Dr. Weeks’ Comment: The lovely Easter lily offers not only beauty and fragrance but a potent anti-cancer remedy as well. Such astonishing design to protect the plant whose trumpet shaped blossom is a vulnerable spot for infection… imagine a bug crawling in, dying and decomposing therein. Rather than perish, the lily has the medicine for that “infection”!
Steroidal glycosides from the bulbs of Easter lily (Lilium longiflorum Thunb.) promote dermal fibroblast migration in vitro.
Abstract
ETHNOPHARMACOLOGICAL RELEVANCE:
Preparations derived from bulbs of various Lilium species have been used to promote the healing of skin abrasions, sores and burns and to aid in healing wounds in Traditional Chinese and Greco-Roman Medicine.
AIM OF THE STUDY:
To evaluate fractionated Easter lily bulb extracts and their steroidal glycosides (1-5) for the promotion of dermal fibroblast migration in vitro, a model for the early events in wound healing.
MATERIALS AND METHODS:
An activity-guided screening approach was used by coupling sequential solvent extraction, gel permeation chromatography (GPC), and semi-preparative reverse-phase high performance liquid chromatography (RP-HPLC) with an in vitro dermal fibroblast migration assay. Cytotoxicity was evaluated with methyl thiazole tetrazolium (MTT). To gain insight into the mode of action of the steroidal glycosides, nitric oxide (NO) production, and expression of genes for transforming growth factor beta-1 (TGF-β) and its receptors were evaluated.
RESULTS:
Fractionated bulb extracts and the two isolated steroidal glycoalkaloids (1) and (2) induced NO production and TGF-β receptor I mRNA expression in fibroblast cell culture. In a cytotoxicity assay, steroidal glycosides (1) and (3) had IC50 values of 8.2 and 8.7 µM, but the natural acetylation of the C-6”³’ hydroxy of the terminal glucose unit in (2) resulted in a 3-fold decrease in cell cytotoxicity when compared with (1). Results from the dermal fibroblast migration assay revealed that the steroidal glycoalkaloids (1) and (2), and the furostanol saponin (3) promoted fibroblast migration from the range of 23.7±5.7 to 37.7±5.1%, as compared with the control.
CONCLUSION:
Collectively, our data demonstrate that the steroidal glycosides present in Easter lily bulbs induce, at least in part, the observed dermal fibroblast migration activity of the bulb extracts. This is the first evidence that steroidal glycosides from Lilium longiflorum may potentially play a role in the wound healing process and may provide a scientific basis for the historical use of lily bulbs for this purpose.
Copyright © 2013 Elsevier Ireland Ltd. All rights reserved.
Antifungal activity and fungal metabolism of steroidal glycosides of Easter lily (Lilium longiflorum Thunb.) by the plant pathogenic fungus, Botrytis cinerea.
Abstract
Botrytis cinerea Pers. Fr. is a plant pathogenic fungus and the causal organism of blossom blight of Easter lily (Lilium longiflorum Thunb.).Easter lily is a rich source of steroidal glycosides, compounds which may play a role in the plant-pathogen interaction of Easter lily. Five steroidal glycosides, including two steroidal glycoalkaloids and three furostanol saponins, were isolated from L. longiflorum and evaluated for fungal growth inhibition activity against B. cinerea, using an in vitro plate assay. All of the compounds showed fungal growth inhibition activity; however, the natural acetylation of C-6”’ of the terminal glucose in the steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-D-glucopyranosyl-(1→4)]-β-D-glucopyranoside (2), increased antifungal activity by inhibiting the rate of metabolism of the compound by B. cinerea. Acetylation of the glycoalkaloid may be a plant defense response to the evolution of detoxifying mechanisms by the pathogen. The biotransformation of the steroidal glycoalkaloids by B. cinerea led to the isolation and characterization of several fungal metabolites. The fungal metabolites that were generated in the model system were also identified in Easter lily tissues infected with the fungus by LC-MS. In addition, a steroidal glycoalkaloid, (22R,25R)-spirosol-5-en-3β-yl O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranoside (6), was identified as both a fungal metabolite of the steroidal glycoalkaloids and as a natural product in L. longiflorum for the first time.
Quantitative analysis of steroidal glycosides in different organs of Easter lily (Lilium longiflorum Thunb.) by LC-MS/MS.
