6477-44-7

Usage

Uses

Apiose is used as a building block in the synthesis of complex carbohydrates and glycoconjugates for research purposes. It is also used in the development of new pharmaceuticals and therapeutic agents targeting various diseases.
Used in Pharmaceutical Industry:
Apiose is used as a key component in the development of novel drugs and therapeutic agents for the treatment of various diseases, including cancer, inflammatory disorders, and infectious diseases. Its unique structure and properties make it a promising candidate for drug discovery and development.
Used in Research and Development:
Apiose is used as a valuable tool in the study of carbohydrate chemistry, glycobiology, and glycoengineering. It helps researchers understand the role of carbohydrates in biological processes and develop new strategies for the synthesis and modification of complex carbohydrates and glycoconjugates.
Used in Food Industry:
Apiose can be used as a natural sweetener and flavor enhancer in the food industry. Its unique taste and properties make it a potential alternative to traditional sweeteners and additives.

Upstream product

• 30572-22-6 4-hydroxymethyl-L-erythro-pentonic acid 4-lactone 
• 70147-50-1 (3S)-O²,O³-isopropylidene-β-L-apiofuranose 
• 1176306-06-1 1-O-3,4-(dihydroxyphenyl)ethyl-β-D-apiofuranosyl-(1->2)-4-O-caffeoyl-β-D-glucopyranoside 
• 1252575-33-9 ent-kauran-3α,16α,17-triol-19-al 3-O-[5-O-vanilloyl-β-D-apiopyranosyl(1->6)]-β-D-glucopyranoside 
• 125085-17-8 C₇₃H₁₁₈O₃₈ 
• 111252-14-3 (23S)-3β-[(O-β-D-apiofuranosyl-(1->2)-O-β-D-glucopyranosyl-(1->2)-O-α-L-arabinopyranosyl-(1->6)-β-D-glucopyranosyl)oxy]-17α,23-epoxy-29-hydroxy-27-norlanost-8-ene-15,24-dione 
• 111252-15-4 muscaroside D₄ 
• 1176306-07-2 1-O-3,4-(dihydroxyphenyl)ethyl-β-D-apiofuranosyl-(1->2)-β-D-xylopyranosyl-(1->3)-4-O-caffeoyl-β-D-glucopyranoside 
• 1217268-01-3 scutellarein-7-O-β-D-apiofuranoside 
• 1217268-02-4 apigenin-7-O-β-D-apiofuranosyl-(1->2)-β-D-apiofuranoside 
• 1191300-10-3 β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-[β-D-apio-D-furanosyl-(1->3)]-α-L-arabinopyranosyl 3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oate 
• 1191300-13-6 β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-{[β-D-apio-D-furanosyl-(1->3)]-4-O-(8-oxo-16-β-[(D-xylopyranosyl)oxy]hexadecanoyl)}-α-L-arabinopyranosyl 3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oate 
• 1191300-14-7 β-D-xylopyranosyl-(1->4)-α-L-rhamnopyranosyl-(1->2)-{[β-D-apio-D-furanosyl-(1->3)]-4-O-(9-oxo-16-β-[(D-xylopyranosyl)oxy]hexadecanoyl)}-α-L-arabinopyranosyl 3-O-β-D-glucopyranosyl-2β,3β,23-trihydroxyolean-12-en-28-oate 
• 1307232-69-4 15,16-dihydroxy-3-[[O-β-D-xylopyranosyl-(1->2)-O-α-L-arabinopyranosyl-(1->6)-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]oxy]-(3β,15α,16α)-olean-12-en-28-oic acid O-D-apio-β-D-furanosyl-(1->3)-O-β-D-xylopyranosyl-(1->2)-O-[β-D-glucopyranosyl-(1->4)]-6-O-[(2E,6R)-6-hydroxy-2,6-dimethyl-1-oxo-2,7-octadienyl]-β-D-glucopyranosyl ester 

Downstream Products

• 109941-37-9 3-hydroxymethyl-[2]tetrosulose-bis-(2,5-dichloro-phenylhydrazone) 
• 34724-16-8 1,2;3,3'-di-O-isopropylidene-3-C-(hydroxymethyl)-α-D-erythrofuranose 
• 10592-17-3 (3S)-2-hydroxymethylbutane-1,2,3,4-tetrol 
• 64481-63-6 methyl 3-C-(hydroxymethyl)-α-L-threofuranoside 
• 64481-62-5 methyl 3-C-(hydroxymethyl)-β-L-threofuranoside 
• 64481-65-8 methyl 3-C-(hydroxymethyl)-β-D-erythrofuranoside 
• 64481-64-7 methyl 3-C-(hydroxymethyl)-α-D-erythrofuranoside 

