1996 Mar;11(2):161-7.

The influence of alpha-Hederin (a saponin isolated from Hedera helix), chlorophyllin, the sodium-copper salt of chlorophyll, and ascorbic acid (vitamin C) on the direct clastogenicity of doxorubicin (Adriamycin) was investigated in vitro in human lymphocytes for the induction of micronuclei. In order to determine a possible mechanism of action responsible for the antimutagenic activity, treatments were performed for the three substances at different times of the culture (pre-treatment, simultaneous and post-treatment). alpha-Hederin (1.3 x 10(-2), 0.13, 1.3 and 13 nmol/ml) and chlorophyllin (0.14, 1.4 and 14 nmol/ml) were found to exert an antimutagenic effect against the clastogenicity of doxorubicin (1.5 x 10(-2) nmol/ml) in all treatments at all concentrations. Ascorbic acid (10 nmol/ml) was effective in reducing the micronucleus levels only in the simultaneous treatment, when it was previously incubated with doxorubicin for 2 h at 37 degrees C before being introduced into the culture. Our results suggested a desmutagenic effect for alpha-Hederin, chlorophyllin and ascorbic acid. Chlorophyllin acted also through a bio-antimutagenic mechanism and alpha-Hederin seemed to induce metabolic enzymes, which inactivated doxorubicin. Preliminary studies showed that the effective antimutagenic concentrations of alpha-Hederin, chlorophyllin and ascorbic acid had no clastogenic or aneugenic effects in human lymphocytes. No cytotoxicity was observed for the three antimutagenic agents either.

Antileishmanial activity of three saponins isolated from ivy, alpha-hederin, beta-hederin and hederacolchiside A1, as compared to their action on mammalian cells cultured in vitro.[Pubmed:10865451]

Planta Med. 2000 May;66(4):343-7.

The in vitro antileishmanial activity of three saponins isolated from ivy, alpha-Hederin, beta-hederin and hederacolchiside A1, was investigated on Leishmania infantum. The assessment of possible targets (membrane integrity, membrane potential, DNA synthesis and protein content) was performed in both Leishmania promastigotes and human monocytes (THP1 cells). Results observed in Leishmania showed that the saponins exhibited a strong antiproliferative activity on all stages of development of the parasite by altering membrane integrity and potential: hederacolchiside A1 appeared to be the most active compound against both promastigotes and amastigotes. Results observed in THP1 cells demonstrated that the saponins exerted also a potent antiproliferative activity against human monocytes, by producing a significant DNA synthesis inhibition. The ratio between antileishmanial activity on amastigotes and toxicity to human cells suggested that the saponins could be considered as possible antileishmanial drugs.

Alpha-hederin, but not hederacoside C and hederagenin from Hedera helix, affects the binding behavior, dynamics, and regulation of beta 2-adrenergic receptors.[Pubmed:19278262]

Biochemistry. 2009 Apr 21;48(15):3477-82.

Hederacoside C, alpha-Hederin, and hederagenin are saponins of dry extracts obtained from the leaves of ivy (Hedera helix L.). Internalization of beta(2)-adrenergic receptor-GFP fusion proteins after stimulation with 1 microM terbutaline was inhibited by preincubation of stably transfected HEK293 cells with 1 microM alpha-Hederin for 24 h, whereas neither hederacoside C nor hederagenin (1 microM each) influenced this receptor regulation. After incubation of A549 cells with 5 nM Alexa532-NA, two different diffusion time constants were found for beta(2)AR-Alexa532-NA complexes by fluorescence correlation spectroscopy. Evaluation of the autocorrelation curve revealed diffusion time constants: tau(bound1) = 1.4 +/- 1.1 ms (n = 6) found for receptor-ligand complexes with unrestricted lateral mobility, and tau(bound2) = 34.7 +/- 14.1 ms (n = 6) for receptor-ligand complexes with hindered mobility. The distribution of diffusion time constants was 24.3 +/- 2.5% for tau(bound1) and 8.7 +/- 4.3% for tau(bound2) (n = 6). A549 cells pretreated with 1 microM alpha-Hederin for 24 h showed dose-dependent alterations in this distribution with 37.1 +/- 5.5% for tau(bound1) and 4.1 +/- 1.1% for tau(bound2). Simultaneously, the level of Alexa532-NA binding was significantly increased from 33.0 +/- 6.8 to 41.2 +/- 4.6%. In saturation experiments, alpha-Hederin did not influence the beta(2)-adrenergic receptor density (B(max)), whereas the K(D) value for Alexa532-NA binding decreased from 36.1 +/- 9.2 to 24.3 +/- 11.1 nM. Pretreatment of HASM cells with alpha-Hederin (1 microM, 24 h) revealed an increased intracellular cAMP level of 13.5 +/- 7.0% under stimulating conditions. Remarkably, structure-related saponins like hederacoside C and hederagenin did not influence either the binding behavior of beta(2)AR or the intracellular cAMP level.

Antioxidant activity of saponins isolated from ivy: alpha-hederin, hederasaponin-C, hederacolchiside-E and hederacolchiside-F.[Pubmed:15241892]

Planta Med. 2004 Jun;70(6):561-3.

The antioxidant activities of alpha-Hederin and hederasaponin-C from Hedera helix, and hederacolchisides-E and -F from Hedera colchica were investigated, in this study. The antioxidant properties of the saponins were evaluated using different antioxidant tests: 1,1-di-phenyl-2-picryl-hydrazyl (DPPH.) free radical scavenging, total antioxidant activity, reducing power, superoxide anion radical scavenging, hydrogen peroxide scavenging, and metal chelating activities. alpha-Hederin, hederasaponin-C, as well as hederacolchisides-E and -F exhibited a strong total antioxidant activity. At the concentration of 75 pg/mL, these saponins showed 94, 86, 88 and 75% inhibition on lipid peroxidation of linoleic acid emulsion,respectively. These various antioxidant activities were compared with model antioxidants such as a-tocopherol, butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT).

alpha-Hederin (α-Hederin) is a water-soluble pentacyclic triterpenoid saponin, possessing several biological properties such as antispasmodic, moliscicidic, anthelmithic and inhibiting cell proliferation，

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