Psychoactive Plant Database - Neuroactive Phytochemical Collection

1. Phytochemistry. 2017 Sep;141:105-113. doi: 10.1016/j.phytochem.2017.04.023.
Epub  2017 Jun 7.

Triterpene saponins from Billia rosea.

De Freitas L(1), Jimenez D(2), Pimentel S(2), Mitaine-Offer AC(3), Pouységu 
L(4), Quideau S(4), Paululat T(5), Gonzalez-Mujica F(6), Rojas LB(7), Rodríguez 
M(2), Lacaille-Dubois MA(8).

Author information:
(1)Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, 
Université de Bourgogne Franche-Comté, 7, Bd. Jeanne d'Arc, BP 87900, F-21079 
Dijon Cedex, France; Laboratorio de Productos Naturales, Escuela de Química, 
Facultad de Ciencias, Universidad Central de Venezuela, Caracas 47102, 
Venezuela.
(2)Laboratorio de Productos Naturales, Escuela de Química, Facultad de Ciencias, 
Universidad Central de Venezuela, Caracas 47102, Venezuela.
(3)Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, 
Université de Bourgogne Franche-Comté, 7, Bd. Jeanne d'Arc, BP 87900, F-21079 
Dijon Cedex, France.
(4)Institut des Sciences Moléculaires, CNRS-UMR 5255 et Institut Européen de 
Chimie et Biologie, Université de Bordeaux, 2 Rue Robert Escarpit, 33607 Pessac 
Cedex, France.
(5)Universität Siegen, OC-II, Naturwissenschaftlich-Technische Fakultät, 
Adolf-Reichwein-Str. 2, D-57076 Siegen, Germany.
(6)Sección de Bioquímica Médica, Instituto de Medicina Experimental, Facultad de 
Medicina, Universidad Central de Venezuela, Caracas 50587, Venezuela.
(7)Laboratorio de Productos Naturales, Departamento de Quimica, Facultad de 
Ciencias, Universidad de los Andes, Mérida 5101, Venezuela.
(8)Laboratoire de Pharmacognosie, PEPITE EA 4267, UFR des Sciences de Santé, 
Université de Bourgogne Franche-Comté, 7, Bd. Jeanne d'Arc, BP 87900, F-21079 
Dijon Cedex, France. Electronic address: m-a.lacaille-dubois@u-bourgogne.fr.

Five previously undescribed triterpene saponins, billiosides A-E, and a known 
analogue, were isolated from the seeds of Billia rosea (Planch. & Linden) C. 
Ulloa & P. Jørg. Their structures were elucidated on the basis of extensive 1D 
and 2D NMR experiments (1H, 13C, DEPT, COSY, TOCSY, NOESY, ROESY, HSQC, and 
HMBC) and mass spectrometry as 
(3β,21β,22α)-3-[(2-O-β-D-glucopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-glucopyranosyl)oxy]-21-[((2E,6S)-2,6-dimethyl-6-hydroxyocta-2,7-dienoyl)oxy]-22-(acetyloxy)-24-hydroxyolean-12-en-28-oic 
acid, 
(3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-β-D-glucopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl 
O-α-L-arabinopyranosyl-(1 → 4)-β-D-glucopyranoside, 
(3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-xylopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl 
O-β-D-glucopyranoside, 
(3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-glucopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl 
O-β-D-glucopyranoside, 
(3β,21β,22α)-3-[(2-O-β-D-galactopyranosyl-O-[α-L-arabinopyranosyl-(1 → 4)]-β-D-glucopyranosyl)oxy]-21,22-dihydroxyolean-12-en-28-yl 
O-β-D-glucopyranosyl-(1 → 6)-β-D-glucopyranoside, and dipteroside A. Billiosides 
B and C exhibited moderate effects when tested as hepatic glucose-6-phosphatase 
inhibitors and as glucose intestinal absorption inhibitors, using in situ rat 
intestinal segments.

Copyright © 2017 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.phytochem.2017.04.023
PMID: 28599241 [Indexed for MEDLINE]


2. Carbohydr Polym. 2015 Jan 22;115:472-7. doi: 10.1016/j.carbpol.2014.09.017.
Epub  2014 Sep 21.

Structural features and antitumor activity of a novel polysaccharide from 
alkaline extract of Phellinus linteus mycelia.

