Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Sci Rep. 2016 Aug 22;6:31743. doi: 10.1038/srep31743.

Pruinosanones A-C, anti-inflammatory isoflavone derivatives from Caragana 
pruinosa.

Zheng C(1), Wang L(1), Han T(1), Xin H(1), Jiang Y(1), Pan L(2), Jia X(2), Qin 
L(1).

Author information:
(1)Department of Pharmacognosy, School of Pharmacy, Second Military Medical 
University, Shanghai 200433, China.
(2)Xinjiang Institute of Chinese Materia Medica and Ethnodrug, Urumqi 830002, 
China.

Pruinosanone A (1), a novel spirochromone, was isolated from the roots of 
Caragana pruinosa. Two biogenetically related isoflavone intermediates, 
pruinosanones B and C (2 and 3), were also isolated, together with five known 
analogs identified as 3-hydroxy-9-methoxypterocarpan (4), 
7,2'-dihydroxy-4'-methoxyisoflavanol (5), retusin-8-methylether (6), 
7,2'-dihydroxy-8,4'-dimethoxy isoflavone (7) and 7,3'-dihydroxy-8,4'-dimethoxy 
isoflavone (8). The structures of 1-3 were elucidated based on extensive 
spectroscopic methods. Notably, 1 is the first example of a spirochromone 
possessing an unprecedented pentacyclic skeleton containing a 
spiro[benzo[d][1,3]dioxole-2,3'-chroman]-4'-one motif, which was confirmed by 
X-ray diffraction analysis. A plausible biosynthetic pathway for 1 was also 
proposed. Compounds 1-8 were tested for their ability to inhibit nitric oxide 
(NO) production in LPS-induced RAW 264.7 macrophages, and compounds 1-3 were the 
most potent inhibitors of NO production, with IC50 values of 1.96, 1.93 and 
1.58 μM, respectively. A structure-activity relationship analysis revealed that 
the fused 2-isopropenyl-2,3-dihydrofuran moiety plays a vital role in the 
potency of these compounds. Moreover, 1 was found to significantly inhibit 
inducible nitric oxide synthase (iNOS) protein expression, which accounts for 
the potent inhibition of NO production by this spirochromone.

DOI: 10.1038/srep31743
PMCID: PMC4992842
PMID: 27545283 [Indexed for MEDLINE]


2. J Ethnopharmacol. 2007 Jan 19;109(2):354-8. doi: 10.1016/j.jep.2006.07.034.
Epub  2006 Aug 4.

Cytotoxic constituents from Butea superba Roxb.

Ngamrojanavanich N(1), Loontaisong A, Pengpreecha S, Cherdshewasart W, 
Pornpakakul S, Pudhom K, Roengsumran S, Petsom A.

Author information:
(1)Research Centre for Bioorganic Chemistry, Faculty of Science, Chulalongkorn 
University, Pyathai Road, Pathumwan, Bangkok, Thailand. nnattaya@chula.ac.th

A carpin (3-hydroxy-9-methoxypterocarpan) (Medicarpin) (1) and four isoflavones, 
7-hydroxy-4'-methoxy-isoflavone (Formononetin) (2); 7,4'-dimethoxyisoflavone 
(3); 5,4'-dihydroxy-7-methoxy-isoflavone (Prunetin) (4) and 
7-hydroxy-6,4'-dimethoxyisoflavone (5) were isolated from the tuber roots of 
Butea superba Roxb. Compounds 2 and 4 showed moderate cytotoxic activity on KB 
cell lines with IC(50) (microM) values of 37.3+/-2.5 and 71.1+/-0.8 and on BC 
cell lines with IC(50) (microM) values of 32.7+/-1.5 and 47.3+/-0.3, 
respectively.

DOI: 10.1016/j.jep.2006.07.034
PMID: 16973318 [Indexed for MEDLINE]


3. Planta Med. 2005 Jul;71(7):683-5. doi: 10.1055/s-2005-871277.

Antimitotic properties of pterocarpans isolated from Platymiscium floribundum on 
sea urchin eggs.

Militão GC(1), Jimenez PC, Wilke DV, Pessoa C, Falcão MJ, Sousa Lima MA, 
Silveira ER, de Moraes MO, Costa-Lotufo LV.

Author information:
(1)Departamento de Fisiologia e Farmacologia, Universidade Federal do Ceará, 
Fortaleza, Ceará, Brasil.

