Psoralenoside
(Synonyms: 补骨脂苷) 目录号 : GC64646Psoralenoside 是源于 Psoralea corylifolia 中的一种苯并呋喃苷。Psoralenoside 对组胺 H1、钙调素和电压门控 l 型钙通道 (E-value≥-6.5 Kcal/mol) 具有较高的亲和力。Psoralenoside 具有雌激素样活性、促进成骨细胞增殖活性、抗肿瘤活性和抗菌活性。
Cas No.:905954-17-8
Sample solution is provided at 25 µL, 10mM.
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Psoralenoside is a benzofuran glycoside from Psoralea corylifolia[1]. Psoralenoside exhibits high binding affinities against histaminergic H1, calmodulin, and voltage-gated L-type calcium channels (E-value≥-6.5 Kcal/mol)[2]. Psoralenoside shows estrogen-like activity, osteoblastic proliferation accelerating activity, antitumor effects and antibacterial activity[3].
[1]. Chun-Feng Qiao, et al.Psoralenoside and isopsoralenoside, two new benzofuran glycosides from Psoralea corylifolia. Chem Pharm Bull (Tokyo). 2006 May;54(5):714-6.
[2]. Muhammad Bilal Riaz, et al. Pharmacological and computational evaluation of fig for therapeutic potential in hyperactive gastrointestinal disorders. BMC Complement Altern Med. 2019 Dec 3;19(1):348.
[3]. Yue-Fei Wang, et al.A UPLC-MS/MS method for in vivo and in vitro pharmacokinetic studies of psoralenoside, isopsoralenoside, psoralen and isopsoralen from Psoralea corylifolia extract. J Ethnopharmacol
Cas No. | 905954-17-8 | SDF | Download SDF |
别名 | 补骨脂苷 | ||
分子式 | C17H18O9 | 分子量 | 366.32 |
溶解度 | DMSO : 100 mg/mL (272.99 mM; Need ultrasonic) | 储存条件 | 4°C, away from moisture and light |
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1 mM | 2.7299 mL | 13.6493 mL | 27.2985 mL |
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10 mM | 0.273 mL | 1.3649 mL | 2.7299 mL |
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[Biotransformation of Psoralenoside and isopsoralenoside in Psoraleae Fructus incubated with human intestinal bacteria flora in vitro]
Zhongguo Zhong Yao Za Zhi 2022 Jul;47(14):3822-3827.PMID:35850840DOI:10.19540/j.cnki.cjcmm.20220325.201.
Absorption is crucial to the resultant efficacy of oral drugs where the intestinal bacteria flora functions as one of the first-pass effects.The present study investigated the biotransformation of Psoralenoside and isopsoralenoside in Chinese medicine Psoraleae Fructus(the dried fruit of Psoralea corylifolia) with the internationally recognized human intestinal bacteria flora model in vitro.Pso-ralenoside and isopsoralenoside were anaerobically incubated with human intestinal bacteria flora at 37 ℃, respectively, and biotransformation products were analyzed and identified using high-performance liquid chromatography-tandem mass spectrometry(HPLC-MS) and comparison with reference standards.The main biotransformation products of Psoralenoside were psoralen and a small amount of 6,7-furano-hydrocoumaric acid, and the main biotransformation products of isopsoralenoside were isopsoralen and a small amount of 5,6-furano-hydrocoumaric acid.
[Pharmacokinetic characteristics of psoralen,isopsoralen,Psoralenoside and isopsoralenoside in rats after oral administration of Psoraleae Fructus extract]
Zhongguo Zhong Yao Za Zhi 2021 Aug;46(16):4244-4251.PMID:34467739DOI:10.19540/j.cnki.cjcmm.20210318.202.
Coumarins are the main active components in Psoraleae Fructus. To study the multi-component pharmacokinetics of Psoraleae Fructus, this study established a sensitive and rapid ultra-pressure liquid chromatography coupled to tandem mass spectrometry(UPLC-MS/MS) method for simultaneous determination of psoralen, isopsoralen, Psoralenoside, and isopsoralenoside in rat plasma. After validation, the method was applied to the investigation of pharmacokinetics of psoralen, isopsoralen, Psoralenoside, and isopso-ralenoside in rats after single and multiple administration of Psoraleae Fructus extract. The results revealed that the exposure of psoralen and isopsoralen in rat plasma was high after a single intragastric administration of Psoraleae Fructus extract, with an AUC_(0-∞) of 443 619-582 680 and 167 314-276 903 ng·mL~(-1)·h~(-1), respectively. Compared with these two compounds, the exposure of Psoralenoside and isopsoralenoside was lower with marked gender difference. After 7-day administration of Psoraleae Fructus extract to rats, the AUC_(0-∞) of psoralen and isopsoralen was 29 701-81 783 and 39 234-89 914 ng·mL~(-1)·h~(-1), respectively, which was significantly lower than that at the first day(P<0.05), and that of Psoralenoside and isopsoralenoside was 7 360-19 342 and 8 823-45 501 ng·mL~(-1)·h~(-1), respectively. There was no significant gender difference in exposure of Psoralenoside and isopsoralenoside in male and female rats. However, the exposure of Psoralenoside and isopsoralenoside in male rats was reduced(P<0.05), and the t_(1/2) and mean residence time(MRT) were shortened, suggesting that the removal of these two compounds from the body was accelerated.
