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TMR Modern Herbal Medicine  2018, Vol. 1 Issue (4): 220-232    DOI: 10.12032/TMRmhm2017B34
Review     
The progress in the chemical constituents of the genus Picrasma during 2007-2017
Zhang Jie1, Yang Jian1, Wang Chuan-Xi2, Gao Hao1,2,*(), Yao Xin-Sheng1,2
1 College of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang, China.
2 Institute of Traditional Chinese Medicine & Natural Products, College of Pharmacy, Jinan University, Guangzhou, China
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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.

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.



Key wordsThe genus Picrasma      Chemical constituents      Alkaloids      Quassinoids      Triterpenoids     
Published: 25 October 2018
Corresponding Authors: Gao Hao     E-mail: tghao@jnu.edu.cn
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# These authors contributed equally to this study.

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Zhang Jie, Yang Jian, Wang Chuan-Xi, Gao Hao, Yao Xin-Sheng. 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

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https://www.tmrjournals.com/mhm/EN/10.12032/TMRmhm2017B34     OR     https://www.tmrjournals.com/mhm/EN/Y2018/V1/I4/220

Figure 1 Chemical structures of 1-21
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]indole 694533-71-6 NO (IC50 = 57.3 mM) P. quassioides [7]
3 1-Ethyl-4-methoxy-β-carboline 26585-14-8 - P. quassioides [7]
4 9H-Pyrido[3,4-b]indole-1-carboxylic acid 26052-96-0 - P. quassioides [7]
5 Picrasidine Y 155416-27-6 - P. quassioides [8, 9]
6 6-Hydroxy-3-methoxycarbonyl-β-Carboline 245662-15-1 AI = 1.5 P. quassioides [8, 12]
7 6,12-Dimethoxy-3-(2-hydroxylethyl)-β-carboline 1131570-92-7 - P. quassioides [8]
8 3,10-Dihydroxy-β-carboline 1233884-59-7 - P. quassioides [8]
9 6,12-Dimethoxy-3-(1-hydroxyethyl)-β-carboline 1233884-60-0 - P. quassioides [8]
10 6,12-Dimethoxy-3-(1,2-dihydroxyethyl)-β-carboline 1131570-91-6 - P. quassioides [8]
11 6-Methoxy-3-(2-hydroxyl-1-ethoxyethyl)-β-carboline 77369-99-4 - P. quassioides [8]
12 6-Methoxy-12-hydroxy-3-methoxycarbonyl-β-carboline 245662-15-1 - P. quassioides [8]
13 3-Hydroxy-β-carboline 19839-52-2 AI = 2 P. quassioides [8, 12]
14 3-(2-Hydroxyethyl)-β-carboline 1131570-92-7 - P. quassioides [8]
15 6-Methoxy-3-(1,2-dihydroxyethyl)-β-carboline 1131570-91-6 - P. quassioides [8]
16 Kumujancine 92631-69-1 - P. quassioides [8]
17 1-(Dimethoxymethyl)-9H-pyrido[3,4-b]indole 1205667-14-6 NO (IC50 = 26.9 ± 2.0 μM) P. quassioides [10]
TNF-α (IC50 = 35.0 ± 2.9 μM)
IL-6 (IC50 = 50.4 ± 4.7 μM)
18 4,8-Dimethoxy-9H-pyrido[3,4-b]indole-1-carboxaldehyde 1131570-87-0 NO (IC50 = 17.4 ± 1.0 μM) P. quassioides [10]
19 6-Hydroxy-9H-pyrido[3,4-b]indole-1-carboxylic acid 1402910-87-5 - P. quassioides [11]
20 1-Hydroxymethyl-8-hydroxy-β-carboline - AI = 6 P. quassioides [12]
21 6-Hydroxy-9H-pyrido[3,4-b]indole-1-carboxylic acid ethyl ester 2122466-76-4 AI = 1.3 P. quassioides [12]
Table 1 β-Carboline alkaloids from the plants of the genus Picrasma
Figure 2 Chemical structures of 22-28.
