The Progress in the Chemical Constituents of the Genus Picrasma During 2007-2017
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TMR Modern Herbal Medicine 2018 October; 1(4): 220-232 Review The progress in the chemical constituents of the genus Picrasma during 2007-2017 Jie Zhang1, Jian Yang1, Chuan-Xi Wang2, Hao Gao1,2*, Xin-Sheng Yao1,2 1College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China. 2Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, China *Correspondence to: Hao Gao, Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, China. Email: [email protected]. Highlights The plants of the genus Picrasma comprise of nine species and are mainly distributed in tropical and subtropical regions of America and Asia. The bark, roots, stems, branches, or leaves of some species in the genus Picrasma are used as traditional herbal medicines for the treatment of anemopyretic cold, sore throat, dysentery, eczema, nausea, loss of appetite, diabetes mellitus, hypertension, and so on. The chemical constituents of the plants of this genus were carried out to isolate 157 compounds before 2007, which were reviewed by Jiao WH et al. From then on, some significant progresses on the plants of the genus Picrasma have been achieved over the last decade, and another 101 compounds with various biological activities are reported. These compounds are assigned to alkaloids, quassinoids, triterpenoids, and others. So far, the chemical investigation on the plants of the genus Picrasma only focus on three species (P. quassioides, P. javanica and P. excelsa). Among them, the most studies on chemical constituents concentrate on the plants of P. quassioides, followed by the plants of P. javanica. Little researches have been done on the plants of P. excelsa. The current results show that there are large differences in the chemical constituents between the species of the genus Picrasma. The updated overview on the chemical constituents of the plants of the genus Picrasma is provided herein after the systematic review by Jiao WH et al. in 2007. Citation: Zhang J, Yang J, Wang CX, et al. The progress in the chemical constituents of the genus Picrasma during 2007-2017. TMR Modern Herbal Medicine, 2018, 1(4): 220-232. DOI: 10.12032/TMRmhm2017B34 Submitted: 9 September 2018Accepted: 15 September 2018, Online: 24 September 2018 Submit a manuscript: https://www.tmrjournals.com TMR Mod Herb Med | October 2018| vol. 1 | no. 4 | 220 TMR Modern Herbal Medicine 2018 October; 1(4): 220-232 Abstract The plants of the genus Picrasma, comprised of nine species, are mainly distributed in tropical and subtropical regions of America and Asia. Some species of this genus are used as traditional medicine resources to cure anemopyretic cold, sore throat, dysentery, eczema, nausea, loss of appetite, diabetes mellitus, hypertension, and so on. A total of 157 chemical constituents identified from Picrasma were reviewed by Jiao WH et al. in 2007. Since then, 101 compounds were reported from the plants of the genus Picrasma. These compounds are assigned to alkaloids, quassinoids, triterpenoids, and others. This review aims to provide an updated overview on the chemical constituents of the plants of the genus Picrasma during 2007-2017. Keywords: The genus Picrasma, Chemical constituents, Alkaloids, Quassinoids, Triterpenoids 摘要 苦树属植物包括 9 个种,主要分布在美洲和亚洲的热带以及亚热带地区。该属某些种的植物作为重要的传 统药物资源用于治疗风热感冒、咽喉肿痛、湿热痢疾、恶心晕船、食欲不振、糖尿病、高血压等疾病。2007 年,焦伟华等人对苦树属植物的化学成分进行了整理,共综述了 157 个化合物。近十年间又有 101 个化学 成分从苦树属植物中被报道,包括生物碱、苦味素、三萜等。本文对 2007-2017 十年间苦树属植物化学成 分的研究进展进行了综述。 关键词:苦树属;化学成分;生物碱;苦味素;三萜 Abbreviation: PDE 4: phosphodiesterase 4; NO: nitric oxide; LPS: lipopolysaccharide; NMR: nuclear magnetic resonance; HPLC: high performance liquid chromatography; CD: circular dichroism; TNF-: tumor necrosis factor ; IL-6: interleukin 6; AI: antiangiogenic index; Vpr: viral protein R; SD: standard deviation; Glc: glucopyranosyl; Api: apiofuranosyl; Xyl: xylopyranosyl. Competing interests: The authors declare that there is no conflict of interests regarding the publication of this paper. Copyright: © 2018 TMR Publishing Group Limited. This is an open access article distributed under the terms of the Creative Commons Attribution Non-Commercial license. Executive Editor: Jing Sun. Submit a manuscript: https://www.tmrjournals.com TMR Mod Herb Med | October 2018| vol. 1 | no. 4 | 221 TMR Modern Herbal Medicine 2018 October; 1(4): 220-232 monocyte-macrophage RAW264.7 cells stimulated by Background lipopolysaccharide (LPS) were evaluated. Only compounds 1 and 2 showed weak inhibitory activities The plants of the genus Picrasma, comprised of nine with IC50 values of 100.0 mM and 57.3 mM, respectively species, are mainly distributed in tropical and subtropical [7]. In 2010, twelve β-carboline alkaloids, picrasidine Y (5), 6-hydroxy-3-methoxycarbonyl-β-carboline (6), regions of America and Asia [1]. The bark, roots, stems, 