No full-text available
To read the full-text of this research,
you can request a copy directly from the authors.
Chemical constituents from the leaves of Viburnum odoratissimum and their chemotaxonomic significance
... The species can be evergreen or semievergreen, deciduous shrubs or small trees. The scientific interest of these plants is due to the chemical components and diverse biological activities as saponin, butaniolide, terpenes and others (carotenoids, polyphenols, and flavonoids) (Cheng-Yu C, 2024;Sharifi-Rad 2021). These biochemical components are what give Viburnum plants their primary biological activities. ...
The genus _Viburnum_ L. (Adoxaceae, formally classified as Caprifoliaceae), contains approximately 163 species of high ecological value, distributed in the temperate and subtropical regions of the Northern Hemisphere and extending to the mountains of South America and Asia. Some species have been considered for contact sensitivity and the pollen allergenicity. The literature shows that some species can give contact hypersensitivity and _V. opulus_ can determine pollen allergy. The pratical implications of this research are destined to the public health practitioners and policymakers, the green desiners, and the public administrations: in fact, the specific knowledgements of the use of _Viburnum_ species in gardening can help to deduce some important considerations about the right destinations of the plants. In particular, in the case of school gardens, children’s green areas or sport areas, some species, as _V. opulus_, _V.plicatum, V. tinus, V. rhytidophyllum,_ wich cause dermatitis in the case of contact, should be avoid.
Myrcia sylvatica (G. Mey) DC. is known as “insulin plant” because local communities use the infusions of various organs empirically to treat diabetes. The leaves of seven specimens of Myrcia sylvatica (Msy-01 to Msy-07) were collected in the Brazilian Amazon. Furthermore, the essential oils were extracted by hydrodistillation and analyzed by gas chromatography coupled to mass spectrometry, and their chemical compositions were submitted to multivariate analysis (Principal Component Analysis and Hierarchical Cluster Analysis). The multivariate analysis displayed the formation of four chemical profiles (chemotypes), described for the first time as follows: chemotype I (specimen Msy-01) was characterized by germacrene B (24.5%), -elemene (12.5%), and �-caryophyllene (10.0%); chemotype II (specimens Msy-03, -06 and -07) by spathulenol (11.1–16.0%), germacrene B (7.8–20.7%), and
-elemene (2.9–7.6%); chemotype III (Msy-04 and -05) by spathulenol (9.8–10.1%),
�-caryophyllene (2.5–10.1%), and �-cadinene (4.8-5.6%); and chemotype IV, (Msy-02) by spathulenol (13.4%), caryophyllene oxide (15.0%), and �-cadinol (8.9%). There is a chemical variability in the essential oils of Myrcia sylvatica occurring in the Amazon region.
Hypericum genus, considered to comprise over 500 species that exhibit cosmopolitan distribution, has attracted human interest since ancient times. The present review aims to provide and summarize the recent literature (2012–2022) on the essential oils of the title genus. Research articles were collected from various scientific databases such as PubMed, ScienceDirect, Reaxys, and Google Scholar. Scientific reports related to the chemical composition, as well as the in vitro and in vivo pharmacological activities, are presented, also including a brief outlook of the potential relationship between traditional uses and Hypericum essential oils bioactivity.
Plant derived oils have recently been found to be more effective in pharmaceutical sectors than synthetic goods since these plants contain physiologically active chemicals with a wide range of therapeutic effects. Essential oil, also known as essence, volatile oil, etheric oil, or aetheroleum, is a complex mixture of volatile elements biosynthesised by living organisms, which is particularly abundant in aromatic plants. This research summarizes facts on the chemistry of essential oil isolated from Cyperus scariosus on the one hand and their most important biological activities on the other. The essential oil components were determined to be a complex mixture of volatile chemicals such as monoterpenes, sesquiterpene hydrocarbons, and their oxygenated derivatives using Gas Chromatography-Mass Spectrometry (GC-MS). Thermoanalytical techniques such as TGA and DSC were used to investigate the oil's stability. Infrared spectroscopy was used to provide further information on the existence of various functional groups. Furthermore, the extracted oil's antibacterial, antioxidant, and antimalarial activities were investigated. The antimalarial activity was tested against Plasmodium falciparum, and the antioxidant and free radical scavenging activity were calculated using the DPPH reagent. This comprehensive study will provide an overview of the chemicals extracted from Cyperus scariosus as well as the plant's convincing pharmacological qualities.
The genus Rosa (Rosaceae family) includes about 200 species spread in the world, and this genus shows unique advantages in medicine and food. To date, several scholars concentrated on compounds belonging to flavonoids, triterpenes, tannins, polysaccharide, phenolic acids, fatty acids, organic acids, carotenoids, vitamins. Pharmacological effects such as antineoplastic and anti-cancer properties, anti-inflammatory, antioxidant, liver protection, regulate blood sugar, antimicrobial activity, antiviral activity, as well as nervous system protection and cardiovascular protection were wildly reported. This article reviews the chemical constituents, pharmacological effects, applications and safety evaluations of Rosa plants, which provides a reference for the comprehensive utilization of medicine and food resources and gives a scientific basis for the development of medicinal plants of the genus Rosa.
