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Nerolidol: a Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities

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Nerolidol: a Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities molecules Review Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities Weng-Keong Chan 1,2, Loh Teng-Hern Tan 1,2, Kok-Gan Chan 3, Learn-Han Lee 1,2,4,* and Bey-Hing Goh 1,2,4,* 1 School of Pharmacy, Monash University Malaysia, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia; [email protected] (W.-K.C.); [email protected] (L.T.-H.T.) 2 Biomedical Research Laboratory, Jeffrey Cheah School of Medicine and Health Sciences, Monash University Malaysia, 47500 Bandar Sunway, Selangor Darul Ehsan, Malaysia 3 Division of Genetics and Molecular Biology, Institute of Biological Sciences, Faculty of Science, University of Malaya, 50603 Kuala Lumpur, Malaysia; [email protected] 4 Center of Health Outcomes Research and Therapeutic Safety (Cohorts), School of Pharmaceutical Sciences, University of Phayao, 56000 Phayao, Thailand * Correspondence: [email protected] or [email protected] (L.-H.L.); [email protected] (B.-H.G.); Tel.: +60-3-5514-5887 or +60-3-5514-4887 (L.-H.L. & B.-H.G.); Fax: +60-3-5514-6364 (L.-H.L. & B.-H.G.) Academic Editor: Luca Forti Received: 24 February 2016; Accepted: 14 April 2016; Published: 28 April 2016 Abstract: Nerolidol (3,7,11-trimethyl-1,6,10-dodecatrien-3-ol) is a naturally occurring sesquiterpene alcohol that is present in various plants with a floral odor. It is synthesized as an intermediate in the production of (3E)-4,8-dimethy-1,3,7-nonatriene (DMNT), a herbivore-induced volatile that protects plants from herbivore damage. Chemically, nerolidol exists in two geometric isomers, a trans and a cis form. The usage of nerolidol is widespread across different industries. It has been widely used in cosmetics (e.g., shampoos and perfumes) and in non-cosmetic products (e.g., detergents and cleansers). In fact, U.S. Food and Drug Administration (FDA) has also permitted the use of nerolidol as a food flavoring agent. The fact that nerolidol is a common ingredient in many products has attracted researchers to explore more medicinal properties of nerolidol that may exert beneficial effect on human health. Therefore, the aim of this review is to compile and consolidate the data on the various pharmacological and biological activities displayed by nerolidol. Furthermore, this review also includes pharmacokinetic and toxicological studies of nerolidol. In summary, the various pharmacological and biological activities demonstrated in this review highlight the prospects of nerolidol as a promising chemical or drug candidate in the field of agriculture and medicine. Keywords: cis-nerolidol; trans-nerolidol; sesquiterpene; essential oil; pharmacological activities 1. Introduction Ever since ancient times, medicinal plants have been explored and used as herbal medicines to treat many diseases [1]. With the advancement of technology, research on herbal medicine has intensified on the efforts to identify the bioactive compounds in medicinal plants that are responsible for their pharmacological and biological activities. Essential oils (EOs) are volatile, natural and complex bioactive compounds which are characterized by a strong odour, and their biological effects are known to be associated to a series of complex interactions with cells, tissues and whole organisms [2]. Besides its well-known application in aromatherapy [3], the uses of EO have been extended into the food, agriculture and pharmaceutical industries [4–6]. Among the plants that are rich in EOs are Baccharis Molecules 2016, 21, 529; doi:10.3390/molecules21050529 www.mdpi.com/journal/molecules Molecules 2016, 21, 529 2 of 40 Molecules 2016, 21, 529 2 of 38 dracunculifoliaBaccharis dracunculifoliaDC, Elettaria DC, cardamomum Elettaria cardamomum(L.) Maton, (L.)Momordica Maton, Momordica charantia L., charantiaPiper aleyreanum L., Piper aleyreanumC. DC and PiperC. DC claussenianum and Piper claussenianum(Miq.) C. DC (Miq.) [7–11 C.]. DC [7–11]. Nerolidol (3,7,11-trimethyl-1,6,10-dodecatrien-3-ol), (3,7,11-trimethyl-1,6,10-dodecatrien-3-ol), also alsoknown known as peruviol, as peruviol, is a naturally is a naturallyoccurring occurringsesquiterpene sesquiterpene alcohol present alcohol in the present EO of in various the EO plants of various with a plantsfloral odour with a[12,13]. floral Nerolidol odour [12 was,13]. Nerolidolfound to exist was as found one of to the exist bioactive as one of compounds the bioactive resp compoundsonsible for responsible the biological for activities the biological demonstrated activities demonstratedby the EOs of the by theaforementioned EOs of the aforementioned plants. plants. Statistics showed showed that that the the global global usage usage of nerolidol of nerolidol per annumper annum rangesranges from