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1. (Article ID: 12021)
Baumeler A, Hesse M, Werner C
Benzoxazinoids - cyclic hydroxamic acids, lactams and their corresponding glucosides in the genus Aphelandra (Acanthaceae)
Phytochemistry 53(2) (2000)
213-222
An improved method of sample preparation and simultaneous HPLC separation was developed that allowed the separation of 2,4-dihydroxy-1,4-benzoxazine-3(4H)-one (DIBOA), 2,4-dihydroxy-7-methoxy-1,4-benzoxazine-3(4H)-one (DIMBOA), 2-hydroxy-1,4-benzoxazine-3(2H)-one (HBOA), 2-hydroxy-7-methoxy-1,4-benzoxazine-3(2H)-one (HMBOA) and their corresponding glucosides as well as the benzoxazolinones BOA and MBOA. The amount and distribution of these compounds was determined in the roots of Aphelandra squarrosa and A. fuscopunctata plants. There is a significant difference in the amount and distribution of this substance class in the two species analyzed. The results are discussed in relation to their function as defence compounds and allelochemicals.
roots, allelopathy, Aphelandra, hydroxamic acids, HPLC separation, benzoxazinoids
NCBI PubMed ID: 10680174Publication DOI: 10.1016/s0031-9422(99)00508-7Journal NLM ID: 0151434Publisher: Elsevier
Correspondence: cwerner

oci.unizh.ch
Institutions: Organisch-chemisches Institut, Universität Zürich, Switzerland
Methods: 13C NMR, 1H NMR, EI-MS, IR, ESI-MS, HPLC, UV, extraction, CI-MS, CC, melting point determination, evaporation
The publication contains the following compound(s):
- Compound ID: 31297
|
b-D-Glcp-(1-2)-Subst
Subst = 2,4-dihydroxy-1,4-benzoxazine-3(4H)-one = SMILES O=C1N({4}O)C2=CC=CC=C2O{2}C1O |
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Structure type: monomer
; 366 [M+Na]+
Trivial name: DIBOA glucoside
Compound class: glycoside
- Compound ID: 31298
|
b-D-Glcp-(1-2)-Subst7Me
Subst = 2,4,7-trihydroxy-1,4-benzoxazine-3(4H)-one = SMILES O{7}C1=CC2=C(C=C1)N(C(=O){2}C(O2)O){4}O |
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Structure type: monomer
; 396 [M+Na]+
Trivial name: DIMBOA glucoside
Compound class: glycoside
- Compound ID: 31299
|
b-D-Glcp-(1-2)-Subst4Me7Me
Subst = 2,4,7-trihydroxy-1,4-benzoxazine-3(4H)-one = SMILES O{7}C1=CC2=C(C=C1)N(C(=O){2}C(O2)O){4}O |
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Structure type: monomer
; 410 [M+Na]+
Trivial name: HDMBOA glucoside
Compound class: glycoside
- Compound ID: 31300
|
b-D-Glcp-(1-2)-Subst
Subst = 2-hydroxy-1,4-benzoxazine-3(2H)-one = SMILES C1=CC=C2C(=C1)NC(=O){2}C(O2)O |
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Structure type: monomer
Trivial name: HBOA glucoside
Compound class: glycoside
- Compound ID: 31301
|
b-D-Glcp-(1-2)-Subst7Me
Subst = 2,7-dihydroxy-1,4-benzoxazine-3(2H)-one = SMILES O{7}C1=CC2=C(C=C1)NC(=O){2}C(O2)O |
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Structure type: monomer
; 380 [M+Na]+
Trivial name: HMBOA glucoside
Compound class: glycoside
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2. (Article ID: 12692)
Sicker D, Frey M, Schulz M, Gierl A
Role of natural benzoxazinones in the survival strategy of plants
International Review of Cytology 198 (2000)
319-346
Benzoxazinoid acetal glucosides are a unique class of natural products abundant in Gramineae, including the major agricultural crops maize, wheat, and rye. These secondary metabolites are also found in several dicotyledonous species. Benzoxazinoids serve as important factors of host plant resistance against microbial diseases and insects and as allelochemicals and endogenous ligands. Interdisciplinary investigations by biologists, biochemists, and chemists are stimulated by the intention to make agricultural use of the benzoxazinones as natural pesticides. These natural products are not only constituents of a plant defense system but also part of an active allelochemical system used in the competition with other plants. This review covers biological and chemical aspects of benzoxazinone research over the last decade with special emphasis on recent advances in the elucidation of the biosynthetic pathway.
biosynthesis, allelopathy, benzoxazinones, cyclic hydroxamic acids, acetal glucosides, defence
NCBI PubMed ID: 10804466Publication DOI: 10.1016/s0074-7696(00)98008-2Journal NLM ID: 2985180RInstitutions: Institute of Organic Chemistry, University of Leipzig, Leipzig, Germany, Institut für Genetik, Technische Universität München, Garching, Germany, Institute of Agricultural Botany, University of Bonn, Bonn, Germany
The publication contains the following compound(s):
- Compound ID: 31373
|
b-D-Glcp-(1-2)-Subst
Subst = 2,4-dihydroxy-1,4-benzoxazine-3(4H)-one = SMILES O=C1N({4}O)C2=CC=CC=C2O{2}C1O |
Show graphically |
Structure type: monomer
Trivial name: DIBOA glucoside
Compound class: glycoside
- Compound ID: 31374
|
b-D-Glcp-(1-2)-Subst7Me
Subst = 2,4,7-trihydroxy-1,4-benzoxazine-3(4H)-one = SMILES O{7}C1=CC2=C(C=C1)N(C(=O){2}C(O2)O){4}O |
Show graphically |
Structure type: monomer
Trivial name: DIMBOA glucoside
Compound class: glycoside
- Compound ID: 32917
Structure type: monomer
Trivial name: DIM2BOA glucoside
Compound class: glycoside
- Compound ID: 32918
Structure type: monomer
Trivial name: HDIBOA glucoside
Compound class: glycoside
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