Monoterpene glycosides from Paeonia hybrida

Monoterpene glycosides (1–5, and 7), together with 14 known compounds, were isolated from the methanol extract of the roots of Paeonia hybrida. These compounds included a paeoniflorin-related glycoside with a hybrid structure of paeoniflorin and paeonovicinoside (1), a monoterpene glucoside biogenetically related to lactiflorin (2), a paeoniflorin-related monoterpene (3), arbiflorin-related monoterpenes (4 and 5), and a tymol-related monoterpene glycoside (7). Their structures were elucidated by extensive spectroscopic examinations.     

Effect of paeoniflorin on acute lung injury induced by influenza A virus in mice. Evidences of its mechanism of action

BackgroundInfluenza often leads to acute lung injury (ALI). Few therapeutics options such as vaccines and other antiviral drugs are available. Paeoniflorin is a monoterpene glucoside isolated from the roots of Paeonia lactiflora Pall. that has showed good anti-inflammatory and anti-fibrotic effects. However, it is not known whether paeoniflorin has an effect on influenza virus-induced ALI.PurposeTo investigative the protective effect and potential mechanism of paeoniflorin on ALI induced by influenza A virus (IAV).Study design and methodsThe anti-influenza activity of paeoniflorin in vitro was investigated. Influenza virus A/FM/1/47 was intranasally infected in mice to induce ALI, and paeoniflorin (50 and 100 mg/kg) was given orally to mice during 5 days, beginning 2 h after infection. On day 6 post-infection, body and lung weights, histology and survival were observed, and the lungs were examined for viral load, cytokine and cellular pathway protein expression.ResultsResults showed that paeoniflorin (50 and 100 mg/kg) reduced IAV-induced ALI. It reduces pulmonary oedema and improves histopathological changes in the lung, and also diminishes the accumulation of inflammatory cells in the lung. It was shown that paeoniflorin (50 and 100 mg/kg) alleviated IAV-induced ALI, as evidenced by improved survival in infected mice (40% and 50%, respectively), reduced viral titer in lung tissue, improved histological changes, and reduced lung inflammation. Paeoniflorin also improves pulmonary fibrosis by reducing the levels of pulmonary fibrotic markers (collagen type IV, alpha-smooth muscle actin, hyaluronic acid, laminin, and procollagen type III) and downregulating the expression levels of type I collagen (Col I) and type III collagen (Col III) in the lung tissues. Additionally, paeoniflorin inhibits the expression of αvβ3, TGF-β1, Smad2, NF-κB, and p38MAPK in the lung tissues.ConclusionThe results showed that paeoniflorin (50 and 100 mg/kg) protected against IAV-induced ALI, and the underlying mechanism may be related to the reduction of pro-inflammatory cytokine production and lung collagen deposition through down-regulation of activation of αvβ3/TGF-β1 pathway in lung tissue.     

A Preliminary Study of the Chemistry and Systematics of Paeoniaceae

Abstract From the root of Paeonia suffruticosa and P. lactiflora seven compounds have been isolated. They are identified as paeoniflorin I, benzoylpaeoniflorin II, oxypaeoniflorin III, paeonol IV, paeonoside V, paeonolide VI and apiopaeonoside VII. The contents of the seven constituents in the root of 23 Paeonia taxa, including 19 species and 6 varieties, are determined by means of the quantitative HPTLC scanning method. The results show that paeoniflorin occurs ubiquitously in all the species examined and is the characteristic constituent of the family Paeoniaceae; The paeonol compounds (IV, V. VI, VII) are found to be restricted to the woody Sect. Moutan and notably absent in the herbaceous Sect. Paeon. This differentiation gives a support to the division of sections in Paeoniaceae. The chemical comparison between Paeoniaceae and 15 possibly related families shows that Paeoniaceae is different from Ranunculaceae, Ranunculales of Magnoliales and is similar to Dilleniaceae, Theaceae and Rosaceae in some respects. The chemical data support the suggestion that Paeoniaceae be elevated to the order rank, Paeoniales.     

