Xanthones et C-glucosides flavoniques du genre Gentiana (sous-genre Gentianella)

Xanthones with 1,3,5,8 or 1,3,4,5,8-oxidation pattern, the C-glucosides mangiferin, isoorientin and swertisin, were isolated from the aerial parts of G. germanica and G. ramosa. The distribution of these compounds within the subgenus Gentianella is given. Phenolic patterns in Gentiana and in Swertia are compared.     

Flavonoid glycoside accumulation trends of Achillea nobilis L. and related species

More than 50 collections of five species forming the Achillea nobilis group were analysed for their leaf flavonoid complement. Major accumulation trends were found to be C-glycosylflavones and flavonol 3-O-glycosides. The most common pattern consisted of the C-8-glycosylfiavones (vitexin and orientin), the C-6-glycosylflavone (isoörientin) together with minor amounts of di-C-glycosylapigenins and quercetin 3-O-glycosides. Additionally, C-6-glycosylflavones (isovitexin) and their 7-methyl ethers swertisin and swertiajaponin were sporadically accumulated, characterizing particularly two subspecies of A. nobilis. Whereas C-glycosylflavone dominated profiles were typical of most species, two taxa exhibited a flavonol dominated profile (A. ligustica; A. virescens p.p.). Regarding the infraspecific and interpopulational variations of flavonoid accumulation trends, their systematic and ecological significance is briefly discussed.     

Lack of altitudinal trends in phytochemical constituents of Swertia franchetiana (Gentianaceae)

Diverse biological characters commonly vary with altitude in species that have a wide altitudinal distribution, partly at least as a result of adaptation to differences in aridity, but whether such variation exists for phytochemical constituents remains unknown. Therefore, levels of seven important phytochemical constituents of Swertia franchetiana (swertiamarin, oleanolic acid, swertisin, mangiferin, 1,5,8-trihydroxy-3-methoxyxanthone, 1,8-dihydroxy-3,7-dimethoxyxanthone and 1,8-dihydroxy-3,5-dimethoxyxanthone) were studied and statistically compared, using materials collected from sites ranging from 2200 to 3960 m in altitude. Swertiamarin was the most abundant in all samples, then mangiferin, oleanolic acid and the other three xanthones. Throughout the distributional range of this species, no altitudinal trend was detected for other constituents except 1,8-dihydroxy-3,7-dimethoxyxanthone, which showed a negative correlation with altitude. However, the concentration of 1,8-dihydroxy-3,7-dimethoxyxanthone and mangiferin showed a significantly latitudinal and longitudinal correlation.     

Flavonoids from Eustoma grandiflorum flower petals

The major flavonoids responsible for flower colours of Eustoma grandiflorum were characterized by TLC, HPLC, spectral and chemical analyses. Anthocyanins were delphinidin 3-rhamnosylgalactoside-5-glucoside and delphinidin 3-galactoside-5-glucoside, each acylated with p-coumaric acid, from the purple cultivar ‘Murasaki no Homare’ and the pelargonidin analogues, each acylated with either p-coumaric or ferulic acids, from the pink cultivar ‘Momo no Mine’. The major flavonol copigments were the 3-rhamnosylgalactoside-7-rhamnoside of myricetin, kaempferol and isorhamnetin and the 3-rhamnosylglucoside-7-rhamnoside of kaempferol and isorhamnetin. Flavonols present acylated with p-coumaric acid were myricetin 3-rhamnosylgalactoside-7-rhamnoside and robinin in both cis and trans forms, and isorhamnetin 3-rhamnosylgalactoside-7-rhamnoside. Robinin also was present acylated with caffeic or ferulic acids. Simulated in vitro colours obtained from the flavonoids present in this germplasm indicated that good blue colours were not attainable. Good blue colours were formed with delphinidin 3-p-coumaroyl-rhamnosylgalactoside-5-glucoside and C-glycosylflavone copigments such as swertisin and isoorientin. These copigments are readily available in other members of the Gentianaceae and this suggests the possibility of genetical engineering endeavours for increasing the colour range of this important new ornamental plant.     

