Morinlongosides A–C, Two New Naphthalene Glycoside and a New Iridoid Glycoside from the Roots of &lt;i&gt;Morinda longissima&lt;/i&gt;

Cường, Nguyễn Mạnh; Hương, Trần Thu; Cuong, To Dao; Van, Doan Thi; Khanh, Pham Ngoc; Hà, Vũ Thị Thu; Tram, Nguyen Cong Thuy; Long, Pham Quoc; Kim, Young Ho

doi:10.1248/cpb.c15-01039

Cited by 14 publications

(7 citation statements)

References 21 publications

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“…With the aid of the DEPT and HSQC NMR spectra, 28 carbon signals in the 13 C NMR spectrum (Table ) were established as one methyl (δ C 21.2), two methylenes (δ C 59.9, 26.4), five methines (δ C 126.0, 126.0, 124.9, 123.0, 123.0), five quaternary carbons (δ C 134.7, 128.3, 128.3, 126.8, 126.6), two oxygenated tertiary carbons (δ C 146.8, 145.1), a carbonyl (δ C 169.8), and two glucopyranosyl units (δ C 105.2, 105.1, 77.1, 76.7, 76.5, 76.3, 74.2, 74.1, 70.4, 69.9, 61.7, 61.0). The NMR data resembled those of morinlongoside A, except for the presence of a carboxylic acid group (δ C 169.8) in 1 replacing a carbomethoxy (δ C 171.3, 53.2) in morinlongoside A. This deduction was supported by 1 H– 1 H COSY, HMBC, and NOESY correlations (Figure ).…”

Section: Resultsmentioning

confidence: 99%

Quinone Derivatives as Promising Anti-Helicobacter pylori Agents from Aerial Parts of Mitracarpus hirtus

Zhou

Heng

et al. 2022

J. Nat. Prod.

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Seven new naphthoquinone diglycosides (1−7), three new anthraquinones (8−10), and eight known analogues were obtained from the aerial parts of Mitracarpus hirtus collected from West Africa in a bioassay-guided phytochemical investigation. All isolated compounds were elucidated by comparison with the literature and interpretation of spectroscopic data, and the absolute configurations of the new naphthoquinone diglycosides (1−10) were confirmed by chemical methods and ECD calculations. Notably, compound 1 was found to be the first naphthoquinone diglycoside containing carboxylic acid and isopentenyl side chains isolated from a species in the genus Mitracarpus. Compounds 6− 18 showed antibacterial activity against multiple Helicobacter pylori strains with MIC values ranging from 0.0625 to 64 μg/mL. Particularly, 1-hydroxybenzoisochromanquinone (17) and benzo[g]isoquinoline-5,10-dione (18), with MIC values of 0.0625 and 0.125 μg/mL, displayed 32−512-fold higher potencies than a positive control, metronidazole. Compound 18 also demonstrated high antibiofilm activity and killed biofilm-encased Helicobacter pylori cells more effectively than metronidazole.

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Section: Resultsmentioning

confidence: 99%

Quinone Derivatives as Promising Anti-Helicobacter pylori Agents from Aerial Parts of Mitracarpus hirtus

Zhou

Heng

et al. 2022

J. Nat. Prod.

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“…The chemical structures of 21 compounds from M. longissima stems and roots were collected from the literature [ 9,10 ] (figure 1) and prepared using Marvin Sketch software (https://chemaxon.com/products/marvin). DFT calculations using ORCA v4.2.1 software at the hybrid Beckee‐3‐Lee‐Yag‐Parr (B3LYP) functional level with def2‐SVP basis set for all atoms were used to optimise the geometry of the compounds [ 13 ] (Figure S1 ‐ Supporting Information‐SI).…”

Section: Methodsmentioning

confidence: 99%

“…Z. Ruan is a valuable medicinal plant belonging to the Rubiaceae family. In North Vietnam, the stems and roots of this hepatoprotective herb are commonly used to treat liver diseases, such as hepatitis and chronic cirrhosis [ 9 ] . This plant contains natural compounds such as iridoids, naphthalene glycosides, and especially anthraquinones and anthraquinone glycosides.…”

Section: Introductionmentioning

confidence: 99%

“…This plant contains natural compounds such as iridoids, naphthalene glycosides, and especially anthraquinones and anthraquinone glycosides. [ 9,10 ] Several compositions of M. longissima stems and roots have been reported to inhibit the in vitro replication of the hepatitis B virus. [ 11,12 ] Thus, the search for TNF‐ α inhibitors from the M. longissima plant and their natural constituents, especially anthraquinone compounds, by molecular docking approaches is necessary for the discovery of potential drug candidates for inflammation‐mediated diseases.…”

