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Rhododendron Molle (Ericaceae): Phytochemistry, Pharmacology, and Toxicology

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Rhododendron Molle (Ericaceae): Phytochemistry, Pharmacology, and Toxicology Chinese Journal of Natural Chinese Journal of Natural Medicines 2018, 16(6): 04010410 Medicines Rhododendron Molle (Ericaceae): phytochemistry, pharmacology, and toxicology CAI Yong-Qing1Δ, HU Jian-Hui2Δ, QIN Jie3, SUN Tao4*, LI Xiao-Li5,6* 1 Department of Pharmacy, Institute of Surgery Research, Daping Hospital, Third Military Medical University, Chongqing 400042, China; 2 Student Brigade Ten Team, Second Military Medical University, Shanghai 200433, China; 3 Student Eleven Camp, Third Military Medical University, Chongqing 400038, China; 4 College of Pharmacy, Chengdu University of Traditional Chinese Medicine, Chengdu 611137, China; 5 College of Pharmacy, Chongqing Medical University, Chongqing 400016, China; 6 Chongqing Key Laboratory of Drug Metabolism, Chongqing 400016, China Available online 20 June, 2018 [ABSTRACT] Rhododendron molle G. Don, belonging to the Ericaceae family, is a traditional Chinese medicinal plant with a wide spectrum of pharmacological effects. This paper aimed to review the phytochemistry, pharmacology and toxicology of R. molle, and to discuss the tendency of future investigations on this plant. A systematic review of literature about R. molle was carried out using re- sources including classic books about Chinese herbal medicine, and scientific data bases including CNKI, Pubmed, SciFinder, Scopus, and Web of Science. Over 67 compounds, including diterpenes, triterpenes, flavonoids, and lignans, had been extracted and identified from R. molle. The extracts/monomers isolated from the root, flower and fruits of this plant were used as effective agents for treating pains, inflammatory diseases, hypertension, and pest, etc. In addition, diterpenes, such as rhodojaponin III, were considered as the toxic agents associated with the toxicities of this plant. These findings will be significant for the discovery of new drugs from this plant and full utilization of R. molle. [KEY WORDS] Rhododendron molle ; Phytochemistry; Pharmacology; Toxicology [CLC Number] R965 [Document code] A [Article ID] 2095-6975(2018)06-0401-10 investigations on R. molle have demonstrated that it possesses Introduction a wide spectrum of pharmacological activities, including an- Rhododendron molle G. Don (R. molle), belonging to the algesics, anti-inflammatory, anti-hypertensive and insecticidal family of Ericaceae, is a small undershrub distributed in the effects [3-4]. Furthermore, previous researches regarding phy- Yangtze River basin and around the south China [1-2]. In addi- tochemistry of R. molle have been done on the roots, flowers tion, the roots, flowers, and fruits of R. molle have been and the fruits of this plant, and over 67 compounds have been commonly recorded in ancient medical monographs as the isolated and identified from this plant, including diterpenes, traditional herbal medicines in China for analgesics, anti-in- triterpenes, flavonoids, and lignans [3-5]. Besides, R. molle is flammatory and insecticides, etc. [3]. Currently, increasing commonly recognized as a poisonous plant, and previous investigations have reported that the diterpenes are the ma- jor toxic components of this plant [4-6]. In the present paper, [Received on] 20-Oct.-2017 a systematic review of literatures about R. molle was per- [Research funding] This study was supported by the National Natu- formed using the available resources, such as classic books ral Science Foundation of China (No. 81302797), Research Project of about Chinese herbal medicine, and scientific data bases Chongqing Science and Technology (No. cstc2015jcyjBX0018), and Research Project of Third Military Medical University (No. 2015XZH19). including CNKI, Pubmed, SciFinder, Scopus, and Web of [*Corresponding author] E-mails: [email protected] (LI Xiao-Li); Science, etc. The phytochemistry, pharmacology and toxi- [email protected] (SUN Tao) cology of R. molle were reviewed, which would be signifi- ΔThese authors contributed equally to this work. cant for finding new drugs from R. molle and full utilization These authors have no conflict of interest to declare. of this plant. Furthermore, the possible tendency and per- Published by Elsevier B.V. All rights reserved spective for future researches of R. molle were also dis- – 401 – CAI Yong-Qing, et al. / Chin J Nat Med, 2018, 16(6): 401410 cussed in this paper. Among these compounds, the diterpenes are the most impor- Phytochemistry tant characteristic constituents in this plant [7-9]. In this section, As a well-known traditional Chinese medicine, many we describe the main chemical constituents of this plant chemical compounds have been isolated from R. molle, mainly (Table 1), including their chemical