scholarly journals OcUGT1-Catalyzed Glucosylation of Sulfuretin Yields Ten Glucosides

Catalysts ◽  
2018 ◽  
Vol 8 (10) ◽  
pp. 416 ◽  
Author(s):  
Shuai Yuan ◽  
Yan-Li Xu ◽  
Yan Yang ◽  
Jian-Qiang Kong

Sulfuretin glucosides are important sources of innovative drugs. However, few glucosides of sulfuretin have been observed in nature. Therefore, it is urgent to diversify sulfuretin glycosides. Herein, glycosyltransferase (GT)-catalyzed glycodiversification of sulfuretin was achieved. Specifically, a flavonoid GT designated as OcUGT1 was used as a biocatalyst for the glucosylation of sulfuretin with UDP-Glc. The OcUGT1-assisted glucosylation of sulfuretin yielded ten glycosylated products, including three monoglucosides, five diglucosides and two triglucosides. The three monoglucosides were thus identified to be sulfuretin 3′-, 4′- and 6-glucoside according to HR-ESI-TOFMS data and their coelution with respective standards. A major diglucoside was assigned as sulfuretin 4′,6-diglucoside by HR-ESI-TOFMS in conjunction with NMR analysis. The exact structure of the other four diglucosides was not well characterized due to their trace amount. However, they were reasonably inferred as sulfuretin 3′,6-diglucoside, sulfuretin 3′,4′-diglucoside and two disaccharide glucosides. In addition, the structural identification of the remaining two triglucosides was not performed because of their small amount. However, one of the triglucosides was deduced to be sulfuretin 3′,4′,6-triglucoside based on the catalytic behavior of OcUGT1. Of the ten sulfuretin glucosides, at least six were new compounds. This is the first time to obtain monoglucosides, diglucosides and triglucosides of sulfuretin simultaneously by a single glycosyltransferase.

2008 ◽  
Vol 86 (8) ◽  
pp. 821-830 ◽  
Author(s):  
Xiang Wan ◽  
Haili Liu ◽  
Xuefeng Huang ◽  
Jianguang Luo ◽  
Lingyi Kong

Biotransformation of caffeic acid with H2O2/Momordica charantia peroxidase at pH 5.0, 25 °C in the presence of acetone has resulted in the isolation of three caffeic acid trimers 1–3, five caffeic acid dimers 4–8, and one monomer 9. Among them, seven (1–7) are new compounds, and two (8 and 9) are known compounds, including one compound (9), which was obtained by biotransformation for the first time. The structures were established by 2D NMR techniques, such as HSQC, HMBC, and NOESY measurements. The possible mechanism for the formation of the products is also discussed. This is the first time that caffeic acid trimers have been obtained through the biotransformation of catalyzed by peroxidase in vitro. Compound 5 has shown much stronger anti-oxidative activity than the other caffeic acid polymers obtained.Key words: Momordica charantia peroxidase, caffeic acid, polymers of caffeic acid, biotransformation, antioxidant activity.


Molecules ◽  
2020 ◽  
Vol 25 (9) ◽  
pp. 2171
Author(s):  
Amna Parveen ◽  
Muhammad Asim Farooq ◽  
Whang Wan Kyunn

