Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. J Ethnopharmacol. 2018 Jan 10;210:260-274. doi: 10.1016/j.jep.2017.08.022.
Epub  2017 Aug 31.

Physalis alkekengi L. var. franchetii (Mast.) Makino: An ethnomedical, 
phytochemical and pharmacological review.

Li AL(1), Chen BJ(2), Li GH(3), Zhou MX(1), Li YR(1), Ren DM(1), Lou HX(1), Wang 
XN(4), Shen T(5).

Author information:
(1)Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, 
Shandong University, Jinan, PR China.
(2)Department of Pharmacy, The Third Hospital of Jinan, Jinan, PR China.
(3)Department of Pharmacy, Jinan Maternity and Child Care Hospital, Jinan, PR 
China.
(4)Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, 
Shandong University, Jinan, PR China. Electronic address: wangxn@sdu.edu.cn.
(5)Key Lab of Chemical Biology (MOE), School of Pharmaceutical Sciences, 
Shandong University, Jinan, PR China. Electronic address: shentao@sdu.edu.cn.

ETHNOPHARMACOLOGICAL RELEVANCE: The calyxes and fruits of Physalis alkekengi L. 
var. franchetii (Mast.) Makino (Physalis Calyx seu Fructus), have been widely 
used in traditional and indigenous Chinese medicines for the therapy of cough, 
excessive phlegm, pharyngitis, sore throat, dysuria, pemphigus, eczema, and 
jaundice with a long history.
AIM OF THE REVIEW: The present review aims to achieve a comprehensive and 
up-to-date investigation in ethnomedical uses, phytochemistry, pharmacology, and 
toxicity of P. alkekengi var. franchetii, particularly its calyxes and fruits. 
Through analysis of these findings, evidences supporting their applications in 
ethnomedicines are illustrated. Possible perspectives and opportunities for the 
future research are analyzed to highlight the gaps in our knowledge that 
deserves further investigation.
MATERIAL AND METHODS: Information on P. alkekengi var. franchetii was collected 
via electronic search of major scientific databases (e.g. Web of Science, 
SciFinder, Google Scholar, Pubmed, Elsevier, SpringerLink, Wiley online and 
China Knowledge Resource Integrated) for publications on this medicinal plant. 
Information was also obtained from local classic herbal literature on 
ethnopharmacology.
RESULTS: About 124 chemical ingredients have been characterized from different 
parts of this plant. Steroids (particularly physalins) and flavonoids are the 
major characteristic and bioactive constituents. The crude extracts and the 
isolated compounds have demonstrated various in vitro and in vivo 
pharmacological functions, such as anti-inflammation, inhibition of tumor cell 
proliferation, antimicrobial activity, diuretic effect, anti-diabetes, 
anti-asthma, immunomodulation, and anti-oxidation.
CONCLUSIONS: P. alkekengi var. franchetii is an important medicinal plant for 
the ethnomedical therapy of microbial infection, inflammation, and respiratory 
diseases (e.g. cough, excessive phlegm, pharyngitis). Phytochemical and 
pharmacological investigations of this plant definitely increased in the past 
half century. The chemical profiles, including ingredients and structures, have 
been adequately verified. Modern pharmacological studies supported its uses in 
the traditional and folk medicines, however, the molecular mechanisms of 
purified compounds remained unclear and were worth of further exploration. 
Therefore, the researchers should be paid more attention to a better utilization 
of this plant.

Copyright © 2017 Elsevier Ireland Ltd. All rights reserved.

DOI: 10.1016/j.jep.2017.08.022
PMID: 28838654 [Indexed for MEDLINE]


2. Biol Pharm Bull. 1995 Dec;18(12):1676-80. doi: 10.1248/bpb.18.1676.

Potentiating effects on pilocarpine-induced saliva secretion, by extracts and 
N-containing sugars derived from mulberry leaves, in streptozocin-diabetic mice.

Chen F(1), Nakashima N, Kimura I, Kimura M, Asano N, Koya S.

Author information:
(1)Department of Chemical Pharmacology, Toyama Medical and Pharmaceutical 
University, Japan.