Traditional Chinese medicines (TCMs) have continued to be a treasure trove. The study of chemodiversity and versatility of bioactivities has always been an important content of pharmacophylogeny. There is amazing progress in the discovery and research of natural components with novel structures and significant bioactivities in 2020. In this paper we review 271 valuable natural products, including terpenoids, steroids, flavonoids, phenylpropanoids, phenolics, nitrogen containing compounds and essential oil, etc., isolated and identified from TCMs published in journals of Chinese Traditional and Herbal Drugs (Zhong Cao Yao) and Chinese Herbal Medicines (CHMs), and focus on their structures, source organisms, and relevant bioactivities, paying special attention to structural characteristics of novel compounds and newly revealed pharmacological properties of known compounds. It is worth noting that natural products with antitumor activity still constitute the primary object of research. Among the reported compounds, two new triterpenoids, i.e., ursolic acid 3-O-β-cis-caffeate and mollugoside E, display remarkable cytotoxicity against PC-9 and HL-60 cell lines, respectively. Three known phenolic compounds, i.e., pyoluteorin, 4-hydroxy-3-methoxy cinnamaldehyde and 3,7-dimethoxy-5-hydroxy-1,4-phenanthrenequinone, exhibit significant cytotoxicity against multiple cell lines. Numerous studies on the free radical scavenging activity of reported compounds are currently underway. In vitro, three known phenolic compounds, i.e., 3,4-O-dicaffeoylquinic acid methyl ester, 3,4,5-O-tricaffeoylquinic acid methyl ester and arbutin, had more considerable antioxidant activities than vitamin C. The anti-inflammatory, anti-diabetic, hypolipidemic, neuroprotective and antimicrobial activities of isolated compounds are also encouraging. The structural characteristics and bioactivities of TCM compounds highlighted here reflect the enormous progress of CHM research in 2020 and will play a positive role in the future drug discovery and development. According to pharmacophylogeny, the phylogenetic distribution of compounds with different natures and flavors can be explored, with view to better mining TCM resources.
A wound is a complicated bioprocess resulting in significant tissue damage, which is worsened by a secondary bacterial infection, commonly Pseudomonas aeruginosa and Staphylococcus aureus. The goal of our study was to investigate the metabolic profile and possible wound-healing effect of Sanguisorba officinalis roots rhoifolin rich fraction (RRF). The LC-ESI-MS/MS analysis of S. officinalis roots crude ethanol extract resulted in a tentative identification of 56 bioactive metabolites, while a major flavonoid fraction was isolated by column chromatography and identified by thin-layer chromatography coupled with electrospray ionization/mass spectrometry (TLC-ESI/MS), where rhoifolin was the major component representing 94.5% of its content. The antibiofilm activity of RRF on the mono-species and dual-species biofilm of P. aeruginosa and S. aureus was investigated. RRF exhibited inhibitory activity on P. aeruginosa and S. aureus mono-species biofilm at 2× minimum inhibitory concentration (MIC) and 4× MIC values. It also significantly inhibited the dual-species biofilm at 4× MIC values. Moreover, the wound-healing characteristics of RRF gel formulation were investigated. Rats were randomly allocated into four groups (eight rats in each): Untreated control; Blank gel; Betadine cream, and RRF gel groups. Animals were anesthetized, and full-thickness ex-cisional skin wounds were created on the shaved area in the dorsal skin. The gels were topically applied to the wound's surface daily for 10 days. The results demonstrated that RRF had a promising wound-healing effect by up-regulating the platelet-derived growth factor (PDGF), vascular en-dothelial growth factor (VEGF), keratinocyte growth factor (KGF), and fibronectin, while metallo-proteinase-1 (MMP-1), interleukin-6 (IL-6), IL-1β, and nitric oxide (NO) levels were suppressed. It also enhanced the immune staining of transforming growth factor (TGF-β) and improved histo-pathological findings. Furthermore, it displayed an immunomodulatory action on lipopolysaccha-ride-induced peripheral blood mononuclear cells. Hence, the wound-healing effect of rhoifolin was confirmed by supporting re-epithelization, angiogenesis, antibacterial, immunomodulatory, and anti-inflammatory activities. Citation: Negm, W.A.; El-Kadem, A.H.; Elekhnawy, E.; Attallah, N.G.M.; Al-Hamoud, G.A.; El-Masry, T.A.; Zayed, A. Wound Healing Potential of Rhoifolin Rich Fraction Isolated from Sanguisorba officinalis Roots Supported by Enhancing Re-Epithelization, Angiogenesis, Anti-Inflammatory, and Antimicrobial Effects. Pharmaceuticals 2022, 15, 178.
Extensive fractionation of n-hexane extract from the dried powdered-trunks of Coffea canephora Pierre ex A.Froehner (Rubiaceae) led to the isolation of a new oleanane-skeleton triterpene, coffecanolic acid (1), along with three known analogues sumaresinolic acid (2), oleanolic acid (3), and 3-O-acetyloleanolic acid (4). The chemical structures were elucidated using FT-IR, 1D and 2D NMR and HR-ESI-MS data analysis. The isolated compounds were assayed for in vitro α-glucosidase inhibitory activity by determining their half-maximal inhibitory concentration (IC50, µM). Compounds 1–4 exhibited higher inhibitory activities when compared with acarbose, a positive control. Compound 1 was found to be the most potent molecule against α-glucosidase, with the IC50 = 83.0 ± 1.2 µM, which improved by 2.5-fold over acarbose (IC50 = 209.8 ± 0.3 µM) in this assay.