赤芍中芍药苷提取工艺的优化

本文提出一条从赤芍中提取芍药苷的工艺,包括醇水溶液回流提取、液液分配、硅胶柱层析等工序,并对各工序的操作条件进行了优化。采用优化后的提取工艺,可得到纯度大于97.0%的芍药苷产品,总回收率超过87.0%。本工艺具有产品纯度高、操作简单、成本低、回收率高、易于工业化等优点。     

Karyotypes of four wild Paeonia species from Greece

The karyotypes of eight wild Greek Paeonia taxa were studied, viz. P. clusii ssp. clusii (2n = 10, 20), P. clusii ssp. rhodia (2n = 10), P. mascula ssp. mascula (2n = 20), P. mascula ssp. hellenica (2n = 20), P. mascula ssp. icarica (2n = 20), P. mascula ssp. russi (2n = 10), P. peregrina (2n = 20) and P. parnassica (2n = 20). P. mascula and P. clusii have a very similar haploid chromosome complement, x = 5, including three metacentric chromosomes, one submetacentric and one subtelocentric. In the chromosome complements of the tetraploid P. peregrina and P. parnassica the same chromosome types are included but their karyotype differ from those of the former two species by a number of characters. The main karyotype differences are concerned with the size differentiation of the chromosomes which in the case of P. peregrina has resulted in the diploidization of the tetraploid karyotype.
From the individuals examined, six were found to have abnormal karyotypes suggesting chromosomal exchanges. These structural aberrations in which mainly submetacentric and subtelocentric chromosomes are involved have also been described and discussed.     

白芍中丹皮酚、芍药苷和苯甲酸的反相薄层色谱分析

建立了对白芍中丹皮酚、芍药苷和苯甲酸同时进行反相薄层色谱分析的新方法。以RP－C18F254S高效反相薄层板,选择了合适的溶剂体系：四氢呋喃／水46／54（0.1%的四丁基溴化铵）,展距仅4.5cm,薄层扫描分析三者。结果准确,重现性好。     

Paeonidanins F–H: Three new dimeric monoterpene glycosides from Paeonia lactiflora and their anti-inflammatory activity

Three new dimeric monoterpene glycosides, paeonidanins F–H (1–3) were isolated from the roots of Paeonia lactiflora. Their structures were elucidated on the basis of spectroscopic evidence and hydrolysis products. Compounds 1–3 showed inhibitory effects against nitric oxide (NO) and pro-inflammatory cytokine TNF-α release in LPS-induced RAW 246.7 macrophages.     

Constituents of flowers of Paeoniaceae plants,Paeonia suffruticosa and Paeonia lactiflora

A new monoterpene glycoside, floralalbiflorin I (1), and a new flavonol glycoside, lactifloraoside I (2), were isolated from the flowers of Paeonia suffruticosa and Paeonia lactiflora (Paeoniaceae) together with 28 known compounds. The chemical structures of the isolated compounds were elucidated on the basis of chemical and physicochemical evidence. Among the major constituents of P. suffruticosa and P. lactiflora flowers, 1,2,3,4,6-penta-O-galloyl-β-d-glucopyranoside (10) [inhibition: 42.4% at 1 μM] and flavonoids having the catechol moiety showed significant inhibitory effect on Cu²⁺-induced low-density lipoprotein (LDL) oxidation.     

Depigmentation and inhibition of cell growth of B-16 melanoma cells by compounds isolated from Paeonia suffruticosa callus

The anther segments of Paeonia suffruticosa Andrews were cultured for callus formation on MS medium supplemented with 2,4-D and BAP(each 1 mg/l) in the dark at 25°C for six weeks. Gallic acid, methyl gallate, ethyl gallate and 1,2,3,4,6-penta-O-galloyl--D-glucose were isolated from the ethanol extract of callus, and paeoniflorin was identified. A dose of 5 g/ml pentagalloyl glucose resulted in depigmentation of B-16 melanoma cells without inhibition of cell propagation.     