The effects of hot water extracts and six compounds of N-containing sugars, 
1-deoxynojirimycin (DNJ), N-methyl-DNJ (N-Me-DNJ), 
2-O-alpha-D-galactopyranosyl-DNJ (GAL-DNJ), fagomine, 
1,4-dideoxy-1,4-imino-D-arabinitol (DAB), and 1,2 alpha,3 beta,4 
alpha-tetrahydroxynortropane (calystegin B2), derived from mulberry leaves 
(Morus alba L.), were investigated on pilocarpine-induced saliva secretion in 
streptozocin (STZ)-induced diabetic mice. The extracts (100 and 200 mg/kg, i.p.) 
significantly potentiated the pilocarpine-induced salivary flow but not the 
protein content. The component compounds (37.5-300 mumol/kg) potentiated the 
saliva secretion, and the potency order was DAB > fagomine > GAL-DNJ. Only 
fagomine significantly increased the protein content in the saliva. The 
potentiation of pilocarpine-induced salivary flow was correlated with 
anti-hyperglycemic effects by the extract and GAL-DNJ from mulberry leaves in 
the same dose ranges.

DOI: 10.1248/bpb.18.1676
PMID: 8787787 [Indexed for MEDLINE]


3. Eur J Biochem. 1995 Apr 15;229(2):369-76. doi:
10.1111/j.1432-1033.1995.0369k.x.

Calystegins of Physalis alkekengi var. francheti (Solanaceae). Structure 
determination and their glycosidase inhibitory activities.

Asano N(1), Kato A, Oseki K, Kizu H, Matsui K.

Author information:
(1)Faculty of Pharmaceutical Sciences, Hokuriku University, Japan.

Five calystegins were extracted from the roots of Physalis alkekengi var. 
francheti (Solanaceae) with hot water and purified to homogeneity by the 
combination of a variety of ion-exchange column chromatographies. Their 
structures have been determined from the 1H- and 13C-NMR spectral data, and two 
of the compounds were identified as calystegins A3 and B2, which have been 
isolated from the roots of Calystegia sepium (Convolvulaceae). Two of the 
remaining three were found to be 1 alpha, 3 alpha, 4 beta-trihydroxy-nor-tropane 
and 1 alpha, 2 alpha, 3 alpha, 4 beta-tetrahydroxy-nor-tropane and given the 
trivial name calystegins A5 and B3, respectively. The last calystegin was 
assigned as 1 alpha, 2 beta, 3 alpha, 6 alpha-tetrahydroxy-nor-tropane, which 
was the same as the relative configuration proposed in the literature for 
calystegin B1 isolated from C. sepium. However, the 13C-NMR spectral data for 
the compound from C. sepium differed substantially from our results. From a 
personal communication with the authors of the original paper on calystegins, it 
was clarified that the 13C-NMR chemical shifts of calystegin B1 in the original 
paper had been erroneous. Since their corrected 13C-NMR data of calystegin B1 
and its 1H-NMR chemical shifts in the original paper are very close to our 
present data, we concluded that both compounds from C. sepium and P. alkekengi 
are identical. Calystegin B2 has been known to be a potent competitive inhibitor 
of almond beta-glucosidase (Ki = 1.2 microM) and coffee bean alpha-galactosidase 
(Ki = 0.86 microM). In this study calystegin B1 (1 alpha, 2 beta, 3 alpha, 6 
alpha-tetrahydroxy-nor-tropane) proved to be a potent competitive inhibitor of 
almond beta-glucosidase (Ki = 1.9 microM) and bovine liver beta-galactosidase 
(Ki = 1.6 microM), but not an inhibitor of alpha-galactosidases. Calystegin A3 
was found to be a weaker inhibitor compared to calystegin B2 but with the same 
inhibitory spectrum. Calystegin A5, a 2-deoxy derivative of calystegin B2, 
showed no activity against any glycosidases tested. Since calystegin B3, a 
2-epimer of calystegin B2, also exhibited only a weak inhibitory activity, it 
was concluded that the equatorially oriented OH group at C2 is the essential 
feature for recognition and strong binding by the active site of 
glycosidases.(ABSTRACT TRUNCATED AT 400 WORDS)

DOI: 10.1111/j.1432-1033.1995.0369k.x
PMID: 7744059 [Indexed for MEDLINE]


4. Carbohydr Res. 1994 Jun 17;259(2):243-55. doi: 10.1016/0008-6215(94)84060-1.

N-containing sugars from Morus alba and their glycosidase inhibitory activities.

Asano N(1), Oseki K, Tomioka E, Kizu H, Matsui K.

Author information:
(1)Faculty of Pharmaceutical Sciences, Hokuriku University, Ishikawa, Japan.