Psoralenoside and isopsoralenoside, two new benzofuran glycosides from Psoralea corylifolia
Chem Pharm Bull (Tokyo) 2006 May;54(5):714-6.PMID:16651775DOI:10.1248/cpb.54.714.
Two new benzofuran glycosides, called Psoralenoside and isopsoralenoside, were isolated from the fruits of Psoralea corylifolia, together with nine known compounds. Their structures were elucidated by detailed spectral analyses including extensive two dimensional (2D) NMR spectra.
A UPLC-MS/MS method for in vivo and in vitro pharmacokinetic studies of Psoralenoside, isopsoralenoside, psoralen and isopsoralen from Psoralea corylifolia extract
J Ethnopharmacol 2014;151(1):609-17.PMID:24315982DOI:10.1016/j.jep.2013.11.013.
Ethnopharmacological relevance: The dried fruit of Psoralea corylifolia L. has been used to prevent and treat vitiligo, osteoporosis, arthralgia and asthma in Traditional Chinese Medicine for some 1600 years. Psoralen (P), isopsoralen (IP), Psoralenoside (PO) and isopsoralenoside (IPO) are the major coumarins and coumarin-related benzofuran glycosides in Psoraleae Fructus, which have been reported to show estrogen-like activity, osteoblastic proliferation accelerating activity, antitumor effects and antibacterial activity. The first aim of this study is to develop a rapid, sensitive and selective ultra performance liquid chromatography tandem mass spectrometry (UPLC-MS/MS) approach for simultaneous determination of PO, IPO, P and IP in rat plasma and samples collected from in vitro incubation experiments. The second aim is to investigate the pharmacokinetic properties of PO, IPO, P and IP after oral administration of Psoralea corylifolia extract (PCE) to rats. The third aim is to confirm the biotransformation of PO to P or IPO to IP under gastrointestinal conditions. Materials and methods: A UPLC-MS/MS method with a C18 column and a mobile phase of methanol-0.1% aqueous formic acid was validated according to the criteria in FDA guidelines about bioanalytical method, which was developed to investigate the pharmacokinetic behavior of PO, IPO, P and IP from PCE and the metabolic pathways of PO to P or IPO to IP. Results: The criteria for establishment of a new UPLC-MS/MS method including selectivity, linearity, accuracy, precision, extraction recovery, matrix effect and stability were validated. This method was successfully applied to the quantitative determination of PO, IPO, P and IP in biological samples collected from both in vitro incubations and in vivo rat experiments. After oral administration of PCE to rat, pharmacokinetic parameters of these four compounds indicated that in vivo biotransformation may occur between PO and P or IPO and IP. Purified benzofuran glycosides fraction (PBGF), containing only PO and IPO, was orally administered to rats to further confirm the biotransformation of PO to P or IPO to IP under gastrointestinal conditions. An in vitro incubation study elucidated that PO and IPO were metabolized to P and IP by intestinal microflora through de-glucosylation. Conclusions: This paper developed a rapid, sensitive and selective UPLC-MS/MS method for simultaneous determination of PO, IPO, P and IP from PCE in biological samples, and investigated on their comprehensive in vivo and in vitro pharmacokinetic studies. These obtained results showed that the metabolism by intestinal bacteria plays an important role in pharmacological effects of orally administered PCE.
Quality assessment of fructus psoraleae
Chem Pharm Bull (Tokyo) 2006 Jun;54(6):887-90.PMID:16755065DOI:10.1248/cpb.54.887.
Two newly-reported benzofuran glycosides, named Psoralenoside and isopsoralenoside, along with two major coumarins, psoralen and isopsoralen, were simultaneously determined in twenty-three samples of Fructus Psoraleae collected from different growth areas in China. The quantitative method was validated, and the mean recovery rates from fortified samples (n=5) of Psoralenoside, isopsoralenoside, psoralen and isopsoralen, were 96.5%, 97.1%, 100.7%, and 99.3% with variation coefficient of 3.1%, 3.6%, 2.3%, and 2.2%, respectively. An interesting biotransformation relationship between the glycosides and the coumarins was revealed on the basis of the quality analysis results. It was also suggested that Psoralenoside and isopsoralenoside should be used as key quality markers for Fructus Psoraleae, together with the commonly used psoralen and isopsoralen.