This study reports the antimitotic effects on sea urchin eggs of five known 
pterocarpans: (+)-3,10-dihydroxy-9-methoxypterocarpan, 
(+)-3,9-dimethoxypterocarpan [(+)-homopterocarpin], 
(+)-2,3,9-trimethoxypterocarpan, (+)-3,4-dihydroxy-9-methoxypterocarpan 
[(+)-vesticarpan] and (+)-3-hydroxy-9-methoxypterocarpan [(+)-medicarpin], 
isolated from the trunk of Platymiscium floribundum, a native tree from Brazil. 
All tested compounds showed strong activity in this assay, with 
2,3,9-trimethoxypterocarpan being the most active (log IC50 of -8.10 +/- 0.02; 
-7.91 +/- 0.01; -7.97 +/- 0.02 M for first and third cleavages, and blastulae 
stages, respectively). These data suggest that the 2-methoxy substituent can be 
an important pharmacophoric unit.

DOI: 10.1055/s-2005-871277
PMID: 16041657 [Indexed for MEDLINE]


4. J Nat Prod. 2005 Mar;68(3):423-6. doi: 10.1021/np049854d.

Cytotoxic flavonoids from Platymiscium floribundum.

Falcão MJ(1), Pouliquem YB, Lima MA, Gramosa NV, Costa-Lotufo LV, Militão GC, 
Pessoa C, de Moraes MO, Silveira ER.

Author information:
(1)Curso de Pós-Graduação em Química Orgânica, Departamento de Química Orgânica 
e Inorgânica, Centro de Ciências, Universidade Federal do Ceará, CP 12200, 
Fortaleza-Ce, 60021-940, Brazil.

Two new isoflavonoids, 7-hydroxy-6,4'-dimethoxy-isoflavonequinone (1) and 
2'-hydroxy-6,4',6' ',4' ''-tetramethoxy-[7-O-7' ']-bisisoflavone (2), and seven 
other known flavonoids, 3-hydroxy-9-methoxypterocarpan (medicarpin), 
3,10-dihydroxy-9-methoxypterocarpan, 3,9-dimethoxypterocarpan (homopterocarpin) 
(3), 2,3,9-trimethoxypterocarpan (4), 3,4-dihydroxy-9-methoxypterocarpan 
(vesticarpan) (5), 2',4,4'-trihydroxychalcone (isoliquiritigenin), and 
7,4'-dihydroxyflavanone (liquiritigenin) (6), were isolated from the heartwood 
of Platymiscium floribundum. The structures of compounds 1 and 2 were 
established by spectroscopic methods. Compounds 3-6 showed cytotoxic activity 
when evaluated against five human cancer cell lines in vitro.

DOI: 10.1021/np049854d
PMID: 15787450 [Indexed for MEDLINE]


5. Plant Physiol. 1978 Feb;61(2):226-30. doi: 10.1104/pp.61.2.226.

Regulation of Phytoalexin Synthesis in Jackbean Callus Cultures: Stimulation of 
Phenylalanine Ammonia-Lyase and o-Methyltransferase.

Gustine DL(1), Sherwood RT.

Author information:
(1)United States Department of Agriculture, Agriculture Research Service, U.S. 
Regional Pasture Research Laboratory and Department of Plant Pathology, The 
Pennsylvania State University, University Park, Pennsylvania 16802.

Jackbean, Canavalia ensiformis (L.), callus tissues synthesized the phytoalexin, 
medicarpin (3-hydroxy-9-methoxypterocarpan), when treated with spore suspensions 
of Pithomyces chartarum (Berk. and Curt.) M. B. Ellis, a nonpathogen of 
jackbean. Medicarpin was isolated from treated callus tissue and identified by 
its ultraviolet and mass spectra. The minimum spore concentration found to 
elicit medicarpin synthesis after 26 hours was 1 x 10(5) spores/ml; levels of 
medicarpin in callus tissue increased linearly up to 1 x 10(7) spores/ml, 
indicating that the recognition sites for presumed elicitors were not saturated. 
Medicarpin was first detected in callus treated with 1 x 10(7) spores/ml, 6 to 
12 hours after application, and the concentration reached a maximum at 48 hours, 
slowly declining thereafter to 72 hours. In callus treated with 3.15 mm HgCl(2), 
medicarpin concentrations were also maximum by 48 hours. Phenylalanine 
ammonia-lyase (EC 4.3.1.5) activity increased 2-fold in spore-treated callus 
after 36 hours. Isoliquiritigenin, daidzein, and genistein o-methyltransferase 
(EC 2.1.1.6) activities were increased 3- to 4-fold in treated callus. Caffeic 
acid and naringenin were more efficient substrates for o-methyltransferase 
activity than the other flavonoids or apigenin, but there was no increase in 
these o-methyltransferase activities in spore-treated callus. The phytoalexin 
response in this callus tissue culture system compares well with natural plant 
systems and should be an excellent system for investigating regulation of 
phytoalexin synthesis.

DOI: 10.1104/pp.61.2.226
PMCID: PMC1091837
PMID: 16660265