Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants

• Karan Malhotra and
• Jakob Franke

Beilstein J. Org. Chem. 2022, 18, 1289–1310, doi:10.3762/bjoc.18.135

• , which plays a central role in the diversification of triterpenoids in eudicots [79]. Members of the CYP716A subfamily were mostly identified as C28 oxidases that catalyse three-step oxidation of α-amyrin (7), β-amyrin (6) and lupeol (10) to ursolic acid, oleanolic acid, and betulinic acid, respectively

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• -3α,12α,16α-triol (6) [15], 3-epimaslinic acid (7) [18], oleanolic acid (8) [19], and ursolic acid (9) [20]. To find potential antineuroinflammatory, neurotrophic, and cytotoxic secondary metabolites from G. hederacea var. longituba, the isolated compounds (1–9) were evaluated for these biological

New sesquiterpenoids from the South China Sea soft corals Clavularia viridis and Lemnalia flava

• Qihao Wu,
• Yuan Gao,
• Meng-Meng Zhang,
• Li Sheng,
• Jia Li,
• Xu-Wen Li,
• Hong Wang and
• Yue-Wei Guo

Beilstein J. Org. Chem. 2019, 15, 695–702, doi:10.3762/bjoc.15.64

• PTP1B inhibitory assay, the inhibitory effects of compounds 1–8 were evaluated against PTP1B, and the result showed that compounds 1, 2 and 4 had a moderate PTP1B inhibitory activity with IC50 values of 18.8, 21.8 and 15.6 μM, respectively. The known PTP1B inhibitor oleanolic acid (IC50 = 3.0 μM) were

Genicunolide A, B and C: three new triterpenoids from Euphorbia geniculata

• Alia Farozi,
• Javid A. Banday and
• Shakeel A. Shah

Beilstein J. Org. Chem. 2015, 11, 2707–2712, doi:10.3762/bjoc.11.291

• ][9][10][11][12][13]. Triterpenoids which have been reported from various species of Euphorbia include β-amyrin [1], β-amyrin acetate [14][18], cycloeucalenol, obtusifoliol, 24-methylenecycloartan-3-β-ol, β-sitosterol, betulin, erythrodiol, oleanolic acid, β-sitosterol glucoside[15], 29-norcycloart-5

Recent progress in the discovery of small molecules for the treatment of amyotrophic lateral sclerosis (ALS)

• Allison S. Limpert,
• Margrith E. Mattmann and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2013, 9, 717–732, doi:10.3762/bjoc.9.82

• . Neymotin et al. [64] tested two related compounds, 2-cyano-3,12-dioxoolean-1,9-dien-28-oic acid-ethylamide (CDDO-EA, 28, Figure 13) and CDDO-trifluoroethylamide (CDDO-TFEA, 29), synthetic triterpenoid analogues derived from oleanolic acid [64] for their ability to activate Nrf2/ARE signaling in cell

Synthesis and antiviral activities of spacer-linked 1-thioglucuronide analogues of glycyrrhizin

• Christian Stanetty,
• Andrea Wolkerstorfer,
• Hassan Amer,
• Andreas Hofinger,
• Ulrich Jordis,
• Dirk Claßen-Houben and
• Paul Kosma

Beilstein J. Org. Chem. 2012, 8, 705–711, doi:10.3762/bjoc.8.79

• reside at the glucuronic acid residues in the β-(1→2)-linked disaccharide unit of GL, with respect to antiviral properties (Figure 1). Previously, ring A modified derivatives of glycyrrhetinic acid were prepared containing 3-amino, 3-thio and 1-thio groups, allowing for an extension of the oleanolic acid

• the concentrations tested. Conclusion 3-Amino and 3-thio derivatives of glycyrrhetinic acid served as versatile scaffolds for the attachment of glycosyl extensions through high-yielding alkylation reactions. The glucuronide derivatives linked via a thioethyl spacer group to the oleanolic acid unit

Efficient oxidation of oleanolic acid derivatives using magnesium bis(monoperoxyphthalate) hexahydrate (MMPP): A convenient 2-step procedure towards 12-oxo-28-carboxylic acid derivatives

• Jorge A. R. Salvador,
• Vânia M. Moreira,
• Rui M. A. Pinto,
• Ana S. Leal and
• José A. Paixão

Beilstein J. Org. Chem. 2012, 8, 164–169, doi:10.3762/bjoc.8.17

• /bjoc.8.17 Abstract A new, straightforward and high yielding procedure to convert oleanolic acid derivatives into the corresponding δ-hydroxy-γ-lactones, by using the convenient oxidizing agent magnesium bis(monoperoxyphthalate) hexahydrate (MMPP) in refluxing acetonitrile, is reported. In addition, a

• : bismuth(III) triflate; δ-hydroxy-γ-lactones; MMPP; oleanolic acid; triterpenoid; Findings The molecular diversity that arises from research into natural products represents a valuable tool for driving drug discovery and development [1][2]. In this context, pentacyclic triterpenoids are currently regarded

• of ring C, a strategy known to increase the anti-inflammatory and cytotoxic activities of oleanolic acid (OA) derivatives [19][21][22]. Oleanolic δ-hydroxy-γ-lactones can be obtained from Δ12-oleananes by oxidative 28,13β-lactonization. This reaction was performed under photochemical irradiation [23