from10 to 100 10 tometric 100 tonnes metric tonnes[14]. For [14 instance,]. For instance, nerolidol nerolidol is frequently is frequently incorporated incorporated in cosmetics in cosmetics(e.g., shampoos (e.g., shampoosand perfumes) and perfumes)and non-cosmetic and non-cosmetic products (e.g., products detergents (e.g., and detergents cleansers) and [13]. cleansers) Besides, [13 nerolidol]. Besides, is also nerolidol widely is used also widelyin the food used industry in the food as a industry flavor enhancer as a flavor in enhancermany food in products many food since products its approval since its by approval U.S. Food by and U.S. FoodDrug andAdministration Drug Administration as a safe food as a flavoring safe food agent. flavoring agent. Principally, this article aims to reviewreview thethe diversediverse rangerange ofof pharmacologicalpharmacological andand biologicalbiological activities of nerolidol which include antioxidant, anti anti-microbial,-microbial, anti-biofilm, anti-biofilm, an anti-parasitic,ti-parasitic, insecticidal, anti-ulcer, skin penetration enhanc enhancer,er, anti-tumor, anti-nociceptive and anti-inflammatory anti-inflammatory properties. properties. The review also covers the chemical structure, physicalphysical properties, and the biosynthesis pathway of nerolidol as the intermediate involved in the mechanismsmechanisms responsible for protection of plants against herbivores and plant pathogens.pathogens. This article also highlights the pharmacokineticpharmacokinetic and toxicologicaltoxicological properties ofof nerolidolnerolidol inin bothboth inin vitrovitro andand inin vivovivo experimentalexperimental models.models. 2. Chemical Chemical Structure Structure and and Physical Physical Properties Properties Nerolidol has four different isomeric forms whichwhich consist of two enantiomers and two geometric isomers [[15].15]. The existence of these isomeric forms is due to the presence of a double bond at the C-6 position and the asymmetricasymmetric center at thethe C-3C-3 position.position. These isomeric forms of ciscis-- andand transtrans-nerolidol-nerolidol are illustrated in Figure1 1.. Besides,Besides, thethe synonymssynonyms forfor ciscis-- andand transtrans-nerolidol-nerolidol areare listedlisted inin TableTable1 .1. Figure 1. Chemical structures of the two enantiomers both for cis- and trans-isomers of nerolidol. Figure 1. Chemical structures of the two enantiomers both for cis- and trans-isomers of nerolidol. Table 1. Synonyms of cis- and trans-nerolidol. Table 1. Synonyms of cis- and trans-nerolidol. Cis-Nerolidol Trans-Nerolidol (i) (±)-cis-nerolidolCis -Nerolidol (i) (±)-trans-nerolidolTrans -Nerolidol (ii) (6Z)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (ii) (6E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-ol (i) (˘)-cis-nerolidol (i) (˘)-trans-nerolidol (ii)(iii) (6 Z(6)-3,7,11-trimethyl-1,6,10-dodecatrien-3-olZ)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol (ii)(iii) (6 (6E)-3,7,11-trimethyl-1,6,10-dodecatrien-3-olE)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol (iii)(iv) (6 (6Z)-3,7,11-trimethyldodeca-1,6,10-trien-3-olZ)-nerolidol (iii)(iv) (6 (6EE)-3,7,11-trimethyldodeca-1,6,10-trien-3-ol)-nerolidol (iv)(v) (6 1,6,10-dodecatrien-3-ol,Z)-nerolidol 3,7,11-trimethyl-, (6Z)- (iv)(v) (61,6,10-dodecatrien-3-ol,E)-nerolidol 3,7,11-trimethyl-, (6E)- (v)(vi) 1,6,10-dodecatrien-3-ol, (Z)-nerolidol 3,7,11-trimethyl-, (6Z)- (v)(vi) 1,6,10-dodecatrien-3-ol, (E)-nerolidol 3,7,11-trimethyl-, (6E)- (vi) (Z)-nerolidol (vi) (E)-nerolidol Molecules 2016, 21, 529 3 of 40 Like other sesquiterpene compounds, nerolidol has high hydrophobicity, thereby allowing easier penetration across the plasma membrane and interaction with intracellular proteins and/or intra-organelle sites [16]. The physical properties of nerolidol (isomer not specified) have been described by Lapczynski et al. [13] as follows: (i) Physical description: A clear pale yellow to yellow liquid having a faint floral odor reminiscent of rose and apple. (ii) Chemical formula: C15H26O (iii) Flash point: >212˝ F; CC. (iv) Boiling point: 276 ˝C. (v) LogKow (calculated): 5.68. (vi) Vapor pressure (calculated): 0.1 mm Hg 20 ˝C. (vii) Specific gravity: 0.8744. (viii) Water solubility (calculated): 1.532 mg/L at 25 ˝C. 3. Sources, Extraction and Analytical Methods of Nerolidol Numerous extraction methods have been employed for extracting EOs from various plant samples [2]. The hydrodistillation method using the Clevenger-type apparatus appears as the most common method used for extracting nerolidol. Table2 summarizes the different extraction methods and the yield of nerolidol from various parts of plants such as leaves, flowers, seeds, fruits, resins, twigs and woods. Based on the literature references, leaves are the most common source for extraction of nerolidol. In terms of the percentage
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