Chemical Constituents of the Vietnamese Marine Sponge Gelliodes sp. and Their Cytotoxic Activities

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

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Compound Identification and In Vitro Cytotoxicity of the Supercritical Carbon Dioxide Extract of Papaya Freeze-Dried Leaf Juice

Processes ◽

10.3390/pr8050610 ◽

2020 ◽

Vol 8 (5) ◽

pp. 610

Author(s):

Kooi-Yeong Khaw ◽

Paul Nicholas Shaw ◽

Marie-Odile Parat ◽

Saurabh Pandey ◽

James Robert Falconer

Keyword(s):

Mass Spectrometry ◽

Carbon Dioxide ◽

Supercritical Carbon Dioxide ◽

Chemical Constituents ◽

Gas Chromatography Mass Spectrometry ◽

Cytotoxic Activities ◽

Compound Identification ◽

Freeze Dried ◽

Leaf Juice ◽

Supercritical Carbon

Carica papaya leaves are used as a remedy for the management of cancer. Freeze-dried C. papaya leaf juice was extracted using a supercritical fluid extraction system. Compound identification was carried out using analytical techniques including liquid chromatography coupled to high-resolution quadrupole time-of-flight mass spectrometry (LC–QToF-MS) and gas chromatography–mass spectrometry (GC–MS). The cytotoxic activities of the scCO2 extract and its chemical constituents were determined using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay on squamous cell carcinoma (SCC25) and human keratinocyte (HaCaT) cell lines. The chemical constituents were quantified by QToF-MS. The supercritical carbon dioxide (scCO2) extract of papaya freeze-dried leaf juice showed cytotoxic activity against SCC25. Three phytosterols, namely, β-sitosterol, campesterol, and stigmasterol, together with α-tocopherol, were confirmed to be present in the scCO2 extract. Quantitative analysis showed that β-sitosterol was the major phytosterol present followed by α-tocopherol, campesterol, and stigmasterol. β-Sitosterol and campesterol were active against SCC25 (half maximal inhibitory concentration (IC50) ≈ 1 µM), while stigmasterol was less active (~33 µM) but was biologically more selective against SCC25. Interestingly, an equimolar mixture of phytosterols was not more effective (no synergistic effect was observed) but was more selective than the individual compounds. The compounds identified are likely accountable for at least part of the cytotoxicity and selectivity effects of C. papaya.

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Cytotoxic Sesterterpenes from Thai Marine Sponge Hyrtios erectus

Marine Drugs ◽

10.3390/md16120474 ◽

2018 ◽

Vol 16 (12) ◽

pp. 474 ◽

Cited By ~ 7

Author(s):

Wirongrong Kaweetripob ◽

Chulabhorn Mahidol ◽

Pittaya Tuntiwachwuttikul ◽

Somsak Ruchirawat ◽

Hunsa Prawat

Keyword(s):

Methyl Ether ◽

Marine Sponge ◽

Indole Alkaloids ◽

Cytotoxic Activities ◽

Spectroscopic Methods ◽

The Absolute ◽

Modified Mosher’S Method

Four sesterterpenes, erectusolides B, C, D, and seco-manoalide-25-methyl ether, two 2-furanone derivatives, erectusfuranones A and B, together with thirteen known sesterterpenes, (6Z)-neomanoalide-24-acetate, two diastereomers of 24-O-methylmanoalide, luffariolide B, manoalide, (6E)- and (6Z)-neomanoalide, seco-manoalide, scalarafuran, 12-acetylscalarolide, 12-epi-O-deacetyl-19-deoxyscalarin, 12-epi-scalarin, and 12-O-deacetyl-12-epi-scalarin, three indole alkaloids, 5-hydroxy-1H-indole-3-carbaldehyde, hyrtiosine A, and variabine B, and one norterpene, cavernosine were isolated from the marine sponge Hyrtios erectus. Their structures were determined by means of spectroscopic methods and the absolute configurations of the asymmetric centers were determined using the modified Mosher’s method. The cytotoxic activities for the isolated compounds have been reported.

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Antipromastigote and cytotoxic activities of some chemical constituents of Hypericum lanceolatum Lam. (Guttifereae)

Journal of Applied Pharmaceutical Science ◽

10.7324/japs.2020.101004 ◽

2020 ◽

Vol 10 (1) ◽

pp. 26-32

Keyword(s):

Chemical Constituents ◽

Cytotoxic Activities

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Chemical Constituents of Viburnum odoratissimum and Their Cytotoxic Activities

Chemistry of Natural Compounds ◽

10.1007/s10600-018-2422-z ◽

2018 ◽

Vol 54 (3) ◽

pp. 600-602 ◽

Cited By ~ 5

Author(s):

Yi-Chao Ge ◽

Hai-Jiang Zhang ◽

Jin-Xiu Lei ◽

Kui-Wu Wang

Keyword(s):

Chemical Constituents ◽

Cytotoxic Activities ◽

Viburnum Odoratissimum

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In Vitro Screening for Cytotoxic, Anti-bacterial, Anti-HIV1-RT Activities and Chemical Constituents of Croton fluviatilis, Croton acutifolius, and Croton thorelii

The Natural Products Journal ◽

10.2174/2210315511666210119125611 ◽

2021 ◽

Vol 11 ◽

Author(s):

Charina Worarat ◽

Wilart Pompimon ◽

Phansuang Udomputtimekakul ◽

Sukee Sukdee ◽

Punchavee Sombutsiri ◽

...

