Bipolenins K-N: New sesquiterpenoids from the fungal plant pathogen Bipolaris sorokiniana

Chin Soon Phan, Hang Li, Simon Kessler, Peter S. Solomon, Andrew M. Piggott, Yit Heng Chooi

Research output: Contribution to journalArticle

Abstract

Chemical investigation of the barley and wheat fungal pathogen Bipolaris sorokiniana BRIP10943 yielded four new sativene-type sesquiterpenoid natural products, bipolenins K-N (1-4), together with seven related known analogues (5-11), and a sesterterpenoid (12). Their structures were determined by detailed analysis of spectroscopic data, supported by TDDFT calculations and comparison with previously reported analogues. These compounds were evaluated for their phytotoxic activity against wheat seedlings and wheat seed germination. The putative biosynthetic relationships between the isolated sesquiterpenoids were also explored.

Original languageEnglish
Pages (from-to)2020-2028
Number of pages9
JournalBeilstein Journal of Organic Chemistry
Volume15
DOIs
Publication statusPublished - 9 Aug 2019

Fingerprint

Pathogens
Biological Products
Seed
sativene

Cite this

Phan, Chin Soon ; Li, Hang ; Kessler, Simon ; Solomon, Peter S. ; Piggott, Andrew M. ; Chooi, Yit Heng. / Bipolenins K-N : New sesquiterpenoids from the fungal plant pathogen Bipolaris sorokiniana. In: Beilstein Journal of Organic Chemistry. 2019 ; Vol. 15. pp. 2020-2028.
@article{9aebab94b1844a32b99f1a1714695270,
title = "Bipolenins K-N: New sesquiterpenoids from the fungal plant pathogen Bipolaris sorokiniana",
abstract = "Chemical investigation of the barley and wheat fungal pathogen Bipolaris sorokiniana BRIP10943 yielded four new sativene-type sesquiterpenoid natural products, bipolenins K-N (1-4), together with seven related known analogues (5-11), and a sesterterpenoid (12). Their structures were determined by detailed analysis of spectroscopic data, supported by TDDFT calculations and comparison with previously reported analogues. These compounds were evaluated for their phytotoxic activity against wheat seedlings and wheat seed germination. The putative biosynthetic relationships between the isolated sesquiterpenoids were also explored.",
keywords = "Bipolaris sorokiniana, Phytotoxicity, Sesquiterpenes, Terpenes",
author = "Phan, {Chin Soon} and Hang Li and Simon Kessler and Solomon, {Peter S.} and Piggott, {Andrew M.} and Chooi, {Yit Heng}",
year = "2019",
month = "8",
day = "9",
doi = "10.3762/bjoc.15.198",
language = "English",
volume = "15",
pages = "2020--2028",
journal = "Beilstein Journal of Organic Chemistry",
issn = "1860-5397",
publisher = "Beilstein Institut",

}

Bipolenins K-N : New sesquiterpenoids from the fungal plant pathogen Bipolaris sorokiniana. / Phan, Chin Soon; Li, Hang; Kessler, Simon; Solomon, Peter S.; Piggott, Andrew M.; Chooi, Yit Heng.

In: Beilstein Journal of Organic Chemistry, Vol. 15, 09.08.2019, p. 2020-2028.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Bipolenins K-N

T2 - New sesquiterpenoids from the fungal plant pathogen Bipolaris sorokiniana

AU - Phan, Chin Soon

AU - Li, Hang

AU - Kessler, Simon

AU - Solomon, Peter S.

AU - Piggott, Andrew M.

AU - Chooi, Yit Heng

PY - 2019/8/9

Y1 - 2019/8/9

N2 - Chemical investigation of the barley and wheat fungal pathogen Bipolaris sorokiniana BRIP10943 yielded four new sativene-type sesquiterpenoid natural products, bipolenins K-N (1-4), together with seven related known analogues (5-11), and a sesterterpenoid (12). Their structures were determined by detailed analysis of spectroscopic data, supported by TDDFT calculations and comparison with previously reported analogues. These compounds were evaluated for their phytotoxic activity against wheat seedlings and wheat seed germination. The putative biosynthetic relationships between the isolated sesquiterpenoids were also explored.

AB - Chemical investigation of the barley and wheat fungal pathogen Bipolaris sorokiniana BRIP10943 yielded four new sativene-type sesquiterpenoid natural products, bipolenins K-N (1-4), together with seven related known analogues (5-11), and a sesterterpenoid (12). Their structures were determined by detailed analysis of spectroscopic data, supported by TDDFT calculations and comparison with previously reported analogues. These compounds were evaluated for their phytotoxic activity against wheat seedlings and wheat seed germination. The putative biosynthetic relationships between the isolated sesquiterpenoids were also explored.

KW - Bipolaris sorokiniana

KW - Phytotoxicity

KW - Sesquiterpenes

KW - Terpenes

UR - http://www.scopus.com/inward/record.url?scp=85071433320&partnerID=8YFLogxK

U2 - 10.3762/bjoc.15.198

DO - 10.3762/bjoc.15.198

M3 - Article

VL - 15

SP - 2020

EP - 2028

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -