Elsevier

Fitoterapia

Volume 74, Issues 1–2, February 2003, Pages 184-187
Fitoterapia

Phytochemical communication
Bioactive constituents of Leptadenia arborea

https://doi.org/10.1016/S0367-326X(02)00314-3Get rights and content

Abstract

The aerial part of Leptadenia arborea has been shown to contain pinoresinol (1), syringaresinol (2), leucanthemitol (3) and E-ferulaldehyde (4). These known compounds are being reported for the first time from this plant. Among them, syringaresinol has shown an inhibitory effect against acetylcholinesterase. The IC50 (the concentration of 50% enzyme inhibition) value of this compound was 200 μg/ml.

Section snippets

Plant.

Leptadenia arborea (Forssk.) Schweinf. Aerial parts collected from (Aswan, south of Egypt), in December 1999, and identified by Dr Arafa Hamed (Faculty of Science, Botany Department, South Valley University). A Voucher specimen of the collection has been deposited in the Herbarium of the University of Aswan.

Uses in traditional medicine.

Many species of the genus Leptadenia are used in India mainly as galactagogue in many pharmaceutical preparations and in folk medicine [1], [2], while the latex of L. hasitata is used as an anti-inflammatory and wound-healing agent [3].

Previously isolated constituents.

From the leaves, stems and fruits of L. arborea: a hydrocarbon C17H36, β-amyrin, α-amyrin, a mixture of campesterol and stigmasterol, a triterpene alcohol and several flavonoids [4].

New-isolated constituents.

From air-dried material (600 g), the MeOH–CH2Cl2 (1:1) extract (15 g), pinoresinol (1) (10 mg), syringaresinol (2) (3 mg), leucanthemitol (3) (50 mg) and E-ferulaldehyde (4) (4 mg) were isolated.

Studied activity.

Inhibition of acetylcholinesterase was assayed according to [5], [6] and syringaresinol gave the best quantitative inhibition with an IC50 value of (200 μg/ml). The other compounds inhibited the enzyme with a range of 20–35% but at higher concentrations.

1H-, 13C-NMR and 2D spectra measured with a Bruker AMX-400 spectrometer, with TMS as an internal standard. EI mass spectra were recorded on a TSQ-70-Triple Stage Quadrupole mass spectrometer (70 eV).

Pinoresinol (1). 1H-NMR (400 MHz, CDCl3): δ

References (6)

  • I.K. Rhee et al.

    J Chrom A

    (2001)
  • G. Narasinhamurthy

    Indian Vet J

    (1969)
  • G.V.P. Krishna et al.

    Planta Med

    (1975)
There are more references available in the full text version of this article.

Cited by (48)

  • Nitric oxide inhibitory phenolic constituents isolated from the roots and rhizomes of Notopterygium incisum

    2022, Bioorganic Chemistry
    Citation Excerpt :

    The resultant CHCl3 fraction were subjected to various CC, RP-HPLC, and chiral HPLC to deliver 14 new compounds (1–7 and 8a) and 12 known compounds (8b and 9–19) (Fig. 1). By comparison of the experimental spectroscopic data with those reported, the known compounds were identified as (2S)-5,4′-dihydroxy-7-O-[(E)-3,7-dimethyl-2,6-octadienyl]flavanone (8b) [7], 3,4′-dimethylresveratrol (9) [8], trimethylresveratrol (10) [8], phenethyl ferulate (11) [9], p-hydroxyphenethyl ferulate (12) [10,11], p-hydroxyphenethyl anisate (13) [12], matairesinol (14) [13], pinoresinol (15) [14], pinoresinol mono-methyl ether (16) [15], 7,4′-dimethoxy-5-hydroxyflavanone (17) [16], 7-methoxy-5,4′-dihydroxyflavanone (18) [17], and 3′,4′-dimethoxy-5,7-dihydroxyflavanone (19) [18]. Notopheninetol A (1), isolated as a white amorphous powder, had a molecular formula of C19H20O5 determined by an HRESIMS deprotonated ion at m/z 327.1230 [M − H]− (calcd for C19H19O5, 327.1232), corresponding to 10 indices of hydrogen deficiency.

  • Evaluation of the neuroprotective and antidiabetic potential of phenol-rich extracts from virgin olive oils by in vitro assays

    2018, Food Research International
    Citation Excerpt :

    In addition, lignans (pinoresinol and acetoxypinoresinol, among others), flavones (luteolin and apigenin) and simple phenolic acids (p-coumaric acid and vanillic acid) can also be found in a minor extent (Reboredo-Rodríguez et al., 2014). Some of these phenolic compounds could be an acceptable resource of enzyme inhibitors, being already addressed to exhibit several remarkable biological activities, including the capacity to inhibit ChEs (Conforti et al., 2010; El-Hassan et al., 2003; Szwajgier & Borowiec, 2012; Tang et al., 2016), 5-LOX (Bekir, Mars, Souchard, & Bouajila, 2013; Lee, Kim, Kim, Lee, & Kang, 2010; Voss, Sepulveda-Boza, & Zilliken, 1992), h-MAO (Bandaruk, Mukai, Kawamura, Nemoto, & Terao, 2012; Chaurasiya, Ibrahim, Muhammad, Walker, & Tekwani, 2014), and/or α-glucosidase and α-amylase (Hadrich, Bouallagui, Junkyu, Isoda, & Sayadi, 2015; Tadera, Minami, Takamatsu, & Matsuoka, 2006). Taken this background into account, as far as we know, this is the first time that the neuroprotective and antidiabetic potential of phenol-rich extracts from monovarietal extra VOOs (obtained from ‘Cornicabra’ and ‘Picual’ varieties, two of the most representative Spanish cultivars) was evaluated using cell-free models as easy tools and a fast approach for initial screening.

  • Antibacterial activity and mechanism of pinoresinol from Cinnamomum Camphora leaves against food-related bacteria

    2017, Food Control
    Citation Excerpt :

    The 1H NMR (CD3OD, 400 MHz) (Fig. 1D) spectrum reveals the presence of a furanone-type lignan skeleton (δH 4.14 (2H, d, J = 4.4 Hz, H-7, 7′), 3.76 (2H, dd, J = 9.0, 6.9 Hz, H-9a, 9’a), 3.32 (2H, m, H-9b, 9’b), 2.50 (2H, m, H-8, 8′)), two typical trisubstituted benzene rings (δH 8.89 (2H, d, J = 1.7 Hz, H-2, 2′), 6.89 (2H, d, J = 8.2, 1.7 Hz, H-6, 6′), 4.61 (2H, d, J = 8.1 Hz, H-5, 5′)) (Shi, Shi, et al., 2015). The 13C NMR (CD3OD, 100 MHz) (Fig. 1E) spectrum shows the presence of 12 aromatic carbon signals (δC 147.5 (C-3, 3′), 145.9 (C-4, 4′), 132.2 (C-1, 1′), 118.6 (C-6, 6′), 115.1 (C-5, 5′), 110.4 (C-2, 2′)), two methoxyls (δC 55.6 (3, 3′OCH3)), four aliphatic methines (δC 85.1 (C-7, 7′), 53.6 (C-8, 8′)), two aliphatic methylene (70.9 (C-9, 9′)) (El-Hassan et al., 2003). The structure of the pinoresinol from Cinnamomum camphora leaves was shown in Fig. 2.

View all citing articles on Scopus
View full text