Literature DB >> 27584856

Melokhanines A-J, Bioactive Monoterpenoid Indole Alkaloids with Diverse Skeletons from Melodinus khasianus.

Gui-Guang Cheng1,2,3, Dan Li1,3, Bo Hou1,3, Xiao-Nian Li1,3, Lu Liu1,3, Ying-Ying Chen1,3, Paul-Keilah Lunga1,3, Afsar Khan1,3,4, Ya-Ping Liu1,3, Zhi-Li Zuo1,3, Xiao-Dong Luo1,3.   

Abstract

The new melokhanines A-J (1-10) and 22 known (11-32) alkaloids were isolated from the twigs and leaves of Melodinus khasianus. The new compounds and their absolute configurations were elucidated by extensive analysis of spectroscopic, X-ray diffraction, and computational data. Melokhanine A (1), composed of a hydroxyindolinone linked to an octahydrofuro[2,3-b]pyridine moiety, is an unprecedented monoterpenoid indole alkaloid. Melokhanines B-H (2-8) possess a new 6/5/5/6/6 pentacyclic indole alkaloid skeleton. Alkaloids 1-16, 25-27, 31, and 32 showed the best antibacterial activity against Pseudomonas aeruginosa (MIC range 2-22 μM). Among the seven dermatophytes tested, compound 1 showed significant inhibitory activity against Microsporum canis, M. ferrugineum, and Trichophyton ajelloi (MIC range 38-150 μM), i.e., half the efficacy of the positive control, griseofulvin.

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Year:  2016        PMID: 27584856     DOI: 10.1021/acs.jnatprod.6b00011

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  4 in total

1.  Origin of High Diastereoselectivity in Reactions of Seven-Membered-Ring Enolates.

Authors:  Olga Lavinda; Collin H Witt; K A Woerpel
Journal:  Angew Chem Int Ed Engl       Date:  2022-02-15       Impact factor: 15.336

2.  Stereocontrolled Synthesis of (±)-Melokhanine E via an Intramolecular Formal [3 + 2] Cycloaddition.

Authors:  Anna E Cholewczynski; Peyton C Williams; Joshua G Pierce
Journal:  Org Lett       Date:  2020-01-07       Impact factor: 6.005

Review 3.  An invocation for computational evaluation of isomerization transforms: cationic skeletal reorganizations as a case study.

Authors:  Alexander W Schuppe; Yannan Liu; Timothy R Newhouse
Journal:  Nat Prod Rep       Date:  2020-09-15       Impact factor: 13.423

Review 4.  Plant-Based Indole Alkaloids: A Comprehensive Overview from a Pharmacological Perspective.

Authors:  Faisal Omar; Abu Montakim Tareq; Ali M Alqahtani; Kuldeep Dhama; Mohammed Abu Sayeed; Talha Bin Emran; Jesus Simal-Gandara
Journal:  Molecules       Date:  2021-04-15       Impact factor: 4.411

  4 in total

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