Concise Synthesis and Antidiabetic Effect of Three Natural Triterpenoid Saponins Isolated from <i>Fadogia ancylantha</i> (Makoni tea)

Feng, Zijian; Wu, Shaoping; Li, Wenhong; Guo, Tiantian; Liu, Qingchao

doi:10.1002/hlca.201500061

Cited by 7 publications

(6 citation statements)

References 40 publications

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“…Synthesis of 12 was started from the peracetyl-β-glucopyranose 6 , which was transformed to the known 1,2-orthoacetate 7 (Scheme ). Without purification, the acetyl protecting groups in 7 were converted into allyl groups to give the compound 8 in 64% yield from 6 . Thioglycosidation of the compound 8 gave the 2- O -acetyl-thioglycoside 9 in 57% yield.…”

Section: Resultsmentioning

confidence: 99%

Water-Soluble Glucosyl Pyrene Photosensitizers: An Intramolecularly Synthesized 2-C-Glucoside and an O-Glucoside

et al. 2018

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Prevalent photosensitizing agents for photodynamic therapy (PDT) suffer from their relatively large molecular weights causing photodermatosis. In this regard, low molecular weight pyrene could be an efficient photosensitizer except for its extreme hydrophobicity. To tackle the insolubility of pyrene, we synthesized 1-carboxypyren-2-yl C-glucoside 4 by a tethered C-glucosylation and 1-pyrenylmethyl O-glucoside 5 by a simple O-glucosylation. Compounds 4 and 5 showed modest water solubilities of 72 and 47 μg/mL, respectively. Whereas compound 4 partially underwent a cyclization reaction at pH 3 to give the corresponding δ-valerolactone 15b in 31% yield after 24 h, it is stable at pH 5–9 for at least a week. The 1O2-producing photosensitizabilities of 4 and 5 were sufficient to apply to PDT. Although compound 5 was uptaken by HeLa cells and showed a good PDT activity, compound 4 showed neither a sufficient cell uptake nor PDT effect. The binding modes of compounds 4 and 5 to concanavalin A were specific and unspecific, respectively. These results demonstrate that compounds 4 and 5 are within a pharmacologically acceptable range as oral drugs and could be a fluorescence imaging probe for α-glucose/mannose receptors and a photosensitizing agent for PDT, respectively.

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Section: Resultsmentioning

confidence: 99%

Water-Soluble Glucosyl Pyrene Photosensitizers: An Intramolecularly Synthesized 2-C-Glucoside and an O-Glucoside

et al. 2018

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“…The method is also applied to dietary supplements claiming to contain F. agrestis. The 11 standard compounds used were geniposidic acid (1), neochlorogenic acid (2), chlorogenic acid (3), 2,4′,6-trihydroxy-4methoxybenzophenone-2-O-β-D-glucoside (4), rutin (5), hyperoside (6), guajavarin (7), 3,4-dicaffeoylquinic acid (8), 3,5-dicaffeoylquinic acid (9), narcissoside (10), and 4,5-dicaffeoylquinic acid (11) (▶ Fig. 1).…”

Section: Quantification Of Phenolic Compounds From Fadogia Agrestis Amentioning

confidence: 99%

“…1)-were purchased from Sigma. 3,4-Dicaffeoylquinic acid (8), 3,5-dicaffeoylquinic acid (9), and 4,5-dicaffeoylquinic acid (11) were purchased from 1Chem. The purity of most of the reference standards were found to be > 95 % except for compound 4…”

Section: Chemicals and Plant Samplesmentioning

confidence: 99%

“…▶ Table 3 Quantitative analysis of phenolic compounds (mg/g) from plant samples of F. agrestis: geniposidic acid (1), neochlorogenic acid (2), chlorogenic acid (3), 2,4′,6-trihydroxy-4-methoxybenzophenone-2-O-β-D-glucoside (4), rutin (5), hyperoside (6), guajavarin (7), 3,4-dicaffeoylquinic acid (8), 3,5-dicaffeoylquinic acid (9), narcissoside (10), and 4,5-dicaffeoylquinic acid (11). P a r t 1 2 3 4 5 6 7 8 9 1 0 1 Nineteen samples of leaves, leaf/twigs, stem, and roots of F. agrestis were obtained from various authentic and commercial sources (▶ Table 1).…”

