(2R)-2-β-d-Glucopyranosyloxy-4-hydroxy-2h-1,4-benzoxazin- 3(4h)-one from Secale cereale

doi:10.1016/S0031-9422(00)90618-6

Phytochemistry

Volume 35, Issue 3, February 1994, Pages 827-828

https://doi.org/10.1016/S0031-9422(00)90618-6 Get rights and content

Abstract

(2R)-2-β-d-Glucopyranosyloxy-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one was isolated from Secale cereale for the first time as a pure substance. The absolute configuration was determined as the 2R-type by spectroscopic methods.

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Data-dependent acquisition-mass spectrometry guided isolation of new benzoxazinoids from the roots of Acanthus mollis L
2022, International Journal of Mass Spectrometry
Citation Excerpt :
The effects of BXs have been reported to range from health protecting, immunoregulatory, antimicrobial, anticancer, and mood improving in mammals to allelopathic and acting as a defense agent in plants [8–11]. The interest in investigating the bioactivity of BXs has led to a range of publications in which the isolation of BXs from plants [12–14] or the production of BXs through organic synthesis has been reported [15–17]. Some of the published isolation procedures for BXs were dedicated to the isolation of formerly known compounds that were required in substantial amounts for use in specific bioassays [15,18–21].
Benzoxazinoids (BXs) are phytochemicals that exert plant-protecting, allelopathic, and human-health-promoting effects. Here, we present a data-dependent acquisition-mass spectrometry based method to locate and annotate BX-conjugates in different fractions of a plant extract. This allows for isolation of compounds present in a much smaller percentage than common for natural products yet still sufficient for subsequent identification through nuclear magnetic resonance (NMR) spectroscopy. The presence of BXs has been extensively studied in monocotyledons, whereas only a limited number of studies have focused on dicotyledons. Here, the presence of hitherto unknown BXs in the roots of the dicotyledonous plant Acanthus mollis L. has been determined. Two acetylated glycosylated BXs, compound 1 2-(6-acetyl-β-D-glucopyranoside)-2,4-dihydroxy-2H-1,4-benzoxazin-3(4H)-one) and compound 2 (-2-(6-acetyl-β-D-glucopyranoside)-2-hydroxy-2H-1,4-benzoxazin-3(4H)-one), and a BX-derived glucoside carbamate olide, compound 3 (2-hydroxy-6-(2-deoxy-β-D-glucopyranosyloxy)-phenyl) carbamic acid 2′-olide), were isolated and identified by NMR. These previously unknown BXs may contribute to the reported biological activities of A. mollis L.
Benzoxazinoid and indoxyl glycosides from Wrightia religiosa
2018, Phytochemistry Letters
Citation Excerpt :
The 1H and 13C NMR spectral data were similar to those of 1 except for the presence of the chemical shifts of C-2 and C-1′ at dC 93.2 and 99.9, respectively (Table 1), suggesting to be a (2S)-diastereomer of 1. Since the stereochemistry at C-2 position of benzoxazinoid glucosides could be determined from the optical rotation value, the positive values are a typical feature of (2R)-configuration (Tietze et al., 1991; Hartenstein and Sicker, 1994; Kanchanapoom et al., 2001a,b). Therefore, the (2S)-stereochemistry of this compound was deduced and confirmed to be (S) from the negative optical value, [α]D26 −105.0 (MeOH, c 0.75), which was different from the positive optical value of 1, [α]D26 +107.2 (MeOH, c 1.00).
A new class of secondary metabolites of the family Apocynaceae, benzoxazinoid, was reported for the first time from Wrightia religiosa. A new benzoxazinoid glycoside, (2S)-2-O-β-d-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (2) and a new indole diglycoside, indoxyl 3-O-β-d-apiofuranosyl-(1 → 6)-β-d-glucopyranoside (4) were isolated, together with twelve known compounds, including benzoxazinoid glycosides (1, 3), simple aromatic glycosides (5–8), a lignan glycoside (9), flavonol glycosides (10–13) and a megastigmane glucoside (14). The structure elucidation of these compounds was based on analyses of physical and spectroscopic data including 1D and 2D NMR experiments. A benzoxazinoid with (2S)-configuration was isolated for the first time from natural source.
Chemical constituents from the roots of Acanthus ilicifolius var. xiamenensis
2014, Biochemical Systematics and Ecology
Citation Excerpt :
