Literature DB >> 15974613

Simplified isolation procedure and interconversion of the diastereomers of nepetalactone and nepetalactol.

Ilme Liblikas1, Ellen M Santangelo, Johan Sandell, Peter Baeckström, Mats Svensson, Ulla Jacobsson, C Rikard Unelius.   

Abstract

Three nepetalactones were isolated from Nepeta racemosa (mussinii) by traditional methods. An improved method was developed to isolate nepetalactones from N. faassénii. An epimerization procedure was used to prepare the fourth 7S-nepetalactone diastereomer. The cis-fused nepetalactols were prepared by reduction of the corresponding nepetalactones, while the trans-fused nepetalactols were unstable and found to undergo ring-opening reactions yielding iridodials. The characterizations and structural assignments by means of NMR agree with quantum chemical density functional calculations.

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Year:  2005        PMID: 15974613     DOI: 10.1021/np049647d

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


  10 in total

Review 1.  Oxidative Cyclization in Natural Product Biosynthesis.

Authors:  Man-Cheng Tang; Yi Zou; Kenji Watanabe; Christopher T Walsh; Yi Tang
Journal:  Chem Rev       Date:  2016-12-12       Impact factor: 60.622

2.  Inverted stereocontrol of iridoid synthase in snapdragon.

Authors:  Hajo Kries; Franziska Kellner; Mohamed Omar Kamileen; Sarah E O'Connor
Journal:  J Biol Chem       Date:  2017-07-12       Impact factor: 5.486

3.  Identification and functional characterization of three iridoid synthases in Gardenia jasminoides.

Authors:  Chong Xu; Peng Ye; Qingwen Wu; Shuangcheng Liang; Wuke Wei; Jinfen Yang; Weiwen Chen; Ruoting Zhan; Dongming Ma
Journal:  Planta       Date:  2022-02-03       Impact factor: 4.116

4.  Benzyl isothiocyanate, a major component from the roots of Salvadora persica is highly active against Gram-negative bacteria.

Authors:  Abier Sofrata; Ellen M Santangelo; Muhammad Azeem; Anna-Karin Borg-Karlson; Anders Gustafsson; Katrin Pütsep
Journal:  PLoS One       Date:  2011-08-01       Impact factor: 3.240

5.  Uncoupled activation and cyclization in catmint reductive terpenoid biosynthesis.

Authors:  Benjamin R Lichman; Mohamed O Kamileen; Gabriel R Titchiner; Gerhard Saalbach; Clare E M Stevenson; David M Lawson; Sarah E O'Connor
Journal:  Nat Chem Biol       Date:  2018-12-10       Impact factor: 16.174

6.  Identification of iridoid synthases from Nepeta species: Iridoid cyclization does not determine nepetalactone stereochemistry.

Authors:  Nathaniel H Sherden; Benjamin Lichman; Lorenzo Caputi; Dongyan Zhao; Mohamed O Kamileen; C Robin Buell; Sarah E O'Connor
Journal:  Phytochemistry       Date:  2017-11-05       Impact factor: 4.004

7.  The evolutionary origins of the cat attractant nepetalactone in catnip.

Authors:  Benjamin R Lichman; Grant T Godden; John P Hamilton; Lira Palmer; Mohamed O Kamileen; Dongyan Zhao; Brieanne Vaillancourt; Joshua C Wood; Miao Sun; Taliesin J Kinser; Laura K Henry; Carlos Rodriguez-Lopez; Natalia Dudareva; Douglas E Soltis; Pamela S Soltis; C Robin Buell; Sarah E O'Connor
Journal:  Sci Adv       Date:  2020-05-13       Impact factor: 14.136

8.  Repellency Assessment of Nepeta cataria Essential Oils and Isolated Nepetalactones on Aedes aegypti.

Authors:  William Reichert; Jadrian Ejercito; Tom Guda; Xujun Dong; Qingli Wu; Anandasankar Ray; James E Simon
Journal:  Sci Rep       Date:  2019-02-06       Impact factor: 4.379

9.  Biocatalytic routes to stereo-divergent iridoids.

Authors:  Néstor J Hernández Lozada; Benke Hong; Joshua C Wood; Lorenzo Caputi; Jérôme Basquin; Ling Chuang; Maritta Kunert; Carlos E Rodríguez López; Chloe Langley; Dongyan Zhao; C Robin Buell; Benjamin R Lichman; Sarah E O'Connor
Journal:  Nat Commun       Date:  2022-08-11       Impact factor: 17.694

10.  An alternative route to cyclic terpenes by reductive cyclization in iridoid biosynthesis.

Authors:  Fernando Geu-Flores; Nathaniel H Sherden; Vincent Courdavault; Vincent Burlat; Weslee S Glenn; Cen Wu; Ezekiel Nims; Yuehua Cui; Sarah E O'Connor
Journal:  Nature       Date:  2012-11-21       Impact factor: 69.504

  10 in total

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