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Medicinal Activities and Nanomedicine Delivery Strategies for Brucea Javanica Oil and Its Molecular Components

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Medicinal Activities and Nanomedicine Delivery Strategies for Brucea Javanica Oil and Its Molecular Components molecules Review Medicinal Activities and Nanomedicine Delivery Strategies for Brucea javanica Oil and Its Molecular Components 1, 1,2, 1,3 2 4 Bo Kyeong Yoon y, Zheng Yi Lim y, Won-Yong Jeon , Nam-Joon Cho , Jeong Hoon Kim and Joshua A. Jackman 1,* 1 School of Chemical Engineering and Biomedical Institute for Convergence at SKKU (BICS), Sungkyunkwan University, Suwon 16419, Korea; [email protected] (B.K.Y.); [email protected] (Z.Y.L.); [email protected] (W.-Y.J.) 2 School of Materials Science and Engineering, Nanyang Technological University, Singapore 637553, Singapore; [email protected] 3 Omni Colab Corporation, Suwon 16229, Korea 4 Department of Health Sciences and Technology, Samsung Advanced Institute for Health Sciences and Technology, Sungkyunkwan University, Seoul 06351, Korea; [email protected] * Correspondence: [email protected]; Tel.: +82-31-290-7243 These authors contributed equally to this work. y Received: 11 September 2020; Accepted: 16 November 2020; Published: 19 November 2020 Abstract: Brucea javanica oil (BJO) is widely used in traditional Chinese medicine to treat various types of cancer and inflammatory diseases. There is significant interest in understanding the medicinal activities of BJO and its molecular components, especially quassinoids, and in exploring how they can be incorporated into nanomedicine delivery strategies for improved application prospects. Herein, we cover the latest progress in developing different classes of drug delivery vehicles, including nanoemulsions, liposomes, nanostructured lipid carriers, and spongosomes, to encapsulate BJO and purified quassinoids. An introduction to the composition and medicinal activities of BJO and its molecular components, including quassinoids and fatty acids, is first provided. Application examples involving each type of drug delivery vehicle are then critically presented. Future opportunities for nanomedicine delivery strategies in the field are also discussed and considered within the context of translational medicine needs and drug development processes. Keywords: Brucea javanica oil; quassinoid; medicinal activity; nanomedicine; emulsion; liposome; spongosome; drug delivery 1. Introduction The field of traditional Chinese medicine (TCM) often incorporates natural products from plant, animal, and mineral sources as medicinally active ingredients for applications such as anticancer, anti-inflammatory, and antimicrobial therapy [1]. Given the use of natural products and historical precedent, there is broad interest in exploring the potential advantages of TCM as an alternative to modern medicine, and potential benefits include greater efficacy, lower costs, fewer side effects, and perceived safety when used judiciously [2]. As shown in Figure1A, Brucea javanica (L.) Merr is a species of evergreen plant shrub from the Simaroubaceae family that grows abundantly throughout Southern China and Southeast Asia [3]. The bitter fruit of B. javanica is oval-shaped, solid, and has a typical length and diameter of around 8 mm and 5 mm, respectively [4] (Figure1B). Listed in the o fficial Chinese Pharmacopoeia that describes TCM ingredients, the B. javanica fruit is often used to treat medical illnesses such as intestinal inflammation, Molecules 2020, 25, 5414; doi:10.3390/molecules25225414 www.mdpi.com/journal/molecules Molecules 2020, 25, x FOR PEER REVIEW 2 of 17 the fruit is also useful to treat ailments such as abdominal pain, hemorrhoids, hyperkeratosis, and ulcers [7]. The fruit and especially its seed oil—termed B. javanica oil (BJO)—contain medicinally active components, including quassinoids as well as fatty acids such as oleic acid and linoleic acid [4,8]. The chemical structures of these compounds are presented in Figure 1C,D. Quassinoids have a tetracyclic triterpene structure that consists of three six-membered carbon rings and a six-membered lactonic Molecules 2020, 25, 5414 2 of 17 ring, which has a variable substituent group that defines the quassinoid identity [9]. Notably, quassinoids are understood to be found exclusively in plants from the Simaroubaceae family [10], a diarrhea,feature malaria,that has andheightened different interest types ofin cancerBJO due [5 ,6to]. the It has wide been range claimed and high that thepotency fruit isof alsomedicinal useful to treatactivities ailments that such quassinoids as abdominal can exhibit pain,, as hemorrhoids, discussed below. hyperkeratosis, and ulcers [7]. FigureFigure 1. 1.