Fr b was purified by preparation HPLC (column: Kromasil 250 × 10 mm, 5 μm; mobile phase: MeOH: H2O = 30:70) to gain 3 (49.5 mg), 4 (202.9 mg), 5 (16.8 mg), and 6 (34.6 mg); FrⅢ was subjected to Sephadex LH-20 to get 7 (29.8 mg). The eleven compounds were identified as 2-benzoxazolinone (1) (Chatterjee et al., 1990), 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one (2) (Atkinson et al., 1991), (2R)-2-O-β-d-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (3) (Tietze et al., 1991), (2R)-2-O-β-d-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one (4) (Hartenstein and Sicker, 1994), (2R)-2-O-β-d-glucopyranosyl-7-hydroxy-2H-1,4-benzoxazin-3(4H)-one (5) (Nagao et al., 1985), lyoniside (6) (Huang et al., 2007), 3′-methoxy-luteolin-7-O-β-d-glucopyranoside (7) (Yang et al., 2007), β-sitosterol-3-O-β-d-glucopyranoside (8) (Zhong et al., 2012), stigmasterol octadecanoate (9) (Zhong et al., 2012), β-sitosterol octadecanoate (10) (Zhong et al., 2012), stigmasterol-3-O-β-d-glucopyranoside (11) (Zhong et al., 2012), respectively, on the basis of their 1H NMR, 13C NMR and EI-MS spectra and by comparison of their data with those reported previously in the related literature (Fig. 1). The present study reported the isolation and identification of eleven secondary metabolites including five alkaloids (1–5), one lignanoid (6), one flavonoid (7) and four steroids (8–11) for the first time from the roots of A. ilicifolius var.
Chemical investigation of Acanthus ilicifolius var. xiamenensis led to the isolation of eleven compounds, and their structures were identified to be 2-benzoxazolinone (1), 2-hydroxy-2H-1,4-benzoxazin-3(4H)-one (2), (2R)-2-O-β-d-glucopyranosyl-2H-1,4-benzox azin-3(4H)-one (3), (2R)-2-O-β-d-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one (4), (2R)-2-O-β-d-glucopyranosyl-7-hydroxy-2H-1,4-benzoxazin-3(4H)-one (5), lyoniside (6), 3′-methoxy-luteolin-7-O-β-d-glucopyranoside (7), β-sitosterol-3-O-β-d-glucopyranoside (8), stigmasterol octadecanoate (9), β-sitosterol octadecanoate (10), stigmasterol-3-O-β-d-glucopyranoside (11) on the basis of mass and NMR spectra. This is the first report on the occurrence of compound 6 and 7 in Acanthaceae. This work also represents the first phytochemical work on the roots of A. ilicifolius var. xiamenensis.
An approach toward the syntheses of triazolo benzoxazines, triazolo quinoxalines, triazolo benzodiazepines, triazolo benzoxazepines, and triazolo benzothiazines via a simple and convenient protocol using basic alumina as solid support
2014, Tetrahedron Letters
Efficient synthesis of [1,2,3]triazolo[5,1-c][1,4]benzoxazines through palladium-copper catalysis
2009, Tetrahedron Letters
Preparative isolation and purification of two benzoxazinoid glucosides from Acanthus ilicifolius L. by high-speed counter-current chromatography
2008, Journal of Chromatography A
The first preparative separation of two benzoxazinoids, (2R)-2-O-β-d-glucopyranosyl-2H-1,4-benzoxazin-3(4H)-one (HBOA-Glc) and (2R)-2-O-β-d-glucopyranosyl-4-hydroxy-2H-1,4-benzoxazin-3(4H)-one (DIBOA-Glc), by means of high-speed counter-current chromatography (HSCCC) from the n-butanol extract of Acanthus ilicifolius L. is presented. The two-phase solvent system containing ethyl acetate–n-butanol–0.5%NH₄OH (2:3:5, v/v/v, system B) was selected for the one-step HSCCC separation of HBOA-Glc and DIBOA-Glc according to the partition coefficient values (K) for target compounds and the separation factor (α) between the two target compounds. In the one-step HSCCC separation using solvent B, from 100 mg n-butanol extract of A. ilicifolius, 6.3 mg HBOA-Glc and 6.8 mg DIBOA-Glc were isolated with purities of 90.3% and 80.2%, respectively. In order to obtain the two target compounds with higher purity, a second separation process was developed comprising two steps. In the two-step separation, the sample was first pre-purified by HSCCC using ethyl acetate–n-butanol–water (2:3:5, v/v/v, system A) solvent system and then purified using solvent system B. A 100-mg amount of the n-butanol extracts of A. ilicifolius was separated to yield 5.8 mg of HBOA-Glc and 4.8 mg of DIBOA-Glc with purities of 97.1% and 94.8%, respectively, which were directly used for NMR analyses.

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Short report(2R)-2-β-d-Glucopyranosyloxy-4-hydroxy-2h-1,4-benzoxazin- 3(4h)-one from Secale cereale

Abstract

Phytochemistry

J. Chromatogr.

Phytochemistry

Zentralbl. Mikrobiol.

Phytochemistry

Acta Chem. Scand.

Acta Chem. Scand.

Chem. Ind.

Acta Chem. Scand.

J. Nat. Prod.

Short report
(2R)-2-β-d-Glucopyranosyloxy-4-hydroxy-2h-1,4-benzoxazin- 3(4h)-one from Secale cereale