Number Name CAS number Activity Plant Reference
22 11-Hydroxycanthin-6-one 75969-83-4 NO (IC50 = 46.3 mM) P. quassioides [7]
23 8-Hydroxycanthin-6-one 66762-19-4 CNE ((IC50 = 56.8 ± 9.7 μM) P. quassioides [13]
Bel-7402 (IC50 = 166.4 ± 41.2 μM)
24 4,5-Dimethoxy-10-hydroxycanthin-6-one 1131570-94-9 CNE (IC50 = 39.2 ± 8.4 μM) P. quassioides [13]
25 3-Methyl-5,6-dioxo-4H-indole[3,2,1-de][1,5]naphthyridinium 1942857-74-0 CNE (IC50 = 94.5 ± 19.3 μM) P. quassioides [13]
26 6-Oxo-6H-indole[3,2,1-de][1,5]naphthyridine-4-butanoic acid 1131570-93-8 NO (IC50 = 47.9 ± 4.1 μM)
TNF-α (IC50 = 25.5 ± 3.3 μM)
IL-6 (IC50 = 67.0 ± 6.6 μM)
P. quassioides [10]
27 5-Methoxy-11-hydroxycanthin-6-one - - P. quassioides [12]
28 Furancanthin - - P. quassioides [12]
Table 2 Canthinone alkaloids from the plants of the genus Picrasma
Figure 3 Chemical structures of 29-40
Number Name CAS number Activity Plant Reference
29 Quassidine A 1207862-36-9 NO (IC50 = 89.4 μM) P. quassioides [14]
TNF-α (IC50 = 88.4 μM)
30 Quassidine B 1207862-37-0 - P. quassioides [14]
31 Quassidine C 1207862-38-1 - P. quassioides [14]
32 Quassidine D 1207862-39-2 - P. quassioides [14]
33 Quassidine E 1393888-72-6 NO (IC50 = 20.5 ± 1.7 μM) P. quassioides [10]
TNF-α (IC50 = 25.6 ± 2.3 μM)
IL-6 (IC50 = 45.4 ± 3.3 μM)
34 Quassidine F 1131570-95-0 NO (IC50 = 9.9 ± 0.8 μM) P. quassioides [10]
IL-6 (IC50 = 24.3 ± 2.2 μM)
35 Quassidine G 1131570-96-1 NO (IC50 = 13.1 ± 1.2 μM) P. quassioides [10]
TNF-α (IC50 = 12.3 ± 1.4 μM)
IL-6 (IC50 = 17.1 ± 1.6 μM)
36 Quassidine H 1393888-73-7 - P. quassioides [10]
37 (+)-Quassidine I 1643689-92-2 HeLa (IC50 = 5.8 μM) P. quassioides [15]
MKN-28 (IC50 = 6.3 μM)
B-16 (IC50 = 10.8 μM)
38 (-)-Quassidine I 1643689-93-3 HeLa (IC50 = 10.5 μM) P. quassioides [15]
MKN-28 (IC50 = 12.3 μM)
B-16 (IC50 = 15.4 μM)
39 (+)-Quassidine J 1643689-94-4 HeLa (IC50 = 4.0 μM) P. quassioides [15]
MKN-28 (IC50 = 4.9 μM)
B-16 (IC50 = 9.3 μM)
40 (-)-Quassidine J 1643689-95-5 HeLa (IC50 = 10.1 μM) P. quassioides [15]
MKN-28 (IC50 = 9.6 μM)
B-16 (IC50 = 14.8 μM)
Table 3 Bis β-carboline alkaloids from the plants of the genus Picrasma
Figure 4 Chemical structures of 41-57.
