Veronicosid,ein neues Iridoidglucosid aus Veronica officinalisL.(Scrophulariaceae)

Veronicoside, a new iridoid glucoside from Veronica officinalis L. (Scrophulariaceae) A new iridoid glucoside, Veronicoside ( 1 ) has been isolated from Veronica officinalis L. The structure of 1 has been determined by chromatographic and spectroscopic analysis as 6-benzoylcatalpol.     

Verproside,a New Iridoid Glucoside from Veronica officinalis L. (Scrophulariaceae)

A new iridoid glucoside, verproside (2) , has been isolated from Veronica officinalis L. and its structure has been established to be 6-O-protocatechuoylcatalpol.     

Ladroside (= 6′-Caffeoyl-mussaenoside), a New Iridoid Glucoside from Veronica officinalis L. (Scrophulariaceae) and the elucidation of the absolute configuration at C(8) of mussaenoside

A new iridoid glucoside, named ladroside, together with mussaenoside (1) [2], has been isolated from Veronica officinalis L . The structure of ladroside (4) and the identity of mussaenoside have been established by spectral analysis. Additionally, the absolute configuration at C(8) carrying the tertiary hydroxyl group has been established by chemical evidence.     

Allobetonicoside and 6-O-Acetylmioporoside: Two new iridoid glycosides from Betonica officinalis L.

A new allose-containing iridoid diglycoside, allobetonicoside ( 1 ), and a new acyl iridoid glucoside, 6-O-acetylmioporoside ( 2 ) have been isolated from the aerial parts of Betonica officinalis L. in addition to two known iridoid glucosides, acetylharpagide ( 3 ) and reptoside ( 4 ). Their structures have been determined by spectroscopic methods as well as by means of chemical evidence.     

Phenylethanoid and iridoid glycosides from Veronica persica

A new phenylethanoid glycoside, persicoside (1) and three known phenylethanoid glycosides, acteoside (2), isoacteoside (3) and lavandulifolioside (4) were isolated from the aerial parts of Veronica persica. On the basis of spectral analyses, the structure of the new compound was elucidated to be 3,4-dihydroxy-beta-phenylethoxy-O-[beta-D-glucopyranosyl-(1-->2)]-[beta-D-glucopyranosyl-(1-->3)]-4-O-caffeoyl-beta-D-glucopyranoside. Persicoside (1) and acteoside (2) exhibited radical scavenging activity against 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. Beside phenylethanoid glycosides, a hexitol, dulcitol (5) and seven known iridoid glucosides, aucubin (6), veronicoside (7), amphicoside (8), 6-O-veratroyl-catalpol (9), catalposide (10), verproside (11) and verminoside (12) were isolated.     

Iridoid glucosides from Veronica hederifolia

A new iridoid glucoside, urphoside A, and six known iridoid glucosides, pikuroside, aucubin, veronicoside, catalposide, amphicoside, and verminoside, were isolated from Veronica hederifolia together with a known megastigmane glucoside, 3-hydroxy-5,6-epoxy-beta-ionol-9-O-beta-D-glucopyranoside, and a hexitol, dulcitol. The structures of the isolated compounds were established by the extensive 1D- and 2D-NMR spectroscopy.     

Headspace Sorptive Extraction (HSSE) in the Headspace Analysis of Aromatic and Medicinal Plants

A new sampling technique, Headspace Sorptive Extraction (HSSE), is here applied for the first time to the headspace sampling of medicinal and aromatic plants. The analyte partition coefficient between HSSE‐PDMS stir bar and sample headspace (K₁), the concentration factor (CF), the reproducibility, and the minimum recoverable amount were determined by analyzing standard solution of high volatility C₅–C₇ compounds with different polarities and structures (cyclohexane, propyl acetate, hexanal, 1‐hexen‐3‐ol, isoamyl acetate, and 2‐heptanol). Four aromatic and medicinal plants, viz. rosemary (Rosmarinus officinalis L.), sage (Salvia officinalis L.), thyme (Thymus vulgaris L.), and valerian (Valeriana officinalis L.) were analyzed by HSSE‐GC with PDMS stir bars, and their concentration capacity was compared with those of S‐HS and HS‐SPME with different fibers. HSSE showed very high concentration capability with both standard and real sample components.     

