Pharmacological Diversity and Structure-Activity Relationship on Anticancer Effects

Hindawi Evidence-Based Complementary and Alternative Medicine Volume 2018, Article ID 9186926, 15 pages https://doi.org/10.1155/2018/9186926 Review Article Oplopanax horridus: Phytochemistry and Pharmacological Diversity and Structure-Activity Relationship on Anticancer Effects Kai Wu,1 Chong-Zhi Wang,2 Chun-Su Yuan ,2 and Wei-Hua Huang 2,3 1 Department of Physiatry, Xiangya Hospital, Central South University, Changsha 410008, China 2Tang Center for Herbal Medicine Research, Te Pritzker School of Medicine, University of Chicago; 5841 South Maryland Avenue, MC4028,Chicago,IL60637,USA 3Department of Clinical Pharmacology, Xiangya Hospital, Central South University, Changsha 410008, China Correspondence should be addressed to Wei-Hua Huang; [email protected] Received 23 June 2018; Accepted 29 August 2018; Published 13 September 2018 Academic Editor: Yoshiyuki Kimura Copyright © 2018 Kai Wu et al. Tis is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. Oplopanax horridus,well-knownasDevil’sclub,isprobablythemostimportant ethnobotanical to most indigenous people living in the Pacifc Northwest of North America. Compared with the long history of traditional use and widespread distribution in North America, the study of O. horridus is relatively limited. In the past decade, some exciting advances have been presented on the phytochemistry and pharmacological diversity and structure-activity relationship on anticancer efects of O. horridus.Todate, no systematic review has been drafed on the recent advances of O. horridus. In this review, the diferent phytochemicals in O. horridus are compiled, including purifed compounds and volatile components. Animal and in vitro studies are also described and discussed. Especially, the potential structural-activity relationship of polyynes on anticancer efects is highlighted. Tis review aimed to provide comprehensive and useful information for researching O. horridus and fnding potential agents in drug discovery. 1. Introduction “wildarmoredAlaskanginseng,”“Alaskanginseng,”or “Pacifc ginseng”, but the marketing is now forbidden in Oplopanax horridus (Sm.) Torr. & A. Gray ex Miq., well- the United States due to the misleading [2]. Such marketing knownasDevil’sclub,anethnobotanical,exclusivelyorig- relies on the presumable speculation that O. horridus share inates and is distributed in northwestern North America. similar chemical ingredients with the herbs in Panax,but Tis understory shrub forming larger populations through the presumption is not supported by related phytochemical layering usually grows in moist, well-drained, dense, and investigation [4]. old-growth forests [1]. Tis herbal plant belongs to the O. horridus has a long history of use for 34 diferent genus Oplopanax, which only consists of three species, the medical ailments by the Pacifc indigenous peoples from remaining of which are O. japonicus Nakai and O. elatus over 38 linguistic groups [7]. Te extracts of Devil’s club are (Nakai) Nakai [2]. O. elatus is mainly distributed in the marketed in North America for respiratory stimulant and temperate regions of Northern China, the south of Primorye, expectorant, rheumatoid arthritis, autoimmune conditions, northern part of the Korean Peninsula, and Russia [3], eczema, type II diabetes, external infections, and internal while O. japonicus is endemic to central Japan [4]. Te infections [7]. Te Pacifc native tribes also use O. horridus genus Oplopanax is classifed to the Araliaceae family, which for spiritual stimulant, while Shaman use it in their religion comprises some world-known botanicals such as Panax ceremonial practices. Table 1 summarizes that diferent part ginseng (Asian ginseng, Chinese or Korean ginseng), P. of O. horridus is used for many various ailments by the quinquefolius (American ginseng), and P. noto g in s e ng (Sanqi) indigenous people. It implies that the main phytochemicals [5–8]. Occasionally, O. horridus is sometimes marketed as in diferent parts of O. horridus are signifcantly varied. 