Polyphenols and alkaloids from piper species

doi:10.1016/S0031-9422(98)00208-8

Phytochemistry

Volume 49, Issue 4, 27 October 1998, Pages 1069-1078

https://doi.org/10.1016/S0031-9422(98)00208-8 Get rights and content

Abstract

Thirty eight compounds of different types have been isolated from twelve Piper species. The ether extract of the leaves of P. aduncum yielded eleven compounds, out of which 2,6-dimethoxy-4-(2-propenyl)phenol was isolated for the first time from the genus Piper and 2-acetoxy-1,3-dimethoxy-5-(2-propenyl)benzene is a new compound. The petrol extract of the stems and leaves of P. attenuatum furnished a novel long chain alcohol, 14-benzo1, 3dioxol-5-yl-tetradecan-2-ol. From P. betle, β-sitosteryl palmitate was isolated for the first time from the genus Piper. A novel amide, 3-(3,4-dimethoxyphenyl)propanoyl pyrrole has been obtained from P. brachystachyum. Nerolidol was isolated for the first time from P. falconeri. From the methanol extract of the stems and leaves of P. khasiana, piperlonguminine, piperine, apigenin dimethyl ether and β-sitosterol were obtained. Retrofractamide A was obtained for the first time from P. longum; the structure of (+)-asarinin, isolated from P. longum, was confirmed by X-ray crystallographic studies. Retrofractamide A, apigenin dimethyl ether, tetratriacontanol and tectochrysin were isolated from P. manii. P. pedicellosum furnished β-sitosterol, pellitorine, piperlonguminine, cepharadione A and furacridone, the last compound being isolated for the first time from the genus Piper.

Introduction

Piper species, widely distributed in the tropical and subtropical regions of the world are used medicinally in various manners 1, 2. In continuation of our previous investigations on various Indian Piper species, we undertook the phytochemical examination of P. khasiana, P. manii, P. pedicellosum and P. thomsoni which have not earlier been investigated phytochemically along with P. acutisleginum, P.aduncum, P. attenuatum, P. betle, P. brachystachyum, P.falconeri, P. longum and P. peepuloides. This is the second report on the phytochemical investigation of P. acutisleginum [3]. Thirty eight compounds were isolated, out of which 2,6-dimethoxy-4-(2-propenyl)benzene (10), β-sitosteryl palmitate (18) and furacridone (29) are being reported for the first time from the genus Piper and 2-acetoxy-1,3-dimethoxy-5-(2-propenyl)benzene (13), 14-benzo1, 3dioxol-5-yl-tetradecan-2-ol (14) and 3-(3,4-dimethoxyphenyl)-propanoylpyrrole (21) are new compounds.

Section snippets

Results and discussion

Thirty eight compounds were isolated in all from twelve Piper species, these are listed in a comprehensive manner in Table 1. Compound 13 was isolated as an oil from P. aduncum. Its ¹H NMR spectrum revealed the presence of an allyl group (δ 3.35, 5.0–5.10 and 5.90–6.01) and an acetoxy group (δ 2.32). A singlet at δ 3.80 indicated two identical methoxy groups and a singlet at δ 6.44 indicated two identical aromatic protons stemming from a symmetrically tetrasubstituted benzenoid compound. On

General

Mps were determined in a bath and are uncorrected. The ¹H NMR and ¹³C NMR spectra were recorded on a Bruker AC-250 spectrometer, chemical shifts are relative to TMS. Mass spectra were determined at 70 eV on a Jeol AX505 W or a Varian MAT 311A mass spectrometer. Silica gel (60–80 mesh) was used for column chromatography and silica gel G for TLC.

Isolation procedure

All the plant materials, except for P. aduncum, P. attenuatum and P.longum, were collected from the forests around Botanical Survey of India(BSI, Eastern

Acknowledgements

—We thank the Danish International Development Agency (Danida), the Council of Scientific and Industrial Research (CSIR, New Delhi, India) and the British Council Division, New Delhi, India for financial assistance. We are grateful to Professor Dr Kurt Torssell for giving the plant material of P. aduncum from his collections and to Professor Dr Per M Boll for encouragement and suggestions during the course of this work.

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Presences of dihydroxyphenolics and hydroxydopamine have been observed in the extract from Piper longum seeds (Mouhajir et al., 2001). D asparatic acid, cysteine, n-eicosane, p methoxyacetophenone, n-Heneicosane, methyl 3,4,5 trimethoxycinnamate, n-octadecane, β phenylethanol, serine, n-triacontane, and L-tyrosine has also been reported in P. longum (Parmar et al., 1998). The modern world is now relaying over nanoparticles for treatment of various disease, as they offer special advantage of organ targeting, enhanced bioavailability and many more.
Piper longum, commonly referred as ‘Pippali’, has found its traditional use in India, Malaysia, Singapore and other South Asian countries as an analgesic, carminative, anti-diarrhoeic, immunostimulant, post childbirth to check postpartum hemorrhage and to treat asthma, insomnia, dementia, epilepsy, diabetes, rheumatoid arthritis, asthma, spleen disorder, puerperal fever, leprosy etc.
This review offers essential data focusing on the traditional use, phytochemistry and pharmacological profile of Piper longum thereby identifying research gaps and future opportunities for investigation on this plant.
This systematic survey was accomplished as per the PRISMA guidelines. The information was collected from books, and electronic search (PubMed, Science Direct, Lilca and Scielo) during 1967–2019.
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Amongst various activities, bioscientific clarification in relation to its ethnopharmacological perspective has been evidenced mainly for anti-amebic, anthelminthic, anti-tumor and anti-diabetic activity. However, despite traditional claims, insufficient scientific validation for the treatment of insomnia, dementia, epilepsy, rheumatoid arthritis, asthma, spleen disorder, puerperal fever and leprosy, necessitate future investigations in this direction. It is also essential and critical to generate toxicological data and pharmacokinetics on human subjects so as to confirm its conceivable bio-active components in the body.

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