Anthocyanins from red flowers of Camellia cultivar 'Dalicha'

Five anthocyanins, cyanidin 3-O-(2-O-β-xylopyranosyl-6-O-(Z)-p-coumaroyl)-β-galactopyranoside (2), cyanidin 3-O-(2-O-β-xylopyranosyl-6-O-(E)-p-coumaroyl)-β-galactopyranoside (3), cyanidin 3-O-(2-O-β-xylopyranosyl-6-O-(E)-caffeoyl)-β-galactopyranoside (4), cyanidin 3-O-(2-O-β-xylopyranosyl-6-O-acetyl)-β-galactopyranoside (5), and cyanidin 3-O-(2-O-β-xylopyranosyl-6-O-acetyl)-β-glucopyranoside (6), together with the known cyanidin 3-O-(2-O-β-xylopyranosyl)-β-galactopyranoside (1), were isolated from red flowers of Camellia cultivar ‘Dalicha’ (Camellia reticulata) by chromatography using open columns. Their structures were subsequently determined on the basis of spectroscopic analyses, i.e., ¹H NMR, ¹³C NMR, HMQC, HMBC, HR ESI-MS and UV-vis.     

Anthocyanins from red flower tea (Benibana-cha), Camellia sinensis

Three anthocyanins were isolated from the leaves of red flower tea (Benibana-cha), Camellia sinensis, and their structures were determined by means of chemical and spectroscopic analyses. Two are the anthocyanins, delphinidin and cyanidin 3-O-beta-D-galactosides, respectively. Whereas the third, delphinidin 3-0-beta-D-(6-(E)-p-coumaryl)galactopyranoside. The anthocyanins were also contained in the flowers of Benibana-cha in different compositions.     

Anthocyanins from flowers of Cichorium intybus

From the blue perianth segments of Cichorium intybus we isolated four anthocyanins. The pigments were identified as delphinidin 3,5-di-O-(6-O-malonyl-beta-D-glucoside) and delphinidin 3-O-(6-O-malonyl-beta-D-glucoside)-5-O-beta-D-glucoside and the known compounds were delphinidin 3-O-beta-D-glucoside-5-O-(6-O-malonyl-beta-D-glucoside) and delphinidin 3,5-di-O-beta-D-glucoside. In addition 3-O-p-coumaroyl quinic acid has been identified.     

Anthocyanins from the scarlet flowers of Anemone coronaria

Three acylated anthocyanins were isolated from the scarlet flowers of Anemone coronaria 'St. Brigid Red' along with a known pigment, pelargonidin 3-lathyroside. The structures of the acylated pigments were based on a pelargonidin 3-lathyroside skeleton acylated at different positions with malonic acid. The first pigment was identified as pelargonidin 3-O-[2-(beta-D-xylopyranosyl)-6-O-(malonyl)-beta-D-galactopyranoside], the second was pelargonidin 3-O-[2-O-(beta-D-xylopyranosyl)-6-O-(methyl-malonyl)-beta-D-galactopyranoside], and the third was (6'-O-(pelargonidin 3-O-[2'-O-(beta-D-xylopyranosyl)-beta-D-galactopyranosyl]))((4-O-(beta-D-glucopyranosyl)-trans-caffeoyl)-O-tartatryl)malonate.     

金花茶花化学成分的研究

采用反复硅胶柱色谱法、Sephadex LH-20柱色谱法、ODS柱色谱法、反复重结晶等方法对金花茶花的化学成分进行分离纯化,并通过理化常数测定和波谱分析等方法进行结构鉴定.从金花茶花的乙醇提取物中分离得到13个化合物,分别鉴定为:槲皮素(1)、槲皮素-7-O-β-D-葡萄糖苷(2)、槲皮素-3-O-β-D-葡萄糖苷(...     