Keyword(s):

Ethyl Acetate ◽

Ethyl Acetate Extract ◽

Biological Activities ◽

Chemical Constituents ◽

Bacterial Activity ◽

Cytotoxic Activities ◽

Separation And Purification ◽

Crude Extracts ◽

Cytotoxicity Activities

Background: Although the chemical constituents and biological activities of a large number of plants in the Croton genus have been studied, there are still recently discovered plants to be investigated. Objective: 1. To investigate the anti-bacterial, anti-HIV1-RT, and cytotoxicity activities of crude extracts from these plants. 2. To investigate the chemical constituents of Croton fluviatilis, Croton acutifolius, and Croton thorelii. Method: The anti-bacterial, anti-HIV1-RT, and cytotoxicity of the three plants were evaluated by standard techniques. Extraction, separation, and purification of extracts from the three plants were undertaken. Results: The ethyl acetate extract of C. fluviatilis showed low anti-bacterial activity against E. aerogenes, E. coli 0157: H7, and P. mirabilis, together with the ethyl acetate extract of C. acutifolius displayed low anti-bacterial activity against E. aerogenes, while all the crude extracts of C. thorelii were inactive. The ethyl acetate extracts of C. thorelii, and C. fluviatilis showed strong inhibited HIV1-RT, whereas the ethyl acetate extract of C. acutifolius, and the hexane extract of C. fluviatilis displayed moderate inhibited HIV1-RT. Cytotoxic properties of three Croton plants were specific to KKU-M213, MDA-MB-231, A-549, and MMNK-1. Especially, the ethyl acetate extract of C. acutifolius exhibited strong cytotoxic activities against MDA-MB-231, A-549, and MMNK-1. Furthermore, the ethyl acetate extract of C. thorelii showed high cytotoxic activities against KKU-M213, and MDA-MB-231. Compounds 1, and 4 were found in C. fluviatilis. Compounds 2 and 4 were also found in C. acutifolius. Moreover, compound 3 was only found in C. thorelii. Conclusion: The present study revealed that the three Croton species are good sources of flavonoid compounds and further investigation of the chemical constituents from these plants may prove to be fruitful to discover more active compounds to be tested as potential medicines.

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Chemical constituents from the thorns of Gleditsia sinensis and their cytotoxic activities

Journal of Asian Natural Products Research ◽

10.1080/10286020.2020.1731799 ◽

2020 ◽

Vol 22 (12) ◽

pp. 1121-1129

Author(s):

Yu-Bo Zhang ◽

Kar-Ho Lam ◽

Li-Feng Chen ◽

Hei Wan ◽

Guo-Cai Wang ◽

...

Keyword(s):

Chemical Constituents ◽

Cytotoxic Activities ◽

Gleditsia Sinensis

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Biological Activity and Chemical Constituents of Essential Oil and Extracts of Murraya microphylla

Natural Product Communications ◽

10.1177/1934578x1501000935 ◽

2015 ◽

Vol 10 (9) ◽

pp. 1934578X1501000

Author(s):

Hai-Ning Lv ◽

Ke-Wu Zeng ◽

Bing-Yu Liu ◽

Yun Zhang ◽

Peng-Fei Tu ◽

...

Keyword(s):

Essential Oil ◽

Human Cancer ◽

Biological Activities ◽

Chemical Constituents ◽

Cytotoxic Activities ◽

Active Components ◽

Human Cancer Cell Lines ◽

Total Oil ◽

Promising Development ◽

Carbazole Alkaloids

Murraya microphylla is the most closely related species to M. koenigii (Curry tree). Inspired by the traditional effects of M. koenigii, the antioxidant, anti-inflammatory, and cytotoxic activities of the essential oil and extracts of M. microphylla were evaluated for the first time. The light petroleum and chloroform extracts were found to be able to scavenge DPPH free radicals, inhibit linoleic acid peroxidation, and nitric oxide production, as well as to present cytotoxicity to the human cancer cell lines HepG2, Bel7402, Bel7403, and Hela, but the essential oil only showed moderate activities. Chemical analysis of the active extracts by LC-DAD-MSn indicated that carbazole alkaloids were the main constituents. GC-MS analysis of the essential oil resulted in identification of 91 constituents, representing 96.9% of the total oil, with ( E)-caryophyllene (18.4%) and terpinen-4-ol (12.6%) as the major constituents. These results demonstrate that M. microphylla has similar biological activities, as well as chemical constituents to M. koenigii, and the carbazole alkaloids were disclosed to be the main potential active components. A promising development as a flavor and potential therapeutic agent could thus be predicated for this plant.

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