Chemical constituents from Lagopsis supina (Steph.) Ik.-Gal. ex Knorr

doi:10.1016/j.bse.2015.07.010

Biochemical Systematics and Ecology

Volume 61, August 2015, Pages 424-428

https://doi.org/10.1016/j.bse.2015.07.010 Get rights and content

Highlights

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Phytochemical investigation of the whole plants of Lagopsis supina led to the isolation of 18 compounds.
•
Lagopsides A and B were identified as new phenylethanoid glycosides.
•
Five compounds were isolated from the Labiatae family for the first time.
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Ten compounds were identified from the genus Lagopsis for the first time.
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The chemotaxonomic significance of the isolates was discussed.

Abstract

Phytochemical investigation of the whole plants of Lagopsis supina (Steph.) Ik.-Gal. ex Knorr. led to the isolation of 18 compounds (1–18), including ten phenylethanoid glycosides (1–10), one phenylmethanoid glycoside (11), four megastigmane glycosides (12–15), and three monoterpenoid glycosides (16–18). Lagopsides A (1) and B (2) were identified as new phenylethanoid glycosides. This is the first report of compounds 7, 11, 12, 15, and 16 from the Labiatae family, while compounds 4–6, 8–10, 13–14, and 17–18 were isolated from the genus Lagopsis for the first time. The chemotaxonomic significance of these isolated compounds was summarized.

Section snippets

Subject and source

The genus Lagopsis belongs to the Labiatae family, and three Lagopsis species are native to China. Lagopsis supina is a perennial herbaceous plant and widely distributed in northeast Asia (Editorial Committee of CAS “Flora of China”, 1977). The whole plant, also known as “Xiazhicao” in Chinese, has been used in traditional Chinese medicine for the treatment of gynecologic disorders such as menorrhagia, irregular menstruation, and painful menstruation, as well as edema in acute and chronic

Previous work

Previous chemical investigations on the whole plants of Lagopsis supina have revealed the presence of phenylethanoid glycosides (Yang et al., 2001), flavonoid glycosides (Li et al., 2002), and labdane diterpenoids (Li et al., 2014) in L. supina.

Present study

The air-dried and powdered whole plants of L. supina (3.0 kg) were extracted with acetone (20 L × 3) and MeOH (12 L × 2) by maceration at room temperature for 2 days. After filtration, combination, and solvent evaporation, the residue (313.8 g) was dissolved in 90% aqueous MeOH and successively partitioned with n-hexane and CH₂Cl₂ to afford n-hexane (71.0 g), CH₂Cl₂ (30.4 g), and water (197.5 g) extracts, respectively. The water extract (197.5 g) was subjected to D101 macroporous resin column

Chemotaxonomic significance

This report discusses the isolation and identification of ten phenylethanoid glycosides (1–10), one phenylmethanoid glycoside (11), four megastigmane glycosides (12–15), and three monoterpenoid glycosides (16–18) from the whole plants of L. supina. Lagopsides A (1) and B (2) were identified as new phenylethanoid glycosides. Besides, this is the first report of compounds 7, 11, 12, 15, and 16 from the Labiatae family, while compounds 4–6, 8–10, 13–14, and 17–18 were isolated from the Lagopsis

Acknowledgments

The project was financially supported by Program for New Century Excellent Talents in University (NCET-13-0693, to J. Li), a grant from Beijing University of Chinese Medicine (2013-JYBZZ-JS-136, to J. Li), and the Scientific Research Foundation for the Returned Overseas Chinese Scholars, State Education Ministry (to J. Li).

