3615-37-0

Usage

Uses

Used in Pharmaceutical Industry:
D-(+)-Fucose is used as a therapeutic agent for its potential anti-inflammatory, antiviral, and anticoagulant properties. It has been found to modulate immune responses and exhibit anti-cancer effects by inhibiting tumor growth and metastasis.
Used in Food Industry:
D-(+)-Fucose is used as a functional ingredient in food products due to its prebiotic properties, promoting the growth of beneficial gut bacteria and supporting overall gut health.
Used in Cosmetic Industry:
D-(+)-Fucose is used as a skin conditioning agent in cosmetic formulations, helping to improve skin hydration, elasticity, and overall appearance.
Used in Research:
D-(+)-Fucose is used as a research tool for studying the structure and function of glycoproteins and glycolipids, as well as their role in various biological processes and disease mechanisms.
Used in Brown Algae-derived Products:
D-(+)-Fucose is used as a key component in fucoidan polysaccharide, which is derived from brown algae and has been associated with various health benefits, such as immune modulation, anti-inflammatory effects, and anticoagulant properties. Fucoidan-rich products are used in dietary supplements and nutraceuticals for their potential health-promoting effects.

Purification Methods

Crystallise D(+)-fucose from EtOH or 95% EtOH. Its 1,2:3,4-diisopropylidene derivative has b 83-84o/0.45mm and crystallises on seeding with m 37o and[]19 -52o (melt). [Schmidt Methods in Carbohydrate Chemistry I 191 1962, Academic Press, Haskett et al. J Am Chem Soc 61 1658 1939, Beilstein 31 H 76, 1 IV 4265.]

InChI:InChI=1/C6H12O5/c1-2-3(7)4(8)5(9)6(10)11-2/h2-10H,1H3/t2-,3+,4+,5-,6-/m1/s1

Upstream product

• 15814-59-2 (2S,3S,4S,5S,6R)-2-methoxy-6-methyltetrahydro-2H-pyran-3,4,5-triol 
• 1051388-66-9 (1β,3β,5β,25S)-spirostan-1,3-diol 1-[α-L-rhamnopyranosyl-(1->2)-β-D-fucopyranoside] 
• 1166398-39-5 8,3'-dihydroxy-3,7,4'-trimethoxy-6-O-[α-L-rhamnopyranosyl-(1->2)]-β-D-glucopyranoside flavone 
• 1253285-17-4 26-O-β-D-glucopyranosyl-(25R)-5α-furostan-20(22)-en-3β,26-diol-3-O-β-D-xylopyranosyl-(1→2)-[β-D-xylopyranosyl-(1→3)]-β-D-glucopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-galactopyranoside 
• 22324-77-2 quercitrin 

Downstream Products

• 634-74-2 D,L-rhamnose 
• 128613-99-0 trimethylsilyl ether of 6-deoxymannose-anti-O-benzyloxime 
• 128614-00-6 trimethylsilyl ether of 6-deoxymannose-syn-O-benzyloxime 
• 50705-55-0 Methyl β-L-rhamnofuranosid 
• 50705-54-9 methyl-α-L-rhamnofuranoside 
• 14917-55-6 methyl 6-deoxy-α-L-mannopyranoside 
• 42214-00-6 (2S,3R,4R,5R,6S)-2-Methoxy-6-methyl-tetrahydro-pyran-3,4,5-triol 
• 6422-34-0 L-idomethylonic acid 
• 99881-07-9 L-xylo-6-deoxy-[2]hexosulose-bis-phenylhydrazone 
• 71202-84-1 D-fucose-(toluene-4-sulfonylhydrazone) 
• 100300-50-3 D-Fucose-benzylphenylhydrazon 
• 128614-01-7 trimethylsilyl ether of 6-deoxygalactose-anti-O-benzyloxime 
• 13322-79-7 methyl 2,6-dideoxy-α-D-lyxo-hexopyranoside 
• 139756-72-2 methyl 2,6-dideoxy-β-D-lyxo-hexopyranoside 

Relevant academic research and scientific papers

Pro-apoptotic activity of new triterpenoid saponins from the roots of Albizia adianthifolia (Schumach.) W.Wight