Number Name CAS number Activity Plant Reference
41 2'-Isopicrasin A 1314868-60-4 PANC-1 (IC50 = 3.9 μM) P. quassioides [16,17]
HeLa (IC50 = 4.0 μM) and P. javanica
42 Picrajavanicin A 1831840-53-9 153% ± 5% (2.5 μM) * P. javanica [3,18]
43 Picrajavanicin B 1831840-54-0 156% ± 5% (2.5 μM) * P. javanica [3,18]
44 Picrajavanicin C 1831840-55-1 168% ± 2% (2.5 μM) * P. javanica [3,18]
45 Picrajavanicin D 1831840-56-2 166% ± 4% (2.5 μM) * P. javanica [3,18]
46 Picrajavanicin E 1831840-57-3 136% ± 5% (2.5 μM) * P. javanica [3,18]
47 Picrajavanicin F 1831840-58-4 138% ± 1% (2.5 μM) * P. javanica [3,18]
48 Picrajavanicin G 1831840-59-5 140% ± 6% (2.5 μM) * P. javanica [3,18]
49 Picrajavanicin H 1854048-28-4 PANC-1 (IC50 = 4.3 μM) P. javanica [17,18]
HeLa (IC50 = 9.5 μM)
147% ± 3% (2.5 μM) *
50 Picrajavanicin I 1854048-29-5 PANC-1 (IC50 = 17.4 μM) P. javanica [17,18]
137% ± 5% (2.5 μM) *
51 Picrajavanicin J 1854048-30-8 PANC-1 (IC50 = 10.0 μM) P. javanica [17,18]
126% ± 6% (2.5 μM) *
52 Picrajavanicin K 1854048-31-9 PANC-1 (IC50 = 3.3 μM) P. javanica [17,18]
155% ± 4% (2.5 μM) *
53 Picrajavanicin L 1854048-32-0 PANC-1 (IC50 = 8.5 μM) P. javanica [18]
54 Picrajavanicin M 1854048-33-1 PANC-1 (IC50 = 7.4 μM) P. javanica [17,18]
HeLa (IC50 = 37.4 μM)
138% ± 3% (2.5 μM) *
55 Nigakilactone P - - P. quassioides [19]
56 Picraqualide F 2172834-22-7 - P. quassioides [19]
57 Nigakilactone Q - - P. quassioides [19]
Table 4 Quassinoids from the plants of the genus Picrasma
Figure 5 Chemical structures of 58-87.
Number Name CAS number Activity Plant Reference
58 Picraquassin A 1967020-60-5 - P. quassioides [20]
59 Picraquassin B 1973484-12-6 MKN-28 (IC50 = 2.5 μM) P. quassioides [20]
A-549 (IC50 = 5.6 μM)
MCF-7 (IC50 = 9.1 μM)
60 Picraquassin C 1973484-13-7 - P. quassioides [20]
61 Picraquassin D 1973484-15-9 - P. quassioides [20]
62 6β-Hydroxypicraquassin C 1973484-16-0 - P. quassioides [20]
63 Picraquassin E 1973484-16-0 MKN-28 (IC50 = 8.8 μM) P. quassioides [20]
64 Picraquassin F 1973484-17-1 MKN-28 (IC50 = 9.8 μM) P. quassioides [20]
65 Picraquassin G 1973484-18-2 P. quassioides [20]
66 Picraquassin H 1973484-20-6 - P. quassioides [20]
67 Picraquassin I 1973484-21-7 MKN-28 (IC50 = 7.9 μM) P. quassioides [20]
A-549 (IC50 = 8.3 μM)
68 Picraquassin J 1967020-22-8 - P. quassioides [20]
69 21β-Ethoxybourjotinolone A 1967020-61-6 - P. quassioides [20]
70 6-Oxo-21β-ethoxybourjotinolone A 1967020-62-7 MKN-28 (IC50 = 8.2 μM) P. quassioides [20]
71 9,11-Dehydrotoonaciliatin K 1967020-63-8 MKN-28 (IC50 = 8.3 μM) P. quassioides [20]