Two new sesquiterpenoids, isocyperotundone (1) and 1,4-epoxy-4-hydroxy-4,5-seco-guain-11-en-5-one (2), together with 6 known sesquiterpenoids, cyperotundone (3), cyperenoic acid (4), sugetriol triacetate (5), cyperusol A 3 (6), cyperusol A 2 (7), and cyperusol A 1 (8), were isolated from the methanol extract of the rhizomes of Cyperus rotundus L. High-resolution electrospray ionization mass spectrometry and 1-dimensional (1D) and 2D nuclear magnetic resonance spectroscopy were used to establish the structures of all the compounds. All the compounds were tested for activity on nuclear factor kappa-light-chain-enhancer of activated B cells (NF- κB) signaling. Compounds 1-7 exhibited inhibitory activity on tumor necrosis factor- α-induced activation of the NF- κB pathway, with half-maximal inhibitory concentration values ranging from 34.5 to 73.7 μmol/L.
20-Hydroxy-3-oxolupan-28-oic acid (HOA), a lupane-type triterpene, was obtained from the leaves of Mahonia bealei, which is described in the Chinese Pharmacopeia as a remedy for inflammation and related diseases. The anti-inflammatory mechanisms of HOA, however, have not yet been fully elucidated. Therefore, the objective of this study was to characterize the molecular mechanisms of HOA in lipopolysaccharide (LPS)-stimulated RAW264.7 cells. HOA suppressed the release of nitric oxide (NO), pro-inflammatory cytokine tumor necrosis factor α (TNF-α), and interleukin 6 (IL-6) in LPS-stimulated RAW264.7 macrophages without affecting cell viability. Quantitative real-time reverse-transcription polymerase chain reaction (RT-qPCR) analysis indicated that HOA also suppressed the gene expression of inducible NO synthase (iNOS), TNF-α, and IL-6. Further analyses demonstrated that HOA inhibited the phosphorylation of upstream signaling molecules, including p85, PDK1, Akt, IκBα, ERK, and JNK, as well as the nuclear translocation of nuclear factor κB (NF-κB) p65. Interestingly, HOA had no effect on the LPS-induced nuclear translocation of activator protein 1 (AP-1). Taken together, these results suggest that HOA inhibits the production of cytokine by downregulating iNOS, TNF-α, and IL-6 gene expression via the downregulation of phosphatidylinositol 3-kinase (PI3K)/Akt and mitogen-activated protein kinases (MAPKs), and the inhibition of NF-κB activation. Our findings indicate that HOA could potentially be used as an anti-inflammatory agent for medical use.
Among the classes of identified natural products, triterpenoids, one of the largest families, have been studied extensively for their diverse structures and variety of biological activities, including antitumor effects. In the present study, a phytochemical study of the green walnut husks of Juglans mandshurica Maxim led to the isolation of a new dammarane triterpene, 12β, 20(R), 24(R)-trihydroxydammar-25-en-3-one (6), together with sixteen known compounds, chiefly from chloroform and ethyl acetate extracts. According to their structural characteristics, these compounds were divided into dammarane-type, oleanane- and ursane-type. Dammarane-type triterpenoids were isolated for the first time from the Juglans genus. As part of our continuing search for biologically active compounds from this plant, all of these compounds were also evaluated for their cytotoxic activities against the growth of human cancer cells lines HepG-2 by the MTT assay. The results were shown that 20(S)-protopanaxadiol, 2α,3β,23-trihydroxyolean-12-en-28-oic acid and 2α,3β,23-trihydroxyurs-12-en-28-oic acid exhibited better cytotoxicity in vitro with IC50 values of 10.32 ± 1.13, 16.13 ± 3.83, 15.97 ± 2.47 μM, respectively. Preliminary structure-activity relationships for these compounds were discussed.
In the present study a new flavoniod 1 along with Betulin 2 Betulinic acid 3, Oleanolic acid 4 and Ursolic acid 5 were isolated from the aerial part of Viburnum grandiflorum Wall. ex DC as white amorphous powder from the chloroform fraction. On the bases of different modern spectroscopic techniques such as EIMS, UV, IR, NMR, HSQC, HMBC, COSY and NOESY the structure of compound 1 was elucidate as 6,7-bis (propenyloxy)-2-ethoxy-5-hydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one (Grandinoid).
Betulinic acid is a known natural product which has gained a lot of attention in the recent years since it exhibits a variety of biological and medicinal properties. This review provides the most important biological properties of betulinic acid.
A new stigmasterol type natural product, viburodorol A (1), along with eleven known sterols and terpenoids (2–12), were isolated from the aerial parts of Viburnum odoratissimum. The structure of 1 was elucidated on the basis of comprehensive spectroscopic analysis. It’s noteworthy that compound 2, the major constituent of this plant, can significantly stimulate glucose absorption in insulin resistant HepG2 cells without affecting cell viability. Furthermore, this compound can also restore the glucose absorption in DXMS-induced insulin resistant 3T3-L1 cells.
Graphical Abstract
Electronic supplementary material
The online version of this article (doi:10.1007/s13659-014-0021-7) contains supplementary material, which is available to authorized users.
The cytotoxicity of a hexanic fraction produced from the ethanolic crude extract, obtained from Jatropha ribifolia (Pohl) Baill, Euphorbiaceae, roots was evaluated against ten human cancer cell lines (MCF-7, NCI-ADR/RES, OVCAR-3, PC-3, HT-29, NCI-H460,786-O, UACC-62, K-562, U251) compared with doxorrubicine as positive control. Compounds jatrophone and cyperenoic acid were isolated from the hexanic extract and characterized by spectroscopic techniques (NMR of 1H, 13C and IR). The in vitro antiproliferative activity of jatrophone showed selectivity in a concentration dependent way with Total Inhibition growth of: glioma 0.57 µg mL-1 (U251), breast cancer 9.2 µg mL-1 (MCF-7), adriamycin-resistant ovarian cancer 0.96 µg mL-1 (NCI-ADR/RES), kidney 4.2 µg mL-1 (786-0), prostate cancer 8.4 µg mL-1 (PC-3), colon cancer 16.1 µg mL-1 (HT29) and leukemia 0.21 µg mL-1 (K-562).