As part of our study of the proapoptotic function of saponins from Cameroonian's Albizia genus, phytochemical investigation of the roots of Albizia adianthifolia led to the isolation of three new triterpenoid saponins, named adianthifoliosides G–I (1–3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H-, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid-28-O-β-D-xylopyranosyl-(1 → 3)-[5-O-acetyl-α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (1), 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-(β-D-quinovopyranosyl)octa-2,7-dienoyl]}acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (2), and 3-O-[β-D-glucopyranosyl-(1 → 2)-β-D-fucopyranosyl-(1 → 6)-β-D-glucopyranosyl]-21-O-{(2E,6S)-2-(hydroxymethyl)-6-methyl-6-O-{4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-4-O-[(2E,6S)-2,6-dimethyl-6-O-(β-D-quinovopyranosyl)octa-2,7-dienoyl]-β-D-quinovopyranosyl}-2,6-dimethylocta-2,7-dienoyl}acacic acid 28-O-β-D-xylopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-1 → 4)]-α-L-rhamnopyranosyl-(1 → 2)-β-D-glucopyranosyl ester (3). The apoptotic effect of saponins 1–3 was evaluated on the A431 human epidermoid cancer cell. Flow cytometric analyses showed that saponins 1–3 induced apoptosis of human epidermoid cancer cell (A431) in a dose-dependent manner.

Nebulosides A-B, novel triterpene saponins from under-ground parts of Gypsophila arrostii Guss. var. nebulosa

A bioassay-guided phytochemical analysis of the triterpene saponins from under ground parts of Gypsophila arrostii var. nebulosa allowed the isolation of two triterpene saponins; nebuloside A, B based on gypsogenin and quillaic acid aglycone. Two new oleanane type triterpenoid saponins (nebuloside A, B) and three known saponins (1-3) were isolated from the root bark of Gypsophila arrostii var. nebulosa. The structures of the two new compounds were elucidated as 3-O-β-d-galactopyranosyl-(1→2)-[β-d-xylopyranosyl-(1→3)]- β-d-glucuronopyranosyl quillaic acid 28-O-β-d-glucopyranosyl- (1→3)-[β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)] -α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside A) and 3-O-β-d-xylopyranosyl-(1→3)-[β-d- galactopyranosyl(1→3)-β-d-galactopyranosyl-(1→2)] -β-d-glucuronopyranosyl gypsogenin 28-O-β-d-glucopyranosyl-(1→3)- [β-d-xylopyranosyl-(1→3)-β-d-xylopyranosyl-(1→4)] -α-l-rhamnopyranosyl-(1→2)-β-d-fucopyranosyl ester (nebuloside B), on the basis of extensive spectral analysis and chemical evidence. Nebuloside A and B showed toxicity enhancing properties on saporin a type-I RIP without causing toxicity by themselves at 15 μg/mL.

Three new spirostanol glycosides from Helleborus thibetanus

An ongoing chemical investigation on n-BuOH extract of roots and rhizomes of Helleborus thibetanus afforded three new spirostanol glycosides (1–3). Their structures were elucidated by extensive analysis of 1 D, 2 D NMR spectra, together with IR and MS met

Cytotoxic triterpenoid saponins from husks of Aesculus californica (Spach) Nutt.

Fifteen polyhydroxyoleanene saponins, aesculiosides C1-C15 (1-15), were isolated from husks of Aesculus californica. Their structures were established by extensive spectroscopic and chemical analyses. The triterpenoid saponins from A. californica have greater structural diversity than those from any other investigated species thus far in the genus Aesculus. The chemotaxonomic characteristic of aesculiosides C1-C15 is that the unit attached to the C-3 of the aglycone is a glucopyranosyl moiety, instead of a glucuronopyranosyl group in the saponins that have been isolated from other Aesculus species. The saponins isolated from A. californica then provide important evolutionary and chemotaxonomic knowledge of the Aesculus genus, a well-known intercontinental disjunct genus in the Northern hemisphere. Aesculiosides C1-C15 (1-15) showed cytotoxicity to human non-small cell lung tumor (A549) with GI50 ranged from 3.76 to >25 μM.

