Labdanes and Withanolides from Physalis coztomatl

Pérez‐Castorena, Ana‐L.; Oropeza, Ruth F.; Vázquez, Alfredo Macías; Martínez, Mahinda; Maldonado, Emma

doi:10.1021/np0601354

Cited by 32 publications

(39 citation statements)

References 19 publications

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“…Increasing the p electron conjugated system leads to p ? p* at the lower energy state and redshifting of k max (224-320 nm) as in withanolides with aromatic rings (Tettamanzi et al 2001) and a 2,4-diene-1-oxo in skeleton structure (Pérez-Castorena et al 2006). Versus the characteristic absorption (225 nm) of the usual dimethyl-substituted a, bunsaturated d-lactone in withanolides, the large substituent groups will break down the conjugated system and result in k max blueshifting from 215 to 224 nm, e.g., withanolides with a 27a-hydroxymethyl (Khan et al 1999a, b;Liu et al 2006).…”

Section: Spectral Generalization Of Withanolidesmentioning

confidence: 96%

Phytochemistry and biosynthesis of δ-lactone withanolides

et al. 2015

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Withanolides are highly oxygenated natural products. These C 28 steroids with ergostane-based skeletons functionalized at C-22 and C-26 form sixmembered d-lactone rings. Withanolides containing a d-lactone side chain often occur in Solanaceae and have a variety of biological activities because of their complicated structures. Characteristic spectroscopic behaviors and biosynthesis of withanolides are conducive to their structural elucidation and ''biomimetic synthesis'', respectively. However, the last review to summarize their spectroscopic features and biosynthesis was in 1996. Since then, many withanolides with novel structures have been described by their spectra with biosynthesis investigated with many bioassays. This review surveys d-lactone withanolides and emphasizes their spectral features, configurations and biosynthetic genes. The period reviewed includes through January 2014. We also include phytochemical species.

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Section: Spectral Generalization Of Withanolidesmentioning

confidence: 96%

Phytochemistry and biosynthesis of δ-lactone withanolides

et al. 2015

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“…With the same procedure, 52 g of I. sonorae were extracted with 600 mL methanol. These methanolic extracts were submitted to a partition with n-hexane and ethyl acetate as described by Pérez-Castorena et al [18]. Each extract was dissolved in 200 mL methanol in a 500 mL separating funnel.…”

Section: Preparation Of Plant Extractsmentioning

confidence: 99%

Cytotoxic Effect of Methanol Extracts and Partitions of Two Mexican Desert Plants against the Murine Lymphoma L5178Y-R

Quintanilla-Licea¹,

Gómez-Flores²,

Samaniego-Escamilla³

et al. 2016

AJPS

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Pachycereus marginatus (DC.) Britton & Rose and Ibervillea sonorae (S. Watson) Greene have been used in the Mexican traditional medicine for the treatment of various diseases, including cancer. The present study aims to investigate the cytotoxic activity of these plants against a murine lymphoma. Soxhlet extraction of dried and powdered plant material was performed with methanol. Also, a further partitioning of these methanolic extracts with hexane and ethyl acetate was achieved. The in vitro cytotoxic activity against the murine lymphoma L5178Y-R cell line was assessed via the colorimetric MTT assay. The methanol extract from P. marginatus exhibited high cytotoxic activity (up to 94%) at concentrations ranging from 3.9 to 500 µg/mL; however, hexane and ethyl acetate partitions from this methanolic extract showed lower but significant (p < 0.05) concentration-dependent cytotoxicity (hexane partition up to 94% at 500 µg/mL; ethyl acetate partition up to 94% at 65.5 µg/mL). The methanolic extract and partitions derived from I. sonorae also showed significant (p < 0.05) and concentration-dependent cytotoxicity against L5178Y-R cells at concentrations ranging from 7.81 to 500 µg/mL (methanolic extract up to 63% at 500 µg/mL; hexane partition up to 76% at 250 µg/mL; ethyl acetate partition up to 73% at 500 µg/mL). These results demonstrate that the methanol extracts and partitions from P. marginatus and I. sonorae possess significant cytotoxic activity against the murine lymphoma L5178Y-R and validate the ethnobotanical use of these plants for the treatment of diseases consistent with cancer symptomatology. Previous scientific reports describe the isolation of isoquinoline alkaloids of P. margi-* Corresponding author. R. Quintanilla-Licea et al. 1522natus as well as cucurbitacins from I. sonorae, phytochemicals that could be responsible for their observed cytotoxic activity in this research. The direct extraction with methanol of medicinal plants allows extracting of both high and low-polarity compounds, contrary to the simple extraction with water that only allows obtaining compounds of high polarity. The subsequent partition of the methanol extract with a solvent of low polarity (hexane) and another of medium polarity (ethyl acetate) allows making a preliminary fractionation of the bioactive molecules present in the plant that will facilitate the bioguided chromatographic isolation of the pure compounds responsible for the biological activity of the plant.

