A structure and an absolute configuration of (+)-alternamin, a new coumarin from Murraya alternans having antidote activity against snake venom

Min, Hla Myoe; Aye, Mya; Taniguchi, Tohru; Miura, Nobuaki; Monde, Kenji; Ohzawa, Kazuhiko; Nikai, Toshiaki; Niwa, Masayuki; Takaya, Yoshiaki

doi:10.1016/j.tetlet.2007.06.156

Cited by 31 publications

(21 citation statements)

References 21 publications

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“…168 The odorous 2-substituted-3(2H)-furanones (+)-152 and (+)-153 had their absolute congurations determined for the rst time as R by using VCD in combination with B3PW91/6-31G(d,p) calculated spectra. Klaivanolide is actually the known molecule acetylmelodorinol (159). 169 The absolute conguration of two tautomers of homofuraneol (+)-154 and (+)-155, with unique keto-enol structures, was determined as R by direct measurement of the VCD spectra of their methyl ether derivatives compared with B3PW91/6-31(d,p) calculations.…”

Section: Miscellaneousmentioning

confidence: 99%

Recent advances in the use of vibrational chiroptical spectroscopic methods for stereochemical characterization of natural products

2015

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Section: Miscellaneousmentioning

confidence: 99%

Recent advances in the use of vibrational chiroptical spectroscopic methods for stereochemical characterization of natural products

2015

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“…The majority of these molecules were investigated by the groups of Stephens 11,[124][125][126][127][128] and Joseph-Nathan, [129][130][131][132][133][134][135][136][137][138][139] but additional groups in natural-product research have begun to take advantage of VCD for AC determinations. [140][141][142][143][144][145][146][147][148][149] Nafie published an extensive review on the AC determination of natural products by VCD in 2008, 10 and as a result only a few more recent examples are described in this section.…”

Section: Determination Of Absolute Configuration Of Natural Product Mmentioning

confidence: 99%

Determination of Absolute Configuration of Chiral Molecules Using Vibrational Optical Activity: A Review

Wang²,

Dukor³

et al. 2011

Appl Spectrosc

291

218

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Determination of the absolute handedness, known as absolute configuration (AC), of chiral molecules is an important step in any field related to chirality, especially in the pharmaceutical industry. Vibrational optical activity (VOA) has become a powerful tool for the determination of the AC of chiral molecules in the solution state after nearly forty years of evolution. VOA offers a novel alternative, or supplement, to X-ray crystallography, permitting AC determinations on neat liquid, oil, and solution samples without the need to grow single crystals of the pure chiral sample molecules as required for X-ray analysis. By comparing the sign and intensity of the measured VOA spectrum with the corresponding ab initio density functional theory (DFT) calculated VOA spectrum of a chosen configuration, one can unambiguously assign the AC of a chiral molecule. Comparing measured VOA spectra with calculated VOA spectra of all the conformers can also provide solution-state conformational populations. VOA consists of infrared vibrational circular dichroism (VCD) and vibrational Raman optical activity (ROA). Currently, VCD is used routinely by researchers in a variety of backgrounds, including molecular chirality, asymmetric synthesis, chiral catalysis, drug screening, pharmacology, and natural products. Although the application of ROA in AC determination lags behind that of VCD, with the recent implementation of ROA subroutines in commercial quantum chemistry software, ROA will in the future complement VCD for AC determination. In this review, the basic principles of the application of VCD to the determination of absolute configuration in chiral molecules are described. The steps required for VCD spectral measurement and calculation are outlined, followed by brief descriptions of recently published papers reporting the determination of AC in small organic, pharmaceutical, and natural product molecules.

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“…5,10 Male ddY mice of 20 g average weight were used for this experiment. Test solutions were prepared as follows: Crude snake venom solution of P. flavoviridis (0.14 mg/mL in saline, 50 lL) and sample solution in 10% dimethylsulfoxide (DMSO)-saline, 50 lL) were mixed and incubated at 37°C for 10 min.…”

Section: Anti-hemorrhagic Activity Assaymentioning

confidence: 99%

Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage

Aung

Furukawa

Nikai

et al. 2011

Bioorganic & Medicinal Chemistry

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A structure and an absolute configuration of (+)-alternamin, a new coumarin from Murraya alternans having antidote activity against snake venom

Cited by 31 publications

References 21 publications

Recent advances in the use of vibrational chiroptical spectroscopic methods for stereochemical characterization of natural products

Recent advances in the use of vibrational chiroptical spectroscopic methods for stereochemical characterization of natural products

Determination of Absolute Configuration of Chiral Molecules Using Vibrational Optical Activity: A Review

Contribution of cinnamic acid analogues in rosmarinic acid to inhibition of snake venom induced hemorrhage

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