Thaixylomolins O–R: four new limonoids from the Trang mangrove, Xylocarpus moluccensis

Dai, Yi-Guo; Li, Wan-Shan; Pedpradab, Patchara; Liu, Junjun; Wu, Jun; Shen, Li

doi:10.1039/c6ra14721f

Cited by 16 publications

(17 citation statements)

References 26 publications

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“…Mangroves or their associates were the sources of a moderately antiplasmodial embelin analogue 1301 (Aegiceras corniculatum), 748 two dolabranes tagalsin V 1302 and W 1303 (Ceriops tagal), 749 a new tirucallane 1304 and two tetranortriterpenes 1305 and 1306 (seeds of Xylocarpus moluccensis), 750 a further eight tetranortriterpenoids 1307-1314 (leaves and twigs of X. granatum), 751 and limonoids 1315-1318 (X. moluccensis). 752 The structures of xylogranatumin A 1308 and thaixylomolins O 1315 and P 1316 are notable, with the former containing an unusual oxygen-bridging arrangement, and the latter two with their orthoacetate bridge. Absolute congurations were assigned to 1307 and 1318 by TDDFT calculated ECD analysis, to 1315 and 1307 by single crystal X-ray diffraction studies and to 1316 by comparison of ECD spectra.…”

Section: Mangrovesmentioning

confidence: 99%

Marine natural products

et al. 2018

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Covering: 2016. Previous review: Nat. Prod. Rep., 2017, 34, 235-294This review covers the literature published in 2016 for marine natural products (MNPs), with 757 citations (643 for the period January to December 2016) referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms. The emphasis is on new compounds (1277 in 432 papers for 2016), together with the relevant biological activities, source organisms and country of origin. Reviews, biosynthetic studies, first syntheses, and syntheses that led to the revision of structures or stereochemistries, have been included.

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Section: Mangrovesmentioning

confidence: 99%

Marine natural products

et al. 2018

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“…In addition, granaxylocarpins C, D , and E were inactive against both the P-388 and A-549 cell lines [ 30 ]. Besides, antitumor activities of thaixylogranins A–H exhibited weak cytotoxicity against the breast MDA-MB-231 cell line [ 61 ], with the concentration of IC 50 values of 49.4, 58.3, 53.6, 61.1, 57.9, 44.6, 40.6, and 38.5 mM, respectively, whereas thaixylogranin E showed weak cytotoxicity against the HCT-8/T cell with an IC 50 value of 36.4 mM. Compound thaixylogranins C and D exhibited weak cytotoxicity against the melanoma A375 cell with IC 50 values of 47.1 and 41.9 mM, respectively; and in gastric cancer AGS cell line, thaixylogranins C and D showed same cytotoxic effect with IC50 values of 41.7 and 35.0 mM, respectively [ 29 ].…”

Section: Resultsmentioning

confidence: 99%

Ethnomedicinal Use, Phytochemistry, and Pharmacology of Xylocarpus granatum J. Koenig

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Hossain

et al. 2021

Evidence-Based Complementary and Alternative Medicine

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The mangrove plants are the potential sources of foods and remedies for people living in the forests and nearby communities. Xylocarpus granatum J. Koenig is traditionally used to treat various diseases including diarrhea, cholera, dysentery, fever, malaria, and viral infections, among others. To summarize critically the taxonomy, ethnomedicinal, phytochemistry, and pharmacological activities of X. granatum, information was collected from different databases. An up-to-date search (till June 2020) was carried out with the help of various scientific web resources from databases such as PubMed, Science Direct, Google Scholar, and various patent offices (e.g., WIPO, CIPO, and USPTO) using the keywords “Xylocarpus granatum” and then paired with ethnomedicinal use and phytochemical, phytochemistry, and pharmacological activity (in vitro, ex vivo, and in vivo studies). Findings revealed that seeds, fruits, stem bark, leaf, and twigs of X. granatum exhibited a wide range of key phytochemicals including limonoids, phragmalin, limonoid-based alkaloids, mexicanolides, protolimonoids, flavonols, and lactones. The plant possessed potent antioxidant, anticancer, antidiabetic, antimicrobial, antimalarial, antifeedant, and neuroprotective activities. No clinical studies have been reported in the databases. Ethnomedicinal assessment indicated the application of X. granatum in various fields of medical science specially to treat various human ailments, and this was attributed to the presence of enormous alkaloids as confirmed by pharmacological studies. However, to understand the mechanism of action in-depth studies are required. In view of these findings, more research is necessary to explore and characterize the chemical compounds and toxicological aspects of this medicinal mangrove plant. Overall, it can be stated that X. granatum may be one of the hopeful medicinal herbs for the treatment of various diseases in human beings.

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“…Phragmalins 8,9,12- ortho esters, called thaixylomolins O–P ( 163, 164 ); 9,10- seco mexicanolide named thaixylomolin Q ( 165 ); and thaixylomolin R ( 166 ), a limonoid with 6-oxabicyclo[3.2.1]octan-3-one, were discovered in the seed of X. moluccensis . Compound 164 exhibited antitumor against ovarian A2780/T cell and A2780 with an IC 50 value of 37.5 μM [ 97 ].…”

Section: The Secondary Metabolites From the Seed Of Mangrovementioning

confidence: 99%

Exploring the Mangrove Fruit: From the Phytochemicals to Functional Food Development and the Current Progress in the Middle East

et al. 2022

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Nowadays, the logarithmic production of existing well-known food materials is unable to keep up with the demand caused by the exponential growth of the human population in terms of the equality of access to food materials. Famous local food materials with treasury properties such as mangrove fruits are an excellent source to be listed as emerging food candidates with ethnomedicinal properties. Thus, this study reviews the nutrition content of several edible mangrove fruits and the innovation to improve the fruit into a highly economic food product. Within the mangrove fruit, the levels of primary metabolites such as carbohydrates, protein, and fat are acceptable for daily intake. The mangrove fruits, seeds, and endophytic fungi are rich in phenolic compounds, limonoids, and their derivatives as the compounds present a multitude of bioactivities such as antimicrobial, anticancer, and antioxidant. In the intermediary process, the flour of mangrove fruit stands as a supplementation for the existing flour with antidiabetic or antioxidant properties. The mangrove fruit is successfully transformed into many processed food products. However, limited fruits from species such as Bruguiera gymnorrhiza, Rhizophora mucronata, Sonneratia caseolaris, and Avicennia marina are commonly upgraded into traditional food, though many more species demonstrate ethnomedicinal properties. In the Middle East, A. marina is the dominant species, and the study of the phytochemicals and fruit development is limited. Therefore, studies on the development of mangrove fruits to functional for other mangrove species are demanding. The locally accepted mangrove fruit is coveted as an alternate food material to support the sustainable development goal of eliminating world hunger in sustainable ways.

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Thaixylomolins O–R: four new limonoids from the Trang mangrove, Xylocarpus moluccensis

Abstract: Four new limonoids, including two novel phragmalin 8,9,12-orthoesters, were identified from the seeds of Thai mangrove, Xylocarpus moluccensis.

Cited by 16 publications

References 26 publications

Marine natural products

Marine natural products

Ethnomedicinal Use, Phytochemistry, and Pharmacology of Xylocarpus granatum J. Koenig

Exploring the Mangrove Fruit: From the Phytochemicals to Functional Food Development and the Current Progress in the Middle East

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