Quebrachitol

Alphen, J. van

doi:10.1021/ie50493a041

Cited by 32 publications

(12 citation statements)

References 13 publications

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“…D-Pinitol was isolated from sugar pine (Pinus lambertiana Dougl) heartwood (24), while L-quebrachitol came from an exudate of the rubber tree (Hevea brasiliensis) (25) (27)] was prepared by the procedure of Jiang and Baker (28). Cyclohexanone dimethylketal (1,1-dimethoxycyclohexane) was from CTC Organics (Atlanta) and m-chloroperoxybenzoic acid was from Sigma.…”

Section: Methodsmentioning

confidence: 99%

“…An LKB 2138 Uvicord S, equipped with a microflow cell and a 254-nm filter, was used to monitor the effluent. For preparative HPLC, a stainless steel column (5.1 x 50 cm) (HT Chemicals, Saint Louis) was packed manually with Merck LiChroprep RP-18 (25)(26)(27)(28)(29)(30)(31)(32)(33)(34)(35)(36)(37)(38)(39)(40) ,um) (EM Scientific, Cherry Hill, NJ) and eluted with methanol/water at a flow rate of 20 or 25 ml/min. The UV detector was equipped with a preparative flow cell, and solvents were mixed and delivered by a Waters Prep LC3000 system fitted with a 15-ml injection loop.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Chiral synthesis of D- and L-myo-inositol 1,4,5-trisphosphate.

Tegge

Ballou

1989

Proc. Natl. Acad. Sci. U.S.A.

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Chiral inositols (D-chiro-inositol from Dpinitol and L-chiro-inositol from L-quebrachitol) were converted to the 3,4-di-O-benzyl ethers, which were selectively benzoylated to yield the 1,2,5-tri-O-benzoyl-3,4-di-O-benzylchiro-inositols. The free hydroxyl group in each derivative was inverted by way of the trifluoromethane sulfonate ester to provide D-and L-1,2,4-tri-O-benzoyl-5,6-di-O-benzyl-myoinositol. Hydrogenolysis to remove the benzyl ether groups gave the enantiomeric 1,2,4-tri-O-benzoyl-myo-inositols, which were phosphorylated by a dibenzylphosphite triester method. After hydrogenolysis and saponification of the derivatives, the D-and L-myo-inositol 1,4,5-trisphosphates were isolated as the crystalline cyclohexylammonium salts in gram quantity.myo-Inositol-containing phospholipids were isolated from bovine brain by Folch in 1942 (1) and from soybeans by Woolley in 1943 (2), and a more highly phosphorylated form was obtained from brain tissue in 1949 (3). Folch called the latter preparation "diphosphoinositide" because it yielded an "inositol metadiphosphate" following strong acid hydrolysis, but the known susceptibility of inositol phosphates to acid-catalyzed migration suggests that the product must have been a mixture. The general nature of the inositol phosphates from brain lipids was reported by Grado and Ballou (4) and Dittmer and Dawson (5) in 1960, who concluded that it was composed of myo-inositol mono-, di-, and triphosphates. Characterization of the myo-inositol monophosphate from soybean inositol phospholipid (6), synthesis of its enantiomer (7), and characterization of the myo-inositol polyphosphates from brain inositol phospholipid (8, 9) followed, and the exact nature of the phospholipid complex was reported by Brockerhoff and Ballou in 1961 (10). These results were confirmed by Brown and Stewart (11).Although the brain inositol phospholipid complex was shown to have an active metabolism in tissue slices with respect to the turnover of the monoesterified phosphate groups (12-15), studies reported by Hokin and Hokin (16) failed to establish a specific physiological role for the inositides. Regardless, these workers are recognized for promoting the hypothesis that the inositol phospholipids were involved in specific cellular processes. Developments of the last decade that have elucidated the role of myo-inositol polyphosphates as second messengers have given new focus to this field of lipid metabolism (17), and the renewed interest has stimulated the development of synthetic procedures for the preparation of such derivatives. In studies published to date (18-23), the syntheses have started with myo-inositol, a meso compound, and have yielded racemic products that must be resolved to provide the natural isomer. In this report, we describe chiral syntheses of myo-inositol 1,4,5-trisphosphate that yield the optical antipodes directly and that follow a synthetic strategy that should facilitate the preparation of other useful derivatives. (27)] was prepared by the procedure of Jiang and Ba...

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Chiral synthesis of D- and L-myo-inositol 1,4,5-trisphosphate.

Tegge

Ballou

1989

Proc. Natl. Acad. Sci. U.S.A.

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“…As a chiral building block, QCT was further expanded by its availability in high concentrations from rubber tree. Then in 1932, QCT had been prepared on a larger collection by Rhodes and Wiltshire [ 6 ]. Afterwards, QCT was separated out of the red oil of Minnesota Wild Hemp [ 7 ].…”

Section: The Source Of Qctmentioning

confidence: 99%

“…Afterwards, QCT was separated out of the red oil of Minnesota Wild Hemp [ 7 ]. The first systematic method of extracting QCT was reported by Jan van Alphen [ 6 ]. Because QCT is seldom coexisted with its isomer d -pinitol in the same plant family, isolation from natural source provides an excellent way to obtain pure compound.…”

Section: The Source Of Qctmentioning

confidence: 99%

Quebrachitol: Global Status and Basic Research

Wang

Zhang

Chang

et al. 2017

Nat. Prod. Bioprospect.

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Recently, there has been a renewed interest in the natural-products-inspired drugs. Quebrachitol (QCT) is one of naturally occurring optically active cyclitols that has now received considerable attention. Until the last decade, it came to be a starting point for the lead discovery. In this review, we had a discussion on the basic research of QCT, including its source, structure, properties, and the recent advances on its application. The biological activities and QCT-inspired leads that are potentially effective for treating human diseases were also discussed.

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“…is a good source of quebrachitol). 11 It has also been recently isolated from the leaves of Allophylus cobbe L. in Vietnam. 13 In nature, quebrachitol has been suggested to be a major contributor to osmotic pressure 14 and a cryoprotective agent for plants.…”

mentioning

confidence: 99%