structures and their iso- including diterpenes, triterpenes, flavonoids and lignans. lation parts of this plant (Figs. 1-5). Table 1 Chemical compounds isolated from R. molle Classification No. Chemical component Part of plant Reference 1 Rhodomolleins I flower [10] 2 Rhodomolins A flower [17] 3 Rhodomolleins XII flower [10] 4 Rhodomolins C flower [16] 5 Rhodomosides A roots [18-19] 6 Rhodomosides B roots [19] 7 1β-rhodomoside root [22] 8 Grayanotoxin II flower [10, 16] 9 Rhodomolleins XIX flower [21] 10 Rhodomolins B flower [17] 11 Rhodomolleins XI (III) flower [10, 13] 12 Rhodomolleins XIII flower [10] 13 Rhodojaponin VI roots, fruits [10, 12, 22] 14 Rhodomolleins XVI fruits [12] 15 Grayanotoxin I flower [16] 16 Grayanotoxin III flower [11] 17 Rhodojaponin II flower [10] Diterpenes 18 Rhodojaponin III root, flower [13] 19 Rhodomolleins IX flower [10] 20 Rhodomolleins XVIII fruits [12] 21 Rhodomolleins X flower [10] 22 Rhodomolleins XX fruits [21] 23 Rhodomolleins XVII fruits [12] 24 Secorhodomollolides A flower [14] 25 Secorhodomollolides B flower [14] 26 Secorhodomollolides C flower [14] 27 Secorhodomollolides D flower [14] 28 Kalmanol flower [10] 29 Rhodomolleins XV fruits [12] 30 Rhodomolleins XIV flower [10] 31 Rhodomolleins F flower [15] 32 Rhodomolleins G flower [15] 2α, 10α-epoxy-3β, 5β, 6β, 14β, 33 flower [29] 16α-hexahydroxy-grayanane 34 Mollolide A roots [33] 35 Quercetin flower [24] 36 Quercitrin flower [24] Flavonoids 37 Isoquercitrin leave [20] 38 Quercetin-3-O-α-L-arabinoside flower [24] 39 Hyperoside flower [20, 24] – 402 – CAI Yong-Qing, et al. / Chin J Nat Med, 2018, 16(6): 401410 Continued Classification No. Chemical component Part of plant Reference 40 Quercetin-3-rhamnoside-2"-gallate flower [24] 41 Kaempferol flower [24] 42 Kaempferol-7-O-α-L-rhamnoside flower [24] 43 Isorhamnetin flower [24] 44 Caryatin flower [24] 45 Phloretin flower [25] Flavonoids 46 Phlorezin 4'-methyl ether flower [25] 47 Phloretin 4'-yl-β-D-glucopyranoside flower [25] 48 Phloretin 4'-methyl ether flower [25] 49 Phloretin 6'-methyl ether flower [25] 50 Epicatechin leave [26] 51 Vitexin flower [27] 7S, 8S-threo-4, 9, 9'-trihydroxy-3, 3'-dimethoxy-8- 52 roots [22] O-4'-neolignan-7-O-β-glucopyranoside 7S, 8S-erythro-4, 9, 9'-trihydroxy-3, 3'-dimethoxy- 53 roots [22] 8-O-4'-neolignan-7-O-β-glucopyranoside 7R, 8R-threo-4, 7, 9, 9'-tetrahydroxy-3-methoxy-8- 54 roots [22] Lignans O-4'-neolignan-3'-O-β-glucopyranoside 55 (+)-lyoniresionl roots [22] 56 (+)-lyoniresionl-3α-O-β-glucopyranoside roots [22] 57 (+)-lyoniresionl-3α-O-α-rhamnopyranoside roots [22] 58 (−)-lyoniresionl-3α-O-β-glucopyranoside roots [22] 59 Oleanolic acid flower [27] 60 2α-hydroxy-oleanolic acid flower [27] Triterpenes 61 Asiatic acid flower [27] 62 Taraxerol roots [28] 63 β-sitosterol flower [27] 64 2E, 4Z abscisic acid flower [27] 65 Benzyl glucoside flower [27] Other compounds 66 Steraric acid flower [27] Benzyl 2, 6-dihydroxybenzoate-6-O-α-L-rhamno- 67 flower [29] pyranosyl-(1→3)-β-D-glucopyranoside Diterpenes rhodomolleins X (21), secorhodomollolides A (24), secor- Diterpenes, existing in numerous natural plants, have been hodomollolides B (25), secorhodomollolides C (26), secor- reported to possess various pharmacological activities. Previous hodomollolides D (27), kalmanol (28), rhodomolleins XIV investigations have reported that abundant diterpenes are (30), rhodomolleins F (31), rhodomolleins G (32), and 2α, isolated from the roots, flowers, and leaves of R. molle, and 10α-epoxy-3β, 5β, 6β, 14β, 16α-hexahydroxy-grayanane the diterpenes are recognized as the characteristic constituents (33) [10-17]. Furthermore, from other parts of R. molle (roots of this plant. As a known folk medicine, called Rhododendri and fruits), abundant diterpenes have also been isolated and Mollis Flos, the chemical constituents of the flowers of R. identified as rhodomosides A (5), rhodomosides B (6), molle have been comprehensively studied, and researchers 1β-rhodomoside (7), rhodojaponin VI (13), rhodomolleins have obtained various diterpenes from its flowers. These XVI (14), rhodojaponin III (18), rhodomolleins XVIII (20), structurally unique diterpenes are mainly Grayanane type rhodomolleins XX (22), rhodomolleins XVII (23), rhodo- diterpenes, and have a broad spectrum of activities, such as molleins XV (29) mollolide A (34) [18-22] (Fig. 1). anti-nociceptive effect, insecticidal effect, and antihypertensive Flavonoids effects. Diterpenes in this plant mainly include rhodomolleins Flavonoids are common constituents with various phar- I (1), rhodomolins A (2), rhodomolleins XII (3), rhodomolins macological activities in natural plant and herbal world, such C (4), grayanotoxin II (8), rhodomolleins XIX (9), rhodo- as antioxidant, anti-tumor and anti-inflammatory effects [23]. So molins B (10), rhodomolleins XI (III) (11), rhodomolleins far, over 16 common flavonoids have
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