Lipoxygenase inhibiting and antioxidant oligostilbene and monoterpene galactoside from Paeonia emodi

Paeoninol and paeonin C, oligostilbene and monoterpene galactoside, have been isolated from the methanolic extract of the fruits of Paeonia emodi. Their structures have been assigned on the basis of spectral analysis including 1D and 2D NMR techniques. In addition, 4-hydroxybenzoic acid 3, gallic acid 4 and methyl gallate 5 have also been reported for the first time from this species. Compounds 1 and 2 have displayed potent inhibitory potential against enzyme lipoxygenase in a concentration-dependent fashion with the IC(50) values 0.77 and 99.5 microM, along with ABTS(.+) radical quenching activity with IC(50) values of 147.5 and 498.2 microM, respectively.     

RP-HPLC detection of a sulphiting-induced artefact from paeoniflorin in dried roots of Paeonia lactiflora

Paeoniflorin is one of the bioactive ingredients of the roots of Paeonia lactiflora (Paeoniaceae). A comparative study of processed and non-processed commercial samples of dried roots of P. lactiflora indicated a very low level of paeoniflorin in the processed sample and the formation of a new more polar component, sodium paeoniflorin sulphonate, during treatment of the roots with sulphiting agents.     

Stereoisomeric pattern of lilac aldehyde in Silene latifolia, a plant involved in a nursery pollination system

The monoterpene lilac aldehyde is found in floral scent of several plants species, among them Silene latifolia. This plant is involved in a nursery pollination system, because a noctuid moth, Hadena bicruris, is not only pollinator but also seed predator. Lilac aldehyde is the key floral scent compound of S. latifolia for attracting Hadena. This monoterpene has three stereogenic centers, and eight different isomers are possible. Here, we analysed the ratio of lilac aldehyde isomers from plants originating from 18 different populations of S. latifolia using enantioselective multidimensional GC-MS (enantio-MDGC-MS), and compared resulting variability with variability found in total scent emitted by specimen under study. Though variability in total emitted scent was high, ratio of lilac aldehyde isomers was a more conservative trait. There was no correlation between the ratio of lilac aldehyde isomers and the total emitted floral scent pattern. Both, ratio of stereoisomers and total emitted scent were independent from the geographic origin of the plants. In conclusion, the ratio of lilac aldehyde stereoisomers in S. latifolia is a reliable trait, and may used by the nursery pollinator H. bicruris for host-plant detection.     

Protective effect of a molecular chaperone inducer, paeoniflorin, on the HCl- and ethanol-triggered gastric mucosal injury

AimsWe previously found that paeoniflorin, a major constituent of Paeonia lactiflora Pall, could induce heat shock proteins (HSPs) in cultured mammalian cells without apparent toxicity (Yan et al. 2004). We here investigated the induction of HSPs by paeoniflorin in mouse stomach and the effect of paeoniflorin on the HCl- and ethanol-triggered gastric mucosal injury in mouse.Main methodsPaeoniflorin and quercetin were intraperitoneally administered in mouse and Hsp70 and other proteins in mouse tissues were detected by western blotting.Key findingsThe intraperitoneal administration of paeoniflorin clearly induced Hsp70 in mouse stomach, and paeoniflorin had a protective effect on the HCl- and ethanol-triggered gastric mucosal injury. When quercetin was injected before paeoniflorin administration, the induction of Hsp70 was suppressed and the protective effect of paeoniflorin was also diminished. Thus, the expression level of Hsp70 was well correlated with the extent of protection against irritant-induced gastric mucosal injury. Oral injection of HCl activated nuclear factor kappa B (NF-κB) and elicited the expression of cyclooxygenase-2 (COX-2) in gastric mucosa. Prior administration of paeoniflorin, however, suppressed these effects. No apparent systemic side effect of paeoniflorin has been observed so far. Hsp70 was also induced in the liver, heart, and brain by paeoniflorin.SignificanceFrom these results, it is suggested that paeoniflorin and paeoniflorin-containing herbal medicines might be used clinically as HSP inducers for the prevention and treatment of diseases associated with protein conformation and of various other pathological states, such as stress ulcers and irritant- or ischemia-induced injuries.     