Natural product studies explore potential and interesting new compounds to discover innovative drugs. Nigella sativa (N. sativa) (Ranunculaceae) is traditionally used to treat diabetes. Flavonoids and triterpenoid mostly show anti-diabetic activity. The current study aim to identify new compounds by a systematic study of the anti-oxidant and anti-diabetic activity of aerial parts of N. sativa concerning. Phytochemicals were isolated from the methanolic extract of aerial parts of the plant by column chromatography and identified by nuclear magnetic resonance spectroscopy and mass spectroscopy. A new triterpenoid saponin glycoside was isolated along with flavonoids. The anti-diabetic study was carried out by DPPH, ABTS, α -glucosidase, and protein tyrosine phosphatase 1B assays at doses of 12.5 to 250 µM. The isolated phytochemicals were identified as 3-O-(β-d-xylopyranosyl-(1-3)-α-l-rhamnopyrnaosyl-(1-2)-α-l-arabinopyranosyl]-28-O-(α-l-rhamno-pyranosyl-(1-4)-β-d-glucopyranosyl-(1-6)-β-d-glucopyranosyl] hederagenin (1), flaccidoside III (2), catechol (3), quercetin-3-gentiobiosides (4), magnoflorine (5), nigelflavonoside B (6), nigelloside (7), quercetin sphorotrioside (8), kaempferol-3, 7-diglucoside (9), kaempferol 3-O-rutinoside (10), rutin (11), 3-O-[α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranpsylhederagenin (12), 3β,23,28-trihydroxyolean-12-ene-3-O-α-l-arabinopyranoside(1→4)-a-rhamnopyranosyl,(1→4)-β-d-gluco-pyranoside (13), 3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranpsyl]-28-O-β-d-gluco-pyranosyl hederagenin (14), and α-hederin (15). These were isolated and are reported for the first time in this study. Compared 13 was identified as a new compound. Compound 2 was isolated for first time from the genus Nigella. Compound 6 was found to be the most active in the DPPH, and ABTS assays and compound 10 was found to be the most active in the α-glucosidase assay, with IC50 32.7 ± 0.1, 95.18 ± 0.9, 214.5 ± 0.0 µΜ, respectively. Compound 12, at a dose of 125 µΜ, showed anti-diabetic activity in a PTP1B assay with IC50 91.30 ± 2.5 µΜ. In conclusion, the anti-diabetic activity of N. sativa is due to its flavonoids and TTSGs. Therefore, our studies suggest that the aerial parts of N. sativa are also a valuable and alternate source of valuable phytochemicals that could be used to develop anti-oxidant and anti-diabetic medicines.


2016 ◽  
Vol 11 (2) ◽  
pp. 1934578X1601100
Author(s):  
Yasuko Okamoto ◽  
Mizuho Taniguchi ◽  
Katsuyuki Nakashima ◽  
Xun Gong ◽  
Ryo Hanai ◽  
...  

The chemical constituents of Ligularia wilsoniana were studied for the first time, using four samples collected in Chongqing City, China. Two new compounds, 6β-(2′,3′-epoxy-2′-methylpropanoyloxy)-1β,10β-epoxyfuranoeremophilane and 11αH-6β-(2′-hydroxymethylacryloyloxy)-1β,10β;7β,8β-diepoxyeremophilanolide, as well as eight known compounds, were isolated from one of the samples, while three to four known furanoeremophilanes were isolated from the other three samples. No compound was common to the two classes of the samples, demonstrating the presence of at least two chemotypes of this species.


2018 ◽  
Vol 13 (8) ◽  
pp. 1934578X1801300 ◽  
Author(s):  
Biljana Nikolić ◽  
Marina Todosijević ◽  
Mihajlo Ratknić ◽  
Iris Đorđević ◽  
Jovana Stanković ◽  
...  

Simultaneous hydrodistillation and extraction of Pinus cembra needles from Slovakia was done (via Likens Nickerson apparatus) for the first time. In essential oil extracts 55 compounds were identified, comprising 99.6% of the extract. The most abundant were monoterpene hydrocarbons (71.0%). In the terpene profile α-pinene, limonene/β-phellandrene, germacrene D, β-pinene, and δ-cadinene dominated (53.2%, 11.4%, 9.4%, 4.6%, and 4.3%, respectively). Seven new compounds for P. cembra, such as methyl daniellate (0.5%), 1,8 cineole (0.2%) and trans-cadina-1(6),4-diene (0.2%), etc. were found. In needle cuticular wax of P. cembra the amount of nonacosan-10-ol was 75.8%. n-Alkanes ranged from C20 to C35 with the most dominant C31, C 29 and C33 (33.4%, 16.9%, and 9.6%, resp.). Differences in terpene profiles between Slovakian and Greece from one side and Romanian and Polish cembran pines on the other side could be the consequence of its disjuncted areal in Carpathian Mountains caused by glaciation and survival of species in different ecological niches. Obtained differences in n-alkane profiles among our and literature results could be the consequence of different age of trees.


