Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. J Agric Food Chem. 2006 Jun 28;54(13):4646-50. doi: 10.1021/jf060900k.

Biocatalytic synthesis of butein and sulfuretin by Aspergillus alliaceus.

Sanchez-Gonzalez M(1), Rosazza JP.

Author information:
(1)Division of Medicinal and Natural Products Chemistry, Center for Biocatalysis 
and Bioprocessing, College of Pharmacy, University of Iowa, Iowa City, Iowa 
52242, USA.

Aspergillus alliaceus UI315 was examined for its potential to catalyze 
biotransformation reactions of chalcones that mimic plant biosynthetic 
processes. 3-(4' '-Hydroxyphenyl)-1-(2',4'-dihydroxyphenyl)propenone 
(4,2',4'-trihydroxychalcone, isoliquiritigein) (1) was efficiently transformed 
to two major metabolites that were isolated chromatographically and identified 
by spectroscopic methods as 3-(3' ',4' 
'-dihydroxyphenyl)-1-(2',4'-dihydroxyphenyl)propenone (butein) (7) and 
2-[(3,4-dihydroxyphenyl)methylene]-6-hydroxy-3(2H)benzofuranone 
(7,3',4'-trihydroxyaurone, sulfuretin) (10). Inhibition experiments suggested 
that initial C-3 hydroxylation of 1 to 7 was catalyzed by a cytochrome P450 
enzyme system. A second A. alliaceus enzyme, partially purified and identified 
as a catechol oxidase, catalyzed the oxidation of the catechol butein (7) likely 
through an ortho-quinone (8) that cyclized to the aurone product 10. This work 
showed that A. alliaceus UI315 contains oxidative enzyme systems capable of 
converting phenolic chalcones such as 1 into aurones such as 10 in a process 
that mimics plant biosynthetic pathways.

DOI: 10.1021/jf060900k
PMID: 16787010 [Indexed for MEDLINE]


2. Yao Xue Xue Bao. 2002 Feb;37(2):121-3.

[Studies on water-soluble constituents of Echinacea prupurea].

[Article in Chinese]

Li JR(1), Wang B, Qiao L, Ai TM, Zhao YY.

Author information:
(1)Department of Natural Medicine, School of Pharmaceutical Sciences, Peking 
University, Beijing 100083, China.

AIM: To study the water-soluble constituents of Echinacea purpurea.
METHODS: The compounds were isolated by chromatography method and their 
structures were identified on the basis of spectral analyses.
RESULTS: Five compounds were identified as 
2-(4-hydroxylphenyl)-ethyl-O-alpha-L-rhamnopy-ranoasyl-(1-->6)-beta-D- 
glucopyranoside, named echipuroside A 1); (6S, 
9R)-6-hydroxy-3-one-alpha-inonol-9-O-beta-D-glucopyranoside 2), 
ampelopsisionoside 3); 
phenylmethyl-6-O-beta-D-xylopyranosyl(1-->6)-beta-D-glucopyranoside 4) and 
phyenylmethyl-beta-D-glucopyranoside 5).
CONCLUSION: Compound 1 is a new compound, the others were isolated from this 
plant for the first time.

PMID: 12579956 [Indexed for MEDLINE]


3. J Med Chem. 1997 May 9;40(10):1407-16. doi: 10.1021/jm970167b.

Discovery and synthesis of 
[6-hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(4-hydroxyphenyl)]b 
enzo[b]thiophene: a novel, highly potent, selective estrogen receptor modulator.

Palkowitz AD(1), Glasebrook AL, Thrasher KJ, Hauser KL, Short LL, Phillips DL, 
Muehl BS, Sato M, Shetler PK, Cullinan GJ, Pell TR, Bryant HU.

Author information:
(1)Lilly Research Laboratories, Eli Lilly and Company, Indianapolis, Indiana 
46285, USA.

Raloxifene,[2-(4-hydroxyphenyl)-6-hydroxybenzo[b]thien-3-yl] 
[4-[2-(1-piperidinyl)ethoxy]phenyl]methanone hydrochloride (2), is 
representative of a class of compounds known as selective estrogen receptor 
modulators (SERMs) that possess estrogen agonist-like actions on bone tissues 
and serum lipids while displaying potent estrogen antagonist properties in the 
breast and uterus. As part of ongoing SAR studies with raloxifene, we found that 
replacement of the carbonyl group with oxygen 
([6-hydroxy-3-[4-[2-(1-piperidinyl)ethoxy]phenoxy]-2-(4-hydroxyphenyl)]b 
enzo[b]thiophene hydrochloride, 4c) resulted in a substantial (10-fold) increase 
in estrogen antagonist potency relative to raloxifene in an in vitro estrogen 
dependent cell proliferation assay (IC50 = 0.05 nM) in which human breast cancer 
cells (MCF-7) were utilized. In vivo, 4c potently inhibited the uterine 
proliferative response to exogenous estrogen in immature rats following both sc 
and oral dosing (ED50 of 0.006 and 0.25 mg/kg, respectively). In ovariectomized 
aged rats, 4c produced a significant maximal decrease (45%) in total cholesterol 
at 1.0 mg/kg (p.o.) and showed a protective effect on bone relative to controls 
with maximal efficacy at 1.0 mg/kg (p.o.). These data identify 4c as a novel 
SERM with greater potency to antagonize estrogen in uterine tissue and in human 
mammary cancer cells compared to raloxifene, tamoxifen or ICI-182,780.