2 Evidence-Based Complementary and Alternative Medicine Table 1: Te uses of O. horridus for various treatments. Part of O. Application Preparation References horridus Respiratory, cardiovascular, gastrointestinal, cold Inner barks Decoction; infusion [2, 7, 92] or infection, diabetes, arthritis, and cancer Stems Respiratory Decoction [2, 7, 93] Roots Respiratory, diabetes, and arthritis Decoction; infusion [2, 4, 94] Berries Gastrointestinal Paste [7, 19] Leaves Arthritis Decoction; infusion [7, 29] Recently, pharmacological studies showed that O. horridus possessed anticancer, antibacterial, antidiabetes, antip- soriasis, antiarthritis, and antifungal and anticonvulsant activities [2]. In the past fve years, most of animal and in vitro studies on O. horridus focused on its anticancer efects. At the same time, extensive investigation on the chemical constituents of O. horridus has led to the isola- tion and identifcation of compounds -, which include polyynes (polyacetylenes), phenylpropanoids (aglycones and glycosides), lignan glycosides, triterpenoids, sesquiterpenes, and some other compounds. Additionally, forty-eight volatile compounds were identifed from the volatile oil by GC/MS. Among these components, polyynes, e.g., falcarindiol (FAD), and oplopantriol A (OPT), have been mostly reported as (A) potentially anticancer natural products from O. horridus. In the past decade, some exciting advances have been presented on the phytochemistry, pharmacological diversity, and structure-activity relationship on anticancer efects of O. horridus. To date, no systematic review has been drafed on the recent advances of O. horridus. In this review, the diferent phytochemicals in O. horridus are compiled, including purifedcompoundsandvolatilecomponents.Animaland in vitro studies are also described and discussed. Especially, the potential structural-activity relationship of polyynes on anticancer efects is highlighted. Tis review aimed to provide comprehensive and useful information for researching O. horridus and fnding potential agents in drug discovery. (B) 2. Ethnobotanical and Ethnopharmacology Figure 1: Geographic distribution of O. horridus. O. horridus isdistributedfromAlaskaalongthePacifcCoast down to Oregon, Idaho, and Montana in the south and east to the southwestern Yukon Territory, while some isolated O. horridus has been used for both spiritual and medical populations grow around Michigan and the islands in Lake practices by the native tribes of Alaska and British Columbia Superior (Figure 1) [7, 9]. O. horridus generally is from 1 to for centuries. Traditionally, the native tribes drink the aque- 1.5 m tall, while it can grow to 3 to 5 m in some undisturbed ous decoction of the root or stem bark of O. horridus for the moist rainforest. Te spines appear around the stems and treatments of colds, fever, burns, stomach trouble, body pains, along the upper and lower surfaces of its leaves, which are sore throats, swollen glands, constipation, and tuberculosis palmately lobed with 5-13 lobes, 20 to 40 cm across, and [11].Teinnerbarkoftherootandstemhasbeenused arespirallylocatedonthestems(upto3cmdiameter).Te to stop infection on wounds and reduce swelling [12]. Te fowers are blooming in dense umbels from 10 to 20 cm Alaska Natives from the Alaskan southeast coast, Cook Inlet, diameter with fve greenish-white petals. Te fruit is a small Kodiak, Kenai, Prince William Sound, and Tanana Valley use red drupe with 4 to 7 mm diameter. Te root without spines is the inner bark of the root and stem to treat colds, cough, similar to the stem [9]. Te plant grows and reproduces slowly and fever [13]. Te traditional preparations of O. horridus and take many years to reach seed bearing maturity, and it is include either applying the heated inner bark to the wounded very sensitive to human impact [10]. area and bandaging it or chewing the root or stem bark Evidence-Based Complementary and Alternative Medicine 3 9 10 HO 3.1. Polyynes (Polyacetylenes). Polyynes, also known as polyacetylenes, possess a long chain of carbon atoms with 3 8 1 OH alternating double and triple bonds between them, which 2 occur in natural products containing more than two acety- . Oplopantriol A (17) 18 lene groups. Meanwhile, polyynes comprising two to four 17 acetylene groups are usually found in higher plants, most of . Oplopantriol B OH which contain conjugated diyne in the highly unsaturated HO 9 10 lipid chains [16]. Tese highly unsaturated hydrophobic compounds are generated in the Araliaceae family, which 3 8 1 OH have a high concentration in the roots and a small content in 2 thestembarks.Tepolyyneswhichareunstableandoxidized 3. 9,17-octadecadiene-12,14- 18 in dried plant material, contain seventeen or eighteen carbons diyne-1,11,16-triol, 1-acetate (17) O 17 (C17 or C18) in the skeleton chain, and are mostly found in the 4. Oplopandiol acetate O Araliaceae. 9 10 HO To date, seven polyynes have been purifed and identifed from the root bark of O. horridus,fveofwhicharealso 1 3 8 R discovered from the stem bark of O. horridus [17, 18]. 2 Te identifed C17 and C18 polyynes from O. horridus, . Falcarindiol (1) R = OH –, are oplopantriol A, oplopantriol B, (11S,16S,9Z)-9,17- 6. Oplopandiol R = OH 17 octadecadiene-12,14-diyne-1,11,16-triol,1-acetate, oplopandiol . Falcarinol (1) R = H acetate, falcarindiol, falcarinol, and oplopandiol (Figure 2). Polyyne

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