Anthocyanins from red cabbage--stability to simulated gastrointestinal digestion

Anthocyanins were the main polyphenol components in extracts of fresh and pickled red cabbage. The composition of anthocyanins in red cabbage was studied using liquid chromatography mass-spectrometry. Eleven major peaks absorbing at 520 nm were discerned, which represented 18 different anthocyanin structures. Another five minor anthocyanin components could be identified by searching at their respective m/z values but only in anthocyanin-enriched concentrates produced by sorption to solid phase extraction matrices. The predominant anthocyanins were constructed of cyanidin-3-diglucoside-5-glucoside "cores" which were non-acylated, mono-acylated or di-acylated with p-coumaric, caffeic, ferulic and sinapic acids. Pelargonidin-3-glucoside and novel forms of cyanidin-3-O-triglucoside-5-O-glucoside di-acylated with hydroxycinnamic acids were also detected in extracts of raw red cabbage, commercially pickled red cabbage and anthocyanin-enriched concentrates. The stability of the anthocyanins to simulated gastrointestinal digestion was assessed. The anthocyanins were effectively stable in the acidic gastric digestion conditions but the total recovery after simulated pancreatic digestion was around 25% compared to around 100% recovery of phenol content. As anthocyanins make up the majority of red cabbage polyphenols, this suggested that anthocyanins broke down to form new phenolic components. The recovery of the individual anthocyanins was monitored by LC-MS(n). All of the anthocyanins were reduced in content after pancreatic digestion but acylated forms were notably more stable than non-acylated forms. There was also a relationship between the type of acylated hydroxycinnamic acid and stability to pancreatic digestion.     

Anthocyanins from flowers of the orchids Dracula chimaera and D. cordobae

The main anthocyanins from flowers of the orchids Dracula chimaera and D. cordobae were isolated from a purified methanolic extract by preparative HPLC. Their structures were determined to be cyanidin 3-O-(6"-O-malonyl-beta-glucopyranoside), cyanidin 3-O-(6"-O-alpha-rhamnopyranosyl-beta-glucopyranoside), cyanidin 3-O-beta-glucopyranoside, peonidin 3-O-(6"-O-alpha-rhamnopyranosyl-beta-glucopyranoside) and peonidin 3-O-(6"-O-malonyl-beta-glucopyranoside). The structure determinations were mainly based on extensive use of 2D and 1D NMR spectroscopy, UV-vis spectroscopy and MS. The anthocyanin contents of species belonging to the subtribe Pleurothallidinae including genus Dracula Luer (Orchidaceae) have previously not been determined. The high content of anthocyanin rutinosides found in D. chimaera and D. cordobae (78 and 28% of the total anthocyanin content, respectively) differs from previously analysed orchid species, in which glucose is found as the only anthocyanin sugar moiety.     

Anthocyanins and flavonols from the flowers of Amherstia nobilis endemic to Myanmar

Three anthocyanins (1–3) and eight flavonols (4–11) were isolated from the flowers of Amherstia nobilis endemic to Myanmar. Anthocyanins were identified as cyanidin 3-O-glucoside (1), 3-O-xyloside (2), and peonidin 3-O-glucoside (3). On the other hand, flavonols were identified as isorhamnetin 3-O-glucoside (4), 7-O-glucoside (5), 3,7-di-O-glucoside (6) and 3-O-rutinoside (7), quercetin 3-O-rutinoside (8) and 3-O-glucoside (9), and kaempferol 3-O-rutinoside (10) and 3-O-glucoside (11). Although an anthocyanin, pelargonidin 3-O-pentoside, has been reported from the flowers of A. nobilis, it was not found in this survey. The presence of flavonols in A. nobilis was reported in this survey for the first time. Flavonoid composition of Amherstia was chemotaxonomically compared with those of phylogenetically related genera Cynometra and Brownea.     