Molecular cloning and characterization of 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase (CaHDR) from Camptotheca acuminata and its functional identification in Escherichia coli

Camptothecin is an anti-cancer monoterpene indole alkaloid. The gene encoding 1-hydroxy-2-methyl-2-(E)-butenyl 4-diphosphate reductase (designated as CaHDR), the last catalytic enzyme of the MEP pathway for terpenoid biosynthesis, was isolated from camptothecin-producing Camptotheca acuminata. The full-length cDNA of CaHDR was 1686 bp encoding 459 amino acids. Comparison of the cDNA and genomic DNA of CaHDR revealed that there was no intron in genomic CaHDR. Southern blot analysis indicated that CaHDR belonged to a low-copy gene family. RT-PCR analysis revealed that CaHDR expressed constitutively in all tested plant organs with the highest expression level in flowers, and the expression of CaHDR could be induced by 100 microM methyl-jasmonate (MeJA), but not by 100 mg/L salicylic acid (SA) in the callus of C. acuminata. The complementation of CaHDR in Escherichia coli ispH mutant MG1655 demonstrated its function.     

Effects of paeoniflorin on the cerebral infarction, behavioral and cognitive impairments at the chronic stage of transient middle cerebral artery occlusion in rats

In the present study, the effects of paeoniflorin (PF), a characteristic monoterpene glucoside isolated from Paeoniae Radix, on cerebral infarction, neurological symptoms, tongue protrusion (TP) and performance in the water maze were examined at the chronic stage (4 weeks) of transient cerebral ischemia using a rat middle cerebral artery occlusion (MCAO) model. One-day (10 mg/kg, twice, s.c.) or seven-day (2.5-10 mg/kg, twice a day, s.c.) injection of PF significantly reduced the infarct volume as well as ameliorated the deficits in neurological symptoms caused by transient MCAO at chronic stage. Transient MCAO also induced impairments in TP and performance in the water maze. Treatment with PF was able to reverse or alleviate these impairments. These results indicate that PF may be effective for treatment of stroke.     

Effects of soil disturbance,fire and litter accumulation on the establishment of Cistus clusii seedlings

Cistus clusii is an early successional shrub, the most drought-resistant species of Cistus which colonises perturbed areas in the southern Iberian Peninsula and regenerates entirely from seeds after a fire. Some of the factors controlling germination and seedling establishment were examined in a field experiment in which we tested the effect of soil disturbance, fire, and litter accumulation on seedling emergence. In a first experiment, soil disturbance and fire were applied to plots in the field with a factorial design in April 1992. In a second experiment, we measured the effect of adding C. clusii litter. The number of seedlings, annual plants and grasses, and the coverage of mosses were recorded in 1993 and 1994.Soil disturbance increased the number of C. clusii seedlings almost seven-fold but did not change the number of grasses, annual plants nor moss cover. Fire significantly increased the number of C. clusii seedlings only in combination with soil disturbance, and it did not affect the presence of annuals, grasses nor moss cover. Litter increased the number of C. clusii seedlings in the following two years.Overall, soil disturbance as a single factor had the most significant effect on seedling emergence, though plots disturbed and treated with fire had the highest number of seedlings, implying that germination of C. clusii seeds was enhanced by processes that alter the hard seed coat and break the physical dormancy imposed by the testa. In addition, recruitment of C. clusii was dependent on rainfall, as drought significantly reduced the number of seedlings appearing in winter.     