2012 ◽  
Vol 39 (2) ◽  
pp. 217-233 ◽  
Author(s):  
J. David Archibald

Studies of the origin and diversification of major groups of plants and animals are contentious topics in current evolutionary biology. This includes the study of the timing and relationships of the two major clades of extant mammals – marsupials and placentals. Molecular studies concerned with marsupial and placental origin and diversification can be at odds with the fossil record. Such studies are, however, not a recent phenomenon. Over 150 years ago Charles Darwin weighed two alternative views on the origin of marsupials and placentals. Less than a year after the publication of On the origin of species, Darwin outlined these in a letter to Charles Lyell dated 23 September 1860. The letter concluded with two competing phylogenetic diagrams. One showed marsupials as ancestral to both living marsupials and placentals, whereas the other showed a non-marsupial, non-placental as being ancestral to both living marsupials and placentals. These two diagrams are published here for the first time. These are the only such competing phylogenetic diagrams that Darwin is known to have produced. In addition to examining the question of mammalian origins in this letter and in other manuscript notes discussed here, Darwin confronted the broader issue as to whether major groups of animals had a single origin (monophyly) or were the result of “continuous creation” as advocated for some groups by Richard Owen. Charles Lyell had held similar views to those of Owen, but it is clear from correspondence with Darwin that he was beginning to accept the idea of monophyly of major groups.


2018 ◽  
Vol 52 (2) ◽  
pp. 455-462 ◽  
Author(s):  
G. Ya. Doroshina ◽  
I. A. Nikolajev

Sphagnum mires on the Greater Caucasus are rare, characterized by the presence of relict plant communities of glacial age and are in a stage of degradation. The study of Sphagnum of Chefandzar and Masota mires is carried out for the first time. Seven species of Sphagnum are recorded. Their distribution and frequency within the North Caucasus are analyzed. Sphagnum contortum, S. platyphyllum, S. russowii, S. squarrosum are recorded for the first time for the study area and for the flora of North Ossetia. The other mosses found in the study area are listed.


2018 ◽  
Author(s):  
Amir Forouharfar

The paper was shaped around the pivotal question: Is SE a sound and scientific field of research? The question has given a critical tone to the paper and has also helped to bring out some of the controversial debates in the realm of SE. The paper was organized under five main discussions to be able to provide a scientific answer to the research question: (1)<b> </b>is “social entrepreneurship” an oxymoron?, (2) the characteristics of SE knowledge, (3) sources of social entrepreneurship knowledge, (4) SE knowledge: structure and limitations and (5) contributing epistemology-making concepts for SE.<b> </b>Based on the sections,<b> </b>the study relied on the relevant philosophical schools of thought in <i>Epistemology </i>(e.g. <i>Empiricism</i>, <i>Rationalism</i>, <i>Skepticism</i>, <i>Internalism</i> vs. <i>Externalism</i>,<i> Essentialism, Social Constructivism</i>, <i>Social Epistemology, etc.</i>) to discuss these controversies around SE and proposes some solutions by reviewing SE literature. Also, to determine the governing linguistic discourse in the realm of SE, which was necessary for our discussion,<i> Corpus of Contemporary American English (COCA)</i> for the first time in SE studies was used. Further, through the study, SE buzzwords which constitute SE terminology were derived and introduced to help us narrowing down and converging the thoughts in this field and demarking the epistemological boundaries of SE. The originality of the paper on one hand lies in its pioneering discussions on SE epistemology and on the other hand in paving the way for a construction of sound epistemology for SE; therefore in many cases after preparing the philosophical ground for the discussions, it went beyond the prevalent SE literature through meta-analysis to discuss the cases which were raised. The results of the study verified previously claimed embryonic pre-paradigmatic phase in SE which was far from a sound and scientific knowledge, although the scholarly endeavors are the harbingers of such a possibility in the future which calls for further mature academic discussion and development of SE knowledge by the SE academia.


Author(s):  
Caroline Durand

Al-Qusayr is located 40 km south of modern al-Wajh, roughly 7 km from the eastern Red Sea shore. This site is known since the mid-19th century, when the explorer R. Burton described it for the first time, in particular the remains of a monumental building so-called al-Qasr. In March 2016, a new survey of the site was undertaken by the al-‘Ula–al-Wajh Survey Project. This survey focused not only on al-Qasr but also on the surrounding site corresponding to the ancient settlement. A surface collection of pottery sherds revealed a striking combination of Mediterranean and Egyptian imports on one hand, and of Nabataean productions on the other hand. This material is particularly homogeneous on the chronological point of view, suggesting a rather limited occupation period for the site. Attesting contacts between Mediterranean merchants, Roman Egypt and the Nabataean kingdom, these new data allow a complete reassessment of the importance of this locality in the Red Sea trade routes during antiquity.