中华蜜蜂在滇山茶上的访花行为研究

对中华蜜蜂在滇山茶上的访花行为的研究表明,中华蜜蜂全天在滇山茶上的访花过程呈现出单峰型的节律,高峰在13:00～14:00.在31朵观察的样花上,中华蜜蜂全天共到访613次,访花627次,对花的连续访问率为2.23％,每朵花平均被访20.23次,每次到访花停留时间均值为10.23 s,全天在样花上总的累计停留时间为6 270 s,单花累计访问时间达到202.26 s.蜜蜂全天访花累计时间占全部访花昆虫总访花的累计停留时间的比例达到97.80％.在滇山茶访花昆虫中,中华蜜蜂具有明显的优势度,是绝对的优势种.对滇山茶花蜜的研究表明,其单花1天的花蜜分泌量平均为69.5 μL(n=100);花蜜含糖量(124.95～200.64) mg/mL.花蜜成分以多糖为主,占66％以上,此外还含有单糖,占1.9％～33％,其他未知名的组分占16％～22％,部分花蜜中含有山梨醇,占11％.对滇山茶花的挥发物分析结果表明,总的挥发物有59种,萜烯类、酯类和醇类是滇山茶花的主要挥发物成分,分别占46.468％、27.035％和21.609％.     

Anthocyanins from red wine--their stability under simulated gastrointestinal digestion

The stability of anthocyanins from red wine was assessed using an in vitro digestion system that simulated the physiochemical changes that occur in the upper gastrointestinal tract. Anthocyanins in red wine were stable to gastric conditions whereas there was a small loss in total phenol content. After pancreatic digestion, the total anthocyanins were very poorly recovered compared to the bulk phenols in the IN sample, which was previously described as the "serum-available" fraction, and the majority of the anthocyanins and phenols were recovered in the OUT fraction, previously described as the "colon-available" fraction. Removing alcohol from the wine samples prior to the procedure did not markedly affect this pattern. The composition of anthocyanins in the post gastric, IN and OUT samples was analysed using liquid chromatography mass-spectrometry. The red wine used contained over 20 identifiable anthocyanins of which the main components were 3-O-glucosides of malvidin, peonidin, petundin, delphidin and cyanidin. Coumaroylated-glucoside derivatives of malvidin, petundin, peonidin, and delphinidin were observed and acetylated glucosides of peonidin, petundin and malvidin were also identified. Anthocyanins with modified aglycones similar to vitisin A derivatives of delphinidin, peonidin, petunidin and malvidin were also identified. After the in vitro digestion procedure, only five anthocyanins could be detected in the IN (serum-available) and the OUT (colon-available) fractions, which were confirmed as malvidin-3-O-glucoside and the vitisin A adducts of malvidin-3-O-glucoside, malvidin-3-O-acetylglucoside, malvidin-3-O-coumaroylglucoside and peonidin-3-O-glucoside. Malvidin-3-O-glucoside was recovered at 0.2% in the IN fraction and 0.9% in the OUT fraction. However, the vitisin derivatives were much more stable to pancreatic digestion. Assuming that the vitisin A derivatives display similar biological properties to their parent anthocyanins, their enhanced gastrointestinal stability could lead to enhanced bioavailability and bio-effectiveness in vivo.     

Anthocyanins and flavonols from the blue flowers of six Meconopsis species in Bhutan

Blue flowers of six Bhutani Meconopsis species, M. bhutanica, M. bella, M. horridula, M. simplicifolia, M. primulina and M. polygonoides, were surveyed for anthocyanins and other flavonoids. Four anthocyanins were isolated and identified as cyanidin 3-O-sambubioside-7-O-glucoside (1), cyanidin 3-O-[xylosyl-(1 → 2)-(6″-malonylglucoside)]-7-O-glucoside (2), cyanidin 3-O-sambubioside (4) and cyanidin 3-O-[xylosyl-(1 → 2)-(6″-malonylglucoside)] (5). On the other hand, 12 flavonols were isolated from their Meconopsis species with various combination and characterized as kaempferol 3-O-glycosides (8–12), kaempferol 3,7-O-glycosides (13–16), quercetin 3-O-glycosides (17 and 18) and isorhamnetin 3-O-glycoside (19). Of six Meconopsis species which were surveyed in this experiment, anthocyanin and flavonol composition of five species except for M. horridula was clarified for the first time. Their Meconopsis species showed the different flavonoid profiles, respectively, and flavonoid diversity within the glycosylation level of Meconopsis flowers were indicated.     

