Lipids of the roots ofAconitum septentrionale and of their processing wastes

The compositions of the lipids and fatty acids of the roots ofAconitum septentrionale and of their processing wastes have been investigated. A high level of the 18:2 and 18:3 acids has been found in the root lipids. A technological stage that concentrates in the wastes lipids that can be used as a complex of biologically active substances has been determined.Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent, fax (3712) 89 14 75. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 701–704, September-October, 1996. Original article submitted March 11, 1996.     

Qualitative mass spectrometric analysis of the total diterpene bases from the roots ofAconitum kusnezoffi

A quantitative analysis of the roots ofAconitum kusnezoffi has been made by a group of mass-spectrometric methods. Twelve diterpene bases have been studied of which ten have been identified as beiwutine, aconitine. mesaconitine, 3-deoxyaconitine, hypaconitine, neoline, songorine, isotalatisidine, talatisidine, and 10-hydroxyneoline.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 89–92, January–February, 1996. Original article submitted August 7, 1995.     

Lipids of the wastes from the processing ofAconitum leucostomum

It has been established that the wastes from the production of the drug allapinin from the epigeat pan ofAconitum leucostomum consist of nonpolar and polar lipids with a high content of phospho- and glycolipids and free fatty acids.Translated from Khimiya Prirodnykh Soedinenii, No. 1, pp. 37–40, January–February, 1995.     

Iridoids from the roots of Valeriana jatamansi and their biological activities

A new iridoid, jatamandoid A (1), and four known analogues (2-5) were isolated from the roots of Valeriana jatamansi. Their structures were elucidated on the basis of extensive spectroscopic analysis (IR, ESI-MS, HR-ESI-MS, 1-D and 2-D NMR). Five compounds were evaluated and compounds 1, 2 and 5 showed moderate neuroprotective effects against MPP(+)-induced neuronal SH-SY5Y cell death.     

Withanolide derivatives from the roots of Withania somnifera and their neurite outgrowth activities

Five new withanolide derivatives (1, 9-12) were isolated from the roots of Withania somnifera together with fourteen known compounds (2-8, 13-19). On the basis of spectroscopic and physiochemical evidence, compounds 1 and 9-12 were determined to be (20S,22R)-3 alpha,6 alpha-epoxy-4 beta,5 beta,27-trihydroxy-1-oxowitha-24-enolide (1), 27-O-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside (withanoside VIII, 9), 27-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranosyl (1-->6)-beta-D-glucopyranoside (withanoside IX, 10), 27-O-beta-D-glucopyranosylpubesenolide 3-O-beta-D-glucopyranoside (withanoside X, 11), and (20R,22R)-1 alpha,3 beta,20,27-tetrahydroxywitha-5,24-dienolide 3-O-beta-D-glucopyranoside (withanoside XI, 12). Of the isolated compounds, 1, withanolide A (2), (20S,22R)-4 beta,5 beta,6 alpha,27-tetrahydroxy-1-oxowitha-2,24-dienolide (6), withanoside IV (14), withanoside VI (15) and coagulin Q (16) showed significant neurite outgrowth activity at a concentration of 1 microM on a human neuroblastoma SH-SY5Y cell line.     

Alkaloids from the roots of Stemona tuberosa and their anti-tobacco mosaic virus activities

Stemtuberlines A (1) and B (2), two new alkaloids with a unique tricyclic pyrrolo [3,2,1-jk]benzazepine-12-one nucleus, three new croomine-type alkaloids, stemtuberlines C-E (3–5), together with seven known ones were isolated from the roots of Stemona tuberosa. The structures of the new alkaloids were elucidated based on a comprehensive spectroscopic data analysis. The absolute configurations of 1 and 2 were determined by quantum ECD calculations. The anti-tobacco mosaic virus activity of the Stemona alkaloids was firstly evaluated and compound 11 exhibited significant anti-tobacco mosaic virus activity with the curative inhibition rate of 84.6% at concentration of 50?μg/mL.     

Alkaloids of the epigeal part ofAconitum kirinense

Lepenine and the new alkaloid lepenine N-oxide have been isolated from the epigeal part ofAcontium kirinense. Institute of the Chemistry of Plant Substances, Academy of Sciences of the Republic of Uzbekistan, Tashkent. Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 734–736, September–October, 1993.     