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“…1). Except for subfraction FC3 of SC2, where the 1 H-NMR spectrum showed signals for aromatic protons and many signals for methoxy groups (3.5-4.5 ppm) typical for high oxygenated flavonoids (Wollenweber et al, 1997;Horie et al, 1998), all other subfractions are mixtures of long-chain alkanes and labdane-type diterpenes at different ratios, thus in their 1 H-NMR spectra it is easy to recognize the strong signal at 1.27 ppm typical for a long methylene chain or the five singlets (between 1.7 and 0.7 ppm) associated with the methyl groups of a labdane diterpene (Pérez-Castorena et al, 2006).…”

Section: Chemical Nature Of Gymnosperma Glutinosum Active Fractionsmentioning

confidence: 99%

Long‐chain Alkanes and ent‐Labdane‐type Diterpenes from Gymnosperma glutinosum with Cytotoxic Activity Against the Murine Lymphoma L5178Y‐R

Gómez-Flores

Quintanilla-Licea

Verde-Star

et al. 2012

Phytotherapy Research

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The antitumor potential of Gymnosperma glutinosum was previously reported using the in vitro and in vivo L5178Y-R lymphoma murine model. The present study was carried out to isolate and identify the cytotoxic compounds present in the Gymnosperma glutinosum leaf hexane extract. Gymnosperma glutinosum was collected in the semi-arid region of Escobedo, State of Nuevo León, México, but it is commonly found in northeastern Mexico; it is traditionally used as a treatment for diarrhea, ulcers and rheumatism. G. glutinosum leaves were extracted with hexane and further fractioned and subfractioned over silica gel by gradient elution with hexane, chloroform, ethyl acetate and methanol. The cytotoxicity of fractions and subfractions was assessed in vitro against L5178Y-R lymphoma cells. Structure elucidation of the active compounds was determined by spectroscopic methods. Fractions and subfractions showed significant (p < 0.05) and concentration-dependent 20% to 56% cytotoxicity against L5178Y-R cells at concentrations ranging from 7.8 µg/mL to 500 µg/mL. The bioassay-guided fractionation of the hexane extract resulted in the isolation and identification of the alkane hentriacontane and the diterpene ent-labd-7-en-13S,14R,15-triol as the metabolites responsible for the activity.

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Labdanes and Withanolides from Physalis coztomatl

Cited by 32 publications

References 19 publications

Phytochemistry and biosynthesis of δ-lactone withanolides

Phytochemistry and biosynthesis of δ-lactone withanolides

Cytotoxic Effect of Methanol Extracts and Partitions of Two Mexican Desert Plants against the Murine Lymphoma L5178Y-R

Long‐chain Alkanes and ent‐Labdane‐type Diterpenes from Gymnosperma glutinosum with Cytotoxic Activity Against the Murine Lymphoma L5178Y‐R

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