Metabolism of maculosin, a host-specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa)

Sang Ho Park; Andrea Stierle; Gary A. Strobel

doi:10.1016/S0031-9422(00)90516-8

Metabolism of maculosin, a host-specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa)

Sang Ho Park, Andrea Stierle, Gary A. Strobel

Montana State University

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

19 Scopus citations

Abstract

Maculosin [the diketopiperazine, cyclo (l-Pro-l-Tyr)] is a host-specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa) [(Proc. Natn. Acad. Sci. U.S.A., 85, 8008-8011 (1988)]. The metabolism of maculosin was analysed after the application of [U-¹⁴C]maculosin on the detached leaves of spotted knapweed. The extracts of treated leaves as early as one day after [¹⁴C]maculosin treatment indicated that it was converted to at least three polar compounds. The neutral metabolite was purified and identified as a novel compound, maculosin β-O-glucoside. The glucoside is not phytotoxic towards spotted knapweed or any of several other plants tested.

Original language	English
Pages (from-to)	101-106
Number of pages	6
Journal	Phytochemistry
Volume	35
Issue number	1
DOIs	https://doi.org/10.1016/S0031-9422(00)90516-8
State	Published - Dec 22 1993

Keywords

Maculosin
diketopiperazine
maculosin β-O-glucoside
phytotoxins
plant disease.
spotted knapweed

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10.1016/S0031-9422(00)90516-8

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title = "Metabolism of maculosin, a host-specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa)",

abstract = "Maculosin [the diketopiperazine, cyclo (l-Pro-l-Tyr)] is a host-specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa) [(Proc. Natn. Acad. Sci. U.S.A., 85, 8008-8011 (1988)]. The metabolism of maculosin was analysed after the application of [U-14C]maculosin on the detached leaves of spotted knapweed. The extracts of treated leaves as early as one day after [14C]maculosin treatment indicated that it was converted to at least three polar compounds. The neutral metabolite was purified and identified as a novel compound, maculosin β-O-glucoside. The glucoside is not phytotoxic towards spotted knapweed or any of several other plants tested.",

keywords = "Maculosin, diketopiperazine, maculosin β-O-glucoside, phytotoxins, plant disease., spotted knapweed",

author = "{Ho Park}, Sang and Andrea Stierle and Strobel, {Gary A.}",

note = "Funding Information: Acknowledgements-The authors acknowledge the financial help of the Montana Weed Trust Fund, the NSF and the Montana Agricultural Experiment Station. Dr Joe Sears is thanked for his help in obtaining mass spectral data .",

year = "1993",

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doi = "10.1016/S0031-9422(00)90516-8",

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AU - Ho Park, Sang

AU - Stierle, Andrea

AU - Strobel, Gary A.

N1 - Funding Information: Acknowledgements-The authors acknowledge the financial help of the Montana Weed Trust Fund, the NSF and the Montana Agricultural Experiment Station. Dr Joe Sears is thanked for his help in obtaining mass spectral data .

PY - 1993/12/22

Y1 - 1993/12/22

N2 - Maculosin [the diketopiperazine, cyclo (l-Pro-l-Tyr)] is a host-specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa) [(Proc. Natn. Acad. Sci. U.S.A., 85, 8008-8011 (1988)]. The metabolism of maculosin was analysed after the application of [U-14C]maculosin on the detached leaves of spotted knapweed. The extracts of treated leaves as early as one day after [14C]maculosin treatment indicated that it was converted to at least three polar compounds. The neutral metabolite was purified and identified as a novel compound, maculosin β-O-glucoside. The glucoside is not phytotoxic towards spotted knapweed or any of several other plants tested.

AB - Maculosin [the diketopiperazine, cyclo (l-Pro-l-Tyr)] is a host-specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa) [(Proc. Natn. Acad. Sci. U.S.A., 85, 8008-8011 (1988)]. The metabolism of maculosin was analysed after the application of [U-14C]maculosin on the detached leaves of spotted knapweed. The extracts of treated leaves as early as one day after [14C]maculosin treatment indicated that it was converted to at least three polar compounds. The neutral metabolite was purified and identified as a novel compound, maculosin β-O-glucoside. The glucoside is not phytotoxic towards spotted knapweed or any of several other plants tested.

KW - Maculosin

KW - diketopiperazine

KW - maculosin β-O-glucoside

KW - phytotoxins

KW - plant disease.

KW - spotted knapweed

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JF - Phytochemistry

IS - 1

ER -

Metabolism of maculosin, a host-specific phytotoxin produced by Alternaria alternata on spotted knapweed (Centaurea maculosa)

Abstract

Keywords

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