Asymmetric Nitrogen-Containing Dimer from Aerial Parts of &lt;i&gt;Mercurialis leiocarpa&lt;/i&gt; and Its Synthesis by Mimicking Generation Process through Radical Intermediates

Kondo, Yuto; Nakamura, Seikou; Ino, Sayaka; Yamashita, Haruka; Nakashima, Souichi; Yamashita, Masayuki; Matsuda, Hisashi

doi:10.1248/cpb.c20-00058

Cited by 6 publications

(2 citation statements)

References 22 publications

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“…Our study group has been conducting research to discover new compounds ( Kondo et al, 2020 ; Nakamura et al, 2021 ) and anti-HSV-1 active natural compounds ( Ogawa et al, 2018 ; Yoneda et al, 2018 ). Triterpenes are known to contain a number of anti-HSV-1 compounds.…”

Section: Introductionmentioning

confidence: 99%

Effective Search of Triterpenes with Anti-HSV-1 Activity Using a Classification Model by Logistic Regression

et al. 2021

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Natural products are an excellent source of skeletons for medicinal seeds. Triterpenes and saponins are representative natural products that exhibit anti-herpes simplex virus type 1 (HSV-1) activity. However, there has been a lack of comprehensive information on the anti-HSV-1 activity of triterpenes. Therefore, expanding information on the anti-HSV-1 activity of triterpenes and improving the efficiency of their exploration are urgently required. To improve the efficiency of the development of anti-HSV-1 active compounds, we constructed a predictive model for the anti-HSV-1 activity of triterpenes by using the information obtained from previous studies using machine learning methods. In this study, we constructed a binary classification model (i.e., active or inactive) using a logistic regression algorithm. As a result of the evaluation of predictive model, the accuracy for the test data is 0.79, and the area under the curve (AUC) is 0.86. Additionally, to enrich the information on the anti-HSV-1 activity of triterpenes, a plaque reduction assay was performed on 20 triterpenes. As a result, chikusetsusaponin IVa (11: IC50 = 13.06 μM) was found to have potent anti-HSV-1 with three potentially anti-HSV-1 active triterpenes. The assay result was further used for external validation of predictive model. The prediction of the test compounds in the activity test showed a high accuracy (0.83) and AUC (0.81). We also found that this predictive model was found to be able to successfully narrow down the active compounds. This study provides more information on the anti-HSV-1 activity of triterpenes. Moreover, the predictive model can improve the efficiency of the development of active triterpenes by integrating many previous studies to clarify potential relationships.

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Section: Introductionmentioning

confidence: 99%

Effective Search of Triterpenes with Anti-HSV-1 Activity Using a Classification Model by Logistic Regression

et al. 2021

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“…5 Recently, we have reported the isolation and synthesis of heterocycles, including pyrroles and pyrrole dimers. [7][8][9][10][11][12][13][14] On the other hand, several N-substituted pyrroles are contained in Allium plants as colored components. Homogenized onion (bulb of Allium cepa) or garlic (bulb of A. sativum) is known to form colored components.…”

Section: Introductionmentioning

confidence: 99%

Detection of New 3,4-Dimethylpyrrole Derivatives upon the Incubation of Exogenous Amines with Extract of Onion (Allium cepa) and Crude Alliinase from Garlic (A. sativum)

Nakamura¹,

Yoneda²,

Okui³

et al. 2021

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Seven new N-substituted 3,4-dimethylpyrroles were obtained in situ through the reaction of an amine ((L)-phenylalanine, (L)-tryptophan, (L)-leucine, (L)-methionine, 1-phenethylamine, aniline or dodecylamine) and a mixture of unstable sulfur-containing compounds derived from the reaction of amino acids in Allium cepa and plant enzyme alliinase. In addition, a plausible reaction mechanism for the synthesis of N-substituted 3,4-dimethylpyrroles was displayed.

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Sutherland

2020

Nat. Prod. Rep.

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Asymmetric Nitrogen-Containing Dimer from Aerial Parts of <i>Mercurialis leiocarpa</i> and Its Synthesis by Mimicking Generation Process through Radical Intermediates

Cited by 6 publications

References 22 publications

Effective Search of Triterpenes with Anti-HSV-1 Activity Using a Classification Model by Logistic Regression

Effective Search of Triterpenes with Anti-HSV-1 Activity Using a Classification Model by Logistic Regression

Detection of New 3,4-Dimethylpyrrole Derivatives upon the Incubation of Exogenous Amines with Extract of Onion (Allium cepa) and Crude Alliinase from Garlic (A. sativum)

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