Characterization by Empirical and Computational Methods of Dictyospiromide, an Intriguing Antioxidant Alkaloid from the Marine Alga Dictyota coriacea

Pengcheng Yan; Ge Li; Chaojie Wang; Jianzhang Wu; Zhongmin Sun; Gary E. Martin; Xiao Wang; Mikhail Reibarkh; Josep Sauri; Kirk R. Gustafson

doi:10.1021/acs.orglett.9b02856

Characterization by Empirical and Computational Methods of Dictyospiromide, an Intriguing Antioxidant Alkaloid from the Marine Alga Dictyota coriacea

Pengcheng Yan
, Ge Li
, Chaojie Wang
, Jianzhang Wu
, Zhongmin Sun
, Gary E. Martin
, Xiao Wang
, Mikhail Reibarkh
, Josep Sauri
, Kirk R. Gustafson

Research output: Indexed journal article › Article › peer-review

25 Citations (Scopus)

Abstract

The challenging structural motif of dictyospiromide (1), a spirosuccinimide alkaloid with antioxidant properties that are associated with activation of the Nrf2/ARE signaling pathway, was assigned using contemporary NMR experiments complemented with anisotropic NMR, chiroptical, and computational methodologies. Anisotropic NMR parameters provided critical orthogonal verification of the configuration of the difficult to assign spiro carbon and the other stereogenic centers in 1.

Original language	English
Pages (from-to)	7577-7581
Number of pages	5
Journal	Organic Letters
Volume	21
Issue number	18
DOIs	https://doi.org/10.1021/acs.orglett.9b02856
Publication status	Published - 20 Sept 2019
Externally published	Yes

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 14 Life Below Water

Keywords

C-13 chemical-shifts
Structure elucidation
Natural-products
Nmr experiments
Validation
H-1
Configuration
Tool
Sensitivity
Prediction

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10.1021/acs.orglett.9b02856

Cite this

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title = "Characterization by Empirical and Computational Methods of Dictyospiromide, an Intriguing Antioxidant Alkaloid from the Marine Alga Dictyota coriacea",

abstract = "The challenging structural motif of dictyospiromide (1), a spirosuccinimide alkaloid with antioxidant properties that are associated with activation of the Nrf2/ARE signaling pathway, was assigned using contemporary NMR experiments complemented with anisotropic NMR, chiroptical, and computational methodologies. Anisotropic NMR parameters provided critical orthogonal verification of the configuration of the difficult to assign spiro carbon and the other stereogenic centers in 1.",

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doi = "10.1021/acs.orglett.9b02856",

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T1 - Characterization by Empirical and Computational Methods of Dictyospiromide, an Intriguing Antioxidant Alkaloid from the Marine Alga Dictyota coriacea

AU - Yan, Pengcheng

AU - Li, Ge

AU - Wang, Chaojie

AU - Wu, Jianzhang

AU - Sun, Zhongmin

AU - Martin, Gary E.

AU - Wang, Xiao

AU - Reibarkh, Mikhail

AU - Sauri, Josep

AU - Gustafson, Kirk R.

PY - 2019/9/20

Y1 - 2019/9/20

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AB - The challenging structural motif of dictyospiromide (1), a spirosuccinimide alkaloid with antioxidant properties that are associated with activation of the Nrf2/ARE signaling pathway, was assigned using contemporary NMR experiments complemented with anisotropic NMR, chiroptical, and computational methodologies. Anisotropic NMR parameters provided critical orthogonal verification of the configuration of the difficult to assign spiro carbon and the other stereogenic centers in 1.

KW - C-13 chemical-shifts

KW - Structure elucidation

KW - Natural-products

KW - Nmr experiments

KW - Validation

KW - H-1

KW - Configuration

KW - Tool

KW - Sensitivity

KW - Prediction

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Characterization by Empirical and Computational Methods of Dictyospiromide, an Intriguing Antioxidant Alkaloid from the Marine Alga Dictyota coriacea

Abstract

UN SDGs

Keywords

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