DOI: 10.1021/jm970167b
PMID: 9154963 [Indexed for MEDLINE]


4. Cancer Res. 1983 Oct;43(10):4956-65.

New approach for visualizing estrogen receptors in target cells using inherently 
fluorescent ligands and image intensification.

Martin PM, Magdelenat HP, Benyahia B, Rigaud O, Katzenellenbogen JA.

Four fluorescent estrogen ligands were investigated as agents for visualization 
of estrogen receptors in cells: 
2-(2,4-dihydroxyphenyl)-6-hydroxy-3-benzofurancarboxylic acid delta-lactone 
(coumestrol) and 9(11)-dehydro-12-oxoestradiol 
[12-oxo-1,3,5-(10),9(11)-estratetraene-3, 17 beta-diol] (12-oxoestradiol), which 
are inherently fluorescent compounds; and tamoxifen 
[Z)-1-[4-(2-dimethylaminoethoxy)phenyl]-1,2-diphenyl-1-butene) and 
4-hydroxytamoxifen [Z)-1-[4-(2-dimethylaminoethoxy) 
phenyl]-1-(4-hydroxyphenyl)-2-phenyl-1-butene), which become maximally 
fluorescent only after ultraviolet irradiation. By conventional fluorescence 
techniques, these agents can be detected down to 10(-8) M in water, but only to 
10(-6) to 10(-7) M in protein solutions; however, by photon-counting 
spectrofluorimetry, coumestrol and 12-oxoestradiol can be detected in protein 
solutions down to 5 X 10(-10) M. Three of these compounds have good affinity for 
the estrogen receptor: coumestrol (20%); 12-oxoestradiol (12%); and 
4-hydroxytamoxifen (37%), relative to estradiol (100%). Under conditions where 
autoradiographic controls indicate that most of the estrogen receptor of MCF-7 
human breast cancer cells is in the nucleus, we could demonstrate nuclear 
fluorescence using 10(-9) M concentrations of coumestrol, 12-oxoestradiol, and 
4-hydroxytamoxifen. This nuclear fluorescence was abolished by a 200-fold excess 
of diethystilbestrol and could only be observed through a fluorescence 
microscope equipped with a microchannel image intensifier and a video camera 
detector that together provide a sensitivity enhancement of approximately 10(4). 
These studies indicate that the estrogen receptor in breast cancer cells can be 
visualized by fluorescence techniques, provided that the visualizing ligands 
have adequate affinity and specificity for the receptor and appropriate 
fluorescence characteristics, and provided that the fluorescence instrument has 
adequate sensitivity to observe fluorescence emission from cells treated with nM 
concentrations of the fluorescent agents.

PMID: 6883346 [Indexed for MEDLINE]


5. Xenobiotica. 1976 Feb;6(2):125-34. doi: 10.3109/00498257609151621.

Urinary excretion of c-hydroxy derivatives of methaqualone in man.

Burnett D, Reynolds CN, Wilson K, Francis JR.

1. Six monohydroxy metabolites of methaqualone have been identified by 
g.l.c.-mass spectrometry in the urine of healthy human subjects who received 
therapeutic doses (250 mg) of the drug (Melsed) daily for ten day. 2. The three 
major metabolites were 2-methyl-3-(2'-hydroxymethylphenyl)-4(3H)-quinazolinone, 
2-methyl-3-(2'-methyl-3'-hydroxyphenyl)-4(3H)-quinazolinone and 
2-methyl-3-(2'-methyl-4'-hydroxyphenyl)-4(3H)-quinazolinone. Three minor 
metabolites in descending order of importance were 
2-hydroxymethyl-3-o-tolyl-4(3H)-quinazolinone, 
2-methyl-6-hydroxy-3-o-tolyl-4(3H)-quinazolinone and 
2-methyl-8-hydroxy-3-o-tolyl-4(3H)-quinazolinone. 3. The 8-hydroxy metabolite is 
identified as a urinary metabolite or methaqualone in humans for the first time.

DOI: 10.3109/00498257609151621
PMID: 1274374 [Indexed for MEDLINE]