Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

Muraoka, Osamu; Yoshikai, Kazuya; Takahashi, Hideo; Minematsu, Toshie; Lu, Guoming; Tanabe, Genzoh; Wang, Tao; Matsuda, Hisashi; Yoshikawa, Masayuki

doi:10.1016/j.bmc.2005.08.040

Cited by 58 publications

(33 citation statements)

References 40 publications

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“…), JNM-LA500 (500 MHz), and JEOL ECA-600K (600 MHz) spectrometers;13 C NMR spectra, JEOL EX-270 (68 MHz), JNM-LA500 (125 MHz), and JEOL ECA-600K (150 MHz) spectrometers with tetramethylsilane as an internal standard; EIMS and HREIMS, JEOL JMS-GCMATE mass spectrometer; FABMS and HRFABMS, JEOL JMS-SX 102A mass spectrometer; HPLC detector, Shimadzu RID-6A refractive index and SPD-10A UV-VIS detectors. HPLC column, YMC-Pack Polyamine II (YMC Inc., 250 × 4.6 mm i.d.)…”

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confidence: 99%

Salaprionol and Ponkoranol with Thiosugar Sulfonium Sulfate Structure from Salacia prinoides and a-Glucosidase Inhibitory Activity of Ponkoranol and Kotalanol Desulfate

Yoshikawa¹,

Xu²,

Nakamura³

et al. 2008

HETEROCYCLES

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The methanolic extract from the roots and stems of Indian Salacia prinoides and its water-eluted fraction of Diaion HP-20 column were found to exhibit inhibitory activities against α-glucosidase. From the water-eluted fraction, two new unique constituents with thiosugar sulfonium sulfate, salaprinol (1) and ponkoranol (2), were isolated together with 10 known constituents including salacinol and kotalanol. The structures of 1 and 2 were elucidated on the basis of chemical and physicochemical evidence. Furthermore, ponkoranol (2) and kotalanol desulfate (14) were found to show potent inhibitory activities against αglucosidase.In the course of our studies on antidiabetogenic compounds from natural medicines, 1-5 we have isolated two potent α-glucosidase inhibitors, salacinol (3) and kotalanol (4), with unique thiosugar sulfonium sulfate inner salt structure from the roots, stems, and leaves of Salacia reticulata, 6-14 S. oblonga, 15 and S. chinensis [16][17][18][19][20] in Sri Lanka, India, and Thailand. As a continuation of our studies on Salacia species plant, 21 we have found that the methanolic extract from the roots and stems of Indian S. prinoides exhibited inhibitory activity against α-glucosidase. This plant is called as "Kushan" in Sanskrit and is widely distributed in India, Sri Lanka, and Southeast Asia countries. The roots and stems of this plant are extensively used for the treatment of diabetes and also used as an abortifacient in Indian traditional medicine. Through bioassay-guided separation using α-glucosidase inhibitory activities, we isolated two new constituents named salaprinol (1) and ponkoranol (2) together with 10 known constituents including salacinol and kotalanol. In this paper, we describe the isolation and structure elucidation of salaprinol (1) and ponkoranol (2), as well as the inhibitory activities of 2 and related compounds on α-glucosidase.

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Salaprionol and Ponkoranol with Thiosugar Sulfonium Sulfate Structure from Salacia prinoides and a-Glucosidase Inhibitory Activity of Ponkoranol and Kotalanol Desulfate

Yoshikawa¹,

Xu²,

Nakamura³

et al. 2008

HETEROCYCLES

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“…[1c, 2b] In conclusion, we have established an ew divergent synthetic methodology to construct the key sulfonium salt structure of Salacia-derived natural products (5)(6)(7)(8). In the meantime,after the same treatment on 34,t he resulting unprotected sulfonium salt was subjected to ar eductive ring-opening reaction to give 7 in ay ield of 52 %a fter three steps.S pectroscopic properties of the synthesized 6 and 7 were in exact accordance with those of the authentic sample.…”

Section: Angewandte Chemiementioning

confidence: 99%

Practical Route to Neokotalanol and Its Natural Analogues: Sulfonium Sugars with Antidiabetic Activities

Huang

Gao

et al. 2019

Angew Chem Int Ed

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An efficient and divergent approacht owardt he synthesis of all four de-O-sulfonated sulfonium type aglucosidase inhibitors,o riginally isolated from plants of genus Salacia, is reported for the first time.T he key strategy features ac oupling reaction between thiol derivatives and ad iiodide counterpart. The newly designed thiol coupling partner presents high chemical stability,w hile the diiodide partner could be easily obtained with increased overall yields compared with conventional routes.T he intermolecular nucleophilic substitution reaction followed by adiastereoselective intramolecular cyclization provided the target fivemember sulfonium salt structure,w hich was connected in an a-orientation to ap olyhydroxylated side-chain moiety.

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“…38 Compound 26 was not an effective inhibitor of this enzyme. This suggests that both the hydroxyl group at C-2 0 and the hydroxymethyl group at C-3 0 are essential for a-glucosidase inhibitory activity.…”

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Synthesis of phosphate derivatives related to the glycosidase inhibitor salacinol

Bhat¹,

Kumar²,

Pinto³

2007

Carbohydrate Research

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Synthesis and biological evaluation of deoxy salacinols, the role of polar substituents in the side chain on the α-glucosidase inhibitory activity

Cited by 58 publications

References 40 publications

Salaprionol and Ponkoranol with Thiosugar Sulfonium Sulfate Structure from Salacia prinoides and a-Glucosidase Inhibitory Activity of Ponkoranol and Kotalanol Desulfate

Salaprionol and Ponkoranol with Thiosugar Sulfonium Sulfate Structure from Salacia prinoides and a-Glucosidase Inhibitory Activity of Ponkoranol and Kotalanol Desulfate

Practical Route to Neokotalanol and Its Natural Analogues: Sulfonium Sugars with Antidiabetic Activities

Synthesis of phosphate derivatives related to the glycosidase inhibitor salacinol

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