The reexamination of N-containing sugars from the roots of Morus alba by 
improved purification procedures led to the isolation of eighteen N-containing 
sugars, including seven that were isolated from the leaves of Morus bombycis. 
These N-containing sugars are 1-deoxynojirimycin (1), 
N-methyl-1-deoxynojirimycin (2), fagomine (3), 3-epi-fagomine (4), 
1,4-dideoxy-1,4-imino-D-arabinitol (5), 1,4-dideoxy-1,4-imino-D-ribitol (6), 
calystegin B2 (1 alpha,2 beta,3 alpha,4 beta-tetrahydroxy-nor-tropane, 7), 
calystegin C1 (1 alpha,2 beta,3 alpha,4 beta,6 alpha-pentahydroxy-nor-tropane, 
8), 1,4-dideoxy-1,4-imino-(2-O-beta-D-glucopyranosyl)-D-arabinitol (9), and nine 
glycosides of 1. These glycosides consist of 2-O- and 
6-O-alpha-D-galactopyranosyl-1-deoxynojirimycins (10 and 11, respectively), 
2-O-, 3-O- and 4-O-alpha-D-glucopyranosyl-1-deoxynojirimycins (12, 13, and 14, 
respectively), and 2-O-, 3-O-, 4-O- and 
6-O-beta-D-glucopyranosyl-1-deoxynojirimycins (15, 16, 17, and 18, 
respectively). Compound 4 is a new member of polyhydroxylated piperidine 
alkaloids, and the isolation of 6 is the first report of its natural occurrence. 
It has recently been found that the polyhydroxy-nor-tropane alkaloids possess 
potent glycosidase inhibitory activities. Calystegin A3 is the 
trihydroxy-nor-tropane, and calystegins B1 and B2 are the 
tetrahydroxy-nor-tropane. Calystegin C1, a new member of calystegins, is the 
first naturally occurring pentahydroxy-nor-tropane alkaloid. The inhibitory 
activities of these compounds were investigated against rat digestive 
glycosidases and various commercially available glycosidases.

DOI: 10.1016/0008-6215(94)84060-1
PMID: 8050098 [Indexed for MEDLINE]


5. Arch Biochem Biophys. 1993 Jul;304(1):81-8. doi: 10.1006/abbi.1993.1324.

Calystegins, a novel class of alkaloid glycosidase inhibitors.

Molyneux RJ(1), Pan YT, Goldmann A, Tepfer DA, Elbein AD.

Author information:
(1)Western Regional Research Center, United States Department of Agriculture, 
Albany, California 94710.

The alkaloid extract from roots of naturally growing Convolvulus arvensis, 
purified by ion-exchange chromatography, showed significant inhibitory activity 
toward beta-glucosidase and alpha-galactosidase. The demonstrated occurrence of 
polyhydroxy-nortropane alkaloids, the calystegins, in C. arvensis and their 
structural similarity to known polyhydroxy alkaloid glycosidase inhibitors, 
suggested that these might be responsible for the observed activity. Pure 
calystegins, isolated from transformed root cultures of the related plant 
species Calystegia sepium, were tested for glycosidase inhibitory activity. The 
purity of the alkaloids was established by gas chromatography and their identity 
confirmed by their mass spectrometric fragmentation patterns. The trihydroxy 
alkaloid, calystegin A3, was a moderately good inhibitor of beta-glucosidase (Ki 
= 4.3 x 10(-5) M) and a weak inhibitor of alpha-galactosidase (Ki = 1.9 x 10(-4) 
M). An increased level of hydroxylation, as in the tetrahydroxy calystegins B, 
consisting of 27% calystegin B1 and 73% calystegin B2, resulted in greatly 
enhanced inhibitory activity. The calystegins B were potent inhibitors of 
beta-glucosidase (Ki = 3 x 10(-6) M) and alpha-galactosidase (Ki = 7 x 10(-6) 
M). These levels of activity are comparable with those of the polyhydroxy 
indolizidine alkaloids castanospermine and swainsonine toward alpha-glucosidase 
and alpha-mannosidase, respectively, and of the polyhydroxy pyrrolizidine 
alkaloid australine toward alpha-glucosidase. The calystegins therefore compose 
a new structural class of polyhydroxy alkaloids, the nortropanes, possessing 
potent glycosidase inhibitory properties.

DOI: 10.1006/abbi.1993.1324
PMID: 8323301 [Indexed for MEDLINE]