Glycosides of polygalacic acid from the stem barks of Piper guineense Schum and Thonn

In a continuation of our study on constituents of P. guineense now focusing on the search for saponins, phytochemical investigation of the n-BuOH fraction of P. guineense stem bark led to the isolation of three previously undescribed triterpenoid saponins, named guineenosides A─C (1─3). Their structures were established on the basis of extensive analysis of 1D and 2D NMR (1H, 13C NMR, DEPT, COSY, TOCSY, NOESY, HSQC, HSQC-TOCSY and HMBC) and HRESIMS experiments, and by chemical evidence as 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (1), 3-O-{α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl-(1 → 2)-α-L-arabinopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-[α-L-arabinofuranosyl-(1 → 4)]-α-L-rhamnopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-β-D-glucopyranosyl-(1 → 3)-α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (2), and 3-O-{α-L-rhamnopyranosyl-(1 → 2)-β-D-xylopyranosyl-(1 → 3)-β-D-fucopyranosyl} polygalacic acid 28-O-[α-L-rhamnopyranosyl-(1 → 4)-α-L-rhamnopyranosyl-(1 → 3)-β-D-xylopyranosyl ester (3). This is the first report of triterpenoid saponins from P. guineense.

Two new saponins from Thalictrum fortunei

Two new cycloartane glycosides were isolated from the aerial parts of Thalictrum fortunei (Ranunculaceae). The chemical structures of these compounds were elucidated as 3-O-β-D-glucopyranosyl (1 → 4)-β-D- fucopyranosyl-(22S,24Z)-cycloart-24-en-3β,22,26,30

Dolabellane diterpene and three cycloartane glycosides from Thalictrum squarrosum

A new dolabellane diterpene glycoside, named squoside A, and three new cycloartane glycosides, named squarrosides V, VI, and VII, have been isolated from the dried aerial parts of Thalictrum squarrosum (Ranunculaceae). Their structures were determined by

Dammarane-type saponins from leaves of Ziziphus spina-christi

Phytochemical profiling of Ziziphus spina-christi leaves led to the characterization of 10 dammarane-type saponins and 12 phenolic compounds. Isolation was achieved by gel chromatography on Sephadex LH20, open column chromatography on silica gel, and semi-preparative HPLC with PDA and ELSD detectors. Structural characterization was performed by extensive 1D and 2D NMR, mass spectrometry, and by GC-MS of sugar derivatives. A biosynthetic pathway leading to three previously undescribed sapogenins is proposed. The saponin profiles in Z.?spina-christi leaves of four different origins were compared by means of HPLC-ESIMS.

Flavonoids isolated from the fresh sweet fruit of Averrhoa carambola, commonly known as star fruit

Thirteen flavonoids were isolated from the fresh sweet fruit of Averrhoa carambola L. (Oxalidaceae), commonly known as star fruit, and their structures were determined by spectroscopic and chemical methods. 8-Carboxymethyl-(+)-epicatechin methyl ester, pinobanksin 3-O-β-D-glucoside, and carambolasides M–Q were undescribed structures. (+)-Epicatechin, aromadendrin 3-O-β-D-glucoside, helicioside A, taxifolin 3′-O-β-D-glucoside, galangin 3-O-rutinoside, and isorhamnetin 3-O-rutinoside were reported from this species for the first time. Pinobanksin 3-O-β-D-glucoside and carambolasides M–Q showed more potent 2,2′-azinobis-(3-ethylbenzthiazoline-6-sulphonic acid) (ABTS) radical cation scavenging activity (IC50 = 5.3–2.3 μM) than L-ascorbic acid (10.5 μM). Further, (+)-epicatechin, pinobanksin 3-O-β-D-glucoside, isorhamnetin 3-O-rutinoside, and carambolasides O–Q exhibited weak porcine pancreatic lipase inhibitory activity.

Furostane Series Asterosaponins and Other Unusual Steroid Oligoglycosides from the Tropical Starfish Pentaceraster regulus

Seven new asterosaponins, pentaregulosides A-G (1-7), including two furostane-type steroid oligoglycosides (2, 3), along with four previously known compounds (8-11) were isolated from the ethanolic extract of the starfish Pentaceraster regulus, collected off the coast of Vietnam. The structures of 1-7 were elucidated by extensive NMR and ESIMS techniques as well as chemical transformations. The aglycons of compounds 1 and 3 have not previously been observed in starfish steroid oligoglycosides, while the aglycons of compounds 2 and 4-6 are very rare for this structural group. Compound 1 exhibited cytotoxic activity with an IC50 value of 6.4 ± 0.3 μM against RAW 264.7 murine macrophages. In contrast, nontoxic asterosaponins 3, 4, and 5 showed a potential immunomodulatory action at a concentration of 5 μM, reducing by 40%, 28%, and 55%, respectively, reactive oxygen species formation in the RAW 264.7 cells, co-stimulated with the pro-inflammatory endotoxic lipopolysaccharide from E. coli.