Flavonoids in the leaves of <Emphasis Type="Italic">Oxalis corniculata </Emphasis>and sequestration of the flavonoids in the wing scales of the pale grass blue butterfly, <Emphasis Type="Italic">Pseudozizeeria </Emphasis><Emphasis Type="Italic">maha</Emphasis>

Three C-glycosylflavones in the leaves of Oxalis corniculata, the host plant of the lycaenid butterfly pale grass blue (Pseudozizeeria maha), were identified as 6-C-glucosylluteolin (isoorientin), 6-C-glucosylapigenin (isovitexin) and isovitexin 7-methyl ether (swertisin). Comparative spectral and HPLC analyses between the leaf extract of the host plants and the wings of P. maha showed selective uptake of the host-plant flavonoid isovitexin to the wings of the butterfly.     

Xanthones and flavonoids from <Emphasis Type="Italic">Gentiana algida</Emphasis> Pall

This article is devoted to phytochemical investigation of xanthones and flavonoids from the Gentiana algida Pall. (cold gentian, the Gentianaceae family). The following xanthones and flavones have been isolated from the top of the gentian: bellidifolin, isobellidifolin, swerchirin, 1,5,8-tirhydroxy-3,4-dimethoxyxanthone, swertisin, and swertianolin (flavone-C-glycoside). The isolated compounds have been identified on the basis of their chemical conversions and by their UV, mass, ¹H, and ¹³C NMR spectra. Derivatives of 1,3,5,8-tetrahydroxyxanthone were mainly found in the top of the cold gentian.     

当药黄素抗抑郁作用研究

研究当药黄素的抗抑郁作用及其可能的作用机制。研究采用动物行为绝望模型评价当药黄素抗抑郁活性;采用药物交互作用模型探讨其主要作用环节及其可能的作用机制。结果显示当药黄素没有中枢神经兴奋性,能缩短小鼠悬尾和强迫游泳的不动时间;增加5-HTP诱导的小鼠甩头次数,可拮抗利血平引起的小鼠体温下降和眼睑下垂,对育亨宾毒性具有增强作用,但对盐酸色胺所致大鼠惊厥无影响。上述结果表明当药黄素具有抗抑郁活性,其抗抑郁活性可能与抑制5-羟色胺重摄取、增强脑内神经递5-HT神经功能和影响去甲肾上腺素有关;而与抑制体内单胺氧化酶活性无关。     

Studies on the Flavonoid of Iridaceae

Flavoayamenin (I), C₂₈H₃₂O₁₅, mp 258~9°C, a new C-glycosyl flavone isolated from ethanolic extracts of the petals of Iris Nertshinskia Loddiges form, alubiflora Honda (Iridaceae), has now been formulated as genkwanin-6-C-β-d-glucopyranosyl-x″-O-mono-d-glucoside. Basides, two other C-glycosyl flavones have also been isolated from the same extract by chromatography on a Nylon column, and identified as swertisin and swertia-japonin, respectively.     

Separation of C-glycoside flavonoids from Aleurites moluccana using chitin and full N-acetylated chitin

This paper describes a comparative study using different chromatographic supports (fully N-acetylated chitin, chitin and silica gel) to separate the flavonoids swertisin and 2"-O-rhamnosylswertisin from Aleurites moluccana. The results show that the flavonoids have apparently been separated by the hydrogen bond between the stationary phase (chitin and chitin-100) and flavonoids under the conditions studied.     

Novel pigments and copigmentation in the blue marguerite daisy

The blue colour of the petals of the blue marguerite daisy, Felicia amelloides, has been found to arise from copigmentation between a novel malonylated delphinidin triglycoside, delphinidin 3-O-neohesperidoside 7-O- (6-O-malonyl-glucoside), and a new flavone C-glycoside, swertisin 2″-O-rhamnoside-4′-O-glucoside. Recombination, in vitro, of these two petal components at pH 6 recreates the blue petal colour.     