Radical scavenging activities of flavonoids from roots of Akschindlium godefroyanum

Chemical constituents of crude ethyl acetate extract of roots of Akschindlium godefroyanum (Kuntze) H. Ohashi were investigated and seven flavonoids were isolated. Their structures were identified based on spectroscopic methods as well as by comparison with spectral data reported in the literature as six flavanonols and a flavonol including 7,4′-dihydroxy-5,3′-dimethoxyflavanonol (1), neophellamuretin (2), taxifolin (3), erycibenin D (4), geraldol (5), fustin (6) and garbanzol (7). Compounds 2, 4 and 7 were found in the genus Akschindlium for the first time. Compounds 3, 5 and 6 appeared to have free radical scavenging activities using DPPH assay with IC₅₀ of 21, 40 and 15 μg/mL, respectively.     

Alkaloids ofAconitum kirinense the structure of akiramine

The known alkaloid tuguaconitine and a new base, which has been called akiramine, have been isolated from the epigeal part ofAconitum kirinense Nakai. The structure of akiramine as 4-acetoxy-1,8-dihydroxy-6,14,16-trimethoxy-N-ethylaconitine has been established by a study of its spectral characteristics.Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 498–501, July–August, 1999.     

Alkaloids of the epigeal part ofAconitum karakolicum

The dynamics of the accumulation of alkaloids in the epigeal part ofAconitum karakolicum according to vegetation periods has been studied. It has been established that the highest content of alkaloids is found in the early period. On separating the combined alkaloids, the aporphine alkaloid isoboldine has been isolated from this plant for the first time and a new base has been obtained — napelline N-oxide, the structure of which has been shown on the basis of the results of a study of spectral characteristics and direct transition to napelline.     

Three new triterpenoid saponins from the roots of Ardisia crenata and their cytotoxic activities

Three new triterpenoid saponins, ardisicrenoside O (1), ardisicrenoside P (2) and ardisicrenoside Q (3) together with three known compounds, 3β,16α-dihydroxy-30-methoxy-28, 30-epoxy-olean-12-en, cyclamiretin A 3-O-β-d-glucopyranosyl-(1→2) -α-l-arabinopyranoside and cyclamiretin A 3-O-β-d-glucopyranosyl-(1→4) -α-l-arabinopyranoside were isolated from the roots of Ardisia crenata Sims. Their structures were determined by one- and two-dimensional NMR techniques, including HSQC, HMBC and TOCSY experiments, as well as acid hydrolysis and GC analysis. All isolates were evaluated for the cytotoxic activities on two human cancer cell lines and compounds 3, 5 and 6 showed significant cytotoxicity.     

Terpene glycosides from the roots of Sanguisorba officinalis L. and their hemostatic activities

Guided by a hemostasis bioassay, seven terpene glycosides were isolated from the roots of Sanguisorba officinalis L. by silica gel column chromatography and preparative HPLC. On the grounds of chemical and spectroscopic methods, their structures were identified as citronellol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (1), geraniol-1-O-α-L-arabinofuranosyl-(1→6)-β-D-glucopyranoside (2), geraniol-1-O-α-Larabinopyranosyl-(1→6)-β-D-glucopyranoside (3), 3β-[(α-L-arabinopyranosyl)oxy]-19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (4), 3β-[(α-L-arabinopyranosyl)-oxy]-19α-hydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (ziyu-glycoside I, 5), 3β,19α-hydroxyolean-12-en-28-oic acid 28-β-D-glucopyranoside (6) and 3β,19α-dihydroxyurs-12-en-28-oic acid 28-β-D-glucopyranoside (7). Compound 1 is a new mono-terpene glycoside and compounds 2, 3 and 5 were isolated from the Sanguisorba genus for the first time. Compounds 1–7 were assayed for their hemostatic activities with a Goat Anti-Human α2-plasmin inhibitor ELISA kit, and ziyu-glycoside I (5) showed the strongest hemostatic activity among the seven terpene glycosides. This is the first report that ziyu-glycoside Ι has strong hemostatic activity.     

Antimalarial and cytotoxic activities of pregnene-type steroidal alkaloids from Holarrhena pubescens roots

The phytochemical investigation of an alkaloidal extract of Holarrhena pubescens roots led to the isolation and identification of a new pregnene-type alkaloid, mokluangin D (1), together with nine known steroidal alkaloids (2–10). The structure of the new metabolite was determined on the basis of spectroscopic analyses including 1D- and 2D-NMR spectroscopy and mass spectrometry. Compounds 3 and 4 showed potent antimalarial activity against Plasmodium falciparum K1 stain with IC₅₀ values of 1.2 and 2.0 μM, respectively, and showed weak cytotoxic activity against the NCI-H187 cell line with IC₅₀ values of 27.7 and 30.6 μM, respectively. The substituent groups at C-3 and the carbonyl group at C-18 are important for the activity against the P. falciparum K1 stain.     

