(±)-Galgravin

The flowers of Magnolia biondii

Rapid purification of diastereoisomers from Piper kadsura using supercritical fluid chromatography with chiral stationary phases.[Pubmed:28641835]

J Chromatogr A. 2017 Aug 4;1509:141-146.

Supercritical fluid chromatography (SFC) with chiral stationary phases (CSPs) is an advanced solution for the separation of achiral compounds in Piper kadsura. Analogues and stereoisomers are abundant in natural products, but there are obstacles in separation using conventional method. In this paper, four lignan diastereoisomers, (-)-Galbelgin, (-)-Ganschisandrin, (±)-Galgravin and (-)-Veraguensin, from Piper kadsura were separated and purified by chiral SFC. Purification strategy was designed, considering of the compound enrichment, sample purity and purification throughput. Two-step achiral purification method on chiral preparative columns with stacked automated injections was developed. Unconventional mobile phase modifier dichloromethane (DCM) was applied to improve the sample solubility. Four diastereoisomers was prepared at the respective weight of 103.1mg, 10.0mg, 152.3mg and 178.6mg from 710mg extract with the purity of greater than 98%.

Neolignans from Nectandra megapotamica (Lauraceae) Display in vitro Cytotoxic Activity and Induce Apoptosis in Leukemia Cells.[Pubmed:26184150]

Molecules. 2015 Jul 15;20(7):12757-68.

Nectandra megapotamica (Spreng.) Mez. (Lauraceae) is a well-known Brazilian medicinal plant that has been used in folk medicine to treat several diseases. In continuation of our ongoing efforts to discover new bioactive natural products from the Brazilian flora, this study describes the identification of cytotoxic compounds from the MeOH extract of N. megapotamica (Lauraceae) leaves using bioactivity-guided fractionation. This approach resulted in the isolation and characterization of eight tetrahydrofuran neolignans: calopeptin (1), machilin-G (2), machilin-I (3), aristolignin (4), nectandrin A (5), veraguensin (6), ganschisandrin (7), and (±)-Galgravin (8). Different assays were conducted to evaluate their cytotoxic activities and to determine the possible mechanism(s) related to the activity displayed against human leukemia cells. The most active compounds 4, 5 and 8 gave IC50 values of 14.2 +/- 0.7, 16.9 +/- 0.8 and 16.5 +/- 0.8 microg/mL, respectively, against human leukemia (HL-60) tumor cells. Moreover, these compounds induced specific apoptotic hallmarks, such as plasma membrane bleb formation, nuclear DNA condensation, specific chromatin fragmentation, phosphatidyl-serine exposure on the external leaflet of the plasma membrane, cleavage of PARP as well as mitochondrial damage, which as a whole could be related to the intrinsic apoptotic pathway.

Moderation of hematological and plasma biochemical indices of sub-chronic salt-loaded rats by aqueous extract of the sclerotia of Pleurotus tuberregium (Fr) Sing's: implications for the reduction of cardiovascular risk.[Pubmed:24055467]

J Ethnopharmacol. 2013 Nov 25;150(2):466-76.