Phytochemical investigation of Daphne penicillata Rehd led to the isolation of twenty-eight compounds, including eighteen lignans (1–18), nine monoterpenes (19–21, 23–28) and one butanolide (22). According to spectroscopic data analysis and comparison with the previously reported literature, their structures were determined. All of these compounds were isolated from D. penicillata for the first time and eighteen compounds (1, 4, 6, 8, 14–27) were firstly reported from the family Thymelaeaceae. In addition, the study introduced the chemotaxonomic significance of these compounds from D. penicillata.
Twenty-seven compounds, including six new iridoids, valeransins A−F (1−6), were isolated from the n-BuOH soluble fraction of Valeriana jatamansi. Structurally, compounds 1 and 2 are rare 8, 11-epoxy iridoids, and their absolute configuration was determined based on their experimental and calculated electronic circular dichroism (ECD) spectra. In addition, compounds 5 and 24 exhibited significant anti-influenza virus activities, with IC50 values of 7.23 and 19.83 μM, respectively. Additionally, compound 24 showed inhibition of NO production stimulated by lipopolysaccharide in RAW 264.7 cells, with an IC50 value of 27.22 μM.
A systematic analysis of the root bark of Zanthoxylum chalybeum was conducted to establish the antidiabetic potential of isolated compounds based on its ethnomedicinal use to manage diabetes. Chromatographic separation of alkaloid extracts led to isolation of three undescribed amides, chaylbemide A (1), chalybemide B (2) and chalybemide C (3) alongside the known fagaramide (4); four known benzophenanthridine alkaloids skimmianine (5), norchelerythrine (6), 6-acetonyldihydrochelerythrine (7) and 6-hydroxy-N-methyl decarine (8). The alkaloid free extracts yielded three known lignans, ailanthoidol (9), 2,3-epoxy-6,7-methylenedioxy coniferyl alcohol (10), sesamine (11), together with five known triterpenoids, lupeol (12), lupanone (13), 3α,20-dihydroxy-28-lupanoic acid (14), 20-hydroxy-3-oxo-28-lupanoic acid (15) and 3α,20,28-trihydroxylupane (16). The structures of the compounds were established based on 1D and 2D NMR spectroscopic and mass spectrometric experiments. Compounds 1-8 displayed inhibitory activities against both α-amylase and α-glycosidase in the range of IC50 = 43.22-49.36 μM which showed no significant (p ˃ 0.05) difference to the positive control acarbose (IC50 = 42.67; 44.88 μM). The results confirmed anti-hyperglycemic potential of alkaloids from Z. chalybeum which lends credence to its use towards management of diabetes susceptibilities.
Two new compounds, adinandrolide (1) and adipoiloside (2), together with twelve known compounds 3–14, were isolated and identified from Adinandra poilanei leaves. In the α-glucosidase activity evaluation, compounds 5–7 and 10 strongly inhibited enzyme activity with IC50 values ranging from 1.29 ± 0.03 μg/mL to 3.13 ± 0.07 μg/mL. Compounds 9, 11, and 13–14 showed significant inhibition with IC50 values of 13.01 ± 0.32 μg/mL to 16.00 ± 0.35 μg/mL, while adipoiloside (2) displayed moderate inhibitory activity. In addition, pomolic acid (10) showed strong cytotoxicity against four tested cancer cell lines.
Multi- drug resistant microbial pathogens are a serious global health problem and thus new antibacterial agents, which are effective both alone and in combination with traditional antibiotics, are urgently needed. Hence, the objective of the present study was to investigate the antibacterial activity of 6β-hydroxy-3-oxolup-20(29)-en-28-oic acid (6β-hydroxy betunolic acid) isolated from the bark of Schumacheria castaneifolia and its effect when combined with oxacillin. Antibacterial potential of 6β-hydroxy betunolic acid alone was performed using broth micro dilution assay against sixteen bacterial strains which included eight standard strains [Staphylococcus aureus (ATCC 29213 and ATCC 25923), Enterococcus faecalis (ATCC 29212), Escherichia coli (ATCC 35218 and ATCC 25922), carbapenemase producing Kebsiella pneumonia (ATCC BAA 1705), carbapenemase non-producing K. pneumonia (ATCC BAA 1706) and Pseudomonas aeruginosa (ATCC 27853)] and four strains each of clinically isolated meropenem resistant Acinetobactor sp. and methicillin resistant S. aureus (MRSA) which were included in the urgent threat list and serious threat list, respectively in 2019 by the Centers for Disease Control and Prevention in the United States. Its effect when combined with oxacillin was tested against S. aureus (ATCC 29213) and MRSAs using a checkerboard dilution method. The results indicated that 6β-hydroxy betunolic acid had antibacterial activity against the tested Gram positive organisms with MICs ranging from 16-32 mg L⁻¹ (MIC of oxacillin and meropenem ranged from 0.25-16 and 0.03-128 mg L⁻¹ respectively). The high MIC values (>1024 mg L⁻¹) of 6β-hydroxy betunolic acid against Gram negative strains indicated a likely lack of activity. Further, 6β-hydroxy betunolic acid exhibited synergistic effect with oxacillin against Staphylococcus aureus (0.49) and showed an additive effect against all the tested MRSAs. The present study suggested that the antibacterial activity of the 6β-hydroxy betunolic acid is restricted to Staphylococcus isolates and possibly Enterococcus faecalis. Further testing on different types of Gram positives and identification of the exact mechanism of action would be of importance.