Abstract
The bulbs of the Easter lily ( Lilium longiflorum Thunb.) are regularly consumed in Asia as both food and medicine, and the beautiful white flowers are appreciated worldwide as an attractive ornamental. The Easter lily is a rich source of steroidal glycosides, a group of compounds that may be responsible for some of the traditional medicinal uses of lilies. Since the appearance of recent reports on the role steroidalglycosides in animal and human health, there is increasing interest in the concentration of these natural products in plant-derived foods. A LC-MS/MS method performed in multiple reaction monitoring (MRM) mode was used for the quantitative analysis of two steroidal glycoalkaloids and three furostanol saponins, in the different organs of L. longiflorum. The highest concentrations of the total five steroidal glycosides were 12.02 ± 0.36, 10.09 ± 0.23, and 9.36 ± 0.27 mg/g dry weight in flower buds, lower stems, and leaves, respectively. The highest concentrations of the two steroidal glycoalkaloids were 8.49 ± 0.3, 6.91 ± 0.22, and 5.83 ± 0.15 mg/g dry weight in flower buds, leaves, and bulbs, respectively. In contrast, the highest concentrations of the three furostanol saponins were 4.87 ± 0.13, 4.37 ± 0.07, and 3.53 ± 0.06 mg/g dry weight in lower stems, fleshy roots, and flower buds, respectively. The steroidal glycoalkaloids were detected in higher concentrations as compared to the furostanol saponins in all of the plant organs except the roots. The ratio of the steroidal glycoalkaloids to furostanol saponins was higher in the plant organs exposed to light and decreased in proportion from the aboveground organs to the underground organs. Additionally, histological staining of bulb scales revealed differential furostanol accumulation in the basal plate, bulb scale epidermal cells, and vascular bundles, with little or no staining in the mesophyll of the bulb scale. An understanding of the distribution of steroidal glycosides in the different organs of L. longiflorum is the first step in developing insight into the role these compounds play in plant biology and chemical ecology and aids in the development of extraction and purification methodologies for food, health, and industrial applications. In the present study, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside, (22R,25R)-spirosol-5-en-3β-yl O-α-l-rhamnopyranosyl-(1→2)-[6-O-acetyl-β-d-glucopyranosyl-(1→4)]-β-d-glucopyranoside, (25R)-26-O-(β-d-glucopyranosyl)furost-5-ene-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1→2)-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside, (25R)-26-O-(β-d-glucopyranosyl)furost-5-ene-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranosyl-(1→3)-β-d-glucopyranoside, and (25R)-26-O-(β-d-glucopyranosyl)furost-5-ene-3β,22α,26-triol 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-xylopyranosyl-(1→3)-β-d-glucopyranoside were quantified in the different organs of L. longiflorum for the first time.
Isolation and structural determination of steroidal glycosides from the bulbs of easter lily (Lilium longiflorum Thunb.).
Abstract
The bulbs of the Easter lily ( Lilium longiflorum Thunb.) are used as a food and medicine in several Asian cultures, and they are cultivated as an ornamental plant throughout the world. A new steroidal glycoalkaloid and two new furostanol saponins, along with two known steroidalglycosides, were isolated from the bulbs of L. longiflorum. The new steroidal glycoalkaloid was identified as (22R,25R)-spirosol-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1–>2)-[6-O-acetyl-beta-d-glucopyranosyl-(1–>4)]-beta-d-glucopyranoside. The new furostanol saponins were identified as (25R)-26-O-(beta-d-glucopyranosyl)-furost-5-en-3beta,22alpha,26-triol 3-O-alpha-l-rhamnopyranosyl-(1–>2)-alpha-l-arabinopyranosyl-(1–>3)-beta-d-glucopyranoside and (25R)-26-O-(beta-d-glucopyranosyl)-furost-5-en-3beta,22alpha,26-triol 3-O-alpha-l-rhamnopyranosyl-(1–>2)-alpha-l-xylopyranosyl-(1–>3)-beta-d-glucopyranoside. The previously known steroidal glycosides, (22R,25R)-spirosol-5-en-3beta-yl O-alpha-l-rhamnopyranosyl-(1–>2)-beta-d-glucopyranosyl-(1–>4)-beta-d-glucopyranoside and (25R)-26-O-(beta-d-glucopyranosyl)-furost-5-en-3beta,22alpha,26-triol 3-O-alpha-l-rhamnopyranosyl-(1–>2)-beta-d-glucopyranosyl-(1–>4)-beta-d-glucopyranoside were identified in L. longiflorum for the first time. These new compounds from L. longiflorum and the isolation methodologies employed can be used for studies on the biological role of steroidal glycosides in plant development and plant-pathogen interactions, as well as for studies in food and human health, for which little is known.
Constituents in Easter lily flowers with medicinal activity.
Abstract
Easter lily (Lilium longiflorum) flowers have been used in traditional medicine for alleviating many ailments. However, the chemical basis of its bioactivity has not been investigated. We have determined bioactive components in Easter lily flowers using lipid peroxidation and cyclooxygenase enzyme inhibitory assays and found to be kaempferol (1), kaempferol glycosides (2, 3, 4, 8, 9 and 10), quercetin glycosides (5, 6 and 7), a regaloside (11), a chalcone (12) and a fatty acid fraction (13). The structures of compounds were determined by NMR, IR, UV/VIS and mass spectroscopic studies. Compound 1 showed the highest COX-1 inhibition (94.1%) followed by 3, 8 and 12 with 38.7, 30.8 and 32.4%, respectively. Only compound 1 inhibited COX-2 enzyme by 36.9% at 80 ppm. In lipid peroxidation inhibitory assay, kaempferol showed 37 and 100 % inhibitions at 1 and 10 ppm, respectively. At 10 ppm, more than 20% inhibition was observed for compounds 4, 7, 10, 11 and 12 and 53% for compound 3. The compounds reported in here are isolated for the first time from Easter lily flowers including novel compounds 10, 11 and 12. Our results suggest that kaempferol and quercetin flavonoids contributed to the anecdotal medicinal properties of Easter lily flowers.