The isolation and characterization of indole alkaloids from the fruits of Kopsia officinalis

Sixteen alkaloids have been isolated from the fruits of Kopsia officinalis Tsiang and P. T. Li (Apocynaceae), a plant commonly used in folk medicine for treating tonsillitis and rheumatism. Ten of them were identified as known alkaloids — eburnamenine ( 1 ), kopsanone ( 2 ), 5, 18-dioxokopsan ( 3 ), kopsinilam ( 4 ), kopsinine ( 5 ), pleiocarpine ( 6 ), kopsamine ( 7 ), N-carbomethoxy-12-methoxykopsinaline ( 8 ), N-carbomethoxy-11, 12-dimethoxykopsinaline ( 9 ) and (+)-vincadifformine ( 13 ). The other three have now been proved to be new. They are N-carbomethoxy-11-hydroxy-12-methoxy-kopsinaline ( 10 ), N-carbomethoxy-11-methoxy-12-hydroxykopsinaline ( 11 ) and kopsamine N-oxide ( 12 ).     

Steroidal glycosides from Veronica chamaedrys L. Part I. The structures of chamaedrosides C, C1, C2, E, E1 and E2

Two new spirostane glycosides, chamaedrosides C (1) and C1 (2), two new furostane glycosides, chamaedrosides E (4) and E1 (5), and two new furospirostane glycosides, chamaedrosides C2 (3) and E2 (6), have been isolated from Veronica chamaedrys L. plants. Their structures were determined on the basis of chemical evidence and extensive spectroscopic methods, including 1D- and 2D-NMR experiments, as well as MS analysis. The given compounds have been found for the first time.     

Antimelanogenic and Antimigration Properties of the Ethyl Acetate Fraction of Calendula officinalis Flowers on Melanoma Cells

Calendula officinalis L., commonly known as marigold, is not only cultivated for ornamental purposes but is also used as a traditional medicinal herb. Its flowers have been used to treat various skin diseases, including rashes, burns, cuts and bruises, since ancient times. However, to our knowledge, the impact of C. officinalis L. on melanoma and its mechanism have not been clarified. The aim of this work was to investigate the chemical characterization and antimelanogenic and antimigration activities of the ethyl acetate fraction of C. officinalis flowers (EFC), as well as elucidate the potential mechanism. The obtained results showed that EFC markedly decreased α‐MSH‐induced melanin production and the cell migration ability of melanoma cells in a dose‐dependent manner. Additionally, EFC significantly inhibited the activity and expression of matrix metalloproteinase 2 (MMP‐2) via suppressing the mitogen‐activated protein kinase (MAPK) signaling pathway. Taken together, the present study demonstrated that C. officinalis flowers can be used as a natural source of antimelanogenisis and antimigration regent to treatment or prevent skin diseases.     

Increased synthesis of a new oleanane-type saponin in hairy roots of marigold (Calendula officinalis) after treatment with jasmonic acid

Native plant of marigold (Calendula officinalis L.) synthesizes oleanolic acid saponins classified as glucosides or glucuronides according to the first residue in sugar chain bound to C-3 hydroxyl group. Hairy root culture, obtained by transformation with Agrobacterium rhizogenes strain 15834, exhibit a potent ability of synthesis of oleanolic acid glycosides. The HPLC profile of saponin fraction obtained from C. officinalis hairy roots treated with plant stress hormone, jasmonic acid, showed the 10-times increase of the content of one particular compound, determined by NMR and MALDI TOF as a new bisdesmoside saponin, 3-O-β-d-glucuronopyranosyl-28-O-β-d-galactopyranosyl-oleanolic acid. Such a diglycoside does not occur in native C. officinalis plant. It is a glucuronide, whereas in the native plant glucuronides are mainly accumulated in flowers, while glucosides are the most abundant saponins in roots. Thus, our results revealed that the pathways of saponin biosynthesis, particularly reactions of glycosylation, are altered in C. officinalis hairy root culture.     

