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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 |
Show graphically |
Structure type: monomer
; 380 [M+Na]+
Trivial name: HMBOA glucoside
Compound class: glycoside
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