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Review Article Phytochemical and Pharmacological Studies on the Genus Psoralea: a Mini Review

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Review Article Phytochemical and Pharmacological Studies on the Genus Psoralea: a Mini Review View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Crossref Hindawi Publishing Corporation Evidence-Based Complementary and Alternative Medicine Volume 2016, Article ID 8108643, 17 pages http://dx.doi.org/10.1155/2016/8108643 Review Article Phytochemical and Pharmacological Studies on the Genus Psoralea: A Mini Review Cong-Cong Li,1 Teng-Long Wang,1 Zhong-Qun Zhang,1 Wen-Qiang Yang,2 Yue-Fei Wang,1 Xin Chai,1 Chun-Hua Wang,1,3 and Zheng Li3 1 Tianjin Key Laboratory of Modern Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, China 2CollegeofPharmacy,LinyiUniversity,Linyi276000,China 3College of Pharmaceutical Engineering of Traditional Chinese Medicine, Tianjin University of Traditional Chinese Medicine, Tianjin 300193, China Correspondence should be addressed to Xin Chai; [email protected] and Chun-Hua Wang; [email protected] Received 9 September 2016; Revised 9 October 2016; Accepted 17 October 2016 Academic Editor: Wenyi Kang Copyright © 2016 Cong-Cong Li et al. This 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. The genus Psoralea, which belongs to the family Fabaceae, comprises ca. 130 species distributed all over the world, and some of the plants are used as folk medicine to treat various diseases. Psoralea corylifolia is a typical example, whose seeds have been widely used in many traditional Chinese medicine formulas for the treatment of various diseases such as leucoderma and other skin diseases, cardiovascular diseases, nephritis, osteoporosis, and cancer. So, the chemical and pharmacological studies on this genus were performed in the past decades. Here, we give a mini review on this genus about its phytochemical and pharmacological studies from 1910 to 2015. 1. Introduction 2. Phytochemistry The genus Psoralea, which belongs to the family Fabaceae, To the best of our knowledge, the first phytochemical inves- comprises ca. 130 species mainly distributed in South Africa, tigation on the genus Psoralea canbetracedbackto1910 North and South America, and Australia, a few of which [4]. In 1933, Jois and his coworkers obtained the first pure are native to Asia and temperate Europe [1]. Among them, compound called psoralen (51)fromP. corylifolia [4]. Up to several species have been widely used as herbal medicine in 2015,thetotalnumberofidentifiedsecondarymetabolites China, India, and other countries. Modern pharmacological from the genus Psoralea amounts to 129, including flavonoids, researches show that the plants in Psoralea genus have coumarins, phenols, benzofurans, benzopyrans, quinines, antimicrobial, antipregnancy, estrogenic, antitumor, antiox- sesquiterpenoids, triterpenoids, steroids, and some other idant, and many other pharmacological activities [1, 2]. For components. The structures of these compounds are shown example, P.corylifolia isthesolespeciesofthegenusdistribut- in Figure 1. Their names and the corresponding plant sources ing in China, and its seeds are used as a famous traditional are compiled in Table 1. Chinese medicine (TCM), having the effects of kidney impo- tence and warming spleen and stopping diarrhea and 2.1. Flavonoids. Previous chemical investigations have indi- included by PharmacopoeiaofPeople’sRepublicofChina[3]. cated that flavonoids were the most frequently occurring con- Here,wereviewtheprogressachievedinphytochemicalstud- stituents of the genus Psoralea. Fifty flavonoids, 1∼50,have ies on the genus Psoralea,listthecompoundsisolatedfrom been isolated and elucidated from the genus Psoralea, this genus over the past decades, and introduce the biological most of which were isolated from P. corylifolia, while iso- activities of these ingredients. vitexin (2)wasgotfromP. pli cata [5]. Various types of 2 Evidence-Based Complementary and Alternative Medicine OH