Identification of a novel hedycaryol synthase gene isolated from Camellia brevistyla flowers and floral scent of Camellia cultivars

Planta - A novel terpene synthase ( Tps ) gene isolated from Camellia brevistyla was identified as hedycaryol synthase, which was shown to be expressed specifically in flowers. Camellia plants are...     

Anthocyanins with 4'-glucosidation from red onion, Allium cepa

The anthocyanins, cyanidin 3-O-(3"-O-beta-glucopyranosyl-6"-O-malonyl-beta-glucopyranoside)-4'-O-beta-glucopyranoside, cyanidin 7-O-(3"-O-beta-glucopyranosyl-6"-O-malonyl-beta-glucopyranoside)-4'-O-beta-glucopyranoside, cyanidin 3,4'-di-O-beta-glucopyranoside, cyanidin 4'-O-beta-glucoside, peonidin 3-O-(6"-O-malonyl-beta-glucopyranoside)-5-O-beta-glucopyranoside and peonidin 3-O-(6"-O-malonyl-beta-glucopyranoside) have been isolated in minor amounts from pigmented scales of red onion, Allium cepa, in addition to six known anthocyanins. The structures were established mainly by extensive use of 2D NMR spectroscopy and electrospray LC-MS. With exception of cyanidin 4'-glucoside and cyanidin 3,4'-diglucoside reported from Hibiscus esculentus with inadequate documentation, this is the first identification of anthocyanins with 4'-glycosidation. Compared to cyanidin 3-glycosides the cyanidin 4'-glucoside derivatives showed hypsochromic shifts of visible lambda(max) and hyperchromic effects on wavelengths around 440 nm, similar to pelargonidin 3-glycosides.     

A New Acylated Anthocyanin from the Red Flowers of Camellia hongkongensis and Characterization of Anthocyanins in the Section Camellia Species

Twelve anthocyanins (1-12) were isolated from the red flowers of Camellia hongkongensis Seem. by chromatography using open columns. Their structures were elucidated on the basis of spectroscopic analyses, that is, proton-nuclear magnetic resonance, carbon 13-nuclear magnetic resonance, heteronuclear multiple quantum correlation, heteronuclear multiple bond correlation, high resolution electrospray ionization mass and ultraviolet visible spectroscopies. Out of these anthocyanins, a novel acylated anthocyanin, cyanidin 3-O-(6-O-(Z)-p-coumaroyl)-β-galactopyranoside (6), two known acylated anthocyanins, cyanidin 3-O-(6-O-(E)-p-coumaroyl)-β-galactopyranoside (7) and cyanidin 3-O-(6-O-(E)-caffeoyl)-β-galactopyranoside (8), and three known delphinidin glycosides (10-12) were for the first time isolated from the genus Camellia. Furthermore, pigment components in C. japonica L., C. chekiangoleosa Hu and C. semiserrata Chi were studied.The results indicated that the distribution of anthocyanins was differed among these species. Delphinidin glycoside was only detected in the flowers of C. hongkongensis, which is a special and important species in the section Camellia. Based on the characterization of anthocyanins in the section Camellia species, there is a close relationship among these species,and C. hongkongensis might be an important parent for creating new cultivars with bluish flower color.     

A New Acylated Anthocyanin from the Red Flowers of Camellia hongkongensis and Characterization of Anthocyanins in the Section Camellia Species