Separation of flavonoids from Aleurites moluccana leaves using chitosan modified with heptaldehyde

Heptaldehyde-modified chitosan (heptyl-chitosan, CH-Hp) was investigated as adsorbent for chromatograhic separation of the flavonoids from A. moluccana. The amount of 2"-O-rhamnosylswertisin isolated (30.0 mg) was approx. twice as high as swertisin (17.5 mg). The improved surface hydrophobicity effected by the heptyl groups promoted the separation of flavonoids. From the results obtained, CH-Hp seems to be more suitable for separation of glycosylated flavonoids than other flavonoids. Thus, modified chitosan described here can be used for hydrophobic interaction chromatography as sucessfully illustrated with flavonoids.     

On the Xanthone Glycosides and Flavonoid Glucoside from Swertia franchetiana H. Smith

Three xanthone glycosides, a flavonoid glucoside and a triterpen acid have been isolated from Swertia franchetiana H. Smith (Gentianaceae). One of them is a new xanthone glyco- side and its stucture is established as 1-O-[β-D-xylopyranosyl-(1-6)-β-D-glucopyranosyl] 3, 5-dimethoxyxanthone (Ⅺ), Others are identified as swertianolin, swertisin, mangiferin and oleanolic acid by chemical and spectral means, respectively.     

Study on the Chemical Constituents of Comastoma pulmonarium (Turcz.) Toyohuni

Eight compounds were isolated from Comastoma pulmonarium (Gentianaceae). Theirstructures are identified as1,8-dihydroxy-3,5-dimethoxyxanthone(Ⅰ),1,8-dihydroxy-3,7-dimetho-xyxanthone(Ⅱ), 1-hydroxy-3,7,8-trimethoxyxanthone(Ⅲ),8-hydroxy-l,3,5-trimethoxyxanthone(Ⅳ), 1,3,8-trihydroxy-7-methoxyxanthone(Ⅴ), 1-O-β-D-glucopyranosyl-3,8-dihydroxy-7-methxy-xanthone(Ⅵ), oleanolic acid(Ⅶ) and swertisin(Ⅷ) by means of chemical methods andUV, IR, NMR and MS respectively. The compound Ⅵ is a new natural product. It wasnamed as comastomaside.     

LC‐ESI‐QTOF‐MS for the Profiling of the Metabolites and in Vitro Enzymes Inhibition Activity of Bryophyllum pinnatum and Oxalis corniculata Collected from Ramechhap District of Nepal

The objective of this study was to profile the chemical components and biological activity analysis of crude extract of Bryophyllum pinnatum and Oxalis corniculata. Results revealed that the analyzed plant materials encompass the high amount of total phenolic and flavonoids content and have significant antioxidant activities. Furthermore, methanol extracts are the potential source of α‐amylase, α‐glucosidase, lipase, tyrosinase and elastase inhibitors. High resolution mass spectrometry revealed the presence of diverse metabolites such as quercetin 3‐O‐α‐L‐rhamnopyranoside, myricetin 3‐rhamnoside, bersaldegenin 1,3,5‐orthoacetate, bryophyllin C, syringic acid, caffeic acid, p‐coumaric acid, and quercetin in B. pinnatum and isoorientin, swertisin, apigenin 7,4′‐diglucoside, vitexin, 4‐hydroxybenzoic acid, vanillic acid, ethyl gallate, 3,3′,4′‐trihydroxy‐5,7‐dimethoxyflavone, and diosmetin‐7‐O‐β‐D‐glucopyranoside in O. corniculata. Our finding suggested that these two plant species have high medicinal importance and are potential source of inhibitors for modern pharmaceuticals, nutraceuticals and cosmetics industries.     