Determination of Oleanolic, Betulinic and Ursolic Acid in Lamiaceae and Mass Spectral Fragmentation of Their Trimethylsilylated Derivatives

Phytochemical investigations of different species of Lamiaceae family (rosemary-Rosmarinus officinalis L., sage-Salvia officinalis L., winter savory-Satureja montana L., clary sage-Salvia sclarea L. and sticky sage-Salvia glutinosa L.), using gas chromatography and mass spectrometry (GC-MS) were performed. The studies were focused on oleanolic, betulinic and ursolic acid. Since oleanolic and ursolic acid are position isomers with very similar structures, the difficulties in their separation and identification have been reported by several authors. However, both compounds can be well distinguished by order of elution during gas chromatography and by intensities of the fragment ion signals in their mass spectra, where the retro-Diels-Alder reaction was primarily observed. A combination of ultrasonic extraction, solid phase extraction, size exclusion chromatography, trimethylsilylation, and GC-MS resulted in simultaneous separation, identification and quantification of the mentioned compounds. The compounds have been identified by retention time and comparison of mass spectra with those of pure standards. The mass spectral fragmentation behavior of all three derivatised acids was investigated. The obtained characteristic fragment patterns are discussed in the presented work. Good linearity over the concentration range 1–50 mg L⁻¹ for all three compounds was confirmed. The correlation coefficients (r ² ) were in the range of 0.9980–0.9983. Quantitative analyses of different Lamiaceae extracts showed that the oleanolic acid content ranged from 0.09 to 0.9% dry weight, content of betulinic acid ranged from traces to 0.6%, and that of ursolic acid varied from 0.09 to 1.6% dry weight.     

New cucurbitacine glycosides fromGratiola officinalis L.

Summary Eight new cucurbitacine glycosides were isolated from hedgehyssopGratiola officinalis L. Their structures were determined by two-dimensional NMR techniques and mass spectrometry. For the first time cucurbitacine I derivatives with an acetyl group in position 16 are described.

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Neue Cucurbitacinglycoside ausGratiola officinalis L.

Zusammenfassung Acht neue Cucurbitacinglycoside wurden aus der DrogeGratiola officinalis L. isoliert. Ihre Strukturen wurden durch zweidimensionale NMR-Spektroskopie und Massenspektrometrie geklärt. Erstmalig wurden Cucurbitacin I-Derivate mit einer Acetylgruppe an C 16 identifiziert.

     

A new isoflavane-4-ol derivative from Melilotus officinalis (L.) Pall.

A new isoflavane derivative, melilofficinaside together with seven other metabolites including coumarin, uridine, methyl-α-d-fructofuranoside, and flavonoid glucosides were isolated from the aerial parts of Melilotus officinalis (L.) Pall.     

Two New Iridoids from the Roots of Valeriana officinalis

Valeriana officinalis is the official species used in Europe as sedatives and tranquilizers for centuries. Two new iridoids, volvaltrates C and D ( 1 and 2 ) were isolated from the ethanol extract as a mixture from the roots of V. officinalis. Their structures were elucidated by spectroscopic evidence including MS, 1D and 2D‐NMR spectra.     

Chemical composition of the endocarps of fruits of Styrax officinalis L.

Endocarps of fruits of Styrax officinalis L. have been subjected to a phytochemical investigation. Five compounds, americanin A (1), egonololeat (2), egonol-2?-metil butanoat (3), egonolgentiobiside (4) and homoegonolgentiobiside (5) were isolated. Their structures were elucidated by using spectroscopic methods and comparison with the literature data. This is the first report of the presence of compound 1 and compound 2 in the genus Styrax (Styracaceae family) and S. officinalis L. species, respectively.     

