Microbial Metabolism. Part 8. The Pyranocoumarin, Decursin

Herath, Wimal; Reddy, N Mohan; Khan, Ikhlas A.

doi:10.1248/cpb.55.1512

Cited by 9 publications

(4 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The m / z ratio of the metabolite was determined to be 247 [M + H] + (calcd for C 14 H 15 O 4 , 247). Both 1 H NMR spectra and molecular mass data were in accordance with published data for decursinol − . Thus, the isolated metabolite was successfully identified as decursinol.…”

Section: Resultssupporting

confidence: 84%

“…Decursinol has been prepared by organic synthesis , , which started from the commercially available compounds umbelliferone and esculetin and resulted in the desired product but required 8 and 10 reaction steps, respectively . Synthesis of decursinol has been recently achieved more efficiently by using a microbial system . Herath et al reported the production of decursin metabolites by microbial transformation.…”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Biotransformation of Plant Secondary Metabolite Decursin by Mycobacterium sp. PYR1001

Kim¹,

Lee²,

Cha³

2010

J. Agric. Food Chem.

View full text Add to dashboard Cite

Decursin and its structural isomer decursinol angelate are major secondary metabolites in the root of Angelica gigas Nakai which possess several chemotherapeutic properties. We isolated bacteria capable of transforming decursin and determined metabolites and biotransformation kinetics. Decursinol angelate was not metabolized to any significant extent. Resting cells of Mycobacterium sp. PYR1001 were able to transform decursin. After 24 h incubation, 5 mM of decursin was completely transformed to a metabolite, the structure of which was determined by NMR and mass spectral analyses to be decursinol. This conversion was shown to be catalyzed by an esterase activity, and the activity was found to be specific for decursin. These results suggest that strain PYR1001 can be successfully used to transform decursin for the production of decursinol, a compound known to have cancer chemopreventive activity.

show abstract

Section: Resultssupporting

confidence: 84%

Section: Resultsmentioning

confidence: 99%

Biotransformation of Plant Secondary Metabolite Decursin by Mycobacterium sp. PYR1001

Kim¹,

Lee²,

Cha³

2010

J. Agric. Food Chem.

View full text Add to dashboard Cite

show abstract

“…However, little is known about the systemic exposure of decursin after administration because the pharmacokinetics of decursin has not been characterized well in vivo as compared to its in vitro pharmacological activity. The only exception is the observation that decursin may be metabolized to decursinol which is also pharmacologically active [5,18,19]. Decursinol has as well various pharmacological activities, including analgesic, serotonergic, antiangiogenic, and anticancer effects [20][21][22][23].…”

mentioning

confidence: 99%

First-pass Metabolism of Decursin, a Bioactive Compound of Angelica gigas, in Rats

Park

Kim

et al. 2012

Planta Med

View full text Add to dashboard Cite

Decursin is considered the major bioactive compound of Angelica gigas roots, a popular Oriental herb and dietary supplement. In this study, the pharmacokinetics of decursin and its active metabolite, decursinol, were evaluated after the administration of decursin in rats. The plasma concentration of decursin decreased rapidly, with an initial half-life of 0.05 h. It was not detectable at 1 h after intravenous administration at an area under the plasma concentration-time curve of 1.20 µg · mL-1·h, whereas the concentration of decursinol increased rapidly reaching a maximum concentration of 2.48 µg · mL-1 at the time to maximum plasma concentration of 0.25 h and an area under the plasma concentration-time curve of 5.23 µg · mL-1·h. Interestingly, after oral administration of decursin, only decursinol was present in plasma, suggesting an extensive hepatic first-pass metabolism of decursin. The extremely low bioavailability of decursin after its administration via the hepatic portal vein (the fraction of dose escaping first-pass elimination in the liver, FH = 0.11) is indicative of extensive hepatic first-pass metabolism of decursin, which was confirmed by a tissue distribution study. These findings suggest that decursin is not directly associated with the bioactivity of A. gigas and that it may work as a type of natural prodrug of decursinol.

show abstract

“…Spinosin, a C-glycoside flavonoid of semen Zizhiphi Spinozae, potentiated pentobarbital-induced sleep in mice via a serotonergic mechanism (Wang et al, 2008). Microbial transformation with Sepedonium chrysospermem of decursin yielded two metabolites, decursinol and cis-decursidinol (Herath et al, 2007). It was shown that decursinol may act as a chemopreventive agent to suppress the uncontrolled growth and invasive potential, angiogenic and metastatic targets, of prostate cancer (Singh & Agarwal, 2006).…”

Section: Discussionmentioning

confidence: 99%

Blockade of vascular angiogenesis by Aspergillus usamii var. shirousamii-transformed Angelicae Gigantis Radix and Zizyphus jujuba

et al. 2009

View full text Add to dashboard Cite

The matrix metalloproteinases (MMP) play an important role in tumor invasion, angiogenesis and inflammatory tissue destruction. Increased expression of MMP was observed in benign tissue hyperplasia and in atherosclerotic lesions. Invasive cancer cells utilize MMP to degrade the extracellular matrix and vascular basement membrane during metastasis, where MMP-2 has been implicated in the development and dissemination of malignancies. The present study attempted to examine the antiangiogenic activity of the medicinal herbs of Aspergillus usamii var. shirousamii-transformed Angelicae Gigantis Radix and Zizyphus jujube (tAgR and tZj) with respect to MMP-2 production and endothelial motility in phorbol 12-myristate 13-acetate (PMA)- or VEGF-exposed human umbilical vein endothelial cells (HUVEC). Nontoxic tAgR and tZj substantially suppressed PMA-induced MMP-2 secretion. In addition, 25 µg/mL tAgR and tZj prevented vascular endothelial growth factor-stimulated endothelial cell transmigration and tube formation. The results reveal that tAgR and tZj dampened endothelial MMP-2 production leading to endothelial transmigration and tube formation. tAgR and tZj-mediated inhibition of endothelial MMP may boost a therapeutic efficacy during vascular angiogenesis.

show abstract

Microbial Metabolism. Part 8. The Pyranocoumarin, Decursin

Abstract: Microbial transformation of the cancer chemopreventive agent, decursin (1) with Sepedonium chrysospermem (ATCC 13378) yielded two metabolites, (؉)-decursinol (2) and (؊)-cis-decursidinol (3). The structures were established by spectroscopic data.

Cited by 9 publications

References 13 publications

Biotransformation of Plant Secondary Metabolite Decursin by Mycobacterium sp. PYR1001

Biotransformation of Plant Secondary Metabolite Decursin by Mycobacterium sp. PYR1001

First-pass Metabolism of Decursin, a Bioactive Compound of Angelica gigas, in Rats

Blockade of vascular angiogenesis by Aspergillus usamii var. shirousamii-transformed Angelicae Gigantis Radix and Zizyphus jujuba

Contact Info

Product

Resources

About