Two New isoquinoline alkaloids from the bark of Alphonsea cylindrica King and their antioxidant activity

doi:10.1016/j.phytol.2018.11.022

Phytochemistry Letters

Volume 29, February 2019, Pages 110-114

https://doi.org/10.1016/j.phytol.2018.11.022 Get rights and content

Highlights

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A total of seven alkaloids were isolated from bark of Alphonsea cylindrica King.
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Two new alkaloids 1 and 2 were successfully identified.
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Compounds 1, 3 and 4 showed higher activity against DPPH radical scavenging assay.

Abstract

Two new isoquinoline alkaloids, iraqiine (1) and kareemine (2), along with five known alkaloids, muniranine (3), kinabaline (4), O-methylmoschatoline (5), atherospermidine (6) and N-methylouregidione (7), were purified from the dichloromethane crude extract of Alphonsea cylindrica bark. The structures of these compounds were elucidated through extensive 1D and 2D NMR, IR and LC–MS studies and comparison with previously reported data. Compounds (1–5 and 7) were tested for their antioxidant activity using in vitro DPPH radical scavenging assay, and 1, 3 and 4 showed the highest antioxidant activities with IC₅₀ values of 48.77 ± 1.01, 44.51 ± 1.12 and 64.28 ± 0.93 μg/ml, respectively.

Graphical abstract

Introduction

Alphonsea is a small genus belonging to the Annonaceae family. According to The Plant List (2013), approximately 37 Alphonsea species have been discovered thus far, and these species are mostly scattered in the Indo–Malayan regions and China (Talip et al., 2017, Aldulaimi et al., 2018). Alphonsea cylindrica King, locally known as ‘mempisang’, is mainly found in lowland forests and not widely dispersed. Previous studies have reported that Alphonsea species present various properties, such as antifungal (Dsd et al., 2018), antioxidant, anticancer (Dsd et al., 2018; Doddapaneni et al., 2018), anti-inflammatory (Attiq et al., 2017) and antibacterial (Talip et al., 2017) activities. Moreover, the fruits of Alphonsea species are traditionally used as an emmanogogue and in antidiarrheal and antipyretic treatments (Bakri et al., 2017). The species is rich in alkaloids, such as aporphine and oxoaporphine (Tadic et al., 1987). Isoquinoline alkaloids are one of the largest groups of plant alkaloids that derived from the structure that signifies the major type of alkaloids which can be commonly discovered in Annonaceae. They have numbers of crucial pharmaceutical agents such as berbamine (Sankaranarayanan et al., 2018), tetrandrine (Shi et al., 2018), coptisine (Bing et al., 2017). According to Nasrullah et al. (2013) isoquinoline alkaloids have been reported to possess effective in scavenging radicals (antioxidant properties). In 2017, we reported a new azafluorenone alkaloid from A. cylindrica, muniranine (3) (Talip et al., 2017). We believe that different types of interesting alkaloids have yet to be extracted from this species. Therefore, the present work aims to discover new active compounds from the plant. In this paper, two rare oxoaporphine and bisbenzylisoquinoline alkaloids are reported.

Section snippets

Results and discussion

The DCM crude extract of the bark of A. cylindrica was purified through open column chromatography (CC) over silica gel to produce two new alkaloids together with five known alkaloids. The known alkaloids were identified by spectroscopic techniques and comparison with previously reported data; these alkaloids include muniranine (3) (Talip et al., 2017), kinabaline (4) (Tadic et al., 1987), O-methylmoschatoline (5) (Kimia, 2015; Taha et al., 2018; Albarracin et al., 2017), atherospermidine (6) (

Instruments and reagents

¹H, ¹³C and 2D (COSY, NOESY, HMBC and HMQC) (NMR) spectra were recorded using a JEOL EC X 500 MHz (UPSI) instrument. IR spectra were recorded on a Model 6700 spectrophotometer using an ATR diamond. An Agilent LC–MS system comprising an Agilent 1260 Infinity HPLC coupled to an Agilent 6530 Q–TOF–MS equipped with an ESI source operating a Sunfire analytical C18 column (150 × 2.1 mm²; i.d. 3.5 μm, Waters) was recorded at the University of Paris–Sud France. Dragendorff’s reagent was used to check

Acknowledgements

This research was funded by Universiti Pendidikan Sultan Idris Special Grant Scheme (Fundamental) 2017-0331-101-01.

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Two New isoquinoline alkaloids from the bark of Alphonsea cylindrica King and their antioxidant activity

Highlights

Abstract

Graphical abstract

Introduction

Section snippets

Results and discussion

Instruments and reagents

Acknowledgements

Phytochemistry

Biochem. Syst. Ecol.

J. Ethnopharmacol.

Nat. Prod. Res.

Food Chem.

Biomed. Pharmacother.

Phytochemistry

Phytochem. Lett.

Phytochem. Lett.

Alkaloids from Alphonsea Elliptica Barks and their biological activities

J. Global Pharma Technol.

Annonaceae: Breaking the wall of inflammation

Front. Pharmacol.

Therapeutic Potential of Plant Species Derived from Some Annonaceae Genus

Int. J. Agric. For.