The Glucosides from Swertia mussotii Franch

Swertia mussotii Franch. is a herb used for treatment of liver disease in Qinghai-Tibcran Plateau folk. Further investigation on chemical constituents in aqueous extract of Swertia mussotii Franch. has been reported here. Seven compounds (Ⅰ, Ⅲ–Ⅷ) were achieved except mangiferin (Ⅱ) isolated previously by a chromatograph. They belong in secoiridoids, flavonoids and xanthonoids, respectively. The structures of known compounds were identified as amarogentin(Ⅲ), swertisin(Ⅷ), 8-O-β-D-glucopyranosyl-1, 3, 5-trihydroxyxanthone(Ⅶ) and 8-O-β-D-glucopyranosyl-(1-6)-β-D-glucopyranosyl)-I, 7-dihydroxy-3-methoxyxanthone (Ⅵ). The structures of other three new compounds have been elucidated as 7-O-β-D-xylopy-ranosyl-1, 8-dihydroxy-3-methoxyxanthone (Ⅳ), 7-O-[α-L-rhamnopyranosyl- (1-2)-β-D-xylopyranosyl]-l,8-dihydroxy-3-methoxyxanthone(Ⅰ)and 3-O-β-D-glucopyranosy 1,8-dihydroxy-5-methoxyxanthone (Ⅴ), by means of the chemical and spectral methods. Mangiferin, amarogentin and 7-0- [α-L-rhamnopyranosyl-(1-2)-β-D-xylopyranosyl]-l,8-dihydroxy-3-methoxyxanthone are the principal glucosides in this plant.     

Combination of HPLC chromatogram and hypoglycemic effect identifies isoflavones as the principal active fraction of Belamcanda chinensis leaf extract in diabetes treatment

In previous study, we demonstrated the hypoglycemic effect of aqueous extract of Belamcanda chinensis leaves in rats. Here, we separated the aqueous extract of B. chinensis leaves and investigated the spectrum-effect relationships between HPLC chromatograms and hypoglycemic activities of different isolates from B. chinensis leaf extract. Sequential solvent extraction with petroleum ether, chloroform, acetic ester and n-butanol provided several isolates showing similar hypoglycemic activities, making it difficult to discriminate the active fractions. Stepwise elution through HP20 macroporous resin by water, 40% and 95% ethanol provided isolates with distinct hypoglycemic activities, representing a simple, rapid and efficient preparative separation method. Combination of HPLC chromatogram and pharmacological effect targeted a hypoglycemic activity-related region in HPLC chromatogram. Each peak in this region was analyzed by UV spectrum scan. Most of them were flavonoids in which tectoridin and swertisin were known flavonoids with anti-diabetic activities. In together, this work provides a general model of combination of HPLC chromatography and pharmacological effect to study the spectrum-effect relationships of aqueous extract from B. chinensis leaves, which can be used to find principle components of B. chinensis on pharmacological activity.     

Revision of the Ceratocapsine Renodaeus group: Marinonicoris,Pilophoropsis, Renodaeus,and Zanchisme,with descriptions of four new genera (Heteroptera,Miridae, Orthotylinae)