6,12-dimethoxy-3-(2-hydroxyethyl)-β-carboline (7), branches, or leaves of some species are used as herbal 3,10-dihydroxy-β-carboline (8), medicine resources for the treatment of some diseases, 6,12-dimethoxy-3-(1-hydroxyethyl)-β-carboline (9), such as anemopyretic cold, sore throat, dysentery, eczema, 6,12-dimethoxy-3-(1,2-dihydroxyethyl)-β-carboline (10), nausea, loss of appetite, diabetes mellitus, hypertension, 6-methoxy-3-(2-hydroxyl-1-ethoxyethyl)-β-carboline (11), and so on [2-5]. In fact, the investigations on 6-methoxy-12-hydroxy-3-methoxycarbonyl-β-carboline phytochemistry and pharmacology of the plants of the (12), 3-hydroxy-β-carboline (13), genus Picrasma are mainly focused on Picrasma 3-(2-hydroxyethyl)-β-carboline (14), quassioides (D. Don) Benn and Picrasma javanica 6-methoxy-3-(1,2-dihydroxyethyl)-β-carboline (15), and Blume. kumujancine (16), were obtained from the stems of P. For the chemical constituents and bioactivities of the quassioides by Jiao WH et al. [8]. But the absolute plants of the genus Picrasma, Jiao WH et al. made a configuration of 5 was not be determined at that time. In 2015, its absolute configuration was firstly identified by review in 2007 [6]. Twenty-three β-carboline alkaloids, Koike K et al. on basis of the comparisons of 1H and 13C nine canthinone alkaloids, eleven bis β-carboline nuclear magnetic resonance (NMR) spectral data, specific alkaloids, ninety-four quassinoids, eight triterpenoids, and optical rotation values, High Performance Liquid twelve other compounds were reviewed in that report. In Chromatography (HPLC) analysis using chiral columns, addition, the biological activities of those compounds and and circular dichroism (CD) spectra with the chemically extracts were also reviewed, including anti-bacteria, synthesized stereoisomers of 5 [9]. In 2011, two anti-malaria, anti-hypertension, anti-tumor, β-carboline alkaloids, anti-phosphodiesterase 4 (PDE 4), protect-cardiovascular, 1-(dimethoxymethyl)-9H-pyrido[3,4-b]indole (17), and protect-gastrointestinal mucous membrane [6]. From 4,8-dimethoxy-9H-pyrido[3,4-b]indole-1-carboxaldehyde then on, some significant progresses on the plants of the (18), were obtained from the stems of P. quassioides by genus Picrasma have been achieved over the last decade, Jiao WH et al. [10]. Both of them exhibited potent and 101 compounds with various biological activities inhibitory activities on the production of NO, tumor necrosis factor (TNF-), and interleukin 6 (IL-6) in were reported. These compounds are assigned to mouse RAW264.7 cells stimulated by LPS [10]. In 2014, alkaloids, quassinoids, triterpenoids, and others, which a β-carboline alkaloid, are described herein. 6-hydroxy-9H-pyrido[3,4-b]indole-1-carboxylic acid (19), was isolated from the stems of P. quassioides by Lai ZQ Alkaloids et al., which showed no cytotoxic activities against four human cancer (K-562, SGC-7901, Hep G2, and A-549) Alkaloids are the principal active components of the and one mouse cancer (CT26.WT) cell lines [11]. In 2016, plants of the genus Picrasma. They can be divided into two new β-carboline alkaloids, β-carboline alkaloids, canthinone alkaloids, and bis 1-hydroxymethyl-8-hydroxy-β-carboline (20), -carboline alkaloids. 6-hydroxy-9H-pyrido[3,4-b]indole-1-carboxylic acid ethyl ester (21), along with 6 and 13, were isolated from β-Carboline alkaloids the stems of P. quassioides by Gong G et al. [12]. In 2007, four β-carboline alkaloids, Meanwhile, they exhibited different potency of the 1-methoxy-9H-pyrido[3,4-b]indole (1), anti-angiogenic activities on zebrafish in vivo with 4-methoxy-1-methyl-9H-pyrido[3,4-b]indole (2), antiangiogenic index (AI) >1 [12]. The structures and 1-ethyl-4-methoxy-β-carboline (3), related information of compounds 1-21 are shown in the 9H-pyrido[3,4-b]indole-1-carboxylic acid (4), were Figure 1 and Table 1. isolated from the stems of P. quassioides by Chen M et al. [7]. At the same time, their inhibitory activities on the production of nitric oxide (NO) in mouse Submit a manuscript: https://www.tmrjournals.com TMR Mod Herb Med | October 2018| vol. 1 | no. 4 | 222 TMR Modern Herbal Medicine 2018 October; 1(4): 220-232 Table 1 β-Carboline alkaloids from the plants of the genus Picrasma Number Name CAS number Activity Plant Reference 1 1-Methoxy-9H-pyrido[3,4-b]indole 30151-92-9 NO (IC50 = 100.0 mM) P. quassioides [7] 2 4-Methoxy-1-methyl-9H-pyrido[3,4-b 694533-71-6 NO (IC50 = 57.3 mM) P. quassioides [7] ]indole 3 1-Ethyl-4-methoxy-β-carboline 26585-14-8 - P. quassioides [7] 4 9H-Pyrido[3,4-b]indole-1-carboxylic 26052-96-0 - P. quassioides [7] acid 5 Picrasidine Y 155416-27-6 - P. quassioides [8, 9] 6 6-Hydroxy-3-methoxycarbonyl-β-Car 245662-15-1 AI = 1.5 P. quassioides [8, 12] boline 7 6,12-Dimethoxy-3-(2-hydroxylethyl)- 1131570-92-7 - P. quassioides [8] β-carboline 8 3,10-Dihydroxy-β-carboline 1233884-59-7 - P. quassioides [8] 9 6,12-Dimethoxy-3-(1-hydroxyethyl)- 1233884-60-0 - P.