The structure of calendulosides C and D from the roots of Calendula officinalis

Summary The structure of new triterpene glycosides from the roots of potmarigold calendula (C. officinalis) has been established: oleanolic acid 3-{[galactopyranosido-(13)] [glucopyranosido-(12)]--D-glucopy-ranoside} (calenduloside C) and the 28-acyl--D-glucopyranoside of calenduloside C (calenduloside D).All-Union Scientific-Research Institute of Medicinal Plants. N. D. Zelinskii Institute of Organic Chemistry, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 3, pp. 366–373, May–June, 1975.     

Structure determination of baeckeins C and D from the roots of Baeckea frutescens

Baeckeins C (compound 1) and D (compound 2), a pair of new diastereomeric biflavonoids, were isolated from the roots of Baeckea frutescens. Their structures were elucidated on the basis of spectroscopic analysis, including HR-ESI-MS and one- and two-dimensional NMR spectra ((1)H and (13)C NMR, HSQC, HMBC, and ROESY). The absolute configurations of the 2,3-epoxide moiety for compounds 1 and 2 were determined by circular dichroism spectrometry combined with quantum chemical calculations.     

Synthesis and evaluation of fluorogenic substrates for phospholipase D and phospholipase C

Fluorogenic analogues of phosphatidylcholine and lysophosphatidylcholine, DDPB and lysoDDPB, were synthesized by an enzyme-assisted strategy. The analogues were evaluated as substrates for phospholipases C and D and lysophospholipase D. DDPB was cleaved by bacterial and plant phospholipase D (PLD) enzymes and represents the first direct fluorogenic substrate for real-time measurement of PLD activity. Both fluorogenic substrates have potential in screening for PLD and PC-PLC inhibitors and for monitoring spatiotemporal changes in PLD activity in cells. [structure: see text]     

The hydrophobic amino acids involved in the interdomain association of phospholipase D1 regulate the shuttling of phospholipase D1 from vesicular organelles into the nucleus

Phospholipase D (PLD) catalyzes the hydrolysis of phosphatidylcholine to generate the lipid second messenger, phosphatidic acid. PLD is localized in most cellular organelles, where it is likely to play different roles in signal transduction. PLD1 is primarily localized in vesicular structures such as endosomes, lysosomes and autophagosomes. However, the factors defining its localization are less clear. In this study, we found that four hydrophobic residues present in the N-terminal HKD catalytic motif of PLD1, which is involved in intramolecular association, are responsible for vesicular localization. Site-directed mutagenesis of the residues dramatically disrupted vesicular localization of PLD1. Interestingly, the hydrophobic residues of PLD1 are also involved in the interruption of its nuclear localization. Mutation of the residues increased the association of PLD1 with importin-β, which is known to mediate nuclear importation, and induced the localization of PLD1 from vesicles into the nucleus. Taken together, these data suggest that the hydrophobic amino acids involved in the interdomain association of PLD1 are required for vesicular localization and disturbance of its nuclear localization.     

Two new eremophilenolides from the roots of Ligulariopsis shichuana and their anti-phytopathogenic fungal and antifeedant activities

Two new eremophilenolides, ligushicins A (1) and B (2), and two known compounds including β-sitosterol and ursolic acid were isolated from Ligulariopsis shichuana. The structures of new compounds were established on the basis of 1D and 2D NMR data and HRESIMS data interpretation. The absolute configuration of new compounds was assigned by ECD spectroscopy, and that of ligushicins A (1) was confirmed by X-ray diffraction analysis. The antifungal and antifeedant activities of new compounds were evaluated against four plant pathogenic fungi and third-instar larvae of Plutella xylostella, respectively. Ligushicins A (1) and B (2) exhibited potent antifungal activity against Botrytis cinerea and Fusarium oxysporum with minimum inhibitory concentration (MIC) values ranging from 50 to 100 mg/L, while they also exhibited weak antifeedant activities.     

Three new secoiridoid glycosides from the rhizomes and roots of Gentiana scabra and their anti-inflammatory activities

Three new (1–3) and 17 known (4–20) iridoid and secoiridoid glycosides were isolated from a methanol extract of the rhizomes and roots of Gentiana scabra. Their chemical structures were elucidated from 1D and 2D NMR, IR absorption, and HR-ESI-MS spectra, as well as comparisons of these data with reported values. The effects of the isolated compounds on lipopolysaccharide (LPS)-stimulated bone marrow-derived dendritic cells were investigated. Compounds 6, 10 and 20 exhibited significant inhibitory effects on LPS-induced IL-12 p40 and IL-6 production with IC₅₀ values of 1.62–14.29 μM. Compound 10 also showed a strong inhibitory effect on the LPS-stimulated production of TNF-α with an IC₅₀ value of 10.45 μM.