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Megastigmanes are structurally-diverse molecules that are widely distributed in nature and occurring mainly in plant kingdom. They are oxidative degradation products from β-carotenoids with C13 skeleton and their diversity has been attributed to different functionalization at the carbon atoms, as well as glycosylation pattern. The object of this review is to summarize the published literature on megastigmane glycosides regarding their sources, ¹³C NMR data and biological activities. This review covers the literature published between the first report that appeared in 1968 till May 2022. It combines about 357 megastigmane glycosides with their classification, sources, biological activities, and ¹³C NMR data. The biological activities of megastigmane glycosides have been reported, including anti-melanogenic, anti-inflammatory, neuroprotective, antioxidant, antitumor, antimicrobial, and hepatoprotective. Anti-melanogenic and hepatoprotective activities are the most promising reported bioactivities. Besides, biosynthetic pathways as well as chemotaxonomic significance are also discussed. The present review is expected to provide a comprehensive guide on this particular class of natural products.
Labdane diterpenoids from Lagopsis supina and their anti-neuroinflammatory activity
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In this study, ten labdane-type diterpenoids 1–10 were isolated from a methanol extract of the whole plant Lagopsis supina, including three undescribed compounds 1–3. Their structures were determined by spectroscopic data analyses such as HR-ESI-MS, 1D, and 2D NMR, as well as comparison with literature data. At the same time, the absolute configuration of five compounds 2–5 and 10 was confirmed for the first time by the single crystal X-ray diffraction method. All the compounds were isolated from L. supina for the first time. The CCK-8 assay showed that all compounds had no significant damage to BV-2 microglial cells, and then screened their inhibitory effects of nitric oxide production stimulated by lipopolysaccharide in BV-2 microglial cells. The pharmacological results showed that compound 4 greatly inhibited LPS-stimulated NO release at the concentration of 10 μM, indicating that it has potential anti-neuroinflammatory activity.
Chemical constituents from Lagopsis supina and their chemotaxonomic significance
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Citation Excerpt :
For example, it was isolated from Euphorbia esula (Lu et al., 2008), Euphorbia mellifera (Valente et al., 2012), Trichilia reticulata (Harding et al., 2001) and Aphanamixis grandifolia (Liu et al., 2010). Although phenylpropanoids were found in L. supina, only propenoic acid-type phenylpropanoids have so far been described (Zhang et al., 2015a, 2016). Compounds 12–14 belong to a type of phenylpropanoids not yet described for L. supina, and they are all reported for the first time in Lamiaceae.
Phytochemical study on the whole plant Lagopsis supina led to the isolation of twenty-nine compounds, which consist of five triterpenoids (1–5), six steroids (6–11), three phenylpropanoids (12–14), two flavonoids (15–16), five fatty acid derivatives (17–21), one dipeptide (22), one sesquiterpenoid (23), and six phenols (24–29). Their structures were elucidated based on analysis of spectroscopic data and comparison with literature data. In this work, compounds 1–3, 12–14, 19, 21, and 24 are reported from the Lamiaceae family for the first time, while all compounds except 5, 9 and 15 are reported from the Lagopsis genus for the first time. Compounds 17, 18 and 20 were previously obtained through synthetic methods only, and are therefore discovered as natural products for the first time. Moreover, the chemotaxonomic significance of the isolated compounds is discussed.
Lagopsis supina extract and its fractions exert prophylactic effects against blood stasis in rats via anti-coagulation, anti-platelet activation and anti-fibrinolysis and chemical characterization by UHPLC-qTOF-MS/MS
2020, Biomedicine and Pharmacotherapy
Citation Excerpt :
Therefore, it also used as a substitute for L. japonicus to treating BSS in clinical practice [11]. Previous phytochemical studies conducted with ethanol or acetone crude extract of L. supina have identified the presence of diterpenoids [12], flavonoids [13], phenylpropanoids [14], and monoterpenes [15]. Modern pharmacological studies have been indicated that ethanol crude extract of L. supina have a wide array of biological effects, including improved the blood and lymph microcirculation [15], anti-inflammatory [12], diuretic and antidiuretic [16,17], myocardioprotective [18], antioxidant [19], and antiviral [20] effects.
