The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities—A Review
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molecules Review The Genus Haplophyllum Juss.: Phytochemistry and Bioactivities—A Review Majid Mohammadhosseini 1,* , Alessandro Venditti 2 , Claudio Frezza 3,* , Mauro Serafini 3, Armandodoriano Bianco 2 and Behnam Mahdavi 4 1 Department of Chemistry, College of Basic Sciences, Shahrood Branch, Islamic Azad University, Shahrood 3616713455, Iran 2 Dipartimento di Chimica, Università di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185 Rome, Italy; [email protected] (A.V.); [email protected] (A.B.) 3 Dipartimento di Biologia Ambientale, Università di Roma “La Sapienza”, Piazzale Aldo Moro 5, 00185 Rome, Italy; mauro.serafi[email protected] 4 Department of Chemistry, Faculty of Science, Hakim Sabzevari University, Sabzevar 9617976487, Iran; [email protected] * Correspondence: [email protected] (M.M.); [email protected] (C.F.) Abstract: Herein, a comprehensive review is given focusing on the chemical profiles of the essential oils (EOs), non-volatile compounds, ethnobotany, and biological activities of different Haplophyllum (Rutaceae family) species. To gather the relevant data, all the scientific databases, including Scopus, ISI-WOS (Institute of Scientific Information-Web of Science), and PubMed and highly esteemed publishers such as Elsevier, Springer, Taylor and Francis, etc., were systematically retrieved and reviewed. A wide array of valuable groups of natural compounds, e.g., terpenoids, coumarins, Citation: Mohammadhosseini, M.; alkaloids, lignans, flavonoids, and organic acids have been isolated and subsequently characterized Venditti, A.; Frezza, C.; Serafini, M.; in different organic extracts of a number of Haplophyllum species. In addition, some remarkable Bianco, A.; Mahdavi, B. The Genus antimicrobial, antifungal, anti-inflammatory, anticancer, cytotoxic, antileishmanial, and antialgal Haplophyllum Juss.: Phytochemistry effects as well as promising remedial therapeutic properties have been well-documented for some and Bioactivities—A Review. species of the genus Haplophyllum. Molecules 2021, 26, 4664. https:// doi.org/10.3390/molecules26154664 Keywords: Haplophyllum Juss. genus; Rutaceae; phytochemistry; chemotaxonomy; ethnobotany; bioactivities Academic Editors: Ioannis P. Gerothanassis, Muhammad Iqbal Choudhary and Hina Siddiqui 1. Introduction Received: 30 June 2021 Accepted: 28 July 2021 It is evident that herbal and medicinal plants play a vital role on the life of human Published: 31 July 2021 beings and have unique compartment in their lifestyles. Over the past few decades, a large number of scientific investigations have been carried out on a wide spectrum of Publisher’s Note: MDPI stays neutral herbal plants and these attempts have led to the isolation of a large number of valuable with regard to jurisdictional claims in natural compounds in different plant species [1,2]. In reality, medicinal plants are used in published maps and institutional affil- different scientific disciplines, from food industries to the fragrance and cosmetics domain, iations. to different medicinal and pharmaceutical approaches [3,4]. Haplophyllum Juss. is a genus of plant species belonging to the Rutaceae family and comprises 160 species of which only two are accepted, i.e., Haplophyllum dauricum (L.) G. Don and Haplophyllum suaveolens Ledeb., whereas fifty species are considered to be Copyright: © 2021 by the authors. synonyms and one hundred and eight are unresolved names [5]. Licensee MDPI, Basel, Switzerland. The etymology of the name derives from the union of two Greek words, απλoũV This article is an open access article (haplous), meaning simple, and 'u´λλoν (phýllon), meaning leaf in the sense of a simple distributed under the terms and leaf. These terms refer to the fact that the species belonging to this genus are characterized conditions of the Creative Commons by non-composite leaves. Attribution (CC BY) license (https:// From a botanical standpoint, these species appear mainly as perennial herbs even if low creativecommons.org/licenses/by/ shrubs also exist. They present cymose and bracteate inflorescences, with petals being variably 4.0/). Molecules 2021, 26, 4664. https://doi.org/10.3390/molecules26154664 https://www.mdpi.com/journal/molecules Molecules 2021, 26, x FOR PEER REVIEW 2 of 38 Molecules 2021, 26, 4664 2 of 40 From a botanical standpoint, these species appear mainly as perennial herbs even if low shrubs also exist. They present cymose and bracteate inflorescences, with petals being variably colored from light white to bright yellow. They have ten stamens and have free colored from light white to bright yellow. They have ten stamens and have free filaments filaments which are widely expanded below and