A phytochemical study of the leaves and twigs of Elaeagnus umbellata Thunb. has led to the isolation and identification of 12 compounds, including two flavonoid coumaroyl glycosides (1 and 2), two simple phenolic compounds (3 and 4), one coniferyl alcohol derivative (5), one monoterpene (6), two pairs of enantiomeric neolignans (7a/7b and 8a/8b), and a pair of enantiomeric sesquineolignans (9a/9b). The structures of these compounds were elucidated through the analysis of their MS, ECD, and 1D/2D NMR spectra as well as comparison with previously reported data. This is the first time that 1 and 2 have been isolated from this species, and the first time that 5, 6, 7a, 7b, 8a, 8b, 9a, and 9b have been identified in the Elaeagnaceae family.
Introduction: Pentacyclic triterpenoids (PCTs) are secondary plant metabolites. They are of exceptional interest as biologically active substances and raw materials for a wide range of medications. Thus, the development of a methodology for rapid screening of PCTs in plant biomass is an important task. Objective: The goal of this work was to develop an approach for simultaneous screening and semi-quantitative determination of PCTs in plant tissues by liquid chromatography–tandem mass spectrometry with a precursor ion scan (PrecIS).
Materials and methods: Pressurised liquid extraction (PLE) with methanol was used for the isolation of PCTs from plant biomass. Screening and semi-quantitative determination
of PCTs in the obtained extracts were carried out by reversed phase highperformance liquid chromatography–tandem mass spectrometry in a PrecIS mode.
Results: The product ion at m/z 95 with collision energy of 40 V was used as a diagnostic
ion to identify PCTs by the PrecIS mode. In plant materials, 26 PCTs and their derivatives, such as PCTs esters and glycosides, were detected and identified. Calculation of the relative response factor for nine available PCTs showed that using a betulin calibration curve allows us to estimate the semi-quantitative content of PCTs and their derivatives in plant PLE extracts.
Conclusion: The developed approach can be applied for simultaneous untargeted screening and semi-quantitative determination of PCTs and their derivatives in various plants at sub-parts per million levels.
Ten cardiac glycosides (1-10) including six 20,22-dihydrodigitoxigenin and four gitoxigenin glycosides were isolated from the stems of Vallaris glabra together with six known triterpenoid cinnamates. Spectroscopic data of these previously undescribed compounds are reported. All isolates were evaluated for their growth inhibitory activities against three cancer cell lines, and compound 2 was the most active against KB cells with an IC50 value of 0.03 ± 0.001 μM. Also, compounds 1, 3, 5, and 6 and the triterpenoid cinnamates 11-13 showed inhibitory activity (IC50 < 10 μM) for one or more of the cell lines used.
As a part of our ongoing search for neuroprotective compounds from natural products, two new iridoid glycosides, vibsansuspenside A-B (1-2), along with five known terpenoids (3-7), were isolated from the dry leaves of Viburnum odoratissimum. Their chemical structures were well determined by means of NMR spectroscopic data as well as HRESIMS analysis. All compounds were detected for their neuroprotective effects against H2O2-induced damage in human dopaminergic neuroblastoma cells (SH-SY5Y). Among them, compound 3 displayed the most potent neuroprotective ability, and further investigation by Annexin V/PI and Western blot analysis demonstrated that compound 3 could protect SH-SY5Y cells from oxidative damage through inhibiting cell apoptosis.
Three new neolignans, fordianoles A-C (1–3), characterized as (7S,8R)-4-hydroxy-3,3′,5′-trimethoxy-8′,9′-dinor-8,4′-oxyneolignan-7,7′,9-triol, (7R,8R)-4-hydroxy-3,3′,5′-trimethoxy-8′,9′-dinor-8,4′-oxyneolignan-7,7′,9-triol, and (7R,8R)-4-hydroxy-3,3′,5′-trimethoxy-8,4′-oxyneolignan-7,9,9′-triol-7′-one, together with an unusual γ-lactone, 3-(3,4-dihydroxyphenyl)-4-pentanolide (4), and twenty-five known compounds (5–29) were isolated from the aerial parts of Viburnum fordiae Hance. Their structures including absolute configurations were determined by spectroscopic and chemical methods. Among them, compounds 6, 7, 11–15, 17–28 were isolated from the Viburnum genus for the first time. The anti-inflammatory and antioxidant activities of all compounds were evaluated in vitro. Compounds 15, 19, 20 and 29 showed significant inhibitory activity on NO production in RAW264.7 cells stimulated by LPS with IC50 values ranging from 8.60 to 13.92 μM. Meanwhile, compounds 1–4, 15, 19, 20, 22, 23, 25, 26 and 29 exhibited varying antioxidant activities through DPPH, ABTS free radical scavenging and FRAP assays.
Six new cardenolides (1-6), including three 14-hydroxylated cardenolides and three 14-carbonylated cardenolides were isolated from the dried aerial parts of Nerium oleander Linn in addition to twenty-seven known compounds (7-33). Their structures were elucidated on the basis of extensive spectroscopic evidences and single-crystal X-ray diffraction analysis. Compounds 1, 4, 7-10 and 13 exhibited significant cytotoxicity against four colon cancer cell lines (HCT116, HT29, SW620, RKO), one gastric cancer cell line (GT) and one cervical cancer cell line (HeLa) in vitro.