Twelve anthocyanins （1-12） were isolated from the red flowers of Camellia hongkongensis Seem. by chromatography using open columns. Their structures were elucidated on the basis of spectroscopic analyses, that is, proton-nuclear magnetic resonance, carbon 13-nuclear magnetic resonance, heteronuclear multiple quantum correlation, heteronuclear multiple bond correlation, high resolution electrospray ionization mass and ultraviolet visible spectroscopies. Out of these anthocyanins, a novel acylated anthocyanin, cyanidin 3-O-（6-O-（Z）-p-coumaroyl）-β-galactopyranoside （6）, two known acylated anthocyanins, cyanidin 3-O-（6-O-（E）-p-coumaroyl）-β-galactopyranoside （7） and cyanidin 3-O-（6-O-（E）-caffeoyl）-~- galactopyranoside （8）, and three known delphinidin glycosides （10-12） were for the first time isolated from the genus Camellia. Furthermore, pigment components in C. japonica L., C. chekiangoleosa Hu and C. semiserrata Chi were studied. The results indicated that the distribution of anthocyanins was differed among these species. Delphinidin glycoside was only detected in the flowers of C. hongkongensis, which is a special and important species in the section Camellia. Based on the characterization of anthocyanins in the section Camellia species, there is a close relationship among these species, and C. hongkongensis might be an important parent for creating new cultivars with bluish flower color.     

Anthocyanins from red onion,Allium cepa,with novel aglycone

Four anthocyanins with the same novel 4-substituted aglycone, carboxypyranocyanidin, have been isolated from acidified, methanolic extracts of the edible scales as well as from the dry outer scales of red onion, Allium cepa L. The structures of 1 and 2 were identified as the 3-O-beta-glucopyranoside and 3-O-(6"-O-malonyl-beta-glucopyranoside) of 5-carboxypyranocyanidin, respectively. This aglycone, 5-carboxy-2-(3,4-dihydroxyphenyl)-3,8-dihydroxy-pyrano[4,3,2-de]-1-benzopyrylium, is with exception of the substitution pattern on the phenyl ring similar to carboxypyranomalvidin (vitisidin A) recently isolated from red wines. In addition to 1 and 2, two analogues of 2 methylated at the terminal carboxyl group of the acyl moiety (3) or at the aglycone carboxyl (4), respectively, were also identified. These latter compounds are most probably formed by esterification of 2 with the solvent (acidified methanol) during the isolation process. The structures were elucidated by 2D NMR spectroscopy and LC-MS.     

云南山茶(Camellia reticulata) nrDNA ITS序列多态性分析

对云南山茶 (Camellia reticulata) 8个品种的核核糖体DNA内转录间隔区(nrDNA ITS)进行克隆测序,将获得的ITS序列进行GC含量、 5.8S区二级结构的稳定性、替代模式、核苷酸多样性及系统发育关系的相关分析.实验结果显示,云南山茶8个品种的ITS序列存在丰富的基因组内多态性,同时包含中性进化的假基因,表明其ITS序列逃离了一致性进化.云南山茶ITS序列多态性的原因可能来自广泛的种间杂交,以及rDNA位点在基因组中有不确定的物理位置.ITS假基因为品种的物种形成研究提供了更全面的遗传证据,同时也提示了利用ITS假基因进行系统发育分析可能会对其真实的系统关系造成影响.     

Anthocyanins and anthocyanidins in the flowers of Aconitum (Ranunculaceae)

The presence of anthocyanidins and anthocyanins were analyzed in flowers of 30 taxa of Aconitum. Delphinidin was detected as a major anthocyanidin from the hydrolysate of 29 taxa with violet and violet-blue flowers. Pelargonidin was identified as a major anthocyanidin in one taxon with white flowers (partially pale reddish purple; White group N155C by R.H.S. Colour Chart). This is the first reported detection of pelargonidin as a major anthocyanidin from Aconitum flowers. Pelargonidin was also found in ten taxa as a minor anthocyanidin, whereas cyanidin was detected from the flowers of all 30 taxa as a minor anthocyanidin.Two anthocyanins polyacylated by p-hydroxybenzoic acids, violdelphin and monodeacylcampanin were identified from 29 taxa with violet and violet-blue flowers as major anthocyanins. This is the first reported isolation of monodeacylcampanin from Aconitum flowers. The structures of these two anthocyanins were elucidated on the basis of Nuclear Magnetic Resonance (NMR) and Mass Spectrometry (MS).