Osage Orange Pigments. II. Isolation of a New Pigment, Pomiferin

Wolfrom, M. L.; Benton, F. L.; Gregory, A. S.; Hess, W. W.; Mahan, John E.; Morgan, Paul W.

doi:10.1021/ja01265a079

Cited by 22 publications

(16 citation statements)

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“…Millepurone, isolated from Millettia atropurpurea, [9] has antitumor activity. Osajin, (from Millettia auriculata) exhibits anti-oxidant activity [10]. In some parts of Africa, especially in Cameroon, the plants of genus Millettia are used by different communities as potent inhibitor of intestinal parasites in children [11].…”

Section: Introductionmentioning

confidence: 99%

Isolation, spectroscopic and density functional theory studies of 7-(4-methoxyphenyl)-9H-furo[2,3-f]chromen-9-one: A new flavonoid from the bark of Millettia ovalifolia

Rahman

Arfan²,

Mahmood

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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Section: Introductionmentioning

confidence: 99%

Isolation, spectroscopic and density functional theory studies of 7-(4-methoxyphenyl)-9H-furo[2,3-f]chromen-9-one: A new flavonoid from the bark of Millettia ovalifolia

Rahman

Arfan²,

Mahmood

et al. 2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Moreover, this hypothesis was supported by our previous experimental evidences which suggest that the protections/substitution of hydroxyl groups in the isoflavone scaffold may lead to a highest inhibitory activity (lower IC 50 ) towards PDE5 in vitro [8]. The preparation of the methanesulfonate derivative of osajin (1) was straightforwardly carried out adopting and modifying a procedure described by Wolfrom et al [15]. In their work, the authors proposed the preparation of the 4-methylbenzenesulfonate derivatives of osajin (1) and pomiferin, another compound extracted from M. pomifera, and of their cyclized isoosajin and isopomiferin analogues.…”

Section: Extraction Of Osajin (1) and Synthesis Ofmentioning

confidence: 66%

5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one

Ribaudo

Ongaro

Zagotto

2018

Molbank

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Natural and semi-synthetic compounds are being studied as novel phosphodiesterase 5 (PDE5) inhibitors for the treatment of erectile dysfunction, pulmonary hypertension, and lower urinary symptoms. Maclura pomifera is a source of flavonoids, one of the main classes of molecules investigated for these purposes. The extraction of the natural isoflavone osajin and its modification to obtain a semi-synthetic derivative are described in this short note. 1 H and 13 C-nuclear magnetic resonance spectroscopy (NMR), mass spectrometry, high-performance liquid chromatography (HPLC) and spectroscopic characterization of the title compound are also hereby provided. Two-dimensional (2D) nuclear Overhauser effect spectroscopy (NOESY) NMR, supported by in silico conformational studies, was used to achieve a complete assignment of the proton signals, assessing the correct chemical structure of the compound. Heteronuclear single quantum coherence spectroscopy (HSQC) and heteronuclear multiple bond correlation (HMBC) NMR experiments were performed to assign 13 C chemical shifts. Calculated chemical properties and preliminary in silico docking suggest that this molecule might be a promising candidate as PDE5 inhibitor.

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“…The terminal methyl groups are upfield around 14 ppm. The other spectral features of the 13 Aminolysis of the oxirane was more sluggish compared to the oxirane formation even as catalyzed by anhydrous ZnCl 2 under gentle reflux irrespective of the lower scale of reactants used. The reaction was sometimes run overnight to give the poly-α-hydroxydibutylamine triglyceride derivative in excellent yield.…”

Section: ■ Results and Discussionmentioning

confidence: 93%

Osage Orange (Maclura pomifera L.) Seed Oil Poly(α-hydroxydibutylamine) Triglycerides: Synthesis and Characterization

Harry-O’kuru¹,

Tisserat²,

Gordon³

et al. 2015

J. Agric. Food Chem.

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Milled Osage orange seeds (Maclura pomifera (Raf.) Schneid) were Soxhlet extracted with hexane, and portions of the extract were treated with activated carbon before solvent removal. The crude oil was winterized and degummed by centrifugation at low temperature. Decantation of the centrifugate gave an admixture of the triglycerides and free fatty acids. The free fatty acid content of the oil was removed when portions of the admixture were diluted with hexane and shaken with cold aqueous ammonium hydroxide (0.1 M) solution. The desiccant-dried organic phase was concentrated under reduced pressure to give the cleaned Osage orange triglyceride after solvent removal by rotary evaporation at 67 °C. Epoxidation of the resulting cleaned triglyceride was effected by reaction with in situ generated peroxy performic acid in H2O2. The oxirane rings of the derivatized oil were then opened using N,N-dibutylamine catalyzed by anhydrous ZnCl2 to afford the poly(α-hydroxydibutylamine) triglyceride. The purpose of this work was to derivatize and thereby stabilize this highly unsaturated tree oil for its eventual use in lubrication applications.

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Osage Orange Pigments. II. Isolation of a New Pigment, Pomiferin

Cited by 22 publications

References 0 publications

Isolation, spectroscopic and density functional theory studies of 7-(4-methoxyphenyl)-9H-furo[2,3-f]chromen-9-one: A new flavonoid from the bark of Millettia ovalifolia

Isolation, spectroscopic and density functional theory studies of 7-(4-methoxyphenyl)-9H-furo[2,3-f]chromen-9-one: A new flavonoid from the bark of Millettia ovalifolia

5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-6-(3-methylbut-2-enyl)pyrano[2,3-h]chromen-4-one

Osage Orange (Maclura pomifera L.) Seed Oil Poly(α-hydroxydibutylamine) Triglycerides: Synthesis and Characterization

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