The Renodaeus group, a monophyletic assemblage of genera within the New World orthotyline tribe Ceratocapsini, comprising eight genera, including four new ones, is defined; and 48 species are treated, including 26 described as new and 12 transferred from Ceratocapsus Reuter as new combinations. Ceratocapsidea gen. n. is described to accommodate the new species Ceratocapsidea bahamaensis sp. n., from the Bahamas; Ceratocapsidea baranowskii sp. n., from Jamaica; Ceratocapsidea dominicanensis sp. n., from the Dominican Republic; Ceratocapsidea rileyi sp. n., from Texas; Ceratocapsidea taeniola sp. n., from Jamaica; Ceratocapsidea texensis sp. n., from Texas; Ceratocapsidea transversa sp. n., from Mexico (Neuvo León); and Ceratocapsidea variabilis sp. n., from Jamaica; and Ceratocapsus balli Knight, comb. n., Ceratocapsus complicatus Knight, comb. n., Ceratocapsidea consimilis Reuter, comb. n., Ceratocapsus fusiformis Van Duzee, comb. n. (as the type species of the genus), Ceratocapsus nigropiceus Reuter, comb. n., and Ceratocapsus rufistigmus Blatchley, comb. n. [and a neotype designated], Ceratocapsus clavicornis Knight, syn. n. and Ceratocapsus divaricatus Knight, syn. n. are treated as junior synonyms of Ceratocapsus fusiformis Van Duzee. The genus Marininocoris Carvalho and the only included species Marinonicoris myrmecoides Carvalho are redescribed. The genus Pilophoropsis Poppius is redescribed and revised, Renodaeus texanus Knight, comb. n. is transferred into it and the three new species Pilophoropsis bejeanae sp. n., from Sonora, Mexico; Pilophoropsis cunealis sp. n., from Oaxaca, Mexico; Pilophoropsis quercicola sp. n., from Arizona, USA, are described. Pilophoropsidea gen. n. is described to accommodate the 12 new species Pilophoropsidea brailovskyi sp. n., from Federal District, Mexico; Pilophoropsidea cuneata sp. n., from Chiapas, Mexico; Pilophoropsidea dimidiata sp. n., from Durango, Mexico; Pilophoropsidea fuscata sp. n., from Durango, Mexico and Arizona and New Mexico, USA; Pilophoropsidea keltoni sp. n., from Durango, Mexico; Pilophoropsidea maxima sp. n., from Durango, Mexico; Pilophoropsidea pueblaensis sp. n., from Puebla, Mexico; Pilophoropsidea schaffneri sp. n., from Neuvo León and San Luis Potosi, Mexico; Pilophoropsidea serrata sp. n., from Michoacan, Mexico; Pilophoropsidea touchetae sp. n., from Mexico (Puebla); Pilophoropsidea truncata sp. n., from Mexico (Guerrero); Pilophoropsidea tuberculata sp. n., from Mexico (Guerrero); and Ceratocapsus barberi Knight, comb. n., Ceratocapsus camelus Knight, comb. n. (as the type species of the genus), and Ceratocapsus fascipennis Knight, comb. n. Pilophoropsita gen. n. is described to accommodate Pilophoropsidea schaffneri sp. n. from Costa Rica and Mexico (Jalisco, Nayarit, Oaxaca). The genus Renodaeus Distant is redescribed and the new species Renodaeus mimeticus sp. n. from Ecuador is described. The genus Zanchisme Kirkaldy is reviewed and the four known species are redescribed. Zanchismeopsidea gen. n. is described to accommodate Zanchismeopsidea diegoi sp. n. from Argentina (Santiago del Estero). Provided are habitus illustrations for certain adults (Pilophoropsidea camelus, Pilophoropsis brachyptera Poppius, Renodaeus mimeticus, and Zanchisme mexicanus Carvalho & Schaffner), male and female (when available) color digital images and figures of male genitalia of all species, electron photomicrographs of diagnostic characters for selected species, and keys to the genera and their included species. The taxa treated in this paper are arranged alphabetically by genus and species.     

