Isolation and Synthesis of an Insect Resistance Factor from Corn Plants

Smissman, Edward E.; LaPidus, Jules B.; Beck, Stanley D.

doi:10.1021/ja01574a032

Cited by 44 publications

(22 citation statements)

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“…Further evidence for the position of the acetyl group was obtained from the 13 C-NMR, where a substantial downfield shift ∆ δC-3" = 1.20 ppm and the upfield shift of C-2″ and C-4″ (∆ δC-2" =1.66 ppm and (∆ δC-4" = 1.67 ppm) relative to those of 1 were observed. 11 12 In the 13 C-NMR spectrum (Table 1) the seven carbons were resolved as three aromatic methines (δ 99.1, 111.0 and 111.6) assigned to C-7, C-5 and C-4 respectively, three quanternary aromatic carbons (δ 129.9, 146.1 and 154.8) attributed to C-9, C-8 and C-6 respectively, and a fourth quaternary carbon at δ 157.7 assigned to the lactone carbonyl. The 1 H-NMR spectrum (Table 1) showed an ABX system at δ 6.68 (1H, d, J 2.3 Hz), 6.85 (1H, d, J 8.5 Hz) and 6.60 (1H, dd, J 2.3, 8.5 Hz) indicating a trisubstituted aromatic system.…”

Section: Resultsmentioning

confidence: 91%

“…9 However, some of the 13 C-NMR assignments in the latter publication 10 must be revised. The HRCI-MS (M + +1 at m/z 621.161 for the molecular formula C 32 H 28 O 13 ) and other spectral data of 4 (see experimental) indicated an additional acetyl group compared with 1. Complete assignments of the sugar protons could be achieved by a combination of COSY and HMQC experiments.…”

Section: Resultsmentioning

confidence: 99%

“…Even the known 6-methoxybenzoxazolinone is a rare natural product isolated only once from Corn plants. 13 Chemical reactions and solubility in NaOH, followed by recovery after acidification, suggested that 3 is a nitrogenous compound with a lactone function. This was confirmed by the IR absorption bands for carbonyl (1670 cm (Table 1) showed five methine signals and three quaternary carbons.…”

Section: Resultsmentioning

confidence: 99%

“…This clearly distinct the new alkaloid 3 (3,4-dihydroxy-1,4-benzoxazine-2-one) from blepharigenin (2-hydroxy-1,4-benzoxazine-3-one) a compound with very close 1 H-NMR data. 14 carbon signals were clear in the 13 C-NMR spectrum (Table 1), of which 8 signals were accounted for the aglycone part, while the remaining 6 carbon signals were assigned for the sugar moiety. The 1,4-benzoxazine-2-one skeleton was assigned to 5 rather than the 1,4-benzoxazine-3-one as indicated from its reaction with KOH solution and fusion test.…”

Section: Resultsmentioning

confidence: 99%

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Alkaloids and flavone acyl glycosides from Acanthus arboreus

Amer¹,

Abou-Shoer²,

Abdel‐Kader³

et al. 2004

J. Braz. Chem. Soc.

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Section: Resultsmentioning

confidence: 91%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

See 2 more Smart Citations

Alkaloids and flavone acyl glycosides from Acanthus arboreus

Amer¹,

Abou-Shoer²,

Abdel‐Kader³

et al. 2004

J. Braz. Chem. Soc.

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“…In addition, air-dried corn coleoptile tissue was observed to contain 6,7-dimethoxy-2-benzoxazolinone after heating. 7 ) DIMBOA glucoside and MBOA concentrations have been related to corn-plant resistance to the European corn borer 8 ) and to stalk rot. 9 ) A number of analytical procedures for the determination of 2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one glucosides in plant tissues measure concentrations of 2-benzoxazolinones, evaluated as MBOA, in the final steps of the procedures.…”

mentioning

confidence: 99%

6-Methoxy-2-benzoxazolinone Synthesis in 1,3-Butanediol

Richey

Caskey

BeMiller

1976

Agricultural and Biological Chemistry

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3D‐QSAR and scaffold hopping based designing of benzo[d]ox‐azol‐2(3H)‐one and 2‐oxazolo[4,5‐b]pyridin‐2(3H)‐one derivatives as selective aldehyde dehydrogenase 1A1 inhibitors: Synthesis and biological evaluation

Verma

Narendra

Raju

et al. 2022

Archiv der Pharmazie

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Aldehyde dehydrogenase 1 (ALDH1A1), an oxidoreductase class of enzymes, is overexpressed in various types of cancer cell lines and is the major cause of resistance to the Food and Drug Administration (FDA)‐approved drug, cyclophosphamide (CP). In cancer conditions, CP undergoes a sequence of biotransformations to form an active metabolite, aldophosphamide, which further biotransforms to its putative cytotoxic metabolite, phosphoramide mustard. However, in resistant cancer conditions, aldophosphamide is converted into its inactive metabolite, carboxyphosphamide, via oxidation with ALDH1A1. Herein, to address the issue of ALDH1A1 mediated CP resistance, we report a series of benzo[d]oxazol‐2(3H)‐one and 2‐oxazolo[4,5‐b]pyridin‐2(3H)‐one derivatives as selective ALDH1A1 inhibitors. These inhibitors were designed using a validated 3D‐quantitative structure activity relationship (3D‐QSAR) model coupled with scaffold hopping. The 3D‐QSAR model was developed using reported indole‐2,3‐diones based ALDH1A1 inhibitors, which provided field points in terms of electrostatic, van der Waals and hydrophobic potentials required for selectively inhibiting ALDH1A1. The most selective indole‐2,3‐diones‐based compound, that is, cmp 3, was further considered for scaffold hopping. Two top‐ranked bioisosteres, that is, benzo[d]oxazol‐2(3H)‐one and 2‐oxazolo[4,5‐b]pyridin‐2(3H)‐one, were selected for designing new inhibitors by considering the field pattern of 3D‐QSAR. All designed molecules were mapped perfectly on the 3D‐QSAR model and found to be predictive with good inhibitory potency (pIC50 range: 7.5–6.8). Molecular docking was carried out for each designed molecule to identify key interactions that are required for ALDH1A1 inhibition and to authenticate the 3D‐QSAR result. The top five inhibitor‐ALDH1A1 complexes were also submitted for molecular dynamics simulations to access their stability. In vitro enzyme assays of 21 compounds suggested that these compounds are selective toward ALDH1A1 over the other two isoforms, that is, ALDH2 and ALDH3A1. All the compounds were found to be at least three and two times more selective toward ALDH1A1 over ALDH2 and ALDH3A1, respectively. All the compounds showed an IC50 value in the range of 0.02–0.80 μM, which indicates the potential for these to be developed as adjuvant therapy for CP resistance.

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Isolation and Synthesis of an Insect Resistance Factor from Corn Plants

Cited by 44 publications

References 0 publications

Alkaloids and flavone acyl glycosides from Acanthus arboreus

Alkaloids and flavone acyl glycosides from Acanthus arboreus

6-Methoxy-2-benzoxazolinone Synthesis in 1,3-Butanediol

3D‐QSAR and scaffold hopping based designing of benzo[d]ox‐azol‐2(3H)‐one and 2‐oxazolo[4,5‐b]pyridin‐2(3H)‐one derivatives as selective aldehyde dehydrogenase 1A1 inhibitors: Synthesis and biological evaluation

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