Relevant academic research and scientific papers

Two new isoflavones from the barks of Dalbergia hancei Benth

Two new isoflavone compounds, Dalhancei A (1) and Dalhancei B (2), along with a known compound epicatechin (3) were isolated from 80% methanol extract of the barks of Dalbergia hancei Benth. The structures of compounds 1–3 were elucidated by comparison with the literature and physical data analysis, including optical rotation, MS, 1D and 2D NMR spectra. Compounds 1 and 2 showed weak inhibitory activity against tyrosinase at 16.22 mmol/L, with inhibition rates of 42.23 ± 0.18% and 45.68 ± 0.17%, respectively; compound 1 exhibited weak inhibitory activity against α-glucosidase with the inhibition rate of 43.72 ± 0.22% at 5.41 mmol/L, compounds 2 and 3 had better α-glucosidase inhibitory activity than compound 1 with IC50 values of 0.90 ± 0.18 and 0.41 ± 0.17 mmol/L, respectively.

Structural characterization of phenolic constituents from the rhizome of Imperata cylindrica var. major and their anti-inflammatory activity

As one of raw materials, the rhizome of Imperata cylindrica var. major (Nees) C.E. Hubb. is used in kinds of preparations curing inflammation related diseases, while its effective substances are not yet clear. In this paper, its chemical constituents and their anti-inflammatory activities were investigated. As results, ten compounds, named as imperphenoside A (1), imperphenols B (2) and C (3), imperphenosides D–F (4–6), and imperlignanosides A–D (7–10), along with previously reported thirty-seven known ones (11–47) were obtained from it. Their structures were ascertained basing on the extensive spectroscopic methods and electronic circular dichroism data analysis. Meanwhile, compounds 4, 11, 12, 24, 27, 31, 32, 37, 43, 45, and 47 exhibited nitric oxide inhibitory effects in concentration dependent at 3, 10, and 30 μM on lipopolysaccharides induced RAW 264.7 cells. Moreover, the western blot analysis indicated that compounds 4, 11, 43, and 47 could restrain the phosphorylation of nuclear factor kappa-B kinase to down-regulate the protein expression of inflammatory cytokines such as inducible nitric oxide synthase, interleukin-6 and tumor necrosis factor-α. In conclusion, they might play the anti-inflammatory effects through regulating NF-κB signaling pathway.

New Phenolic Glycosides and Lignans from the Roots of Lilium dauricum

Three new phenolic glycosides, carvacrol-2- O - β -D-apiofuranosyl-(1 → 6)- β -D-glucopyranoside (1), 1-methyl-3-isopropylphenol-4- O - β -D-apiofuranosyl-(1 → 6)- β -D-glucopyranoside (2), p -methoxythymol-5- O - β -D-apiofuranosyl-(1 → 6)- β -D-glucopyranoside (3), and a pair of new 8- O -4′ neolignan enantiomers (5a / 5b), together with 26 known compounds (4, 6 - 30) were isolated from the roots of Lilium dauricum. The structures of the new compounds were elucidated based on extensive spectroscopic and chemical methods, and the absolute configurations of 5a and 5b were established by electronic circular dichroism analysis. Nine compounds (1, 3, 4, 8, 9, 17, 25, 29, and 30) exhibited potent α -glucosidase inhibitory activity with IC 50values ranging from 73.4 μM to 988.2 μM. Besides, compound 19 displayed strong anticomplementary activity (CH 50: 71.6 μM).

A new prenylated coumarin diglycoside with insulin-release promoting activity from Clausena dunniana

A new prenylated coumarin diglycoside, 6-prenylcoumarin-7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside (1) and five known flavonoid glycosides (2–6) were isolated from the leaves and stems of Clausena dunniana. The structures of these isolates were elucidated based on comprehensive MS, UV, IR, and NMR spectroscopic data analysis and comparison with the data reported in literature. Compounds 2–6 are obtained from the title plant for the first time. All these isolates were evaluated for their insulin-release promoting effects, and compounds 1, 2, and 4 exhibited significant activities (2.0 to 3.3-fold higher in comparison with the control, p 0.01) at 40 μM. (Figure presented.).

Anti-inflammatory active components of the roots of Datura metel

One new phenolic glycoside, methyl 3,4-dihydroxyphenylacetate-4-O-[2-O-β-D-apisoyl-6-O-(2-hydroxybenzoyl)]-β-D-glucopyranoside (1), together with 10 known compounds (2–11), were isolated from the roots of Datura metel. The structures of these compounds we

Two new flavonol glycosides from Selaginella tamariscina

Two new flavonol glycosides 3,5,7-trimethoxyflavone-4'-O-[5'''-O-p-coumaroyl-β-D-apiofuranoyl-(1'''→2'')-β-D-glucopyranoside] (1) and 3,5,7-trimethoxyflavone ?4'-O-β-D-glucopyranoside (2) were isolated from Selaginella tamariscina. The structures of 1 and 2 were elucidated on the basis of chemical and spectral analysis, including 1D, 2D NMR analyses and HRESIMS spectrometry. Two compounds were evaluated for cytotoxic activities against A-375, MCF-7, MDA-MB-231 and MDA-MB-468 cell lines by MTT assay. Unfortunately, two compounds displayed no cytotoxic activities.