Section: Introductionmentioning

confidence: 99%

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In silico and ADMET study of Morinda longissima phytochemicals against TNF‐α for treatment of inflammation‐mediated diseases

Ha,

Anh,

Khanh

et al. 2023

Vietnam Journal of Chemistry

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Morinda longissima Y. Z. Ruan (“Nhó đông") belongs to the Rubiaceae family. In Vietnam, the stems and roots of this plant are commonly used to treat liver diseases, such as viral hepatitis and acute and chronic cirrhosis. A phytochemical study of this hepatoprotective plant revealed the presence of 21 natural compounds of different classes, including iridoids, naphthalene glycosides, and especially anthraquinones and anthraquinone glycosides. The primary goal of this study was to investigate the anti‐inflammatory potential of bioactive molecules from M. longissima targeted against TNF‐α using a molecular docking approach. The results revealed that two anthraquinone glycosides, morindone‐6‐O‐β‐gentiobioside (1) and lucidin‐3‐O‐β‐primeveroside (2), had good binding affinities (∆G values of ‐9.21 and ‐8.75 kcal/mol, respectively), better than that of the TNF‐α inhibitor, SPD‐304 (‐8.71 kcal/mol). The in silico ADME parameters of (1) and (2) and other compounds showed good bioavailability based on their absorption, distribution, metabolism, and excretion parameters. In addition, the oral toxicity of these compounds was determined to be low and safe. All this evidence showed it is worth further study and the development of potential anthraquinone glycosides from M. longissima roots as TNF‐α natural inhibitors for the treatment of inflammatory diseases such as rheumatoid arthritis, sclerosis, and hepatitis.

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“…)], one olefinic bond at [δ H 5.26 (1H, t, 3.5 Hz, H-12), δ C 123.7 (C-12), and δ C 145.1 (C-13)], one carbonyl carbon at δ C 180.8 (C-28), and remaining aliphatic methines and methylenes. Two anomeric protons at δ H 4.44 (H-1') and δ H 4.62 (H-1'') were in association with the same coupling constants J = 8.0 Hz, thereby indicating two β-glucopyranosyl units[15][16][17].…”

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confidence: 97%

Chemical constituents from the stem barks of polyscias serrata balf

Anh¹,

Hà²,

Tra³

et al. 2022

Vietnam J. Sci. Technol.

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Plants of the genus Polyscias (the family Araliaceae) are represented as perennial shrubs and are commonly cultivated in southeastern Asia and the Pacific regions. Pharmacological studies revealed that Polyscias crude extracts and their isolated compounds exhibited a variety of biological activity, such as antibacterial, antifungal, cytotoxic, immuno-stimulant, wound healing and anti-asthmatic activities. For the first time, phytochemical study on the methanol (MeOH) extract of the stem barks of Vietnamese species Polyscias serrata Balf. (locally named Dinh lang rang) resulted in the isolation and NMR (Nuclear Magnetic Resonance)-determination of six compounds 1-6. They include one nucleobase uracil (1), two nucleosides uridine (2) and adenosine (3), one alkaloid indole-3-carboxylic acid (4), one mono-phenol glucoside koaburside (5), and one saponin randianin (6). The chemical structures of these phytochemicals were elucidated by physicochemical, the 1D-NMR [1H, 13C-NMR, and DEPT (Distortionless Enhancement by Polarization Transfer)], the 2D-NMR [HSQC (heteronuclear single quantum coherence), HMBC (Heteronuclear Multiple Bond Correlation), and COSY (correlation spectroscopy)] spectral, and ESI-MS (Electron Spray Ionization-Mass Spectrum) data. This is the first time that compounds 2-6 have been obtained from the genus Polyscias. In agreement with various reports, the nitrogenous compounds and triterpene saponins can be seen as characteristic metabolites of genus Polyscia

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Morinlongosides A–C, Two New Naphthalene Glycoside and a New Iridoid Glycoside from the Roots of <i>Morinda longissima</i>

Cited by 14 publications

References 21 publications

Quinone Derivatives as Promising Anti-Helicobacter pylori Agents from Aerial Parts of Mitracarpus hirtus

Quinone Derivatives as Promising Anti-Helicobacter pylori Agents from Aerial Parts of Mitracarpus hirtus

In silico and ADMET study of Morinda longissima phytochemicals against TNF‐α for treatment of inflammation‐mediated diseases

Chemical constituents from the stem barks of polyscias serrata balf

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