Merging bioactivity with liquid chromatography-mass spectrometry-based chemometrics to identify minor immunomodulatory compounds from a Micronesian adaptogen, Phaleria nisidai

Kulakowski, Daniel; Wu, Shi‐Biao; Balick, Michael J.; Kennelly, Edward J.

doi:10.1016/j.chroma.2014.08.049

Cited by 23 publications

(21 citation statements)

References 39 publications

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“…Simplexin, acetoxyhuratoxin and huratoxin are known to be acutely toxic, and sometimes deadly, to livestock by damaging the gastrointestinal tract and causing heart failure (Fletcher et al, 2009;Roberts et al, 1975;Wilson et al, 2007). Previous work by our group revealed that these, and other daphnane compounds were present in hydrophobic Phaleria nisidai fractions with immunomodulatory activity (Kulakowski et al, 2014).…”

Section: Discussionmentioning

confidence: 92%

“…We have previously used the production of IFNȖ by peripheral blood mononuclear cells (PBMCs) to guide fractionation of a methanol extract of P. nisidai and found that daphnane-type diterpene orthoesters contribute to the immunostimulatory activity of this plant (Kulakowski et al, 2014), which was the first report of diterpene esters from the Phaleria genus.…”

Section: Bioactivity and Chemistrymentioning

confidence: 99%

“…Table 2 were used to identify two additional daphnanes; huratoxin and acetoxyhuratoxin, in methanol extracts. We have previously identified these compounds in P. nisidai fractions by LC-MS-ToF exact mass analysis (Kulakowski et al, 2014).…”

Section: Cell Proliferationmentioning

confidence: 99%

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Traditional preparation of Phaleria nisidai, a Palauan tea, reduces exposure to toxic daphnane-type diterpene esters while maintaining immunomodulatory activity

Kulakowski

Kitalong

Negrin

et al. 2015

Journal of Ethnopharmacology

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The presence of daphnane diterpene esters in a frequently consumed traditional beverage was initially viewed as a public health concern, though interview data reveal that Palauans do not observe toxicity or side effects associated with their use of P. nisidai tea. Concurrently, daphnanes are present in methanolic extracts but not detected in aqueous preparations indicating that the traditional method of preparation avoids the extraction of these potentially toxic compounds, while still maintaining immunostimulant activity.

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Section: Discussionmentioning

confidence: 92%

Section: Bioactivity and Chemistrymentioning

confidence: 99%

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Traditional preparation of Phaleria nisidai, a Palauan tea, reduces exposure to toxic daphnane-type diterpene esters while maintaining immunomodulatory activity

Kulakowski

Kitalong

Negrin

et al. 2015

Journal of Ethnopharmacology

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“…14 In contrast, Kulakowski et al utilized unsupervised principal component analysis (PCA) and supervised orthogonal partial least-squares discriminatory analysis (OPLS-DA) to correlate bioactivity to LC-MS profiles. 6 PCA can be used to group samples based upon covariance, so fractions with similar profiles will be clustered, while others will be in a different location in the PCA scores plot. PCA is useful for describing chemical differences among samples, but does not provide insight into which of the constituents of these samples are biologically active.…”

mentioning

confidence: 99%

“…OPLS-DA allows for the incorporation of biological data, which were in this case binary classifications, i.e., active/nonactive fractions. 6 OPLS-DA plots appear similar to PCA plots, and an OPLS-DA model can be represented as an S-plot, where each axis represents the covariance and correlation loading variables. 15 Biomarkers with intensities that correlate and covary with the bioactivity appear the furthest from the origin.…”

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confidence: 99%

Biochemometrics to Identify Synergists and Additives from Botanical Medicines: A Case Study with Hydrastis canadensis (Goldenseal)

et al. 2017

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A critical challenge in the study of botanical natural products is the difficulty of identifying multiple compounds that may contribute additively, synergistically, or antagonistically to biological activity. Herein, it is demonstrated how combining untargeted metabolomics with synergy-directed fractionation can be effective toward accomplishing this goal. To demonstrate this approach, an extract of the botanical goldenseal (Hydrastis canadensis) was fractionated and tested for its ability to enhance the antimicrobial activity of the alkaloid berberine (4) against the pathogenic bacterium Staphylococcus aureus. Bioassay data were combined with untargeted mass spectrometry-based metabolomics data sets (biochemometrics) to produce selectivity ratio (SR) plots, which visually show which extract components are most strongly associated with the biological effect. Using this approach, the new flavonoid 3,3′-dihydroxy-5,7,4′-trimethoxy-6,8-C-dimethylflavone (29) was identified, as were several flavonoids known to be active. When tested in combination with 4, 29 lowered the IC50 of 4 from 132.2 ± 1.1 μM to 91.5 ± 1.1 μM. In isolation, 29 did not demonstrate antimicrobial activity. The current study highlights the importance of fractionation when utilizing metabolomics for identifying bioactive components from botanical extracts and demonstrates the power of SR plots to help merge and interpret complex biological and chemical data sets.

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Ultra high performance liquid chromatography coupled with triple quadrupole mass spectrometry and chemometric analysis of licorice based on the simultaneous determination of saponins and flavonoids

Jiang

Wang

Zheng

et al. 2016

J of Separation Science

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Licorice is among the most popular herbal medicines and frequently used in traditional medicine, food products, and cosmetics. In China, only Glycyrrhiza uralensis Fisch., Glycyrrhiza inflata Bat. and Glycyrrhiza glabra L. are officially used and are usually processed with honey prior to use. To maintain the quality of commercially available herbal products, a simple, rapid, and reliable ultra high performance liquid chromatography with triple quadrupole mass spectrometry was developed to investigate the major active constituents of commercially available licorice products. Nineteen components were accurately determined, including eight triterpenoid saponins, one triterpene, and ten flavonoids. Subsequently, multivariate statistical analysis methods were employed to further explore and interpret the experimental data. The results indicated that liquiritin apioside may be considered as a candidate index for the quality control of licorice as well as 18β-glycyrrhizic acid and liquiritin. In addition, both 18β-glycyrrhizic acid and licorice-saponin G2 can be used for discrimination between crude and honey-processed licorice. Furthermore, using 18β-glycyrrhizic acid and liquiritin as markers, this work revealed that the quality of licorice products may have declined in recent years. This highlights the need for additional effort focused on good agricultural practice during the processing of licorice. In summary, this study provides a valuable reference for the quality assessment of licorice.

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Merging bioactivity with liquid chromatography-mass spectrometry-based chemometrics to identify minor immunomodulatory compounds from a Micronesian adaptogen, Phaleria nisidai

Cited by 23 publications

References 39 publications

Traditional preparation of Phaleria nisidai, a Palauan tea, reduces exposure to toxic daphnane-type diterpene esters while maintaining immunomodulatory activity

Traditional preparation of Phaleria nisidai, a Palauan tea, reduces exposure to toxic daphnane-type diterpene esters while maintaining immunomodulatory activity

Biochemometrics to Identify Synergists and Additives from Botanical Medicines: A Case Study with Hydrastis canadensis (Goldenseal)

Ultra high performance liquid chromatography coupled with triple quadrupole mass spectrometry and chemometric analysis of licorice based on the simultaneous determination of saponins and flavonoids

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