Section: Chemicals and Plant Samplesmentioning

confidence: 99%

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Quantification of Phenolic Compounds from Fadogia agrestis and Dietary Supplements using UHPLC-PDA-MS

et al. 2018

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is used in traditional African medicine as an analgesic and for anti-inflammatory and aphrodisiac activities. An ultra-high-performance liquid chromatography method was developed for the determination of 11 chemical constituents from roots and aerial parts of The separation was achieved within 7 min by using C-18 column material and a water/acetonitrile mobile phase, both containing 0.1% formic acid gradient system with a temperature of 45 °C. The method was validated for linearity, repeatability, limits of detection, and limits of quantification. The limits of detection of phenolic compounds were found to be in the range from 0.025 to 0.1 µg/mL. The wavelengths used for quantification with the photodiode array detector were 238, 254, 291, and 325 nm. Twelve of 17 dietary supplements contained phenolic compounds in the range from 0.3 to 2.7 mg/d. The phenolic compounds were not detected in five dietary supplements. Liquid chromatography-mass spectrometry coupled with electrospray ionization interface method is described for the identification and confirmation of compounds from plant samples and dietary supplements claiming to contain. This method involved the use of [M + H] and [M + Na] ions in the positive mode and [M - H] ions in the negative mode with extractive ion monitoring. The developed method is simple, economic, rapid, and especially suitable for quality control and chemical fingerprint analysis of .

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“…The synthesis of 2-O-α-L-rhamnosyl-β-O-glucosidic structure involves the rhamnosylation of 2-O in a glucosyl donor bearing an aglycon at the β-anomeric oxygen. [23][24][25][26][27] The donor can be prepared with high β-stereoselectivity via the glycosylation of a glucosyl donor bearing a participating group, 28) such as an acyl group, at the 2-O position with an aglycon. Another method involves the glycosylation of 2-O-rhamnosyl glucosyl donors with an aglycon.…”

Section: Introductionmentioning

confidence: 99%

β-Selective Glycosylation Using Axial-Rich and 2-<i>O</i>-Rhamnosylated Glucosyl Donors Controlled by the Protecting Pattern of the Second Sugar

Bando

Kawasaki

Nagata

et al. 2021

CHEMICAL & PHARMACEUTICAL BULLETIN

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Herein, we describe two counterexamples of the previously reported β/α-selectivity of 96/4 for glycosylation using ethyl 2-O-[2,3,4-tris-O-tert-butyldimethylsilyl (TBS)-α-L-rhamnopyranosyl]-3,4,6-tris-O-TBS-thio-β-D-glucopyranoside as the glycosyl donor. Furthermore, we investigated the effects of protecting group on the rhamnose moieties in the glycosylation with cholestanol and revealed that β-selectivity originated from the two TBS groups at the 3-O and 4-O positions of rhamnose. In contrast, the TBS group at the 2-O position of rhamnose hampered the β-selectivity. Finally, the β/α-selectivity during the glycosylation was enhanced to ≥99/1. The results obtained herein suggest that the protecting groups on the sugar connected to the 2-O of a glycosyl donor with axial-rich conformation can control the stereoselectivity of glycosylation.

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Concise Synthesis and Antidiabetic Effect of Three Natural Triterpenoid Saponins Isolated from Fadogia ancylantha (Makoni tea)

Cited by 7 publications

References 40 publications

Water-Soluble Glucosyl Pyrene Photosensitizers: An Intramolecularly Synthesized 2-C-Glucoside and an O-Glucoside

Water-Soluble Glucosyl Pyrene Photosensitizers: An Intramolecularly Synthesized 2-C-Glucoside and an O-Glucoside

Quantification of Phenolic Compounds from Fadogia agrestis and Dietary Supplements using UHPLC-PDA-MS

β-Selective Glycosylation Using Axial-Rich and 2-<i>O</i>-Rhamnosylated Glucosyl Donors Controlled by the Protecting Pattern of the Second Sugar

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