Bioassay-guided fractionation of the ethanolic extract of the stem bark of Albizia julibrissin led to the isolation of ten new oleanane-type triterpenoid saponins, julibrosides J37–J46 (1–10), along with six known analogues (11–16). In addition, 11 prosapogenins (17–27) were prepared by mild or strong alkaline hydrolysis of the total saponin. The structures of 1 − 27 were determined by spectroscopic and chemical means, and their cytotoxicities against four human cancer cell lines, BGC-823, A549, HCT-116, and HepG2 were evaluated. Compounds 5–16 exhibited significant inhibitory activity with IC50 values ranging from 2.59 to 9.30 μM, and 8 turned out to be the most active compound with all IC50 values < 5 μM. A preliminary structure-activity relationship of these saponins clearly indicated that the outer monoterpenoid moiety (MT′) is a crucial substituent for cytotoxicity, and the linkage sites of the MT′ unit greatly influenced the activity. It could also be inferred that the existence of 16-OH of the aglycone almost has no effect on cytotoxicity and the N-acetyl-glucosamine moiety at C-3 seems to enhance activity.
Phytochemical investigation of the leaves and twigs of Lithocarpus litseifolius and Lithocarpus corneus resulted in the isolation of four new triterpenoids (1–4), three triterpenoids (5–7) isolated from a natural source for the first time, and six known compounds (8–13). In addition, four known triterpenoids (14–17) were isolated from L. corneus. Compound 1 is a 3,4-seco-lupane-type triterpenoid, and compounds 2–4 are lupane-type triterpenoids in different oxidation states. The structures of all isolated compounds were identified by spectroscopic methods, especially NMR and mass spectrometry data. The absolute configuration of 2 and 3 was confirmed by X-ray single crystallographic analysis. The anti-inflammatory activities of 1–17 and anti-HIV activities of 2–17 were evaluated. Among them, 3-epi-betulinic acid (8) showed a strong anti-HIV activity comparable to abacavir, a drug used for treating HIV/AIDS. 3,4-seco-4(23),20(29)-lupadiene-3,28-dioic acid (5) exhibited potent inhibition of superoxide-anion generation with 86.9 ± 2.8% inhibition at 1 µM.
The bark of Betula platyphylla var. japonica (Betulaceae) has been used to treat pneumonia, choloplania, nephritis, and chronic bronchitis. This study aimed to investigate the bioactive chemical constituents of the bark of B. platyphylla var. japonica. A bioassay-guided fractionation and chemical investigation of the bark of B. platyphylla var. japonica resulted in the isolation and identification of a new lupane-type triterpene, 27-hydroxybetunolic acid (1), along with 18 known triterpenoids (2–19). The structure of the new compound (1) was elucidated on the basis of 1D and 2D NMR spectroscopic data analysis as well as HR-ESIMS. Among the known compounds, chilianthin B (17), chilianthin C (18), and chilianthin A (19) were triterpene-lignan esters, which are rarely found in nature. Compounds 4, 6, 7, 17, 18, and 19 showed significant antioxidant activities with IC50 values in the range 4.48–43.02 μM in a DPPH radical-scavenging assay. However, no compound showed significant inhibition of acetylcholine esterase (AChE). Unfortunately, the new compound (1) exhibited no significance in both biological activities. This study strongly suggests that B. platyphylla var. japonica bark is a potential source of natural antioxidants for use in pharmaceuticals and functional foods.
An update of the Angiosperm Phylogeny Group (APG) classification of the orders and families of angiosperms is presented. Several new orders are recognized: Boraginales, Dilleniales, Icacinales, Metteniusiales and Vahliales. This brings the total number of orders and families recognized in the APG system to 64 and 416, respectively. We propose two additional informal major clades, superrosids and superasterids, that each comprise the additional orders that are included in the larger clades dominated by the rosids and asterids. Families that made up potentially monofamilial orders, Dasypogonaceae and Sabiaceae, are instead referred to Arecales and Proteales, respectively. Two parasitic families formerly of uncertain positions are now placed: Cynomoriaceae in Saxifragales and Apodanthaceae in Cucurbitales. Although there is evidence that some families recognized in APG III are not monophyletic, we make no changes in Dioscoreales and Santalales relative to APG III and leave some genera in Lamiales unplaced (e.g. Peltanthera). These changes in familial circumscription and recognition have all resulted from new results published since APG III, except for some changes simply due to nomenclatural issues, which include substituting Asphodelaceae for Xanthorrhoeaceae (Asparagales) and Francoaceae for Melianthaceae (Geraniales); however, in Francoaceae we also include Bersamaceae, Ledocarpaceae, Rhynchothecaceae and Vivianiaceae. Other changes to family limits are not drastic or numerous and are mostly focused on some members of the lamiids, especially the former Icacinaceae that have long been problematic with several genera moved to the formerly monogeneric Metteniusaceae, but minor changes in circumscription include Aristolochiaceae (now including Lactoridaceae and Hydnoraceae; Aristolochiales), Maundiaceae (removed from Juncaginaceae; Alismatales), Restionaceae (now re-including Anarthriaceae and Centrolepidaceae; Poales), Buxaceae (now including Haptanthaceae; Buxales), Peraceae (split from Euphorbiaceae; Malpighiales), recognition of Petenaeaceae (Huerteales), Kewaceae, Limeaceae, Macarthuriaceae and Microteaceae (all Caryophyllales), Petiveriaceae split from Phytolaccaceae (Caryophyllales), changes to the generic composition of Ixonanthaceae and Irvingiaceae (with transfer of Allantospermum from the former to the latter; Malpighiales), transfer of Pakaraimaea (formerly Dipterocarpaceae) to Cistaceae (Malvales), transfer of Borthwickia, Forchhammeria, Stixis and Tirania (formerly all Capparaceae) to Resedaceae (Brassicales), Nyssaceae split from Cornaceae (Cornales), Pteleocarpa moved to Gelsemiaceae (Gentianales), changes to the generic composition of Gesneriaceae (Sanango moved from Loganiaceae) and Orobanchaceae (now including Lindenbergiaceae and Rehmanniaceae) and recognition of Mazaceae distinct from Phrymaceae (all Lamiales).
