A different type of biologically active compound from Kuji amber (Late Cretaceous, Japan) before the K-Pg boundary [65 million years ago (Ma)] was isolated based on the growth-restoring activity of a mutant yeast involving Ca signal transduction. It was identified as a spirolactone norditerpenoid, (4R*, 5S*, 8R*, 9R*, 10S*)-14,15,16,19-tetranor-labdan-13,9-olide (1) from spectral analyses with high-resolution electron ionization mass spectrometry (HREIMS), 1D and 2D nuclear magnetic resonance (NMR). Although the planar structure of 1 is known as an artificial derivative from marrubiin, it was isolated as a natural product from Kuji amber and its structure was elucidated for the first time. It had a growth-restoring activity against the mutant yeast through the direct or indirect inhibition of calcineurin activity [protein phosphatase, Mg/Mn-dependent 1A (PPM1A) activation]. Furthermore, the compound had potent inhibitory effect against the degranulation of rat basophilic leukemia 2H3 (RBL-2H3) cells.
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Synthesis and structure-activity relationship of kujigamberol B, a dinorlabdane diterpenoid isolated from an ancient Kuji amber.
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Department of Chemistry for Life Sciences and Agriculture, Faculty of Life Sciences, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo, Japan.
The versatile methodology was developed for synthesizing kujigamberol B, a dinorlabdane diterpenoid isolated from the methanol extract of Kuji amber. A highly efficient intramolecular cyclization is followed by a Sonogashira-coupling reaction during the total synthesis. The synthesized compounds were evaluated for the growth-restoring activity against the mutant yeast (zds1Δ erg3Δ pdr1Δ pdr3Δ) and for the degranulation of RBL-2H3 cells.
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Chemical Biology Laboratory, Graduate School of Arts and Sciences, Iwate University, Morioka, Japan.
Kuji amber is fossilized tree resin of the Late Cretaceous in Japan. In this study, new biological activities of ethanol extract of Kuji amber (EtOH ext.) and supercritical carbon dioxide fluid extract of Kuji amber (scCO ext.
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J Antibiot (Tokyo)
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Department of Biological Chemistry and Food Sciences, Iwate University, Morioka, Iwate, 020-8550, Japan.
For the discovery of novel drug candidates and bioprobes, it is important to investigate rare natural sources with unique screening methods. Our group tested 1000 original MeOH extracts from natural sources, such as plants and food ingredients using six types of mutant yeasts. In our experiments, Kuji amber was used as the rare domestic natural source and the growth-restoring activity (positive screening) of mutant yeast involving Ca-signal transduction was used as a unique screening method.
View Article and Find Full Text PDFA novel Ca-signal transduction inhibitor, kujigamberol C, isolated from Kuji amber.
Biosci Biotechnol Biochem
September 2019
a Graduate School of Arts and Sciences, Graduate Course in Biological Chemistry and Food Sciences, Iwate University, Morioka , Japan.
Article Synopsis
- A new compound called kujigamberol C, a labdane type diterpenoid, was extracted from Kuji amber using an improved method to enhance the yield of active substances.
- The compound's structure was identified using advanced techniques like high-resolution electrospray ionization mass spectrometry (HREIMS) and nuclear magnetic resonance (NMR).
- Kujigamberol C demonstrated the ability to restore growth in mutant yeast by activating calcium signal transduction pathways.
Kujigamberoic acid A, a carboxylic acid derivative of kujigamberol, has potent inhibitory activity against the degranulation of RBL-2H3 cells.
Biosci Biotechnol Biochem
July 2019
a Graduate School of Arts and Sciences, Graduate Course in Biological Chemistry and Food Sciences , Iwate University, Morioka , Japan.
The aldehyde and carboxylic acid derivatives of kujigamberol were synthesized using pyridinium dichromate (PDC). The carboxylic acid derivative exhibited lower cytotoxicity and inhibited the degranulation of rat basophilic leukemia-2H3 (RBL-2H3) cells stimulated by thapsigargin more than kujigamberol. The carboxylic acid derivative was detected and isolated from the methanol extract of Kuji amber (MEKA) by the modified isolation procedure.
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