Identification of new flavonol O-glycosides from indigo (Polygonum tinctorium Lour) leaves and their inhibitory activity against 3-hydroxy-3-methylglutaryl-CoA reductase
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Cyanogenic glycosides are an important and widespread class of plant natural products, which are however structurally less diverse than many other classes of natural products. So far, 112 naturally occurring cyanogenic glycosides have been described in the phytochemical literature. Currently, these unique compounds have been reported from more than 2500 plant species. Natural cyanogenic glycosides show variations regarding both the aglycone and the sugar part of the molecules. The predominant sugar moiety is glucose but many substitution patterns of this glucose moiety exist in nature. Regarding the aglycone moiety, four different basic classes can be distinguished, aliphatic, cyclic, aromatic, and heterocyclic aglycones. Our overview covers all cyanogenic glycosides isolated from plants and includes 33 compounds with a non-cyclic aglycone, 20 cyclopentane derivatives, 55 natural products with an aromatic aglycone, and four dihydropyridone derivatives. In the following sections, we will provide an overview about the chemical diversity known so far and mention the first source from which the respective compounds had been isolated. This review will serve as a first reference for researchers trying to find new cyanogenic glycosides and highlights some gaps in the knowledge about the exact structures of already described compounds.
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Five novel steroidal glycosides 2-6 were isolated from the whole plant of Asclepias fruticosa L. (Asclepiadaceae). The structures of these steroidal glycosides were determined on the basis of spectral and chemical evidence. All of these glycosides contain 2,6-dideoxyhexopyranoses as component sugars and their structures were elucidated as polyoxypregnane-type glycosides, which have lineolon as the aglycone moiety.
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The chemical structure of glycoside H1 (I), C56H90O24, mp 182°, [α]24D-22. 83°(EtOH), which was isolated from Bei-Wujiapi (cortex of Periploca sepittm BGE.), was established to be Δ5-pregnene-3β, 20α-diol (3)-[2-O-acetyl-β-D-digitalopyranosyl (1dig→4cym)-β-D-cymaropyranoside](20)-[β-D-glucopyranosyl (1glu→6glu)-β-D-glucopyranosyl (1glu→2dig)-β-D-digitalopyranoside].It should be noted that glycoside H1 is the first example of the pregnane type glycoside whose sugar moiety links to both C-3 and C-20 hydroxyl groups of the aglycone and that the sugar sequences of Asclepiadaceous glycosides are ruled by certain regularity, such as aglycone-(2, 6-dideoxysugar or its 3-O-methyl derivative) 0-l-(6-deoxysugar or its 3-Omethyl derivatives) o_m-(glucose) o-n.
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Ruminants are a diverse group of mammals, both domestic and wild species, that exhibit microbial fermentation prior to gastrointestinal activity. During the digestive process, glycosides and other natural products are exposed to ruminal microorganisms and metabolised as substrates. Most compounds are converted into nutrients but some become toxic metabolites. At least 10 types of toxic glycosides occur in forage species. Glycosides are characterized by the presence of one or more sugars linked to the alcohol or thiol functions of the non-sugar portion of the molecule, which is called the aglycone. The biological activity of the glycoside is usually determined by the chemical nature of the aglycone. The aglycones are released by microbial enzymes and may undergo further enzymatic or non-enzymatic transformations to yield toxic metabolites that can be absorbed from the gastrointestinal tract. Microbial detoxification of the aglycone is also possible. Further biotransformation of the aglycone can occur in the liver. A review is presented on glycosides that are toxic to ruminants. The discussion covers aliphatic nitrocompounds, cyanogenic glycosides, cardiac glycosides, saponins, glucosinolates, diterpenoid glycosides, bracken glycosides, calcinogens, phenolic glycosides and ranunculin. Clinical signs of poisoning and treatment of livestock as well as management strategies for the prevention of poisoning are considered.
