Phenylpropane as an Alternative Dearomatizing Unit of Indoles:Discovery of Inaequalisines A and B Using Substructure-Informed Molecular Networking

Gaëla Cauchie; Elvis Otogo N'nang; Justin J.J. Van Der Hooft; Pierre Le Pogam; Guillaume Bernadat; Jean François Gallard; Brice Kumulungui; Pierre Champy; Erwan Poupon; Mehdi A. Beniddir

doi:10.1021/acs.orglett.0c02153

Phenylpropane as an Alternative Dearomatizing Unit of Indoles:Discovery of Inaequalisines A and B Using Substructure-Informed Molecular Networking

Gaëla Cauchie, Elvis Otogo N'nang, Justin J.J. Van Der Hooft, Pierre Le Pogam, Guillaume Bernadat, Jean François Gallard, Brice Kumulungui, Pierre Champy, Erwan Poupon, Mehdi A. Beniddir^*

^*Corresponding author for this work

Bioinformatics

Research output: Contribution to journal › Article › Academic › peer-review

18 Citations (Scopus)

Abstract

Inaequalisines A and B (1 and 2), the first examples of hybrid alkylated phenylpropane monoterpene indole alkaloids, were isolated from the roots of Callichilia inaequalis, guided by the combined use of molecular networking and substructure annotation. Their structures, including absolute configuration, were elucidated by spectroscopic methods and ECD calculations. A possible biosynthetic pathway for 1 and 2 was postulated.

Original language	English
Pages (from-to)	6077-6081
Journal	Organic Letters
Volume	22
Issue number	15
DOIs	https://doi.org/10.1021/acs.orglett.0c02153
Publication status	Published - 7 Aug 2020

Access to Document

10.1021/acs.orglett.0c02153

Cite this

Cauchie, G., N'nang, E. O., Van Der Hooft, J. J. J., Le Pogam, P., Bernadat, G., Gallard, J. F., Kumulungui, B., Champy, P., Poupon, E., & Beniddir, M. A. (2020). Phenylpropane as an Alternative Dearomatizing Unit of Indoles:Discovery of Inaequalisines A and B Using Substructure-Informed Molecular Networking. Organic Letters, 22(15), 6077-6081. https://doi.org/10.1021/acs.orglett.0c02153

@article{53f97a488acc4d879cf852b13ebd9df4,

title = "Phenylpropane as an Alternative Dearomatizing Unit of Indoles:Discovery of Inaequalisines A and B Using Substructure-Informed Molecular Networking",

abstract = "Inaequalisines A and B (1 and 2), the first examples of hybrid alkylated phenylpropane monoterpene indole alkaloids, were isolated from the roots of Callichilia inaequalis, guided by the combined use of molecular networking and substructure annotation. Their structures, including absolute configuration, were elucidated by spectroscopic methods and ECD calculations. A possible biosynthetic pathway for 1 and 2 was postulated.",

author = "Ga{\"e}la Cauchie and N'nang, {Elvis Otogo} and {Van Der Hooft}, {Justin J.J.} and {Le Pogam}, Pierre and Guillaume Bernadat and Gallard, {Jean Fran{\c c}ois} and Brice Kumulungui and Pierre Champy and Erwan Poupon and Beniddir, {Mehdi A.}",

year = "2020",

month = aug,

day = "7",

doi = "10.1021/acs.orglett.0c02153",

language = "English",

volume = "22",

pages = "6077--6081",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "15",

}

Cauchie, G, N'nang, EO, Van Der Hooft, JJJ, Le Pogam, P, Bernadat, G, Gallard, JF, Kumulungui, B, Champy, P, Poupon, E & Beniddir, MA 2020, 'Phenylpropane as an Alternative Dearomatizing Unit of Indoles:Discovery of Inaequalisines A and B Using Substructure-Informed Molecular Networking', Organic Letters, vol. 22, no. 15, pp. 6077-6081. https://doi.org/10.1021/acs.orglett.0c02153

TY - JOUR

T1 - Phenylpropane as an Alternative Dearomatizing Unit of Indoles:Discovery of Inaequalisines A and B Using Substructure-Informed Molecular Networking

AU - Cauchie, Gaëla

AU - N'nang, Elvis Otogo

AU - Van Der Hooft, Justin J.J.

AU - Le Pogam, Pierre

AU - Bernadat, Guillaume

AU - Gallard, Jean François

AU - Kumulungui, Brice

AU - Champy, Pierre

AU - Poupon, Erwan

AU - Beniddir, Mehdi A.

PY - 2020/8/7

Y1 - 2020/8/7

N2 - Inaequalisines A and B (1 and 2), the first examples of hybrid alkylated phenylpropane monoterpene indole alkaloids, were isolated from the roots of Callichilia inaequalis, guided by the combined use of molecular networking and substructure annotation. Their structures, including absolute configuration, were elucidated by spectroscopic methods and ECD calculations. A possible biosynthetic pathway for 1 and 2 was postulated.

AB - Inaequalisines A and B (1 and 2), the first examples of hybrid alkylated phenylpropane monoterpene indole alkaloids, were isolated from the roots of Callichilia inaequalis, guided by the combined use of molecular networking and substructure annotation. Their structures, including absolute configuration, were elucidated by spectroscopic methods and ECD calculations. A possible biosynthetic pathway for 1 and 2 was postulated.

U2 - 10.1021/acs.orglett.0c02153

DO - 10.1021/acs.orglett.0c02153

M3 - Article

C2 - 32686942

AN - SCOPUS:85089183416

SN - 1523-7060

VL - 22

SP - 6077

EP - 6081

JO - Organic Letters

JF - Organic Letters

IS - 15

ER -

Phenylpropane as an Alternative Dearomatizing Unit of Indoles:Discovery of Inaequalisines A and B Using Substructure-Informed Molecular Networking

Abstract

Access to Document

Fingerprint

Cite this