The genera in the second catalogue (1833–1836) of?Dejean’s Coleoptera collection

All genus-group names listed in the second edition of the catalogue (1833-1836) of Dejean’s beetle collection are recorded. For each new genus-group name the originally included available species are listed and for generic names with at least one available species, the type species and the current status are given. Names available prior to the publication of Dejean’s second catalogue (1833-1836) are listed in an appendix.The following new synonymies are proposed: Cyclonotum Dejean, 1833 (= Dactylosternum Wollaston, 1854) [Hydrophilidae], Hyporhiza Dejean, 1833 (= Rhinaspis Perty, 1830) [Scarabaeidae], Aethales Dejean, 1834 (= Epitragus Latreille, 1802) [Tenebrionidae], Arctylus Dejean, 1834 (= Praocis Eschscholtz, 1829) [Tenebrionidae], Euphron Dejean, 1834 (= Derosphaerus Thomson, 1858) [Tenebrionidae], Hipomelus Dejean, 1834 (= Trachynotus Latreille, 1828) [Tenebrionidae], Pezodontus Dejean, 1834 (= Odontopezus Alluaud, 1889) [Tenebrionidae], Zygocera Dejean, 1835 (= Disternopsis Breuning, 1939) [Cerambycidae], and Physonota Chevrolat, 1836 (= Anacassis Spaeth, 1913) [Chrysomelidae]. Heterogaster pilicornis Dejean, 1835 [Cerambycidae] and Labidomera trimaculata Chevrolat, 1836 [Chrysomelidae] are placed for the first time in synonymy with Anisogaster flavicans Deyrolle, 1862 and Chrysomela clivicollis Kirby, 1837 respectively. Type species of the following genus-group taxa are proposed: Sphaeromorphus Dejean, 1833 (Sphaeromorphus humeralis Erichson, 1843) [Scarabaeidae], Adelphus Dejean, 1834 (Helops marginatus Fabricius, 1792) [Tenebrionidae], Cyrtoderes Dejean, 1834 (Tenebrio cristatus DeGeer, 1778) [Tenebrionidae], Selenepistoma Dejean, 1834 (Opatrum acutum Wiedemann, 1823) [Tenebrionidae], Charactus Dejean, 1833 (Lycus limbatus Fabricius, 1801) [Lycidae], Corynomalus Chevrolat, 1836 (Eumorphus limbatus Olivier, 1808) [Endomychidae], Hebecerus Dejean, 1835 (Acanthocinus marginicollis Boisduval, 1835) [Cerambycidae], Pterostenus Dejean, 1835 (Cerambyx abbreviatus Fabricius, 1801) [Cerambycidae], Psalicerus Dejean, 1833 (Lucanus femoratus Fabricius, 1775) [Lucanidae], and Pygolampis Dejean, 1833 (Lampyris glauca Olivier, 1790) [Lampyridae]. A new name, Neoeutrapela Bousquet and Bouchard [Tenebrionidae], is proposed for Eutrapela Dejean, 1834 (junior homonym of Eutrapela Hübner, 1809).The following generic names, made available in Dejean’s catalogue, were found to be older than currently accepted valid names: Catoxantha Dejean, 1833 over Catoxantha Solier, 1833 [Buprestidae], Pristiptera Dejean, 1833 over Pelecopselaphus Solier, 1833 [Buprestidae], Charactus Dejean, 1833 over Calopteron Laporte, 1836 [Lycidae], Cyclonotum Dejean, 1833 over Dactylosternum Wollaston, 1854 [Hydrophilidae], Ancylonycha Dejean, 1833 over Holotrichia Hope, 1837 [Scarabaeidae], Aulacium Dejean, 1833 over Mentophilus Laporte, 1840 [Scarabaeidae], Sciuropus Dejean, 1833 over Ancistrosoma Curtis, 1835 [Scarabaeidae], Sphaeromorphus Dejean, 1833 over Ceratocanthus White, 1842 [Scarabaeidae], Psalicerus Dejean, 1833 over Leptinopterus Hope, 1838 [Lucanidae], Adelphus Dejean, 1834 over Praeugena Laporte, 1840 [Tenebrionidae], Amatodes Dejean, 1834 over Oncosoma Westwood, 1843 [Tenebrionidae], Cyrtoderes Dejean, 1834 over Phligra Laporte, 1840 [Tenebrionidae], Euphron Dejean, 1834 over Derosphaerus Thomson, 1858 [Tenebrionidae], Pezodontus Dejean, 1834 over Odontopezus Alluaud, 1889 [Tenebrionidae], Anoplosthaeta Dejean, 1835 over Prosopocera Blanchard, 1845 [Cerambycidae], Closteromerus Dejean, 1835 over Hylomela Gahan, 1904 [Cerambycidae], Hebecerus Dejean, 1835 over Ancita Thomson, 1864 [Cerambycidae], Mastigocera Dejean, 1835over Mallonia Thomson, 1857 [Cerambycidae], Zygocera Dejean, 1835 over Disternopsis Breuning, 1939 [Cerambycidae], Australica Chevrolat, 1836 over Calomela Hope, 1840 [Chrysomelidae], Edusa Chevrolat, 1836 over Edusella Chapuis, 1874 [Chrysomelidae], Litosonycha Chevrolat, 1836 over Asphaera Duponchel and Chevrolat, 1842 [Chrysomelidae], and Pleuraulaca Chevrolat, 1836 over Iphimeis Baly, 1864 [Chrysomelidae]. In each of these cases, Reversal of Precedence (ICZN 1999: 23.9) or an applicationto the International Commission on Zoological Nomenclature will be necessary to retain usage of the younger synonyms.