Antimalarial Biflavonoids from the Roots of Ochna serrulata (Hochst.) Walp

Ndoile, Monica M.; Heerden, Fanie R. van

doi:10.9734/irjpac/2018/42440

Cited by 7 publications

(6 citation statements)

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“…In addition, the HMBC cross-peaks of proton resonances at δ H 4.50 (H-3) to C-2″ (δ C 86.4), C-4 (δ C 196.0), C-4″ (δ C 200.5), and C-10 (δ C 122.1) and those at δ H 5.62 (H-2) to C-3″ (δ C 60.2), C-4 (δ C 196.0), C-9 (δ C 166.4), and C-2′/6′ (δ C 129.5) established the C-3–C-3″ linkage of the two flavanone units. Similar C-3–C-3″ linkages were previously reported from other plant species including campylospermone B from Campylospermum mannii , 19 ouratein D from Ouratea spectabilis , 15 4,4,7-tri- O -methylisocapylospermone A from Ochna serrulata , 27 chamaejasmin from Ormocarpum kirkii , 8 and chamaejasmin D from Stellera chamaejasme . 28 The NMR spectroscopic data for compound 1 closely resembled those of campylospermone B 19 and liquiritigeninyl-(1-3,II-3)-naringenin, 8 but had a methoxy group resonating at δ H 3.77 (H-11) and attached to C-7″ (δ C 167.9), indicated by the HMBC cross-peak of H-11 (δ H 3.77) with C-7″ (δ C 167.9).…”

Section: Resultssupporting

confidence: 85%

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Biflavanones, Chalconoids, and Flavonoid Analogues from the Stem Bark of Ochna holstii

et al. 2021

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Two new biflavanones ( 1 and 2 ), three new bichalconoids ( 3 – 5 ), and 11 known flavonoid analogues ( 6 – 16 ) were isolated from the stem bark extract (CH 3 OH–CH 2 Cl 2 , 7:3, v/v) of Ochna holstii . The structures of the isolated metabolites were elucidated by NMR spectroscopic and mass spectrometric analyses. The crude extract and the isolated metabolites were evaluated for antibacterial activity against Bacillus subtilis (Gram-positive) and Escherichia coli (Gram-negative) as well as for cytotoxicity against the MCF-7 human breast cancer cell line. The crude extract and holstiinone A ( 1 ) exhibited moderate antibacterial activity against B. subtilis with MIC values of 9.1 μg/mL and 14 μM, respectively. The crude extract and lophirone F ( 14 ) showed cytotoxicity against MCF-7 with EC 50 values of 11 μg/mL and 24 μM, respectively. The other isolated metabolites showed no significant antibacterial activities (MIC > 250 μM) and cytotoxicities (EC 50 ≥ 350 μM).

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Section: Resultssupporting

confidence: 85%

“…The ECD spectrum is shown in Figure 1 . Similar structures have previously been reported from various Ochna , 27 , 31 , 32 Campylospermum , 22 , 33 and Lophira 34 , 35 species, however without their absolute configuration having been determined.…”

Section: Resultssupporting

confidence: 84%

Biflavanones, Chalconoids, and Flavonoid Analogues from the Stem Bark of Ochna holstii

et al. 2021

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“…There is no previous report on the occurrence of C-3/C-3″-coupled biflavanones in Ouratea species. However, a C-3–C-3″-linked biflavanone has previously been isolated from Ochna serrulata , a species from the Ochnaceae family, namely, 4,4′,7-tri- O -methylisocampylospermone A . Other examples of known C-3–C-3″-bonded biflavanones structurally related to 1 – 4 have been reported, including chamaejasmin, chamaejasmins B and C, and neochamaejasmins A and B, along with isochamaejasmin, isolated from the Stellera species. − In addition, the structurally related sikokianins A and B were isolated from Wikstroemia sikokiana …”

Section: Resultsmentioning

confidence: 99%

(3,3″)-Linked Biflavanones from Ouratea spectabilis and Their Effects on the Release of Proinflammatory Cytokines in THP-1 Cells

et al. 2020

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Ouratea spectabilis is an arborous species traditionally used in Brazil as an anti-inflammatory agent. Four new (3,3″)-linked biflavanone O-methyl ethers, named ouratein A (1), B (2), C (3), and D (4), were isolated from the bark extract of the species. Ouratein A ( 1) is an enantiomer of neochamagesmine A, which has never been described before. The structures were elucidated by extensive spectroscopic data analyses, whereas their absolute configurations were defined by electronic circular dichroism data. Ouratein D (4) inhibited in vitro the release of the pro-inflammatory cytokine CCL2 by lipopolysaccharide-stimulated THP-1 cells (IC 50 of 3.1 ± 1.1 μM), whereas TNF and IL-1β release were not reduced by any of the biflavanones. These findings show ouratein D (4) as a selective CCL2 inhibitor, which may have potential for the development of new anti-inflammatory agents to prevent or treat cardiovascular diseases.

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“…OC from Ochna serrulata (Hochst.) Walp performed the highest antimalarial activity (IC 50 = 17.25 μM), followed by lophirone A (IC 50 = 29.78 μM), 5‐deoxyurundeuvine C (IC 50 = 31.07 μM), lophirone C (IC 50 = 35.31 μM), afzelone B (IC 50 = 39.54 μM), 2″,3″‐dihydroochnaflavone (IC 50 = 61.86 μM), and 3′‐methoxyvitexin‐6″‐O‐acetate (IC 50 = 106.35 μM) (Ndoile & Van Heerden, 2018). Moreover, the antibacterial activity of OC and 7‐O‐methylochnaflavone against Escherichia coli , Pseudomonas aeruginosa , Enterococcus faecalis , and Staphylococcus aureus revealed that gram‐negative bacteria are more vulnerable to chemical intervention than gram‐positive bacteria (Makhafola et al., 2012).…”

Section: Molecular Mechanisms Of Action Of Ochnaflavonementioning

confidence: 99%

Advances in resources, biosynthesis pathway, bioavailability, bioactivity, and pharmacology of ochnaflavone

Lin,

Ganesan,

Vargas‐De‐La‐Cruz

et al. 2024

Future Postharvest and Food

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Ochnaflavone is a naturally occurring biflavonoid mainly isolated from Ochna integerrima, manifests health benefits encompassing antidiabetic, anticancer, anti‐cardiovascular, and anti‐inflammatory activities. However, most bioactivity research has focused on in vitro experiments, rather than in vivo disease models, toxicological assessments, and human clinical trials. Moreover, a comprehensive review of the pharmacological aspects of ochnaflavone is conspicuously lacking. Thus, this review provides a concise and comprehensive summary of existing knowledge on the chemical structure, plant origin, physical properties, biotransformations, and multifaceted biological activities of ochnaflavone along with an in‐depth exploration of the complex molecular mechanisms behind these activities, including signaling pathways and gene expression regulation, with the aim of promoting future theoretical needs for ochnaflavone in clinical trials and providing comprehensive insights into the research and application of this valuable natural compound.

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Antimalarial Biflavonoids from the Roots of Ochna serrulata (Hochst.) Walp

Cited by 7 publications

References 0 publications

Biflavanones, Chalconoids, and Flavonoid Analogues from the Stem Bark of Ochna holstii

Biflavanones, Chalconoids, and Flavonoid Analogues from the Stem Bark of Ochna holstii

(3,3″)-Linked Biflavanones from Ouratea spectabilis and Their Effects on the Release of Proinflammatory Cytokines in THP-1 Cells

Advances in resources, biosynthesis pathway, bioavailability, bioactivity, and pharmacology of ochnaflavone

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