Pei JJ(1), Wang ZB(2), Ma HL(2), Yan JK(3).

Author information:
(1)School of Food & Biological Engineering, Jiangsu University, Zhenjiang 
212013, China.
(2)School of Food & Biological Engineering, Jiangsu University, Zhenjiang 
212013, China; Physical Processing of Agricultural Products Key Lab of Jiangsu 
Province, Zhenjiang 212013, Jiangsu, China.
(3)School of Food & Biological Engineering, Jiangsu University, Zhenjiang 
212013, China; Physical Processing of Agricultural Products Key Lab of Jiangsu 
Province, Zhenjiang 212013, Jiangsu, China. Electronic address: 
jkyan_27@163.com.

A novel high molecular weight polysaccharide (PL-N1) was isolated from alkaline 
extract of the cultured Phellinus linteus mycelia. The weight average molecular 
weight (Mw) of PL-N1 was estimated at 343,000kDa. PL-N1 comprised arabinose, 
xylose, glucose, and galactose in the molar ratio of 4.0:6.7:1.3:1.0. The 
chemical structure of PL-N1 was investigated by FTIR and NMR spectroscopies and 
methylation analysis. The results showed that the backbone of PL-N1 comprised 
(1→4)-linked β-D-xylopyranosyl residues, (1→2)-linked α-D-xylopyranosyl 
residues, (1→4)-linked α-D-glucopyranosyl residues, (1→5)-linked 
β-D-arabinofuranosyl residues, (1→4)-linked β-D-xylopyranosyl residues which 
branched at O-2, and (1→4)-linked β-D-galactopyranosyl residues which branched 
at O-6. The branches consisted of (1→)-linked α-D-arabinofuranosyl residues. 
Antitumor activity assay in vitro showed that PL-N1 could inhibit the growth of 
HepG2 cells to a certain extent in a dose-dependent manner. Thus, PL-N1 may be 
developed as a potential, natural antitumor agent and functional food.

Copyright © 2014 Elsevier Ltd. All rights reserved.

DOI: 10.1016/j.carbpol.2014.09.017
PMID: 25439921 [Indexed for MEDLINE]


3. Pharm Biol. 2014 Jun;52(6):750-5. doi: 10.3109/13880209.2013.869759. Epub 2014
 Mar 12.

Antidiabetic potential of triterpenoid saponin isolated from Primula 
denticulate.

Singh S(1), Farswan M, Ali S, Afzal M, Al-Abbasi FA, Kazmi I, Anwar F.

Author information:
(1)Department of Pharmacology, Siddhartha Institute of Pharmacy , Dehradun, 
Uttarakhand , India .

CONTEXT: Primula denticulate Sm. (Primulaceae), commonly known as drumstick 
primula, is traditionally used to treat diabetes and urinary disorders. In the 
present study, a new triterpenoid saponin was isolated. Triterpenoids generally 
show antidiabetic activity. Considering its traditional use and chemical nature 
of the molecule, the present study was designed to evaluate the antidiabetic 
activity.
OBJECTIVE: Antidiabetic activity of triterpenoid saponin (TTS) isolated from P. 
denticulate.
MATERIALS AND METHODS: A new TTS was isolated from the leaf of P. denticulate by 
column chromatography on CHCl3/MeOH (8.5:1.5) fraction. It was further 
characterized by using NMR, UV, and IR spectroscopic methods. Ethanol and 
aqueous extracts of the leaf were also prepared. Antidiabetic study for TTS, 
ethanol extract, and aqueous extract was carried out in streptozotocin 
(STZ)-induced diabetic rats at doses of 200, 1000, and 1000 mg/kg body weight, 
respectively. A toxicity study was also performed.
RESULTS: Isolated new TTS molecule was characterized as 
3-O[β-d-xylopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-α-l-arabinopyranosyloxy]-16α-hydroxy-13β,28-epoxy-olean-30-al 
by NMR, UV, and IR spectroscopic methods. This new TTS was found to be effective 
in lowering blood-glucose level in the experimental rat model, thus establishing 
its antidiabetic property (168.8   ± 4.58) when compared with disease control 
(258.8 ± 0.60). Its LD50 value was found at a dose of 2000 mg/kg. The level of 
insulin was restored by TTS and ethanol extract up to 31.49 µU/ml and 38.90 
µU/ml, respectively, when compared with disease control (18.45 µU/ml).
DISCUSSION AND CONCLUSION: In conclusion, 
3-O[β-d-xylopyranosyl-(1 → 2)-β-d-glucopyranosyl-(1 → 4)-α-l-arabinopyranosyloxy]-16α-hydroxy-3β,28-epoxy-olean-30-al 
possesses potential glucose lowering properties, i.e., antidiabetic potential 
against STZ-induced diabetic rats.

