Protective effects of cycloartane triterpenoides from Passiflora edulis Sims against glutamate-induced neurotoxicity in PC12 cell

doi:10.1016/j.fitote.2016.09.013

Fitoterapia

Volume 115, December 2016, Pages 122-127

https://doi.org/10.1016/j.fitote.2016.09.013 Get rights and content

Abstract

Four new cycloartane triterpenoids, 1α,3β-dihydroxy-16-keto-24(31)-en-cycloartane (1), 31-methoxyl-passifloic acid (2), cyclopassifloside XIV (3), and cyclopassifloside XV (4), together with six known compounds (5–10) were isolated from Passiflora edulis Sims. Their structures were elucidated on the basis of extensive spectroscopic analysis. All the compounds were evaluated for protective effects against damage of PC12 cell induced by glutamate according to traditional usage of the herbal medicine, and the results indicated that cycloartane triterpenoids maybe one of the active compositions of P. edulis Sims for the treatment of neurodegenerative disease.

Graphical abstract

Protective effects of cycloartane triterpenoides from Passiflora edulis Sims against glutamate-induced neurotoxicity in PC12 cell.

Introduction

The genus Passiflora comprises approximately 500 species and distributed mainly in the warm temperate and tropical regions of America. Southeast Asia, India, Mlaysia, and Australia also distributed and introduced some species [1], [2]. There are 19 species and 3 varieties belonging to Passiflora distributed in China in now time [3]. Various species of Passiflora, including P. edulis and P. edulis var. flavicarpa are cultivated for their edible fruits [4], as to others, are planted mainly as ornamentals for their exotic flowers. Several Passiflora species have been used extensively in the traditional system of therapeutics in many countries [5]. Such as P. incarnate Linn, which originated in North America, is a popular traditional Europe remedy as well as a homoeopathic medicine for insomnia and anxiety [6], [7]. For another example, a number of Passiflora species known as “Maracuja” been used as tranquilizers in Brazil [8], [9], [10], [11].

It was reported that triterpenoids, flavonoids, cyanogenic glycosides, and aroma constituents were the main chemical constituents of P. edulis Sims [5], [12]. Pharmacology studies showed that the leaves of P. edulis Sims have significant anxiolytic, anti-inflammatory and antioxidant health benefits [12], [13], [14], [15]. Previous work on the stems and leaves of the species by us indicated that cycloartane triterpenoids and their saponins as the main bioactive composition possess antidepressant-like effect [16]; otherwise, dideoxyhexosyl-C-glycoside flavones express neurite outgrowth enhancing activities [17]. As part of our ongoing research program with P. edulis and their nervous system activity, n-BuOH part of the 70% aq. acetone extraction of the species was further developed by us. In this paper, we describe the isolation and structural elucidation of four new cycloartane triterpenoids, clopassifloic acid H (1), 31-methoxyl-passifloic acid (2), cyclopassifloside XIV (3) and cyclopassifloside XV (4) (Fig. 1), and their protective effects against glutamate-induced neurotoxicity in PC12 cells.

Section snippets

Generals

Optical rotations were measured on a Jasco P-1020 (Jasco International Co., Ltd., Tokyo, Japan) automatic digital polarimeter. UV spectra were taken on a Shimadzu UV-2401PC (Shimadzu, Kyoto, Japan) spectrophotometer. IR spectra were obtained on a Bruker Tensor 27 FT-IR (Bruker Optics GmbH, Ettlingen, Germany) spectrometer with KBr pellets. NMR spectra were acquired on Bruker AM-400 or DRX-500 (Bruker BioSpin GmbH, Rheinstetten, Germany) instruments, using tetramethylsilane (TMS) as an internal

Result and discussion

The 70% aq acetone extract from the stems and leaves of P. edulis was suspended in water and then partitioned into EtOAc and n-BuOH extracts respectively. A phytochemical study on the n-BuOH extracts by repeated CC over silica gel, MCI-gel and Sephadex LH-20 to give four new cycloartane triterpenoids (1–4), along with 6 known ones (5–10). The new ones were elucidated by extensive spectroscopic methods. Six known compounds were identified as passiflorin (5) [18], cyclopassifloside II and III (6–7

Acknowledgments

This work was financially supported by Yunnan Province (2015HB093 and 2015HA011) and State Key Laboratory of Phytochemistry and Plant Resources in West China (P2016-ZZ04). The authors also thank Ji-Jun Chen team and the staff of analytical group of the State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, for measurements of all spectra.

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Passiflora species are known to possess a large number of functional properties which includes antioxidant (Dhawan, Dhawan, & Sharma, 2004; Zeraik & Yariwake, 2010), anti-diabetic (Colomeu et al., 2014; Saravanan & Parimelazhagan, 2014), anti-inflammatory, antipyretic and analgesic (Saravanan, Arunachalam, & Parimelazhagan, 2014), sedative and hypotensive properties (Cazarin et al., 2014). Recent works also reported that, fruits of Passiflora species have neuroactive, demonstrating antianxiety and anticonvulsant effects (Dembitsky et al., 2011; Porto-Figueira, Freitas, Cruz, Figueira, & Câmara, 2015; Xu et al., 2016). Furthermore, rind flour of Passiflora edulis fruit is used for antiretroviral therapy for the HIV patients (do Socorro Fernandes Marques et al., 2016).
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¹: These authors contributed equally to this work.

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Protective effects of cycloartane triterpenoides from Passiflora edulis Sims against glutamate-induced neurotoxicity in PC12 cell

Abstract

Graphical abstract

Introduction

Section snippets

Generals

Result and discussion

Acknowledgments

Food Chem.

J. Ethnopharmacol.

J. Ethnopharmacol.

J. Ethnopharmacol.

Food Chem.

Fitoterapia

J. Ethnopharmacol.

Food Chem.

Phytochemistry

Phytochemisrry

100 families of flowering plants

Passifloraceae

The edible species of Passiflora

Econ. Bot.