OR4 R3 OH R O HO O O O 2 R O O O 5 HO HO HO HO OH HO R1 H CO O O 3 R1 R2 R3 R4 R5 OH 1 HOH HOH OH O 6 2 OGlc OH H H H OH 3 HHHCH3 H 4 OH H H H HO O HO O OH 5 OCH3 HHH O OH OH O HO 7 OH OH O O O O OH HO O O O 8 9 O 10 OH HO O O O O OH O OH 11 12 R3 R2O O R4 R1 O OR5 R6 R1 R2 R3 R4 R5 R6 13 OH H H H H H 14 HH H H H 15 HH H H H H 16 HH H CHOH H 17 OH H H HCH3 H 18 HCH3 H CHO H H 19 HH HHH 20 HHCH3 HH 21 HGlcH H H H 22 HH H HGlc (6→1)-Rha H (a) Figure 1: Continued. Evidence-Based Complementary and Alternative Medicine 3 H3CO O O HO O HO O O O O O O OH 23 24 25 R1O O HO O HO O O O O O O O R2O R1 R2 26 27 28 HH 29 CH3 H 30 CH3 COCH3 31 COCH3 COCH3 R1 OH R3 OH OH R4O OR2 O OH R5 O R1 R2 R3 R4 R5 32 HH HCH CHO O 3 38 33 HHHCHOCH3 34 HH HH HO OH 35 HH H CH3 O OH 36 OH H HH O 37 HH H CH3 39 OH OH OH OH OH OH HO HO O O OH HO OH O O 41 40 O 42 (b) Figure 1: Continued. 4 Evidence-Based Complementary and Alternative Medicine OH OH OH OH HO O O OH HO OH OH O OH O O 44 45 43 R3 R O R OH O OH OH 1 2 O O 46 R1 R2 R3 47 HHOH 48 CH3 OH H R O OCH3 1 O O O O O O O O O O O R 55 O OH 2 54 49 R1 R2 51 HH 52 OCH3 H 53 H OCH3 OH HO OH O O O O O O O HO O O 56 HO O O 58 57 OH OOCCH3 OH O O O O O O O O O H3CCOO O O O 59 60 61 OH O O OH O OH O O HO HO O O O 62 O O HO O O 63 64 (c) Figure 1: Continued. Evidence-Based Complementary and Alternative Medicine 5 OH OH OH CH2CH3 N O H3CH2C O O CH2OH CHO COOH O 66 O O 67 68 69 65 COOR HO HO HO 72 R = H 70 71 73 R = CH3 O HO HO HO 74 75 76 OH COOCH3 COOCH3 O OH OH HO HO HO 78 79 77 OH O HO HO HO 82 HO OH 81 OH 80 83 COOCH2CH3 COOCH2CH3 O OH OH O 86 87 OH OH 84 85 HO OH HO HO H O O O O OH O O i-Pr i-Pr 91 88 89 90 (d) Figure 1: Continued. 6 Evidence-Based Complementary and Alternative Medicine OH H H H3COOC HO O COOCH H 3 92 HO 93 O O O O OH OH OH OH 94 95 O OH HO 96 O HO OH OH O O HO HO OH 97 O 98 COOCH2CH3 COOCH3 OH O COOCH3 O O 101 99 100 HOOC COOH HOOC OH HO HO O OH OH O O OH O O OH O O O O HO HO OH HO HO 104 102 103 (e) Figure 1: Continued. Evidence-Based Complementary and Alternative Medicine 7 H CH COOC HOOC HOOC 3 2 O OH OH O O O HO O O HO HO OH HO HO O O OH O OH OH 105 107 HO 106 O H3CH2COOC OH O O O HO HO OH O CH3 108 109 O H H O HO H O H 110 111 112 H H H H H H HO 114 OH H 113 O C R O H H2 C H CH2 OH O C O C O R O O R HO C HO OH O 115 116 117 COOH HOOC 118 119 H RO H 120 R = CH3 121 R = CH2CH3 H H 122 R = COCH3 HO 123 (f) Figure 1: Continued. 8 Evidence-Based Complementary and Alternative Medicine O CH2OH OH O O O OH HO OH HO HO HO OH 124 OH OCH3 125 126 OH OH O HO H OH O O OH N HO O O O OH H O HO O N O H OH O HN H OH OH OCH3 127 129 128 (g) Figure 1: Chemical structures of isolated compounds from the genus Psoralea. flavonoids, including flavones1 ( ∼5), flavonols (6∼7), flava- 2.4. Benzofurans and Benzopyrans. Phytochemical stud- nones (8∼11), isoflavones (12∼31), and chalcones (32∼45), ies have afforded ten benzofurans and benzopyrans99 ( ∼ have been isolated and identified. According to Harborne’s 108)fromthegenusPsoralea.Amongthem,Z-Werneria “The Flavonoids Advances in Research Since 1980” [6], chromenes and E-Werneria chromenes (100 and 101,resp.) psorachromene (46), psorachalcones A (47), 4 -O-methyl are benzopyrans and the others are benzofurans. In 1992, one bavachalcone (48), 4,2 -dihydroxy-2 -(1 -methyl ethyl)- new benzofuran, named isocorylifonol (99), was found from 2 -3 -dihydro-(4 ,5 ,3 ,4 )furanochalcone (49), and 7,5 - P. corylifolia [4,18].Theothertwocompounds,psoralenoside dihydroxy-6 ,6 -dimethyl-dihydropyrano-(2 ,3 ,4 ,3 )- (102) and isopsoralenoside (106), were isolated from P. isoflavone (50) have the basic skeleton type of “C6-C3-C6” corylifolia in 2006 [63]. Another two compounds, 107∼108, of flavonoids. So in this review, this kind of compounds is were obtained from P. pli cata [71]. classified as flavonoid. 2.5. Quinones. Two quinones, named -tocopherol quinone 109 110 2.2. Coumarins. Coumarin is another major type of com- methyl ether and -tocopherol quinone ( and ,resp.), pounds in the genus Psoralea.
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