Antifungal activity against Botrytis cinerea of labdane-type diterpenoids isolated from the resinous exudate of Haplopappus velutinus Remy (Asteraceae)

J. Echeverría, M. González-Teuber, A. Urzúa

Research output: Contribution to journalArticle

Abstract

Two labdane diterpenoids were isolated, from the resinous exudate of Haplopappus velutinus Remy (Asteraceae); the main compound was identified as 7,13-(E)-labdadien-15,18-dioic-acid-18-methyl ester (1) and the minor compound identified as 7-labden-15,18-dioic-acid-18-methyl ester (2). Their structures were obtained using FTIR, MS, HRMS and NMR data: 1D NMR (1H, 13C and DEPT-135), 2D homonuclear NMR (COSY and NOESY) and heteronuclear NMR (HSQC and HMBC). The trans stereochemistry of the decalin moiety of compounds 1 and 2 was established through NOESY experiments of the reduction product of 1; 7-labden-15,18-diol (1a). Diterpenoids 1 and 1a are described for the first time and showed antifungal activity, inhibiting approximately 40% mycelial growth of Botrytis cinerea. © 2018 Informa UK Limited, trading as Taylor & Francis Group
LanguageEnglish
Pages1-5
Number of pages5
JournalNatural Product Research
DOIs
Publication statusPublished - 2018

Fingerprint

Haplopappus
Botrytis
Asteraceae
Diterpenes
Exudates and Transudates
Botrytis cinerea
diterpenoids
Esters
esters
Nuclear magnetic resonance
Biomolecular Nuclear Magnetic Resonance
glycols
Acids
acids
stereochemistry
Fourier Transform Infrared Spectroscopy
Stereochemistry
Growth
labdane
Experiments

Keywords

  • antifungal labdanes
  • Botrytis cinerea
  • Haplopappus velutinus
  • labdane diterpenes

Cite this

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title = "Antifungal activity against Botrytis cinerea of labdane-type diterpenoids isolated from the resinous exudate of Haplopappus velutinus Remy (Asteraceae)",
abstract = "Two labdane diterpenoids were isolated, from the resinous exudate of Haplopappus velutinus Remy (Asteraceae); the main compound was identified as 7,13-(E)-labdadien-15,18-dioic-acid-18-methyl ester (1) and the minor compound identified as 7-labden-15,18-dioic-acid-18-methyl ester (2). Their structures were obtained using FTIR, MS, HRMS and NMR data: 1D NMR (1H, 13C and DEPT-135), 2D homonuclear NMR (COSY and NOESY) and heteronuclear NMR (HSQC and HMBC). The trans stereochemistry of the decalin moiety of compounds 1 and 2 was established through NOESY experiments of the reduction product of 1; 7-labden-15,18-diol (1a). Diterpenoids 1 and 1a are described for the first time and showed antifungal activity, inhibiting approximately 40{\%} mycelial growth of Botrytis cinerea. {\circledC} 2018 Informa UK Limited, trading as Taylor & Francis Group",
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author = "J. Echeverr{\'i}a and M. Gonz{\'a}lez-Teuber and A. Urz{\'u}a",
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language = "English",
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AU - González-Teuber, M.

AU - Urzúa, A.

N1 - Export Date: 11 April 2018 Article in Press CODEN: NPRAA Correspondence Address: Echeverría, J.email: javier.echeverriam@usach.cl

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AB - Two labdane diterpenoids were isolated, from the resinous exudate of Haplopappus velutinus Remy (Asteraceae); the main compound was identified as 7,13-(E)-labdadien-15,18-dioic-acid-18-methyl ester (1) and the minor compound identified as 7-labden-15,18-dioic-acid-18-methyl ester (2). Their structures were obtained using FTIR, MS, HRMS and NMR data: 1D NMR (1H, 13C and DEPT-135), 2D homonuclear NMR (COSY and NOESY) and heteronuclear NMR (HSQC and HMBC). The trans stereochemistry of the decalin moiety of compounds 1 and 2 was established through NOESY experiments of the reduction product of 1; 7-labden-15,18-diol (1a). Diterpenoids 1 and 1a are described for the first time and showed antifungal activity, inhibiting approximately 40% mycelial growth of Botrytis cinerea. © 2018 Informa UK Limited, trading as Taylor & Francis Group

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