Pseudostellarins D - F, new tyrosinase inhibitory cyclic peptides from Pseudostellaria heterophylla

doi:10.1016/S0040-4020(01)89612-5

Tetrahedron

Volume 50, Issue 33, 1994, Pages 9975-9982

https://doi.org/10.1016/S0040-4020(01)89612-5 Get rights and content

Abstract

New potent tyrosinase inhibitory cyclic peptides, pseudostellarins D - F, have been isolated from the roots of Pseudostellaria heterophylla and the structures were elucidated by extensive 2D NMR methods, chemical and enzymatic degradation and ESI tandem MS spectroscopic analysis.

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Natural molecules have remarkable potential, as they are regarded to be safe and largely free of side effects. Therefore, the inhibition of tyrosinase by proteins [17], protein hydrolysates [18–20], peptides [21–32], and amino acids [26,33–35] have emerged as a novel focus in the search of natural tyrosinase inhibitors. Some previous studies have shown the effectiveness of natural [22,25,27,30,36,37], synthetic [38,39], and kojic acid [40]/ caffeic acid [31,41] coupled peptides as tyrosinase inhibitors.
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Natural bioeffective cyclooligopeptides from plant seeds of Annona genus
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Diverse cyclopeptides isolated from roots of different plants include brachystemin A-E, arenarin A, psammosilenin A & B, heterophyllin A-C, J, pseudostellarin A-H, silenin A-C, stelladelin A-D, delavayin A-C, dichotomin A-I, stellarin A-H, yunnanin A-F; from seeds of different plants include cherimolacyclopeptides A-G, cyclosquamosins A-I, annosquamosin A, fanlizhicyclopeptides A & B, cyclomontanins A-D, annomuricatin A-L, glaucacyclopeptides A & B, cyclosenegalins A & B, sclerin, glabrins A-D, cycloreticulins A-C, cyclopurpuracin, leiocyclocin A-D, cyclolinopeptide A-I, segetalin A-H; from latex of different plants include chevalierin A-C, curcacycline A-B, cyclogossine A & B, mahafacyclin A & B, podacyclin A & B, pohlianin A-C; from fruits of different plants include cycloleonurinin, cycloleonuripeptide A-D; from stems of different plants include grifficyclocin A, microtoenin A-C; from whole plants include diandrine A-D, drymarin A & B, dianthin A-F, cleromyrine I, arcticumin A-C, arenariphilin A & B, polycarponin A-C, schnabepeptide, crassipin B and from fruit peels of different plants include citrusin I-IV [10]. Plant-derived cyclic peptides possess a variety of biological activities including antiplatelet, immunomodulatory, cytotoxic [11,12], vasorelaxant [13], immunosuppressive [14], tyrosinase inhibitory activity [15,16], antimalarial [17], activity of human cyclophilin B, and estrogen-like activity [18]. Keeping in view the medicinal properties of plant originated cyclopeptides, the focus of the present review is on the exclusive structural features of Annona sp. plant seeds-originated bioactive cyclooligopeptides, with special attention on the structure activity relationship, synthesis and their emerging bioproperties.
The Annona L. is one of the most significant genus of the Annonaceae family due to its widespread medicinal properties. This genus has a variety of active metabolites, including alkaloids, isoquinolines, peptides, acetogenins, lectins, volatile oils etc. Due to the constitution of cyclopeptides with an expanded spectrum of distinctive bioproperties, this genus is predominantly preferred over other species. The cytotoxicity, vasorelaxant activity, anti-inflammatory and other properties exhibited by cyclooligopeptides from seeds of Annona genus plants make these metabolites attractive leads for the drug discovery process. The present review covers the structural characteristics, structure activity relationship, synthesis strategies, pharmacological properties of plant seeds-originated bioactive peptides from Annona genus, which may be vital for the development of novel therapeutics based on peptide skeleton.
Rapid authentication of Pseudostellaria heterophylla (Taizishen) from different regions by Raman spectroscopy coupled with chemometric methods
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Pseudostellaria heterophylla (Miq.) Pax (Family Caryophyllaceae), named as “Taizishen”, is a popular traditional Chinese herbal medicine [1]. According to the records of the provincial plant records, the wild resources of P. heterophylla distributed widely in China, such as Fujian, Zhejiang, Jiangsu, Hebei and Shaanxi provinces [2].
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Determination of the phytochemical composition of Jingning fang and the in vivo pharmacokinetics of its metabolites in rat plasma by UPLC–MS/MS
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Jingning fang (JNF) is an effective Traditional Chinese Medicine (TCM) which is used for the treatment of Attention Deficit Hyperactivity Disorder (ADHD). To clarify the bioactive constituents of JNF, a Thermo Q Exactive™ Plus Orbitrap™ mass spectrometer was used in this study. More than 127 chemical compounds were isolated and identified tentatively in the JNF extract, while 42 prototype constituents with 4 potential metabolites were identified tentatively in rat plasma. A method for simultaneous determination of polygalaxanthone III (PAIII), sibiricose A₅ (A₅), sibiricose A₆ (A₆), 3, 6′-disinapoyl sucrose (3,6′-DISS), tenuifoliside C (TEC), tenuifolin B (TNB), verbascoside (VCE), heterophyllin B (HEB) and schisandrin (SCH) in rat was developed and validated using polydatin (PLN) and psoralen (PSN) as internal standards. All calibration curves proved favorable linearity (R² ≥ 0.9923) in linear ranges. The lower limit of quantification (LLOQ) was 2.5 ng/mL for PAIII, A₅, 3, 6′-DISS, TNB, VCE, HEB and SCH, 1.0 ng/mL for A₆ and TEC, respectively. Intra-day and inter-day precisions didn’t exceed 14.0% for all the analytes. Extraction recoveries and matrix effects of analytes and IS were acceptable. The validated method has been successfully applied to the pharmacokinetics (PK) studies of the nine compounds in JNF. These findings are useful for predicting the bioactive components of JNF, and will aid in optimizing dose regimens of the drug.
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^☆: Cyclic Peptides from Higher Plants. Part 7., Part 6, H. Morita, T. Kayashita, H. Kobata, A. Gonda, K. Takeya and H. Itokawa, Tetrahedron, 1994, 50, 6797.

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Pseudostellarins D - F, new tyrosinase inhibitory cyclic peptides from Pseudostellaria heterophylla☆

Abstract

Tetrahedron

Chem. Lett.

J. Chem. Soc. Perkin Trans. 1

Chem. Pharm. Bull.

Heterocycles

Phytochemistry

Chem. Pharm. Bull.

Chem. Lett.

J. Magn. Reson.

Jpn. J. Dermatol.

Tetrahedron Lett.

Carlsberg Res. Commun.