Iridoide aus Verbascum nigrum L. 182. Mitteilung über organische Naturstoffe

Iridoids from Verbascum nigrum L. Two new iridoid glycosides, nigroside 1 ( ? 6-O-(3-O-einnamoyl-α-L-rhamno-pyranosyl)aucubin (2) , and nigroside 2 (?6-O-(2-O-cinnamoyl-α-L-rhamnopy-ranosyl)aucubin (3) , and the known compound laterioside (1) have been isolated from extracts of the stems of Verbascum nigrum L., and their structures established primarily on the basis of NMR. spectroscopy. Harpagoside (4) , a known iridoid glucoside, was also isolated from the roots of this plant.     

235. Information on the sesquiterpenoid C 12 -Ketones from the essential oil of Vetiveria zizanioides (L.) Nash

Two new C₁₂-ketones, (+)-(1S, 10R)-1,10-dimethylbicyclo[4.4.0]dec-6-en-3-one ( 5 ) and (+)-(6S, 10S)-6,10-dimethylbicyclo[4.4.0]dec-1-en-3-one ( 6 ), have been isolated from Reunion vetiver oil (Vetiveria zizanioides (L.) Nash). Structure and absolute configuration of 5 were established by a four-step synthesis from (+)-isonootkatone ((+)-α-vetivone) ( 1 ). The structure of 6 followed from its spectroscopic properties and was confirmed by direct comparison with an authentic racemic sample. The absolute configuration of 6 was established by chemical correlation with (+)-α-eudesmol ( 13 ).     

Contribution à la phytochimie du genre Gentiana,XIX. Identification de nouveaux C-glucosides flavoniques dans Gentiana pyrenaicaL

Phytochemistry of genus Gentiana, XIX: Identification of new C-glycosylflavones in Gentiana pyrenaica L . Five flavone C-glucosides [6-C-β-D -glucopyranosyl-tricine ( 1 ) or isopyrenine; 7-O-β-D -glucopyranosyl-6-C-β-D -glucopyranosyltricine ( 2 ) or isopyrenine-7-O-glucoside; isoscoparine-7-O-glucoside ( 3 ); 7-O-β-D -glucopyranosyl-6-C-β-D -glucopyranosylacacetine ( 4 ) and isovitexine-7-O-glucoside ( 5 ) or saponarine] as well as the flavonol glucoside isoquercitrine ( 9 ) have been isolated chromatographically, using polyamide and cellulose columns, from the aerial parts of Gentiana pyrenaica L . 1 and 2 are new compounds and the first glycoflavones trisubstituted on cycle B. Compound 4 is also encountered for the first time in nature.     

Oleanane Saponins from Rhizome of Anemone raddeana

Two new oleanolic acid‐type triterpenoid saponins, raddeanosides R₂₂ and R₂₃ ( 1 and 2 , resp.), together with four known saponins were isolated from the rhizome of Anemone raddeana Regel. The structures of the new compounds were elucidated as oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 1 ) and oleanolic acid 3‐O‐α‐L ‐arabinopyranosyl(1→3)‐α‐L ‐rhamnopyranosyl(1→2)[β‐D ‐glucopyranosyl(1→4)]‐α‐L ‐arabinopyranoside ( 2 ). The four known compounds were identified as oleanolic acid 3‐O‐α‐L ‐arabinopyranoside ( 3 ), oleanolic acid 3‐O‐β‐D ‐glucopyranosyl(1→4)‐α‐L ‐arabinopyranoside ( 4 ), hederasaponin B ( 5 ), and hederacholchiside E ( 6 ) on the basis of chemical and spectral evidences. Compound 4 is reported for the first time from the Anemone genus, while the other three known compounds have been already found in this plant.