72 5,6,9,11-Dehydrotoonaciliatin K 1967020-64-9 - P. quassioides [20]
73 21β-Ethoxy-20α-hydroxymelianodiol 1967020-65-0 MKN-28 (IC50 = 9.0 μM) P. quassioides [20]
74 Picraquassin K 1967020-66-1 MKN-28 (IC50 = 9.1 μM) P. quassioides [20]
75 Xanthocerasic acid methyl ester 1967020-67-2 MKN-28 (IC50 = 8.3 μM) P. quassioides [20]
76 11-Oxobrumollisol A 1967023-09-1 - P. quassioides [20]
77 Picraquassin L 1973484-23-9 - P. quassioides [20]
78 Melianodiol 32764-64-0 - P. quassioides [20]
79 (13α,14β,17α,20S,21R,23R,24S)-21,23-Epoxy-21-ethoxy-24,25-dihydroxylanost-7-en-3-one 749849-70-5 - P. quassioides [20]
80 Toonaciliatin K 1142886-12-1 - P. quassioides [20]
81 21-Methoxy-21,23-epoxytirucalla-7,24-dien-3α-ol 1442419-83-1 - P. quassioides [20]
82 Bourjotinolone A 6985-35-9 MKN-28 (IC50 = 6.7 μM) P. quassioides [20]
A-549 (IC50 = 7.0 μM)
MCF-7 (IC50 = 9.9 μM)
83 Sapelin B 26790-94-3 - P. quassioides [20]
84 3β,29-Dihydroxytirucalla-7,24-dien-21-oic acid 262444-39-3 MKN-28 (IC50 = 9.1 μM) P. quassioides [20]
85 Piscidinol A 100198-09-2 MKN-28 (IC50 = 6.9 μM) P. quassioides [20]
A-549 (IC50 = 8.0 μM)
MCF-7 (IC50 = 8.5 μM)
86 Brumollisol B 1431628-61-3 - P. quassioides [20]
87 24S,25-Dihydroxytirucall-7-en-3-one 220864-17-5 MKN-28 (IC50 = 9.1 μM) P. quassioides [20]
Table 5 Triterpenoids from the plants of the genus Picrasma
Figure 6 Chemical structures of 88-101.
Number Name CAS number Activity Plant Reference
88 Calycosin 20575-57-9 - P. quassioides [21]
89 Ononin 486-62-4 - P. quassioides [21]
90 Formononetin 7-O-β-D-apiofuranosyl-(1→6)-β-D-glucopyranoside 857677-78-2 - P. quassioides [21]
91 Kushenol O 19716-26-8 - P. quassioides [21]
92 Umbelliferone 93-35-6 - P. quassioides [21]
93 Emodin 518-82-1 - P. quassioides [21]
94 Maackiain 2035-15-6 - P. quassioides [21]
95 Trifolirhizin 6807-83-6 - P. quassioides [21]
96 Stigmasterol-3-O-β-glucopyranoside 19716-26-8 - P. quassioides [21]
97 Mannitol 87-78-5 - P. quassioides [21]
98 Picrasmalignan A 1314868-59-1 NO (IC50 = 6.4 ± 0.9 μM) P. quassioides [16]
TNF-α (IC50 = 13.4 ± 1.1 μM)
IL-6 (IC50 = 17.3 ± 1.5 μM)
99 Buddlenol A 97399-78-5 NO (IC50 = 14.6 ± 1.4 μM) P. quassioides [16]
TNF-α (IC50 = 19.5 ± 1.6 μM)
IL-6 (IC50 = 24.4 ± 1.7 μM)
100 Buddlenol C 97465-73-1 NO (IC50 = 5.9 ± 0.8 μM) P. quassioides [16]
TNF-α (IC50 = 11.4 ± 1.1 μM)
IL-6 (IC50 = 18.8 ± 2.0 μM)
101 Fisetin 528-48-3 NO (IC50 = 2.9 ± 0.4 μM) P. quassioides [16]
TNF-α (IC50 = 6.6 ± 0.7 μM)
IL-6 (IC50 = 21.1 ± 1.8 μM)
Table 6 Other compounds from the plants of the genus Picrasma
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