Secoiridoid Glucosides from Strychnos spinosa

Itoh, Atsuko; Oya, Naoko; Kawaguchi, Eri; Nishio, Sayo; Tanaka, Yasuhiro; Kawachi, Emi; Akita, Toru; Nishi, Toyoyuki; Tanahashi, Takao

doi:10.1021/np058062w

Cited by 21 publications

(18 citation statements)

References 22 publications

(29 reference statements)

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“…Phytochemicals isolated from Strychnos spinosa include secoiridoids [95], indole, pyridine, and naphthyridine alkaloids [40], sterols and triterpenoids [96] (Table S20). Relatively small pyridine and naphthyridine alkaloids from Strychnos spinosa showed preferential docking to TbPTR1 and/or TbTIM.…”

Section: Resultsmentioning

confidence: 99%

In-silico Investigation of Antitrypanosomal Phytochemicals from Nigerian Medicinal Plants

Setzer

Ogungbe

2012

PLoS Negl Trop Dis

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BackgroundHuman African trypanosomiasis (HAT), a parasitic protozoal disease, is caused primarily by two subspecies of Trypanosoma brucei. HAT is a re-emerging disease and currently threatens millions of people in sub-Saharan Africa. Many affected people live in remote areas with limited access to health services and, therefore, rely on traditional herbal medicines for treatment.MethodsA molecular docking study has been carried out on phytochemical agents that have been previously isolated and characterized from Nigerian medicinal plants, either known to be used ethnopharmacologically to treat parasitic infections or known to have in-vitro antitrypanosomal activity. A total of 386 compounds from 19 species of medicinal plants were investigated using in-silico molecular docking with validated Trypanosoma brucei protein targets that were available from the Protein Data Bank (PDB): Adenosine kinase (TbAK), pteridine reductase 1 (TbPTR1), dihydrofolate reductase (TbDHFR), trypanothione reductase (TbTR), cathepsin B (TbCatB), heat shock protein 90 (TbHSP90), sterol 14α-demethylase (TbCYP51), nucleoside hydrolase (TbNH), triose phosphate isomerase (TbTIM), nucleoside 2-deoxyribosyltransferase (TbNDRT), UDP-galactose 4′ epimerase (TbUDPGE), and ornithine decarboxylase (TbODC).ResultsThis study revealed that triterpenoid and steroid ligands were largely selective for sterol 14α-demethylase; anthraquinones, xanthones, and berberine alkaloids docked strongly to pteridine reductase 1 (TbPTR1); chromenes, pyrazole and pyridine alkaloids preferred docking to triose phosphate isomerase (TbTIM); and numerous indole alkaloids showed notable docking energies with UDP-galactose 4′ epimerase (TbUDPGE). Polyphenolic compounds such as flavonoid gallates or flavonoid glycosides tended to be promiscuous docking agents, giving strong docking energies with most proteins.ConclusionsThis in-silico molecular docking study has identified potential biomolecular targets of phytochemical components of antitrypanosomal plants and has determined which phytochemical classes and structural manifolds likely target trypanosomal enzymes. The results could provide the framework for synthetic modification of bioactive phytochemicals, de novo synthesis of structural motifs, and lead to further phytochemical investigations.

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Section: Resultsmentioning

confidence: 99%

In-silico Investigation of Antitrypanosomal Phytochemicals from Nigerian Medicinal Plants

Setzer

Ogungbe

2012

PLoS Negl Trop Dis

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“…Compound indicating that units A and B were linked, as shown in Figure 1 [4,5]. The linkage was also ascertained by long-range correlations between H-7a 2 at d H 6.64 and C7b 2 at d C 195.0, H-7b 2 at d H 9.18, and C7a 2 at d C 155.8 in the HMBC spectrum ( Figure 2).…”

Section: Resultsmentioning

confidence: 75%

Two novel secoiridoid glucosides from Tripterospermum chinense

Zhang

et al. 2012

Journal of Asian Natural Products Research

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Two novel secoiridoid glucosides, tripterospermumcins C (1) and D (2), were isolated from the aerial parts of Tripterospermum chinense, along with four known compounds, tripterospermumcin B (3), sweroside (4), loganic acid (5), and 8-epi-kingiside (6). Their structures were determined by analysis of 1D and 2D NMR data, as well as by comparison with model compounds. Compound 1 was a rare iridoid tetramer with four glucosides.

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“…Adinoside A from Adina racemosa [21] and stryspinoside from Strychnos spinosa [22] are the only known natural products possessing the carbon skeletons of 1 and 2, reported from species rather than L. japonica. Both the known compounds were also isolated from the ethanol extract of the L. japonica flower buds [18], and an ester of adinoside A coupling with a phenolic glucoside (lonicerjaponin A) from a methanol extract [24].…”

Section: Resultsmentioning

confidence: 99%