ETHNOPHARMACOLOGICAL RELEVANCE: The sclerotia of Pleurotus tuberregium are used in Southern Nigeria for the management of diabetes and hypertension, yet there is scarcity of information in the literature regarding the evaluation of the biochemical basis of its antihypertensive property, as well as the biochemical impact of its administration to the hypertensive. Thus, in this study, the ability of an aqueous extract of the sclerotia of Pleurotus tuberregium to moderate biochemical and hematological indices was investigated in normal and sub-chronic salt-loaded rats. MATERIALS AND METHODS: The normal and treatment control groups received a diet consisting 100% of the commercial feed, while the test control, reference and test treatment groups received an 8% salt-loaded diet. The extract was orally administered daily at 100 and 200 mg/kg body weight; while the moduretics was administered at 1 mg/kg. The normal and test control groups received appropriate volumes of water by the same route. RESULTS: On gas chromatographic analysis of the crude aqueous extract, 29 known flavonoids (mainly 47.71% kaempferol and 37.36% quercetin), four saponins (mainly 72.93% avenacin B1 and 26.80% avenacin A1), six hydroxycinnamic acid derivatives (mainly 57.57% p-coumaric and 42.10% caffeic acid), ten carotenoids (mainly 58.44% carotene and 28.16% lycopene) and seven phytosterols (mainly 98.16% sitosterol) were detected. Also detected were nine benzoic acid derivatives (mainly 44.19% ferulic acid and 25.92% rosmarinic acid), six lignans (mainly 70.88% (±)-Galgravin and 22.69% retusin), three allicins (mainly 71.92% diallyl thiosulphinate and 23.68% methyl allyl thiosulphinate), seven glycosides (mainly 84.86% arbutin and 12.01% ouabain), 31 alkaloids (mainly 48.82% lupanine, 32.26% augustamine) and 24 terpenes (mainly 60.66% limonene and 6.52% geranyl acetate). Compared to test control, the treatment significantly, dose-dependently lowered (P < 0.05) the mean cell volume, atherogenic indices (cardiac risk ratio, atherogenic coefficient and atherogenic index of plasma), plasma alanine and aspartate transaminase activities, mean cell hemoglobin, sodium, bicarbonate, urea, blood urea nitrogen, triglyceride, total-, non-high density lipoprotein-, low density lipoprotein- and very low density lipoprotein cholesterol concentrations, and neutrophils, monocytes and platelets counts of the treated animals. However, it significantly, dose-dependently increased (P < 0.05) the hemoglobin concentration, mean cell hemoglobin, red cells and lymphocytes counts, plasma high density lipoprotein cholesterol, calcium, potassium, chloride, creatinine, albumin and total protein concentrations of the treated animals. CONCLUSIONS: All these results support the use of the plant in traditional health care, for the management of hypertension, and highlight the cardio-protective potential of the sclerotia, whilst suggesting that its antihypertensive activity may be mediated through alteration of plasma levels of sodium and potassium, or increases in muscle tone brought about by changes in plasma calcium levels.

[Chemical constituents from rhizomes of Acorus tatarinowii].[Pubmed:23713285]

Zhongguo Zhong Yao Za Zhi. 2013 Feb;38(4):569-73.

Fifteen compounds were isolated from the rhizomes of Acorus tatarinowii by means of various chromatographic techniques such as silica gel, ODS, Sephadex LH-20 and preparative HPLC, and their structures were elucidated as tatanone A (1), calamusenone (2), acoronene (3), 2-acetyloxyacoronene (4), acorenone (5), alpha-asarone (6), beta-asarone (7), 1,2-dimethoxy-4-(1'Z-propenyl) benzene (8), methyleugenol (9), asarylaldehyde (10), acoramone (11), gamma-asarone (12), 5-hydroxymethyl-2-furaldehyde (13), (±)-Galgravin (14) and eudesmin (15) on the basis of spectroscopic data analysis. Compound 1 was a new compound, and compounds 3-5 were separated from Acorus species for the first time.

Effects of veraguensin and galgravin on osteoclast differentiation and function.[Pubmed:22526488]

Cytotechnology. 2012 May;64(3):315-22.

The dried flower buds of Magnolia sp. are widely used as herbal medicines because of their anti-inflammatory, anti-malarial and anti-platelet activities. Here, we found that veraguensin and (±)-Galgravin, lignan compounds derived from Magnolia sp., dose-dependently inhibited osteoclast formation in co-cultures of bone marrow cells and osteoblastic cells. These compounds also inhibited receptor activator of nuclear factor kappaB ligand (RANKL)-induced osteoclast differentiation in RAW264.7 cells and bone marrow macrophages. In the RANKL-induced signaling pathway, veraguensin and (±)-Galgravin reduced p38 phosphorylation and suppressed the expression of c-Fos, a key transcription factor for osteoclastogenesis. Veraguensin and (±)-Galgravin also inhibited osteoclastic pit formation, which was accompanied by decreased mature osteoclast viability. In conclusion, these results indicate that veraguensin and (±)-Galgravin can inhibit bone resorption and may offer novel compounds for the development of drugs to treat bone-destructive diseases such as osteoporosis.

In vitro antileishmanial and antimalarial activities of tetrahydrofuran lignans isolated from Nectandra megapotamica (Lauraceae).[Pubmed:18688887]

Phytother Res. 2008 Oct;22(10):1307-10.

Seven tetrahydrofuran lignans, isolated from Nectandra megapotamica (Lauraceae), were evaluated for their in vitro antileishmanial and antimalarial activities. Among the evaluated compounds, machilin-G (1a) and veraguensin (2a) showed the highest antileishmanial activities, displaying for both compounds an IC(50) value of 18 microg/mL and an IC(90) value of 36 microg/mL, while (±)-Galgravin (1b), nectandrin-A (1c), nectandrin-B (1d), calopeptin (2b) and ganshisandrine (3) were inactive against Leishmania donovani. In the antimalarial assay against Plasmodium falciparum, it was observed that calopeptin (2b) displayed moderate activity, with IC(50) values of 3800 ng/mL (D6 clone) and 3900 ng/mL (W2 clone), while the lignans 1a-1d, 2a and 3 were inactive. In order to compare the effect on the parasites with toxicity to mammalian cells, the cytotoxic activity of the isolated compounds were evaluated against the Vero cells, showing that all evaluated tetrahydrofuran lignans exhibited no cytotoxicity at the maximum dose tested.

