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Phenolic Compounds from Lavandula angustifolia

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English lavender (Lavandula angustifolia, Labiatae) is indigenous to the Mediterranean region. The first mention of lavender is found in Avicenna’s Canon of Medical Science. The plant is widely used in… Click to show full abstract

English lavender (Lavandula angustifolia, Labiatae) is indigenous to the Mediterranean region. The first mention of lavender is found in Avicenna’s Canon of Medical Science. The plant is widely used in traditional Uyghur medicine. Currently, lavender is extensively cultivated to produce essential oil in Gulja, a Xinjiang province in China. Early investigations focused on essential oils from the plant that were used to manufacture perfume. It consisted of more 100 constituents that were responsible for the aromatic features and determined their biological activity [1]. Nevertheless, the composition of the nonvolatile compounds in lavender is poorly studied. According to the literature, many plants of the family Labiatae are rich in phenolic compounds, which have shown good antioxidant activity [2]. Earlier, caffeic acid and apigenin were isolated from lavender [3, 4]. Herein, we communicate results from studies of phenolic compounds from the aerial part of L. angustifolia collected in June 2014 in Gulja. A total of 15 compounds were isolated from the EtOAc fraction of lavender. Compounds 1–9 and 11–14 were isolated for the first time. Volatile constituents were extracted by steam distillation. Specimens were deposited in the Xinjiang Technical Institute of Physics and Chemistry. Plant material (13 kg) was ground and extracted with EtOH (70%). Then, the extract was evaporated to produce a condensed extract (4.2 kg) that was suspended in H2O and worked up with petroleum ether, CH2Cl2, EtOAc, and n-BuOH. The EtOAc fraction (188 g) was chromatographed over a column of silica gel with elution by CH2Cl2–MeOH to produce six large fractions (EA–EF). Column chromatography of these fractions using silica gel, ODS (octadecylsilyl silica gel), LH-20 Sephadex, and preparative HPLC (MeOH–H2O, 25:75; MeCN–H2O, 20:80) led to isolation of 15 pure compounds (1–15). The structures of 1–15 were established using spectral data (1D and 2D NMR and ESI-MS) and comparison with the literature [3–16]. 4-Hydroxybenzoic acid (1), 12.0 mg, colorless crystals, C7H6O3, mp 214–217°C. Spectral data agreed with those published [5]. 3,4-Dihydroxybenazldehyde (2), 20.1 mg, plate-like crystals, C7H6O3, mp 152–157 Ñ. ESI-MS m/z 137.3 [M – H] –. 1Í NMR spectrum (600 MHz, DMSO-d6, , ppm, J/Hz): 9.78 (2Í, br.s, 3, 4-OH), 9.70 (1H, s, H-7), 7.26 (1H, d, J = 7.7, H-6), 7.23 (1H, s, H-2), 6.90 (1H, d, J = 7.7, H-5). 13C NMR spectrum (150 MHz, DMSO-d6, , ppm): 190.97 (C-7), 152.16 (C-4), 145.85 (C-3), 128.77 (C-1), 124.40 (C-6), 115.47 (C-5), 114.32 (C-2) [6]. 3,4-Dihydroxybenzoic acid (3), 22.3 mg, white needle-like crystals, C7H6O4, mp 198–202°C. Spectral data agreed with those published [7]. 2-Hydroxycinnamic acid (4), 28.6 mg, white powder, C9H8O3, mp 215–219°C. Spectral data agreed with those published [8]. 4-Hydroxycinnamic acid (5), 19.9 mg, white needle-like crystals, C9H8O3, mp 212–214°C. Spectral data agreed with those published [9].

Keywords: data agreed; spectral data; agreed published; chemistry; lavandula angustifolia; phenolic compounds

Journal Title: Chemistry of Natural Compounds
Year Published: 2017

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