The synthesis and stereochemistry of odorine

Babidge, PJ; Massy-Westropp, RA; Pyne, SG; Shiengthong, D.; Ungphakorn, A.; Veerachat, G

doi:10.1071/ch9801841

Cited by 20 publications

(7 citation statements)

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“…The bond distances in (I) are within normal ranges (Allen et al, 1987) and comparable with the related structures which are odorinol (Hayashi et al, 1982) and forbaglin A (Dumontet et al, 1996). The absolute configuration at atoms C15 and C13 or positions 2 and 2′ of the odorine are S,R configurations which agree with the previous stereochemistry of odorine (Babidge et al, 1980).…”

Section: Methodssupporting

confidence: 81%

“…For background to the Aglaia plants and their biological activity, see: Brader et al (1998); Cui et al (1997); Engelmeier et al (2000); Hayashi et al (1982); Inada et al (2001); Nugroho et al (1999); Purushothaman et al 1979); Saifah et al (1993); Shiengthong et al (1979). For related structures, see: Babidge et al (1980); Dumontet et al (1996); Hayashi et al (1982). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986).…”

Section: Related Literaturementioning

confidence: 99%

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Absolute configuration of odorine

et al. 2010

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The title compound, known as odorine or roxburghiline {systematic name: (S)-N-[(R)-1-cinnamoylpyrrolidin-2-yl]-2-methylbutanamide}, C18H24N2O2, is a nitrogenous compound isolated from the leaves of Aglaia odorata. The absolute configuration was determined by refinement of the Flack parameter with data collected using Cu Kα radiation showing positions 2 and 2′ to be S and R, respectively. The pyrrolidine ring adopts an envelope conformation. In the crystal, molecules are linked into chains along [010] by intermolecular N—H⋯O hydrogen bonds.

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Section: Methodssupporting

confidence: 81%

Section: Related Literaturementioning

confidence: 99%

Absolute configuration of odorine

et al. 2010

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“…N-(1'-Oxo-3'-phenylprop-2'-enyl)pyrrolidine-2-carboxylic Acid ( N-cinnamoyl-L-proline, ProCA)-Synthesis of ProCA was completed following a published procedure [42]. Briefly, to a stirred solution of L-proline (5.7 g) in 1N NaOH (50 mL) prepared and maintained at 0 °C was added dropwise phenylpropanoyl chloride (16.7 g, 2 M in 1N NaOH) with stirring.…”

Section: Chemical Synthesismentioning

confidence: 99%

Cinnamoyl-based Nrf2-activators targeting human skin cell photo-oxidative stress

Wondrak¹,

Cabello²,

Villeneuve³

et al. 2008

Free Radical Biology and Medicine

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Strong experimental evidence suggests the involvement of photo-oxidative stress mediated by reactive oxygen species as a crucial mechanism of solar damage relevant to human skin photoaging and photocarcinogenesis. Based on the established role of antioxidant response element (ARE)-mediated gene expression in cancer chemoprevention, we tested the hypothesis that small molecule Nrf2-activators may serve a photo-chemopreventive role by targeting skin cell photo-oxidative stress. A luciferase-based reporter gene assay was used as a primary screen for the identification of novel agents that modulate the Nrf2-Keap1 signaling pathway. A series of cinnamoyl-based electrophilic Michael acceptors including cinnamic aldehyde and methyl-1-cinnamoyl-5-oxo-2-pyrrolidine-carboxylate was identified as potent Nrf2-activators. Hit confirmation was performed in a secondary screen, based on immunodetection of Nrf2 protein upregulation in human Hs27 skin fibroblasts, HaCaT keratinocytes, and primary skin keratinocytes. Bioefficacy profiling of positive test compounds in skin cells demonstrated compound-induced upregulation of hemeoxygenase I and NAD(P)H-quinone oxidoreductase, two Nrf2 target genes involved in the cellular antioxidant response. Pretreatment with cinnamoylbased Nrf2-activators suppressed intracellular oxidative stress and protected against photooxidative induction of apoptosis in skin cells exposed to high doses of singlet oxygen. Our pilot studies suggest feasibility of developing cinnamoyl-based Nrf2-activators as novel photochemopreventive agents targeting skin cell photo-oxidative stress.

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“…The stereochemistry was not determined; thus, no evidence as to the absolute configuration is available. Lacking these data, we have drawn the structure in the same 2'R configuration that has been assigned to odorine by the optical rotation of its hydrolytic products (5) and to odorinol by its X-ray analysis (3). As a natural amide, piriferine would not be basic enough to form a salt with picric acid, so the picrate derivative was not attempted.…”

mentioning

confidence: 99%