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

doi:10.3762/bjoc.15.198

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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

25 Citations (Scopus)

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 language	English
Pages (from-to)	2020-2028
Number of pages	9
Journal	Beilstein Journal of Organic Chemistry
Volume	15
DOIs	https://doi.org/10.3762/bjoc.15.198
Publication status	Published - 9 Aug 2019

Access to Document

10.3762/bjoc.15.198

Cite this

@article{477f0dd2c39c42e7bcf43c59e29113da,

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}",

note = "Publisher Copyright: {\textcopyright} 2019 Phan et al.; licensee Beilstein-Institut.",

year = "2019",

month = aug,

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 Zur Forderung der Chemischen Wissenschaften",

}

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

SN - 1860-5397

VL - 15

SP - 2020

EP - 2028

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this