( A(A)) Picture Picture of Brucea javanica javanica plantplant (Credit: (Credit: Yercaud Yercaud Elango Elango under under CC BY CC-SA BY-SA 4.0 license) 4.0 license);; (B) (B)Picture Picture of of BruceaBrucea javanica javanica fruitfruit (Credit: (Credit: Ruben Ruben C. C.J. Lim J. Lim under under CC CC BY BY-NC-SA-NC-SA 2.0 2.0 license license);); (C) ( C)hemical Chemical structurestructure of aof quassinoid a quassinoid molecule, molecule where, where R denotes R denotes a generic a generic substituent substituent group; group (D) Chemical; (D) Chemical structures ofstructures linoleic acid of linoleic and oleic acid acid and molecules. oleic acid molecules Reproduced. Reproduced with permission with permission from Ref. from [4]. Ref. [4]. TheWhile fruit BJO and and especially its molecular its seed components oil—termed are medicinallyB. javanica oilactive, (BJO)—contain they have a poor medicinally solubility active in components,aqueous solution includings, which quassinoids has motivated as well the development as fatty acids of such B. javanica as oleic oil acidemulsion and linoleic(BJOE) systems acid [4 ,8]. Thethat chemical enable structuresimproved ofsolubility these compounds [11]. BJOE are samples presented are incomp Figureosed1C,D. of oil Quassinoids extracts isolated have a tetracyclicfrom B. triterpenejavanica structurefruit together that consists with a ofnaturally three six-membered sourced lipid carbon emulsifier rings and [12] a. six-memberedTo date, intravenously lactonic ring, whichadministered has a variable BJOE substituenthas been used group clinically that defines, including the in quassinoid China, as identitya standalone [9]. Notably,treatment quassinoids [13] and arein understood combination to wi beth foundradiotherapy exclusively [14] or in chemotherapeutic plants from the Simaroubaceae drugs [15] to improve family cancer [10], a treatment feature that hasefficacy heightened and enhance interest immune in BJO due functions to the wide[16]. However range and, BJOE high potencystill has ofshortcomings medicinal, activities such as thata quassinoidsrelatively low can bioavailability exhibit, as discussed of medicinally below. active compounds, physicochemical stability issues, and potentialWhile BJOadministration and its molecular side effects components such as blood are medicinally vessel irritation active, and they adverse have immune a poor solubilityreactions in aqueous[17,18]. solutions, which has motivated the development of B. javanica oil emulsion (BJOE) systems Such challenges have spurred ongoing efforts to develop innovative nanomedicine strategies that enable improved solubility [11]. BJOE samples are composed of oil extracts isolated from B. javanica that harness the medicinal activity of BJO and its molecular components with nanoparticle carriers. fruit together with a naturally sourced lipid emulsifier [12]. To date, intravenously administered BJOE Key examples of promising nanostructures in various stages of development include nanoemulsions, has been used clinically, including in China, as a standalone treatment [13] and in combination with radiotherapy [14] or chemotherapeutic drugs [15] to improve cancer treatment efficacy and enhance immune functions [16]. However, BJOE still has shortcomings, such as a relatively low bioavailability of medicinally active compounds, physicochemical stability issues, and potential administration side effects such as blood vessel irritation and adverse immune reactions [17,18]. Such challenges have spurred ongoing efforts to develop innovative nanomedicine strategies that harness the medicinal activity of BJO and its molecular components with nanoparticle carriers. Key examples of promising nanostructures in various stages of development include nanoemulsions, liposomes, nanostructured lipid carriers, and spongosomes, which can help to improve bioavailability, Molecules 2020, 25, 5414 3 of 17 Molecules 2020, 25, x FOR PEER REVIEW 3 of 17 liposomes, nanostructured lipid carriers, and spongosomes, which can help to improve controlled release, physicochemical stability, drug loading, and encapsulation efficiency. The objective bioavailability, controlled release, physicochemical stability, drug loading, and encapsulation of this review is to cover the latest progress in the field, starting with an overview of the pharmacological efficiency. The objective of this review is to cover the latest progress in the field, starting with an properties of BJO and its molecular components, followed by a critical presentation of various overview of the pharmacological properties of BJO and its molecular components, followed by a types of cutting-edge nanomedicine strategies and how they are being utilized to deliver BJO critical presentation of various types of cutting-edge nanomedicine strategies and how they are being andutilized purified to deliver quassinoids. BJO and purified quassinoids. 2. Overview of Brucea javanica Oil and Molecular Components 2. Overview of Brucea javanica Oil and Molecular Components BJOBJO is is mainly mainly extracted extracted from fromB.
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