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Two flavone O-glycosides were isolated from allelopathic rice seedlings and have been identified as 5,4'-dihydroxy-3',5'-dimethoxy-7-O-β-glucopyranosylflavone and 7,4'-dihydroxy-3',5'-dimethoxy-5-O-β-glucopyranosylflavone. Considerable levels of these glycosides could be found in allelopathic rice tissues. They could not be detected in the soils growing these allelopathic rice seedlings. Only their aglycone, 5,7,4'-trihydroxy-3',5'-dimethoxyflavone, could be found in the soil. Further experiments showed that two flavone O-glycosides were exuded from allelopathic rice roots to the rihzosphere and then transformed into their aglycone form, that is, 5,7,4'-trihydroxy-3',5'-dimethoxyflavone, with a great diversity of biological activities on associated weeds and microbes by soil interactions once released. The glycosides degraded rapidly (t1/2 < 2 h), whereas their aglycone was more resistant toward degradation in paddy soils, in which the half-life (t1/2) at low (25 μg/g) and high (200 μg/g) doses reached 19.86 ± 3.64 h (r 2 = 0.97) and 28.78 ± 3.72 h (r 2 = 0.98), respectively. Furthermore, the mobility of both glycosides and their aglycone in paddy soil was evaluated by soil TLC with bioassay. The mobility of the glycosides (Rf = 0.418 ± 0.069, n = 18) is higher than that of the aglycone (Rf = 0.361 ± 0.048, n = 18). The results suggested that two flavone O-glycosides are formed in rice biosynthesis and that storage of the allelochemicals and their aglycone 5,7,4'-trihydroxy-3',5'-dimethoxyflavone is the agent of alleloapthic rice which interferes with weeds or microbes in paddy soil. Keywords: Oryza sativa L.; allelopathy; flavone O-glycosides; bioactivity; soil TLC; soil dynamics
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Two new triterpene glycosides, scabraside A (1) and B (2), and a structurally known compound (3), were isolated from the sea cucumber Holothuria scabra (Holothuriidae) collected from the South China Sea. Structure of these compounds was elucidated by spectroscopic and chemical methods. The glycosides 1 and 2 exhibit the same common structural features, i. e., the presence of 12- and 17-hydroxy groups in the holostane-type triterpene aglycone with a 9(11)-ene bond, but are different in the side chains of the triterpene aglycone. The glycosides 1 and 2 had significant in vitro cytotoxicity against four human tumor cell lines in comparison to 10-hydroxycamptothecin.
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Phenolic acid and flavonoid glycosides form a varied class of naturally occurring compounds, characterised by high polarity—resulting from the glycone moiety—and the presence of multiple phenol functionalities, which often leads to strong antioxidant activity. Phenolic glycosides, and in particular flavonoid glycosides, may possess strong bioactive properties with broad spectrum activity. This systematic literature review provides a detailed overview of 28 studies examining the biological activity of phenolic and flavonoid glycosides from plant sources, highlighting the potential of these compounds as therapeutic agents. The activity of glycosides depends upon the biological activity type, identity of the aglycone and the identity and specific location of the glycone moiety. From studies reporting the activity of both glycosides and their respective aglycones, phenolic glycosides appear to generally be a storage/reserve pool of precursors of more bioactive compounds. The glycosylated compounds are likely to be more bioavailable compared to their aglycone forms, due to the presence of the sugar moieties. Hydrolysis of the glycoside in the in vivo environment would release the free aglycone, potentiating their biological activity. However, further high‐quality studies are needed to firmly establish the clinical efficacy of glycosides from many of the plant species studied.
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Glycosides are plant secondary metabolites containing a carbohydrate component linked by anether bond to a non carbohydrate nucleus (theaglycone). They are usually bitter substances. Acids are hydrolyzed to aglycone and sugar. Apart from acidic hydrolysis, it is possible to carry out the enzyme that is more specific. Often the aglycone is released by enzymatic action when the plantt issueis damaged. Glycosides are classified according to the structure of the aglycone (nucleus) constituent. Some of the glycosides of most importance in human and animal nutrition include saponins, glucosinolates, cyanogenicglycosides, cardiac glycosides and glycoalkaloids. An example of non-reducing sugar is trehalose. Detected in shoots, it is still at the beginning of this century. It is spread in various organisms such as bacteria, fungi, plants, insects and invertebrates, and has so far been isolated from them. This paper deals with the properties of glycoside, glycoside synthesis and the experimental part of the work is isolation of trehalose from bakers yeast.
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The structures of two glycosides, named ziyu-glycoside I and ziyu-glycoside II, obtained from Sanguisorbae Radix have been established as I and II respectively by virtue of the soil bacterial hydrolysis method. Furthermore, it has been revaled that the genuine aglycone of the glycosides is pomolic acid (XI) and is not tomentosolic acid (III).
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