DOI: 10.3109/13880209.2013.869759
PMID: 24617737 [Indexed for MEDLINE]


4. Fitoterapia. 2013 Jan;84:295-301. doi: 10.1016/j.fitote.2012.12.017. Epub 2012
 Dec 22.

Sibiricasaponins A-E, five new triterpenoid saponins from the aerial parts of 
Polygala sibirica L.

Song YL(1), Zeng KW, Shi TX, Jiang Y, Tu PF.

Author information:
(1)State Key Laboratory of Natural and Biomimetic Drugs, School of 
Pharmaceutical Sciences, Peking University, Beijing 100191, China.

Five new triterpenoid saponins, named as sibiricasaponins A-E (1-5), were 
isolated and identified from the aerial parts of Polygala sibirica L., together 
with nine known triterpenoid saponins (6-14). The chemical structures of the 
five new triterpenoid saponins (1-5) were elucidated as 
3β,19α-dihydroxyurso-12-ene-23,28-dioic acid 3-O-β-d-glucuronopyranoside (1), 
pomolic acid 3-O-(3-O-sulfo)-α-l-arabinopyranoside (2), pomolic acid 
3-O-(4-O-sulfo)-β-d-xylopyranoside (3), pomolic acid 
3-O-(2-O-acetyl-3-O-sulfo)-α-l-arabinopyranoside (4), and 3-O-β-d-glucopyranosyl 
medicagenic acid 28-O-β-d-galactopyranosyl (1→4)-β-d-xylopyranosyl 
(1→4)-α-l-rhamnopyranosyl (1→2)-(4-O-acetyl)-[β-d-apiofuranosyl 
(1→3)]-β-d-fucopyranosyl ester (5), respectively, on the basis of spectroscopic 
data and physicochemical evidences. These isolated compounds (1-14) were 
evaluated for their anti-ischemic effects on oxygen/glucose deprivation (OGD) 
model in vitro, and only compound 7 showed a weak anti-ischemia effect, with 
EC(50) value of 46.7μM.

Copyright © 2012 Elsevier B.V. All rights reserved.

DOI: 10.1016/j.fitote.2012.12.017
PMID: 23266727 [Indexed for MEDLINE]


5. Org Lett. 2007 Jul 19;9(15):2755-8. doi: 10.1021/ol070720b. Epub 2007 Jun 28.

Highly beta-selective and direct formation of 2-O-glycosylated glucosides by 
ring restriction into twist-boat.

Okada Y(1), Nagata O, Taira M, Yamada H.

Author information:
(1)School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, 
Sanda 669-1337, Japan.

Three disaccharide donors, ethyl 
2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-beta-D-xylopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-beta-D-glucopyranoside, 
ethyl 
2-O-(2,3,4-tris-O-tert-butyldimethylsilyl-alpha-L-rhamnopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-beta-D-glucopyranoside, 
and ethyl 
2-O-(2,3,4,6-tetrakis-O-tert-butyldimethylsilyl-beta-D-glucopyranosyl)-3,4,6-tris-O-tert-butyldimethylsilyl-1-thio-beta-D-glucopyranoside, 
produced a highly beta-selective glycosidation up to alpha/beta = 2/98 using 
MeOTf as the activator and 2,6-lutidine as an additive. The ring conformations 
of the glucose part in these disaccharide donors were all restricted to 3S1, and 
the conformation would lead to the stereoselectivity.

DOI: 10.1021/ol070720b
PMID: 17602562 [Indexed for MEDLINE]