A bioassay survey was conducted of constituents of leaves of Viburnum odoratissimum Ker., a “fish poison” plant. The bioassays led to the isolation of a new piscicidal compound vibsanine A (TLm against Oryzias latipes, 0.18μg/ml), a new plant growth inhibitor vibsanine B (IC50 against root growth of rice seedlings, 57μg/ml) and related compounds vibsanines C, D, E and F.
From Viburnum awabuki K. KOCH (Caprifoliaceae), four new acetyl glucosides of scopoletin, 2'6'-di-o-acetylscopolin (1), 3', 6'-di-O-acetylscopolin (2), 6'-O-acetylscopolin (3) and 2'-O-acetylscopolin (4), and two lupane-type triterpenes, 6α-hydroxylup-20(29)-en-3-on-28-oic acid (6) and its 6β-epimer (7), were isolated. Their structures were elucidated on the basis of physicochemical evidence, including proton and carbon-13 nuclear magnetic resonance spectrometry.
A phytochemical study on the whole plant of Spermacoce latifolia led to the isolation of a new ursane triterpene acid, 3β,6β,23-trihydroxy-urs-12,20(30)-dien-28-oic acid (1), and a new oleanane triterpene acid, 3β,6β,29-trihydroxy-olean-12-en-28-oic acid (2), together with seven known triterpenic acids (3–9). Their structures were established on the basis of detailed spectroscopic analysis, including one- and two-dimensional NMR, ESI–MS and HR–ESI–MS techniques. All the compounds were isolated from S. latifolia for the first time. Compounds 3, 5, 6 and 9 were found to show in vitro growth inhibitory activity against three assayed human cancer cell lines MCF-7, NCI-H460 and HepG-2 with IC50 values from 9.53 to 80.20 mM. Compounds 1 and 3–9 were further revealed to show significantly in vitro α-glucosidase inhibitory activity with IC50 values from 0.009 to 0.422 mM, most of which were more potent than the reference compound acarbose (IC50 0.409 mM).
A new triterpene saponin, gymnocladus saponin D (5), having a glycosyl monoterpene carboxylate and a monoterpene carboxylate group, was isolated and its structure was characterized as the (6S)-2-trans-2, 6-dimethyl-6-hydroxy-2, 7-octadienoate of 2β, 23-dihydroxy-3-O-α-L-rhamno-pyranosyl-21-O-[(6S)-2-trans-2, 6-dimethyl-6-α-L-arabinopyranosyloxy-2, 7-octadienoyl]-acacic acid 28-O-β-D-xylopyranosyl-(1→3)-β-D-xylopyranosyl-(1→2)-[L-rhamnopyranosyl-(1→6)]-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside, on the basis of chemical and physicochemical evidence.
Three new monosubstituted sucrose fatty acid esters, 1–3, were isolated from Equisetum hiemale L., together with nine known compounds, 4–12. Their structures were elucidated by spectroscopic analyses. Compounds 5, 6, and 10–12 were isolated from the title plant for the first time. All these compounds were evaluated for their cytotoxic activity. However, none of them was cytotoxic.
Highlights
► Twelve compounds were isolated from C. venezuelanus. ► This work constitute the first phytochemical report for C. venezuelanus. ► Chemical profile identified in this specie was similar to that of C. icaco. ► This work suggests a chemosystematic relationship between Licania and Chrysobalanus.
The structure of 23-hydroxy-3-oxo-urs-12-en-28-oic acid, isolated from the twigs and leaves of Cussonia natalensis, has been determined by spectrometric methods.
Yellow birch, Betula alleghaniensis, is a dark-barked birch species that is widely utilized in the northeastern region of the United States for pulp and solid wood products. Currently, the bark is used only as a low value fuel source. In this study, the triterpenoid composition of the outer bark of B. alleghaniensis was investigated in order to evaluate potential for use as a resource for specialty chemicals. Seventeen triterpenoids, including four new compounds, were isolated and identified. Previously known compounds included lupeol, lupenone, betulone, betulin, betulonic acid, lupenyl formate, lup-20(29)-ene-30-ol-3-one, lup-20(29)-ene-3β,30-diol, lup-20(29)-ene-28-ol-30-al, 29-norlupan-3β-ol-20-one, lupan-20-ol-3-one, lupan-3β,20-diol, and lupan-3β-ol-29-oic acid. The four new compounds isolated from yellow birch were lup-20(29)-ene-28-ol-3-one-30-al, 29-norlupan-3,20-dione, 29-norlupan-28-ol-3,20-dione, and lupan-20,28-diol-3-one.
