Dactyloidin, a New Diaryl Nonanoid from<i>Myristica Dactyloides</i>

Herath, H. M. T. Bandara; Priyadarshani, A.M.A.; Jamie, Joanne F.

doi:10.1080/10575639808048275

Cited by 10 publications

(4 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Phytochemical investigation of the genus Myristica has led to the isolation and characterization of various classes of phenolic type secondary metabolites such as acylphenols, dimeric acylphenols, flavonoids, lignans, and neolignans [5,8,[15][16][17][18][19][20][21][22][23][24][24][25][26][27][28][29][30][31][32][33]. These phenolic type secondary metabolites have been reported to exhibit numerous pharmacological activities namely cytotoxic activity, nitric oxide inhibitory activity, AMPK activators, anticariogenic activity, LDL antioxidant activity, DPPH free radical scavenging activity, lipid peroxidation activity, anti-quorum sensing activity, acetylcholinesterase inhibitory activity, anti-inflammatory activity, anti-platelet activity, antifungal activity, and COX-2 inhibitory activity [5,8,15,16,18,19,[22][23][24][25][26][30][31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Acylphenols and Dimeric Acylphenols from the Genus Myristica: A Review of Their Phytochemistry and Pharmacology

Othman

Sivasothy

2023

Plants

View full text Add to dashboard Cite

The genus Myristica is a medicinally important genus belonging to the Myristicaceae. Traditional medicinal systems in Asia have employed plants from the genus Myristica to treat a variety of ailments. Acylphenols and dimeric acylphenols are a rare group of secondary metabolites, which, to date, have only been identified in the Myristicaceae, in particular, in the genus Myristica. The aim of the review would be to provide scientific evidence that the medicinal properties of the genus Myristica could be attributed to the acylphenols and dimeric acylphenols present in the various parts of its plants and highlight the potential in the development of the acylphenols and dimeric acylphenols as pharmaceutical products. SciFinder-n, Web of Science, Scopus, ScienceDirect, and PubMed were used to conduct the literature search between 2013–2022 on the phytochemistry and the pharmacology of acylphenols and dimeric acylphenols from the genus Myristica. The review discusses the distribution of the 25 acylphenols and dimeric acylphenols within the genus Myristica, their extraction, isolation, and characterization from the respective Myristica species, the structural similarities and differences within each group and between the different groups of the acylphenols and dimeric acylphenols, and their in vitro pharmacological activities.

show abstract

Section: Introductionmentioning

confidence: 99%

Acylphenols and Dimeric Acylphenols from the Genus Myristica: A Review of Their Phytochemistry and Pharmacology

Othman

Sivasothy

2023

Plants

View full text Add to dashboard Cite

show abstract

“…Various researchers around the world have explored the chemistry and bioactive potentials of a similar species, Myristica fragrans [12]. Despite having the similar pharmacological potential to M. fragrans, M. dactyloides has remained unexplored except for a few early attempts [13][14][15][16][17]. In these reports, Myoinositol, Malabaricone A, B, C, D, Dactyloidin, Acylresorcinols, Arylalkanones, and Lignans were found in various parts of the M. dactyloides Gaertn.…”

Section: Introductionmentioning

confidence: 99%

HR-LC-MS based profiling of phytochemicals from methanol extracts of leaves and bark of Myristica dactyloides Gaertn. from Western Ghats of Karnataka, India

