Short report(2R)-2-β-d-Glucopyranosyloxy-4-hydroxy-2h-1,4-benzoxazin- 3(4h)-one from Secale cereale
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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 SpectrometryCitation 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].
Benzoxazinoid and indoxyl glycosides from Wrightia religiosa
2018, Phytochemistry LettersCitation 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).
Chemical constituents from the roots of Acanthus ilicifolius var. xiamenensis
2014, Biochemical Systematics and EcologyCitation 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.
Efficient synthesis of [1,2,3]triazolo[5,1-c][1,4]benzoxazines through palladium-copper catalysis
2009, Tetrahedron Letters