Three genuine saponins, named kinmoonosides A-C (1-3), have been isolated, together with a new monoterpenoid (4), from a methanolic extract of the fruits of Acacia concinna. The structures of kinmoonosides A-C were elucidated on the basis of spectral analysis as 3-O-{alpha -L-arabinopyranosyl(1-->6)[beta -D-glucopyranosyl(1-->2)]-beta -D-glucopyranosyl)-21-O-{(6R,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2'E)-6'-hydroxyl-2'-hydroxymethyl-6'-methyl-2', 7'-octadienoyl-beta -D-quinovopyranosyl]-2,7-octadienoyl} acacic acid 28-O-alpha -L-arabinofuranosyl(1-->4)-[beta -D-glucopyranosyl(1-->3)]-alpha -L-rhamnopyranosyl(1-->2)]-beta -D-glucopyranosyl ester (1); 3-O-(alpha -L-arabinopyranosyl(1-->6)-[beta -D-glucopyranosyl(1-->2)]-beta -D-glucopyranosyl}-21-O-{(6S,2E)-2-hydroxymethyl-6-methyl-6-O-[4-O-(2'E)-6'-hydroxyl-2'-hydroxymethyl-6'-methyl-2',7'-octadienoyl-beta -D-quinobopyranosyl]-2,7-octadienoyl}acacic acid 28-O-alpha -L-arabinofuranosyl(1-->4)-[beta -D-glucopyranosyl(1-->3)]-alpha -L-rhamnopyranosyl(1-->2)-beta -D-glucopyranosyl ester (2); and 3-O-{alpha -L-arabinopyranosyl(1-->6)-[beta -D-glucopyranosyl(1-->2)]-beta -D-glucopyranosyl}-21-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7- octadienoyl]acacic acid 28-O-alpha -L-arabinofuranosyl(1-->4)-[beta -D-glucopyranosyl(1-->3)]-alpha -L-rhamnopyranosyl-(1-->2)-beta -D-glucopyranosyl ester (3), respectively. The new monoterpenoid 4 was determined as 4-O-[(2E)-6-hydroxyl-2-hydroxymethyl-6-methyl-2,7-octadienoyl] -D-quinovopyranose. Compounds 1-3 showed significant cytotoxicity against human HT-1080 fibrosarcoma cells.
Initial phytochemical investigation of the previously unstudied plant species Sandwithia guyanensis yielded two crystalline compounds that were unambiguously identified by 2D-nmr spectroscopy as cyperenol and cyperenoic acid. The former compound has been reported only once previously, while the latter has never previously been isolated as a natural product. While the two structural characterizations required ca. 40 mg of sample and 16-24 h of spectrometer time, very recent advances should make it possible to carry out similar characterizations with as little as 1-2 mg of sample. The implications of this for strategies of phytochemical research are discussed.
A new lupane type triterpene, 3β,20,25-trihydroxy lupane, was isolated from the petrol extract of the leaves of Rhus taitensis together with the known compounds 3,20-dihydroxylupane, 20-hydroxylupane-3-one, 20,28-dihydroxylupane-3-one, 3,16-dihydroxy lup-20(29)-ene and 28-hydroxy-β-amyrone. Their structures were determined by means of spectral methods.
A new norisoprenoid, (3R,6R,7E)-3-hydroxy-4,7-megastigmadien-9-one, was isolated together with seven known norisoprenoids, (−)-loliolide, (+)-isololiolide, (6R,7E)-4,7-megastigmadien-3,9-dione, (6S,7E)-6-hydroxy-4,7-megastigmadien-3,9-dione, (3S,7E)-3-hydroxy-5,7-megastigmadien-9-one, (3S,5R,6S,7E)-5,6-epoxy-3-hydroxy-7-megastigmene-9-one, (3S,5R,7E,8R)-3,5-dihydroxy-6,7-megastigmadien-9-one and eight known phenolic compounds, trans-ferulic acid, cis-ferulic acid, trans-p-coumaroyl methyl ester, umbelliferone, veratric acid, p-hydroxybenzaldehyde, p-hydroxybenzoic acid, p-methoxybenzoic acid, from the leaves of Viburnum dilatatum. Their structures were established on the basis of chemical evidence and spectral data.
In addition to chloromaloside A, three new steroidal saponins, diuranthosides A–C, were isolated from the fresh roots of Diuranthera major. On the basis of chemical and spectroscopic analysis, the structures of diuranthosides A–C were established as neotigogenin 3-O-β-d-glucopyranosyl(1→2)-[β-d-xylopyranosyl(1→3)]-β-d-glucopyranosyl (1→4)-β-d-galactopyranoside, neohecogenin 3-O-β-d-glucopyranosyl(1→3)-β-d-xylopyranosyl(1→3)-[β-d-glucopyranosyl(1→2)]-β-d-glucopyranosyl(1→4)-β-d-galactopyranoside neohecogenin 3-O-β-d-glucopyranosyl (1→3)-β-d-glucopyranosyl(1→2)-[β-d-glucopyranosyl (1→3)-β-d-xylopyranosyl (1→3)]-β-d-glucopyranosyl(1→4)-β-d-galactopyranoside, respectively.
Olean-12-en-3β,9α,11α-triol was isolated together with the known monoterpene lactone, loliolide, from the whole herb of Euphorbia supina.
From the leaves of Enkianthus campanulatus were isolated three new triterpenes, 3-oxo-19,23,24-trihydroxyurs-12-en-28-oic acid, 3β,6β, 19,23-tetrahydroxyurs-12-en-28-oic acid and 3β,6β,23-trihydroxyurs-12-en-28-oic acid.
From the seeds of Yucca glauca Nutt., sarsasapogenin. markogenin. tigogenin. neo-tigogenin. neo-gitogenin, hecogenin and gloriogenin have been isolated and identified. Sarsasapogenin was the predominant sapogenin. Markogenin and gloriogenin have not been reported in leaves, roots or rhizomes of this species before. Small amounts of a sapogenin believed to be either diosgenin or yamogenin were also detected.