Magnolioside

Antiplasmodial and cytotoxic activity of coumarin derivatives from dried roots of Angelica gigas Nakai in vitro.[Pubmed: 21428713]

Immunopharmacol Immunotoxicol. 2011 Dec;33(4):663-6.

The butanol-soluble fraction of the dried root of Angelica gigas exhibited significant protection against chloroquine-sensitive strains of Plasmodium falciparum using the parasite lactate dehydrogenase assay method.
METHODS AND RESULTS:
Using antiplasmodial activity-guided fractionation, five coumarins, marmesinin (1), nodakenin (2), skimmin (3), apiosylskimmin (4), and Magnolioside (5), were isolated and evaluated for in vitro antiplasmodial activity, as well as for their cytotoxic potential on SK-OV-3 cancer cell lines. Compounds 1 and 5 showed notable growth inhibitory activity against chloroquine-sensitive strains of P. falciparum with IC(50) values of 5.3 and 8.2 μM. The compounds showed no significant cytotoxicity (IC(50) > 100 μM) toward the SK-OV-3 cancer cell line.
CONCLUSIONS:
This is the first report on the antiplasmodial activity of these coumarin derivatives from the dried root of A. gigas.

Chemical composition, antibacterial, antioxidant and tyrosinase inhibitory activities of glycosides from aerial parts of Eryngium tricuspidatum L.[Reference: WebLink]

Phytochemistry Letters, 2016 , 18 :23-28.

Two new phenolic glucosides, together with six known compounds, were isolated from the aerial part of Eryngium tricuspidatum L. (Apiaceae).
METHODS AND RESULTS:
The structures of the new compounds were established as 2-hydroxy- 3,5-dimethyl-acetophenon-4-O-β-d-glucopyranoside (1) and 2,3-dimethyl-4-hydroxymethylphenyl-1-hydroxymethyl-O-β-d-glucopyranoside (2) on the basis of detailed spectroscopic data including MS, 1D, and 2D NMR. The antibacterial, tyrosinase inhibitory and DPPH radical scavenging activities of hydromethanolic extract, fractions, and the eight isolated compounds were evaluated. The antibacterial assay showed a moderate activity for Magnolioside (4) against Staphylococcus aureus CIP 53.154. Compound 7 (quercetin 3-O-β-d-glucopyranosyl-(1 → 6)-O-β-d-galactopyranoside) had moderate DPPH radical scavenging activity whereas compounds 2 exhibited good inhibitory effect against mushroom tyrosinase.

Neuroprotective coumarins from the root of Angelica gigas: structure-activity relationships.[Pubmed: 18087802]

Arch Pharm Res. 2007 Nov;30(11):1368-73.

An n-butanol-soluble fraction of the root of Angelica gigas Nakai (Umbelliferae) exhibited significant protection against glutamate-induced toxicity in primary cultured rat cortical cells.
METHODS AND RESULTS:
Using neuroprotective activity-guided fractionation, nine coumarins; marmesinin (1), nodakenin (2), columbianetin-O-beta-D-glucopyranoside (3), (S)-peucedanol-7-O-beta-D-glucopyranoside (4), (S)-peucedanol-3'-O-beta-D-glucopyranoside (5), skimmin (6), apiosylskimmin (7), isoapiosylskimmin (8) and Magnolioside (9), were isolated from the n-butanol fraction. Of these nine coumarins, three dihydrofuranocoumarins; 1, 2 and 3, exhibited significant neuroprotective activities against glutamate-induced toxicity, exhibiting cell viabilities of about 50% at concentrations ranging from 0.1 to 10 microM. To explore the structure-activity relationships of coumarins, sixteen previously isolated compounds; 10-25, were simultaneously evaluated in the same system.
CONCLUSIONS:
Our results revealed that cyclization of the isoprenyl group, such as dihydropyran or dihydrofuran, or the furan ring at the C-6 position of coumarin, as well as lipophilicity played an important role in the neuroprotective activity of coumarins.