A New Lignan Glucoside from Lagochilus ilicifolius

Abstract

Background:The whole herb of Lagochilus ilicifolius has been used as a folk medicine for treating hemostatic, inflammation and ulcer in China. There were only limited reports on its chemical constituents, and no reports on its pharmacology study.Objective:To isolate compounds from the whole herb of L. ilicifolius and evaluate their cytotoxic activity.Materials and Methods:The column chromatographic techniques were used for separating the constituents of the n-butanol-soluble fraction of the 95% ethanol extract from the whole plant of L. ilicifolius. The structures of one new lignan and two known lignans were elucidated on the basis of spectroscopic analyses and comparison with literature data. The cytotoxic activities of these three lignans were evaluated using the MTT-assay against PC12 cell line derived from rat adrenal pheochromocytoma.Results:The new lignan was identified as erythro-1-[(4-O-β-D-glucopyranosyl-3-methoxyl)-phenyl]-2-[(5’-methoxyl)-pinoresinol]-propane-1,3-diol (1), and two known lignans were identified as tortoside C (2) and sisymbrifolin (3). The new lignan exhibited significant cytotoxic activity against PC12 cell line with IC50 value of 1.22 ± 0.03 μmol/L.Conclusions:A new lignan, erythro-1-[(4-O-β-D-glucopyranosyl-3-methoxyl)-phenyl]-2-[(5’-methoxyl)-pinoresinol]-propane-1,3-diol and two known lignans were isolated from the whole herbs of L. ilicifolius. The two known lignans were reported for the first time in the genus Lagochilus. Three lignans were evaluated for in vitro cytotoxic activity. The new lignan showed relatively strong cytotoxicity against PC12 cell line, while sisymbrifolin and tortoside C exibited no cytotoxicity.

The Genus Lagochilus (Lamiaceae): A Review of Its Diversity, Ethnobotany, Phytochemistry, and Pharmacology

“…The lignans are fiber-associated compounds found in plants, particularly seeds, nuts, grains, and vegetables. Lignans are rare in the Lagochilus genus, with only three lignans named erythro-1-[(4-O-β-D-glucopyranosyl-3-methoxyl)- phenyl]-2-[(5’-methoxyl)-pinoresinol]-propane-1,3-diol ( 132 ), tortoside C ( 133 ), and sisymbrifolin ( 134 ) isolated from L. ilicifolius [ 7 ] ( Table 3 , Figure S8 ). Another three lignans: 1-(4-hydroxy-3-methoxy)-phenyl-2-[4-(1, 2, 3-trihydroxypropyl)-2-methoxy]-phenoxy- 1, 3-propandiol ( 135 ), (+)-isolarisiresinol 3-α-O-β-D-glucopyranoside ( 136 ), and (-)-isolarisiresinol 3-α-O-β-D-glucopyranoside ( 137 ) were isolated from whole herb of L. platyacanthus [ 58 ].…”

“…Another three lignans: 1-(4-hydroxy-3-methoxy)-phenyl-2-[4-(1, 2, 3-trihydroxypropyl)-2-methoxy]-phenoxy- 1, 3-propandiol ( 135 ), (+)-isolarisiresinol 3-α-O-β-D-glucopyranoside ( 136 ), and (-)-isolarisiresinol 3-α-O-β-D-glucopyranoside ( 137 ) were isolated from whole herb of L. platyacanthus [ 58 ]. From L. ilicifolius (+)-syringaresinol ( 138 ) was identified by Qian et al [ 7 ].…”

“…Some other metabolites were also discovered in this genus, such as scopoletin ( 150 ) [ 7 , 27 , 41 ], ascorbic acid ( 151 ), β-caroten ( 152 ) [ 63 ] ( Figure S11 ). The following class of metabolites were identified in Lagochilus species: carbohydrates [ 35 , 64 ], sugars [ 63 ], polysaccharides, pectin, hemicellulose [ 64 , 65 , 71 ], tannins [ 63 ], organic acids, resins [ 63 ], and microelements [ 63 , 72 , 73 ].…”

“…The most reported properties include relaxation, insomnia, dementia, euphoria, and subtle perceptual changes. Lagochilus is also used for the treatment of allergies and skin diseases [ 5 , 6 , 7 , 8 , 9 ]. Pharmacological studies indicated that mainly diterpenoids have hemostatic abilities [ 10 , 11 ].…”

“…However, this effort on the chemical profiling of the plants belonging to the genus led to the isolation and characterization of many diterpenes, flavonoids, iridoids, triterpenes, and polysaccharides. The diterpene lagochiline and its derivatives are among the promising hemostatic agents [ 5 , 7 , 10 , 11 ].…”