[Chemical constituents from stems of Schisandra propinqua].[Pubmed:18536373]

Zhongguo Zhong Yao Za Zhi. 2008 Mar;33(5):521-3.

OBJECTIVE: To study the chemical constituents in the stems of Schisandra propinqua and evaluate their effects on proliferation of vascular smooth muscle cells (VSMCs) in vitro by MTT assay. METHOD: The compounds were isolated and purified by various column chromatographic techniques and their structures were elucidated on the basis of spectral analysis (ESI-MS, 1H-NMR, 13C-NMR). RESULT: Five compounds were isolated and identified as (±)-Galgravin (1), veraguensin (2), octadecanoic acid 2, 3-dihydroxypropyl ester (3), hexadecanoic acid 2, 3-dihydroxypropy ester (4), tetracosanoic acid 2, 3-dihydroxypropyl ester (5). CONCLUSION: All the compounds were isolated for the first time from the plant. 1, 2, 5 showed inhibiting effects on vascular smooth muscle cell (VSMCs) proliferation in vitro.

Tetrahydrofuran lignans via tandem oxidative anionic-radical processes or reductive radical cyclizations.[Pubmed:16986930]

Org Lett. 2006 Sep 28;8(20):4481-4.

Several tetrahydrofuran lignans have become important due to their diverse biological activities. We present initial studies on short syntheses of some of the simplest members of this natural product class. (±)-Galgravin and Veraguensin are obtained in only three or four steps from nitroalkenes and allylic alcohols via a new tandem anionic-radical process, and reductive radical cyclizations of beta-nitro ethers derived from the same precursors are suitable to obtain (±)-Galgravin as well as Galbelgin and Ganschisandrin.

Neuroprotective effects of 2,5-diaryl-3,4-dimethyltetrahydrofuran neolignans.[Pubmed:15684486]

Biol Pharm Bull. 2005 Feb;28(2):289-93.

We previously reported the neurotrophic effects of talaumidin (1) from Aristolochia arcuata MASTERS. In the present study, we compared the neurotrophic and neuroprotective effects of six other 2,5-diaryl-3,4-dimethyltetrahydrofuran neolignans isolated from the same plant, veraguensin (2), (±)-Galgravin (3), aristolignin (4), nectandrin A (5), isonectandrin B (6), and nectandrin B (7), with compound 1 in primary cultured rat neurons. Compounds 3-7 promoted neuronal survival and neurite outgrowth, among which compounds 6 and 7 showed neurotrophic activity comparable with that of 1. Furthermore, compounds 1-7 protected hippocampal neurons against amyloid beta peptide (Abeta25-35)-induced cytotoxicity, while compounds 1 and 4-7 protected against neuronal death from 1-methyl-4-phenylpyridinium ion (MPP+)-induced toxicity in cultured rat hippocampal neurons.

Evaluation of analgesic and anti-inflammatory activities of Nectandra megapotamica (Lauraceae) in mice and rats.[Pubmed:15324487]

J Pharm Pharmacol. 2004 Sep;56(9):1179-84.

The bioactivity-guided phytochemical investigation of the crude hydralcoholic extract of Nectandra megapotamica was carried out using the abdominal constriction test in mice, which led to the isolation of three active compounds: alpha-asarone (1), (±)-Galgravin (2) and veraguensin (3). The crude extract (EBCA, 300 mg kg(-1)) and isolated compounds 1,2, and 3, at different doses, were evaluated using the acetic acid-induced abdominal constriction test in mice, carrageenan-induced paw oedema in rats, and hot plate tests in rats. The EBCA showed a significant effect in the abdominal constriction and hot plate tests, but did not show activity in the rat paw oedema assay. All isolated compounds displayed activity in the abdominal constriction test, but only compound 1 was active in the hot plate test. Compounds 2 and 3 displayed activity in the anti-inflammatory assay. It was suggested that the analgesic effects obtained for EBCA could be due mainly to the presence of its major compound, alpha-asarone (1).

Galgravin is an active compound in Nectandra megapotamica, with anti-inflammatory activity. Galgravin displays in vitro cytotoxic activity and induce apoptosis in leukemia cells.

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