(+)-Menthol and its hydroxy derivatives,novel fungal monoterpenols from the fusicoccin-producing fungi,Phomopsis amygdali F6a and Niigata 2

In our search for new fusicoccins of unique diterpene glucosides from Phomopsis amygdali, we found that a fragrant substance was formed in the early stage of fusicoccin fermentation. This fragrant constituent was isolated and identified as (+)-menthol, which is a novel fungal metabolite as the enantiomer of well-known peppermint (-)-menthol. (+)-7-Hydroxymenthol and new (+)-(6S)-hydroxymenthol were also isolated and identified as fungal metabolites. In addition, p-menthanetriol, which has been reported as the first fungal monoterpene from the fungus, was also isolated. The possible biosynthetic relationship of these metabolites is discussed.     

Effect of Various Essential Oils Isolated from Douglas Fir Needles upon Sheep and Deer Rumen Microbial Activity

The effects of essential oils isolated from Douglas fir needles on sheep and deer rumen microbial activity were tested by use of an anaerobic manometric technique. Rumen microorganisms were obtained from a sheep which had been fed mainly on alfalfa hay and dried range grass. One deer used in this study had access to Douglas fir trees the year around, whereas the other deer had no access to Douglas fir. All of the monoterpene hydrocarbons isolated from Douglas fir needles—α-pinene, β-pinene, limonene, myrcene, camphene, Δ³-carene, and terpinolene—promoted only slightly or had no effect on deer rumen microbial activity, whereas all of them promoted activity in sheep rumen microbes, except Δ³-carene and terpinolene, which inhibited activity. Of the oxygenated monoterpenes, all monoterpene alcohols—α-terpineol, terpinen-4-ol, linalool, citronellol, and fenchyl alcohol—strongly inhibited the rumen microbial activity of both sheep and deer. Monoterpene esters (bornyl acetate) produced mild inhibition for both sheep and deer microbes, and citronellyl acetate inhibited rumen microbial activity in sheep, whereas it promoted activity in both deer. Monoterpene aldehyde (citronellal) inhibited the activity of rumen microbes from both sheep and deer having no access to Douglas fir from the Hopland Field Station, whereas they produced no effect upon the deer having access to Douglas fir from the Masonite forest. Rumen microbial activity for sheep and deer was promoted slightly with aliphatic ester (ethyl-n-caproate). There was a marked difference between sheep and deer rumen microbes as affected by addition of the various essential oils. The monoterpene hydrocarbons promoted activity more on sheep rumen microbes than on deer, and the monoterpene alcohols inhibited sheep rumen microbial activity more than that of deer. Furthermore, the deer rumen microbes from Hopland Field Station were affected more than the deer from Masonite forest.     

Paeoniflorin: A neuroprotective monoterpenoid glycoside with promising anti-depressive properties

BackgroundDepression, as a prevalent and debilitating psychiatric disease, severely decreases the life quality of individuals and brings heavy burdens to the whole society. Currently, some antidepressants are applied in the treatment of severe depressive symptoms, while there are still some undesirable drawbacks. Paeoniflorin is a monoterpenoid glycoside that was firstly extracted from Paeonia lactiflora Pall, a traditional Chinese herb that is widely used in the Chinese herbal formulas for treating depression.PurposeThis review summarized the previous pre-clinical studies of paeoniflorin in treating depression and further discussed the potential anti-depressive mechanisms for that paeoniflorin to be further explored and utilized in the treatment of depression clinically.MethodsSome electronic databases, e.g., PubMed and China National Knowledge Infrastructure, were searched from inception until April 2021.ResultsThis review summarized the effective anti-depressive properties of paeoniflorin, which is related to its functions in the upregulation of the levels of monoaminergic neurotransmitters, inhibition of the hypothalamic-pituitary-adrenal axis hyperfunction, promotion of neuroprotection, promotion of hippocampus neurogenesis, and upregulation of brain-derived neurotrophic factor level, inhibition of inflammatory reaction, downregulation of nitric oxide level, etc.ConclusionThis review focused on the pre-clinical studies of paeoniflorin in depression and summarized the recent development of the anti-depressive mechanisms of paeoniflorin, which approves the role of paeoniflorin plays in anti-depression. However, more high-quality pre-clinical and clinical studies are expected to be conducted in the future.