are pubescent on the inner surface which(Figure are 1) [6]. widely expanded below and are pubescent on the inner surface (Figure1) [6]. Figure 1. The photographs of Haplophyllum suaveolens Ledeb. Figure 1. The photographs of Haplophyllum suaveolens Ledeb. The distribution area of this genus is quite wide, ranging from Morocco and Spain to The distribution area of this genus is quite wide, ranging from Morocco and Spain China and passing through Romania, Somalia, Turkey, Iran, and Central Asia [6]. toAdditionally, China and many passing relevant through species Romania, are endemic Somalia, and some Turkey, even occur Iran, in small, and Central unlinked Asia [6]. Ad- ditionally,populations. many In particular, relevant the specieslatter characteristics are endemic concern and the some Iranian even and occur Central in Asian small, unlinked populations.species, and, for In particular,this reason, thethe lattergenus characteristicsis locally and partially concern considered the Iranian to be and very Central Asian species,susceptible and, to extinction for this [7]. reason, the genus is locally and partially considered to be very susceptibleIn the topresent extinction review [7 ].article, we aimed to cover and discuss the available phytochemicalIn the present knowledge review article,involving we the aimed composition to cover andof the discuss chemical the availableprofiles phytochemicalof Haplophyllum’s essential oils (EOs) as well as the characterized non-volatile compounds knowledgeand their relevant involving biological the activities. composition This wo ofrk the represents chemical an profilesupdating, of anHaplophyllum extension, as ’s essential oilswell (EOs) as a partial as well modification as the characterized of the work non-volatileby Prieto et al. compounds [8] on the phytochemistry and their relevant and biological activities.bioactivities This of the work same represents genus. To ancollect updating, the corresponding an extension, data, as Scopus well as(date a partial of access: modification of the20 January work by 2021 Prieto and revisited et al. [8] on on 06 the June phytochemistry 2021), PubMed (date and of bioactivities access: 10 January of the 2021 same genus. To collectand revisited the corresponding on 05 June 2021), data, ISI-WOS Scopus (date (date of access: of access: 21 January 20 January 2021 and 2021 revisited and revisitedon on 06 June05 June 2021), 2021), PubMed and a number (date ofof access:published 10 re Januaryports dealing 2021 andwith revisiteddifferent aforementioned on 05 June 2021), ISI-WOS aspects were carefully studied. The keywords used for this research were Haplophyllum, (date of access: 21 January 2021 and revisited on 05 June 2021), and a number of published phytochemistry, ethnobotany, ethnopharmacology, pharmacology, and biological reportsactivities, dealing in combination with different between aforementioned Haplophyllum and aspects the rest wereof the carefullymentioned studied. keywords, The keywords usedone by for one. this The research systematic were researchHaplophyllum was also, phytochemistry,conducted considering ethnobotany, all the accepted ethnopharmacology, or pharmacology,unresolved names and of biologicalHaplophyllum activities, species, as in reported combination in www.theplantlist.org, between Haplophyllum accessedand the rest of theon mentioned1 August 2021 keywords, [5], alone or one in bycombination one. The with systematic the previous research terms, was one also by one. conducted All the considering allHaplophyllum the accepted species, or unresolved now taxonomically names of consideredHaplophyllum to be species,synonyms as of reported other species, in www.theplantlist. as orgreported, accessed in www.theplantlist.org, on 24 June 2021 [5 accessed], alone oron in1 August combination 2021 [5], with were the not previous taken into terms, one by consideration for this review. In any case, all the existing works, abiding by these rules, one.were Allinserted the Haplophyllum in spite of the yearsspecies, or types now of taxonomicallypublications. considered to be synonyms of other species, as reported in www.theplantlist.org, accessed on 24 June 2021 [5], were not taken into consideration2. Phytochemistry for this review. In any case, all the existing works, abiding by these rules, were insertedThe inHaplophyllum spite of the species years have or types been studied of publications. for their phytochemical constituents that regard both the EOs and the polar fraction metabolites. 2. Phytochemistry 2.1. EssentialThe Haplophyllum Oils of Haplophyllumspecies Species have been studied for their phytochemical constituents that regardEOs both could the be EOs defined and as the hydrophobic polar fraction liquid mixtures metabolites. usually having a lower density of water and comprising