- Potential role of two cytochrome P450s obtained from Lithospermum erythrorhizon in catalyzing the oxidation of geranylhydroquinone during Shikonin biosynthesis
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Shikonin is a natural naphthoquinone derivative that specifically occurs in boraginaceous plants, and the major active ingredient of the medicinal plant Lithospermum erythrorhizon. Previously, a cytochrome P450 oxygenase (CYP) CYP76B74 catalyzing 3″-hydroxylation of geranylhydroquinone (GHQ) — a key intermediate of shikonin biosynthesis, was identified from cultured cells of Arnebia euchroma. However, the enzymes catalyzing oxidation of the geranyl side-chain of GHQ from L. erythrorhizon remain unknown. In this study, we performed transcriptome analysis of different tissues (red roots and green leaves/stems) from L. erythrorhizon using RNA sequencing technology. Highly expressed CYP genes found in the roots were then heterologously expressed in Saccharomyces cerevisiae and functionally screened with GHQ as the substrate. As the result, two CYPs of CYP76B subfamily catalyzing the oxidation of GHQ were characterized. CYP76B100 catalyzed the hydroxylation of the geranyl side-chain of GHQ at the C-3″ position to form 3″-hydroxyl geranylhydroquinone (GHQ-3″-OH). The enzyme CYP76B101 carried out oxidation reaction of GHQ at the C-3″ position to produce a 3″-carboxylic acid derivative of GHQ (GHQ-3″-COOH) as well as GHQ-3″-OH. This enzyme-catalyzed oxidation reaction with GHQ as the substrate is reported for the first time. This study implicates CYP76B100 and CYP76B101 as having a potential role in shikonin biosynthesis in L. erythrorhizon.
- Liu, Tao,Song, Wan,Zhuang, Yibin
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- (±)-Pabmaragramin, a scalemic meroterpenoid produced by Marasmius graminum via precursor-assisted biosynthesis
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A pair of novel scalemic meroterpenoid dimers, (+)- and (?)-pabmaragramin (1), featuring an unprecedented 6/6/5/6/6/6/5 seven-membered ring system, were obtained from Marasmius graminum via precursor-assisted biosynthesis (PAB). Their structures and absol
- Ren, Panlong,Wang, Jing,Miao, Xinyu,Zhu, Weide,Wu, Yueting,Li, Yun,Gao, Kun,Yang, Yan-Long
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- Avarol derivatives as competitive AChE inhibitors, non hepatotoxic and neuroprotective agents for Alzheimer's disease
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Avarol is a marine sesquiterpenoid hydroquinone, previously isolated from the marine sponge Dysidea avara Schmidt (Dictyoceratida), with antiinflammatory, antitumor, antioxidant, antiplatelet, anti-HIV, and antipsoriatic effects. Recent findings indicate
- Tommonaro, Giuseppina,García-Font, Nuria,Vitale, Rosa Maria,Pejin, Boris,Iodice, Carmine,Ca?adas, Sixta,Marco-Contelles, José,Oset-Gasque, María Jesús
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- Construction of a meroterpenoid-like compound collection by precursor-assisted biosynthesis
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Natural products (NPs) and their derivatives play a pivotal role in drug discovery due to their complexity and diversity. The strategies to rapidly generate NP-like compounds offer unique opportunities to access bioactive compounds. Here we present a new approach, precursor-assisted biosynthesis (PAB), for the creation of NP-like compounds by combination of artificial supplementation of common precursors and divergent post-modifications of precursor-deficient fungi. This method was applied to construct a meroterpenoid-like compound collection containing 43 compounds with diverse molecular scaffolds. Extensive bioactive screening of the collection revealed novel STING (stimulator of interferon genes) inhibitors, cytotoxic and antifungal compounds. This result indicates that PAB is an effective methodology for producing compound collections for the purpose of drug discovery.
- Gao, Kun,Li, Yun,Miao, Xinyu,Ren, Panlong,Tang, Ting,Wang, Jing,Wu, Yueting,Yang, Yan-Long,Zeng, Ying
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- Synthesis and fungicidal activity of hydrated geranylated phenols against botrytis cinerea
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Botrytis cinerea is a ubiquitous fungus that affects hundreds of plants, resulting in economic losses to the horticulture and fruit industry. The search for new antifungal agents is a matter of current interest. Thus, in this work a series of geranylated
- Amesty, ángel,Diaz, Katy,Espinoza, Luis,Estevez-Braun, Ana,Kluepfel, Julia,Olea, Andrés F.,Restrepo, Susana,Soto, Mauricio,Taborga, Lautaro
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- Synthesis of Natural Geranylhydroquinone Analogs
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Hydroquinone was alkylated by geraniol in the presence of aluminum-phenoxide and -isopropoxide catalysts. The reaction products were isolated and characterized. Several features of the process were determined.
- Chukicheva,Fedorova,Koroleva,Kuchin
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p. 1055 - 1058
(2016/02/18)
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- Synthesis of linear geranylphenols and their effect on mycelial growth of plant pathogen Botrytis cinerea
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Natural geranyl compounds are known to exhibit important biological activities. In this work a series of geranylphenols were synthesized to evaluate their effect on the mycelial growth of Botrytis cinerea. Geranyl derivatives were synthesized by direct ge
- Espinoza, Luis,Taborga, Lautaro,Diaz, Katy,Olea, Andres F.,Pena-Cortes, Hugo
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p. 1512 - 1526
(2014/03/21)
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- Synthesis and nmr structure determination of new linear geranylphenols by direct geranylation of activated phenols
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The known geranylhydroquinone 2, geranylorcinol 4 and the derivative (E)-4-(3,7-dimethylocta-2,6-dienyl)-5-methylbenzene-1,3-diol 5, were prepared by Electrophilic Aromatic Substitution (EAS) reactions between the corresponding phenol derivatives containi
- Taborga, Lautaro,Vergara, Alejandra,Fernandez, Maria Jose,Osorio, Mauricio,Carvajal, Marcela,Madrid, Alejandro,Marilaf, Francisco,Carrasco, Hector,Catalan, Luis Espinoza
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p. 1790 - 1796
(2013/09/24)
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- Enantioselective 6-endo-trig Wacker-type cyclization of 2-geranylphenols: Application to a facile synthesis of (-)-cordiachromene
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An enantioselective intramolecular oxidative cyclization of 2-geranylphenols catalyzed by a Pd(II)-spiro bis(isoxazoline) complex is reported. The reaction proceeds in a 6-endo-trig manner to give chromene derivatives in reasonable yields and with moderate enantioselectivities. This transformation can be applied to a protecting-group-free total synthesis of naturally occurring cordiachromene.
- Takenaka, Kazuhiro,Tanigaki, Yugo,Patil, Mahesh L.,Rao, C. V. Laxman,Takizawa, Shinobu,Suzuki, Takeyuki,Sasai, Hiroaki
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p. 767 - 770
(2010/11/04)
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- Total synthesis of polyprenylhydroquinols and benzoquinones
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The total synthesis of polyprenylhydroquinols and benzoquinones is described.First, two appropriate aromatic allyl carbonates (moieties with one and two prenyls) and two activated bifunctional terpenyl derivatives (moieties with two and three prenyls) were synthesized.These molecules were then reacted together using a highly regio- and stereoselective coupling with Pd(PPh3)4 as a catalyst.The synthesis was achieved by functional group elimination and formation of quinonic and hydroquinonic moieties. - Keywords: polyprenylbenzoquinol; polyprenylhydroquinone; allylcarbonate; ?-allyl palladium complex
- Bouzbouz, Samir,Kirschleger, Bernard,Villieras, Jean
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