Phenolic constituents isolated from Senna tora sprouts and their neuroprotective effects against glutamate-induced oxidative stress in HT22 and R28 cells

The consumption of sprouts has been steadily increasing due to their being an excellent source of nutrition. It is known that the bioactive constituents of legumes can be increased after germination. In this study, the extract from Senna tora sprouts is shown to exhibit improved radical scavenging activities and better neuroprotective effects in HT22 hippocampal neuronal (HT22) and R28 retina precursor (R28) cells than those from seeds due to an increased content of phenolic constituents, especially compounds 1 and 3–6. A phytochemical investigation of S. tora sprouts resulted in the isolation of two new naphthopyrone glycosides (1–2) with 27 previously reported compounds. Their structures were determined via interpreting spectroscopic data. Compounds 1 and 3–6 were found to possess radical scavenging activities and neuroprotective effects against oxidative stress in both neuronal cells. Hence, Senna tora sprouts and their constituents may be developed as natural neuroprotective agents via antioxidative effects.

Indole glycosides from calanthe discolor with proliferative activity on human hair follicle dermal papilla cells

A methanol extract from the underground part of Calanthe discolor Lindl. (Orchidaceae) demonstrated significant proliferative activity on human hair follicle dermal papilla cells (HFDPC, % of control: 120.8±0.2%) at 100μg/mL against HFDPC. Through bioassay-guided separation of the extract, a new indole glycoside named 6′-O-β-D-apiofuranosylindican (1) was isolated along with six known compounds (2–7) including three indole glycosides. The stereostructure of 1 was elucidated based on its spectroscopic properties and chemical characteristics. Among the isolates, 1 (110.0±1.0%), glucoindican (3, 123.9±6.8%), and calanthoside (4, 158.6±7.1%) showed significant proliferative activity at 100μM. Furthermore, the active indole glycosides (1, 3, and 4) upregulated the expression of vascular endothelial growth factor (VEGF) and fibroblast growth factor-7 (FGF-7) mRNA and protein in HFDPC, which could be the mechanism of their proliferative activity.

Stable Axially Chiral Isomers of Arylnaphthalene Lignan Glycosides with Antiviral Potential Discovered from Justicia procumbens

Arylnaphthalene lignans (ANLs) were known to have axial chirality due to the biphenyl skeleton with hindered rotation at the single bond. However, the stable ANL atropisomers have not been isolated from nature until the present study. Phytochemical separation of the methanol extract of the stems and barks of Justicia procumbens led to the isolation of 11 ANL glycosides including four pairs of new atropisomers with stable confirmations at room temperature. Their structures were deduced from elucidation of the extensive spectral data, and their absolute configurations were determined by the circular dichroism, electronic circular dichroism, and X-ray methods as well as the total synthesis of one pair of the atropisomers. The ANL compounds were evaluated for their antiviral potential, and it was found that they displayed great antiviral activity discrepancy between a pair of atropisomers due to the geometric orientation. The 1′P-oriented atropisomers showed much more significant antiviral potency than their corresponding 1′M-oriented counterparts. The biological activity discrepancy caused by the axial chirality will not only inspire synthetic design of novel ANL atropisomers to enrich the structural diversity, but also provide important hints to direct the synthetic approaches toward the antiviral drug development of ANL compounds.

Phenolic glycosides and flavonoids with antioxidant and anticancer activities from Desmodium caudatum

Descaudatine A (1), an undescribed phenolic glycoside, along with a known analogue (2) and ten flavonoids (3-12), were isolated from the whole plant of Desmodium caudatum. Compounds 1 and 4 exhibited potent antioxidant activities with the IC50 of 58.59 μM and 31.31 μM, respectively, which were approached to that of the positive control Vitamin C (IC50 = 46.32 μM). Meanwhile, 12 showed moderate antioxidant activity with the IC50 of 173.9 μM. Besides, compounds 3 and 6 inhibited the proliferation of HeLa cells with IC50 values of 56.14 μM and 69.04 μM, respectively. Further studies indicated that 3 and 6 could dose-dependently induce PARP cleavage and might trigger caspase-3, 8, 9 activation to induce apoptosis. RXRα is an ideal anticancer target of nuclear receptor. The reporter gene assay of RXRα indicated that 3 and 6 could inhibited the 9-cis-RA induced RXRα transcription in a concentration-dependent manner.