2016 ◽  
Vol 1 (1) ◽  
Author(s):  
D.G. Shah ◽  
D.N. Mehta ◽  
R.V. Gujar

Bryophytes are the second largest group of land plants and are also known as the amphibians of the plant kingdom. 67 species of bryophytes have been reported from select locations across the state of Gujrat. The status of family fissidentaceae which is a large moss family is being presented in this paper. Globally the family consists of 10 genera but only one genus, Fissidens Hedw. has been collected from Gujarat. Fissidens is characterized by a unique leaf structure and shows the presence of three distinct lamina, the dorsal, the ventral and the vaginant lamina. A total of 8 species of Fissidens have been reported from the state based on vegetative characters as no sporophyte stages were collected earlier. Species reported from the neighboring states also showed the absence of sporophytes. The identification of different species was difficult due to substantial overlap in vegetative characters. Hence a detailed study on the diversity of members of Fissidentaceae in Gujarat was carried out between November 2013 and February 2015. In present study 8 distinct species of Fissidens have been collected from different parts of the state. Three species Fissidens splachnobryoides Broth., Fissidens zollingerii Mont. and Fissidens curvato-involutus Dixon. have been identified while the other five are still to be identified. Fissidens zollingerii Mont. and Fissidens xiphoides M. Fleisch., which have been reported as distinct species are actually synonyms according to TROPICOS database. The presence of sexual reproductive structures and sporophytes for several Fissidens species are also being reported for the first time from the state.


Molecules ◽  
2021 ◽  
Vol 26 (11) ◽  
pp. 3371
Author(s):  
Chao-Qun Wang ◽  
Li-Wei Yi ◽  
Lin Zhao ◽  
Yu-Zhen Zhou ◽  
Fang Guo ◽  
...  

Wild ginseng (W-GS), ginseng under forest (F-GS, planted in mountain forest and growing in natural environment), and cultivated ginseng (C-GS) were compared via HPLC-DAD and HPLC-IT-TOF-MSn. A total of 199 saponins, including 16 potential new compounds, were tentatively identified from 100 mg W-GS (177 saponins in W-GS with 11 new compounds), F-GS (56 saponins with 1 new compound), and C-GS (60 saponins with 6 new compounds). There were 21 saponins detected from all the W-GS, F-GS, and C-GS. Fifty saponins were only detected from W-GS, including 23 saponins found in ginseng for the first time. Contents of ginsenosides Re (12.36–13.91 mg/g), Rh1 (7.46–7.65 mg/g), Rd (12.94–12.98 mg/g), and the total contents (50.52–55.51 mg/g) of Rg1, Re, Rf, Rb1, Rg2, Rh1, and Rd in W-GS were remarkably higher than those in F-GS (Re 1.22–3.50 mg/g, Rh1 0.15–1.49 mg/g, Rd 0.19–1.49 mg/g, total 5.69–18.74 mg/g), and C-GS (Re 0.30–3.45 mg/g, Rh1 0.05–3.42 mg/g, Rd 0.17–1.68 mg/g, total 2.99–19.55 mg/g). Contents of Re and Rf were significantly higher in F-GS than those in C-GS (p < 0.05). Using the contents of Re, Rf, or Rb1, approximately a half number of cultivated ginseng samples could be identified from ginseng under forest. Contents of Rg1, Re, Rg2, Rh1, as well as the total contents of the seven ginsenosides were highest in ginseng older than 15 years, middle–high in ginseng between 10 to 15 years old, and lowest in ginseng younger than 10 years. Contents of Rg1, Re, Rf, Rb1, Rg2, and the total of seven ginsenosides were significantly related to the growing ages of ginseng (p < 0.10). Similarities of chromatographic fingerprints to W-GS were significantly higher (p < 0.05) for F-GS (median: 0.824) than C-GS (median: 0.745). A characteristic peak pattern in fingerprint was also discovered for distinguishing three types of ginseng. Conclusively, wild ginseng was remarkably superior to ginseng under forest and cultivated ginseng, with ginseng under forest slightly closer to wild ginseng than cultivated ginseng. The differences among wild ginseng, ginseng under forest, and cultivated ginseng in saponin compositions and contents of ginsenosides were mainly attributed to their growing ages.


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