Lagopsis supina (Steph.) IK. -Gal. ex Knorr. has been used for centuries as an empiric treatment for blood stasis syndrome in China without scientific validation. The aim of this study was to evaluate for the first time the chemical profiling, efficacy and mechanism of L. supina ethanol extract (LS) and its four fractions (LSA∼D) in Dextran 500-induced acute blood stasis model rats. Oral administration of LS (229.0∼916.0 mg/kg) and LSC (17.6∼70.4 mg/kg) once daily for seven consecutive days significantly improved microcirculation hemodynamics function (blood flow, blood concentration and blood flow velocity), hemorheological parameters (whole blood viscosity, whole blood reduced viscosity, plasma viscosity, platelet aggregation rate, hematokrit, erythrocyte assembling index and erythrocyte deformation index), and coagulation parameters (thrombin time, prothrombin time, activated partial thromboplastin time, fibrinogen and antithrombin III). Furthermore, their markedly down-regulated thromboxane B2 and 6-keto-prostaglandin F1α levels. In addition, it significantly decreased tissue-type plasminogen activator (t-PA), urokinasetype plasminogen activator (u-PA) and plasminogen activator inhibitor-1 (PAI-1) levels, as well as PAI-1/t-PA and PAI-1/u-PA rations. In parallel, 51 chemical constituents were identified from LS based on ultra-high-performance liquid chromatography-quadrupole time-of-flight tandem mass spectrometry (UHPLC-qTOF-MS/MS), and quantitative analysis showed that the two major constituents of stachysoside A and acteoside were present in 0.90 ± 0.01 and 1.36 ± 0.01 mg/g of the L. supina whole plant, respectively. These findings suggest that LS and LSC possess prominent anti-blood stasis effect on rats by modulating the anti-coagulation, anti-platelet activation and anti-fibrinolysis, and supports the traditional folk use of this plant.
Chemical constituents from Phlomis bovei Noë and their chemotaxonomic significance
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ex Willd.) Ikonn.-Gal (Zhang et al., 2015). ( Lamiaceae) and debiloside B from Equisetum debile Roxb.
A phytochemical investigation of the leaves and roots of Phlomis bovei Noë (Lamiaceae) led to the isolation of sixteen compounds, including iridoids (1, 2, 3), megastigmanes (4, 5), phenylpropanoids (6, 7, 8, 9, 10), lignans (11, 12, 13, 14), a nortriterpene (15), and a phenyl glucoside (16). Compounds (1, 2, 4, 5, 6, 10) were obtained from the leaves and compounds (1, 2, 3, 7, 8, 9, 11, 12, 13, 14, 15, 16) were isolated from the roots. Compounds 1 and 2 were found both in the leaves and in roots.
The compounds were identified by analysis of 1D- (¹H, ¹³C), 2D-NMR (¹H–¹H COSY, TOCSY, ROESY, HSQC, HMBC) spectroscopic data, mass spectrometry (ESI- and HR-ESI-MS), and by comparison with previously reported spectral data.
Compounds 5, 9, 10, 13 and 14 were isolated from the genus Phlomis for the first time. All these specialized metabolites were described here for the first time in the Algerian Phlomis bovei Noë species. To the best of our knowledge, no reports have appeared on the constituents of the roots of P.bovei Noë. The chemotaxonomic significance of these compounds was summarized.
Molecular docking and molecular dynamics simulation studies on PLCE1 encoded protein
2019, Journal of Molecular Structure
Citation Excerpt :
Machuca et al. reviewed [13] the clinical and molecular findings in the field of genomics of nephrotic syndrome and provided a suitable understanding of the complex gloumerular filtration barrier physiology. Previous studies were focused on phytochemicals related on nephrotic syndrome like aegeline [14], berberine [15], diterpenoid [16] and roseoside [17]. To the best of our knowledge, reports have not found on molecular docking study both wild type and mutant model of PIPLC_X domain of PLCE1 with aegeline, berberine, diterpenoid and roseoside phytochemicals.
Phospholipase C epsilon gene (PLCE1) is encoded the 1-phosphatidylinositol 4,5- bisphosphate phosphodiesterase ɛ-1 protein. This protein is characterized by the fetal onset of enormous proteinuria following by severe steroid resistance nephrotic syndrome (SRNS). The mutation position is located on the PIPLC_X domain of PLCE1 encoded protein. Molecular docking study was carried out between aegeline, berberine, diterpenoid, roseoside phytochemicals with wild type and mutant of the PIPLC_X domain of the PLCE1 gene encoded protein. From the molecular docking study, it was found that, due to mutation the binding energy was decreased for aegeline, berberine diterpenoid and roseoside with mutant PLCE1 at S1484L compared to wildtype. To achieve the depth analysis, we extended our study by performing the molecular dynamic simulation of 100 ns on wild type and the mutant (S1484L) model of above said domain of the studied protein. In the MD simulation study, we analyzed the result obtained from root mean square deviation, root mean square fluctuation, radius of gyration, salvation accessible surface area, hydrogen bond number and principal component analysis. These dynamical behaviour results of wild type protein show similar behaviour with mutant protein.

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Chemical constituents from Lagopsis supina (Steph.) Ik.-Gal. ex Knorr

Highlights

Abstract

Section snippets

Subject and source

Previous work

Present study

Chemotaxonomic significance

Acknowledgments

Phytochemistry

Phytochemistry

Phytochemistry

Phytochemistry

Chin. J. Magn. Reson.

Nat. Prod. Res.

J. Nat. Med.

Helv. Chim. Acta