Mallikarjunaiah¹,

Nuthan²,

Channarayapatna-Ramesh³

et al. 2021

J App Biol Biotech

View full text Add to dashboard Cite

Untargeted profiling of phytochemicals from plant extracts would aid in the exploration of various groups of compounds and assist in the identification of new bioactive compounds, reducing the redundancy in compound identification. The potential bioactive phytochemicals present in Myristica dactyloides, an endemic ethnomedicinal plant widely used in traditional treatment practices, were explored and cataloged in this study. The untargeted phytochemical profile of active methanolic leaves and bark extracts was assessed by Ultra high-performance liquid chromatography coupled to electrospray ionization and quadrupole time-offlight mass spectrometry. Preliminary screening results highlighted the high efficiency of methanolic extract as an effective antioxidant and anti-inflammatory agent, along with a remarkable amount of total phenolics and flavonoid content. Thus, the methanolic extracts of leaves and bark samples were further subjected to catalog its chemical constituents through untargeted metabolite profiling. Analysis of high-resolution liquid chromatography-mass spectrometer spectra, exhibited 3,813 and 1,797 molecular features in the ESI+ mode with clean retention time-exact mass, resulted in identifying 35 major therapeutically important common compounds for the first time in both leaves and bark extracts of M. dactyloides, fitting to major groups like lignans, neolignans, phenylpropanoids, diarylnonanoid, flavonoids, and others. Our results prove the presence of Myoinositol, Malabaricone B, Malabaricone C, Malabaricone D, and 1-(2,6-dihydroxyphenyl)-9-(4-hydroxy-3-methoxyphenyl) nonan-1-one previously reported from M. dactyloides, along with promising chemical signatures like Monotropein, Austrobailignan 7, Fragransol B, Guaiacin, Myricanone, Nectandrin A, Argenteane, and Epicatechin to the phytochemical catalog of M. dactyloides. Furthermore, our research not only confirms the existence of previously known molecules and adds new phytochemicals, but it also sheds light on the wide application of M. dactyloides for possible bio-prospecting for a new chemical entity.

show abstract

“…Structurally similar compounds have been isolated from the Myristica genus in the plant family Myristicaceae. [11][12][13][14] Mosher ester analysis was used to deduce the absolute configuration of the chiral center (C-5) in compound 1. The Mosher esters, obtained by reacting 1 with both (3R)-and (3S)-MTPA chloride to yield the (4S)-and (4R)-…”

mentioning

confidence: 99%

“…Although the diarylheptanoids are similar in structure, and have been previously isolated from the Dioscoreaceae family, − diarylnonanoids have a 9-carbon chain linking the two aromatic systems. Structurally similar compounds have been isolated from the Myristica genus in the plant family Myristicaceae. − Mosher ester analysis was used to deduce the absolute configuration of the chiral center (C-5) in compound 1 . The Mosher esters, obtained by reacting 1 with both (3 R )- and (3 S )-MTPA chloride to yield the (4 S )- and (4 R )-MTPA ester, respectively, were analyzed using both 1D and 2D NMR spectroscopy.…”

mentioning

confidence: 99%

Constituents of Two Dioscorea Species That Potentiate Antibiotic Activity against MRSA

2020

View full text Add to dashboard Cite

The isolation of two diarylnonanoids from Dioscorea cotinifolia possessing antibiotic-potentiating activity against resistant strains of S. aureus are reported. The diarylnonanoids are a class of natural products similar in structure to the diarylheptanoids, which have a wide spectrum of reported biological activities. One of the diarylnonanoids (1) isolated possesses a chiral center and to deduce its configuration, the modified Mosher ester method was used. Using both 1D and 2D NMR data, as many protons as possible were assigned to both the Rand S-MTPA esters, and the configuration of the chiral center in 1 was determined to be R. Both the chiral and achiral diarylnonanoid (2) exhibited potent antibiotic-potentiating activity with the chiral natural product showing a greater tetracycline-potentiating activity than 2. Interestingly, 2 gave a higher norfloxacinpotentiating activity with a resultant higher efflux pump inhibitory activity. Manipulation of the structure of the diarylnonanoids through synthesis could lead to improved biological activity.

show abstract

Dactyloidin, a New Diaryl Nonanoid fromMyristica Dactyloides

Cited by 10 publications

References 5 publications

Acylphenols and Dimeric Acylphenols from the Genus Myristica: A Review of Their Phytochemistry and Pharmacology

Acylphenols and Dimeric Acylphenols from the Genus Myristica: A Review of Their Phytochemistry and Pharmacology

HR-LC-MS based profiling of phytochemicals from methanol extracts of leaves and bark of Myristica dactyloides Gaertn. from Western Ghats of Karnataka, India

Constituents of Two Dioscorea Species That Potentiate Antibiotic Activity against MRSA

Contact Info

Product

Resources

About