Eight Indole Alkaloids from the Roots of Maerua siamensis and Their Nitric Oxide Inhibitory Effects

Maerua siamensis (Capparaceae) roots are used for treating pain and inflammation in traditional Thai medicine. Eight new indole alkaloids, named maeruanitriles A and B, maeroximes A–C, and maeruabisindoles A–C, were isolated from them. Spectroscopic methods and computational analysis were applied to determine the structure of the isolated compounds. Maeroximes A–C possesses an unusual O-methyloxime moiety. The bisindole alkaloid maeruabisindoles A and B possess a rare azete ring, whereas maeruabisindole C is the first indolo[3,2-b]carbazole derivative found in this plant family. Five compounds [maeruanitriles A and B, maeroxime C, maeruabisindoles B, and C] displayed anti-inflammatory activity by inhibiting nitric oxide (NO) production in the lipopolysaccharide-induced RAW 264.7 cells. Maeruabisindole B was the most active inhibitor of NO production, with an IC50 of 31.1 ± 1.8 μM compared to indomethacin (IC50 = 150.0 ± 16.0 μM) as the positive control.

[1]  O. Theanphong,et al.  Combination of selected Thai traditional pain relief medicinal plants with anti-inflammatory abilities in a protein denaturation assay , 2022, Pharmacia.

[2]  M. Khongkow,et al.  Ethanolic Fenugreek Extract: Its Molecular Mechanisms against Skin Aging and the Enhanced Functions by Nanoencapsulation , 2022, Pharmaceuticals.

[3]  Kaixian Chen,et al.  Bisindole alkaloids with nitric oxide inhibitory activities from an alcohol extract of the Isatis indigotica roots. , 2020, Fitoterapia.

[4]  V. Fogliano,et al.  Aryl hydrocarbon Receptor activation during in vitro and in vivo digestion of raw and cooked broccoli (brassica oleracea var. Italica). , 2020, Food & function.

[5]  J. Vervoort,et al.  Induction of peroxisome proliferator activated receptor γ (PPARγ) mediated gene expression and inhibition of induced nitric oxide production by Maerua subcordata (Gilg) DeWolf , 2020, BMC Complementary Medicine and Therapies.

[6]  Kaixian Chen,et al.  Four undescribed sulfur-containing indole alkaloids with nitric oxide inhibitory activities from Isatis tinctoria L. roots. , 2020, Phytochemistry.

[7]  H. Paik,et al.  Ovalbumin Hydrolysates Inhibit Nitric Oxide Production in LPS-induced RAW 264.7 Macrophages , 2020, Food science of animal resources.

[8]  Powo.  Plants of the World Online. , 2020 .

[9]  Galen P. Miley,et al.  Inducible nitric oxide synthase: Regulation, structure, and inhibition , 2020, Medicinal research reviews.

[10]  Kaixian Chen,et al.  Indole alkaloid glycosides from Isatis tinctoria roots , 2019, Natural product research.

[11]  P. Bednarek,et al.  Glutathione S-Transferases in the Biosynthesis of Sulfur-Containing Secondary Metabolites in Brassicaceae Plants , 2018, Front. Plant Sci..

[12]  B. Mvumi,et al.  Novel Agmatine Derivatives in Maerua edulis With Bioactivity Against Callosobruchus maculatus, a Cosmopolitan Storage Insect Pest , 2018, Front. Plant Sci..

[13]  Saksit Nobsathian,et al.  Larvicidal effect of compounds isolated from Maerua siamensis (Capparidaceae) against Aedes aegypti (Diptera: Culicidae) larvae , 2018, Chemical and Biological Technologies in Agriculture.

[14]  B. Kaina,et al.  The Brassica-derived phytochemical indolo[3,2-b]carbazole protects against oxidative DNA damage by aryl hydrocarbon receptor activation , 2017, Archives of Toxicology.

[15]  N. Nwobodo,et al.  Analgesic, anti-inflammatory and antipyretic activities of methanolic leaf extract of Maerua crassifolia , 2016 .

[16]  M. Wang,et al.  Indole alkaloids from the roots of Isatis indigotica and their inhibitory effects on nitric oxide production. , 2014, Fitoterapia.

[17]  G. Bringmann,et al.  SpecDis: quantifying the comparison of calculated and experimental electronic circular dichroism spectra. , 2013, Chirality.

[18]  Wei‐Lie Xiao,et al.  Four new indole alkaloids from Plantago asiatica , 2012, Natural Products and Bioprospecting.

[19]  Sheng Lin,et al.  Alkaloids from the root of Isatis indigotica. , 2012, Journal of natural products.

[20]  F. Z. Basha,et al.  O-Alkylation of Menthone Oxime: Synthesis and 13C NMR Studies of a Series of Novel Oxime Ethers , 2010 .

[21]  J. Bergman,et al.  Synthetic applications of cyanoacetylated bisindoles: synthesis of novel cycloheptadiindoles, indolocarbazoles, and related aza analogues. , 2007, The Journal of organic chemistry.

[22]  J. Wallace.  Nitric oxide as a regulator of inflammatory processes. , 2005, Memorias do Instituto Oswaldo Cruz.

[23]  Jocelyn C Hall,et al.  Phylogeny of Capparaceae and Brassicaceae based on chloroplast sequence data. , 2002, American journal of botany.

[24]  P. Needleman,et al.  Interactions between the inducible cyclooxygenase (COX-2) and nitric oxide synthase (iNOS) pathways: implications for therapeutic intervention in osteoarthritis. , 1999, Osteoarthritis and cartilage.

[25]  M. Abdel-Mogib.  A lupane triterpenoid from Maerua oblongifolia , 1999 .

[26]  H. Kinashi,et al.  Possible Metabolic Intermediates from IAA to β-Acid in Rice Bran , 1976 .