Chemical Constituents from Flueggea virosa and the Structural Revision of Dehydrochebulic Acid Trimethyl Ester

Chao, Chih‐Hua; Lin, Ying; Cheng, Ju Chien; Huang, Hui; Yeh, Yung Ju; Wu, Tian Shung; Hwang, Syh Yuan; Wu, Yang Chang

doi:10.3390/molecules21091239

Cited by 13 publications

(10 citation statements)

References 16 publications

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“…Compounds with three galloyl groups connected with the glucose core, including gallotannins (Compounds 38, 40, 42, and 43) and ellagitannin (Compound 41) showed GNMT-promoter-enhancing activity. Among them, 1,3,6-tri-O-linkage (43) was the most active compound, two-fold higher in induction activity than 1,4,6-tri-O-linkage (42) and positive control PGG. This finding suggested that the substituted position of galloyl groups is crucial for GNMT-promoter-enhancing activity.…”

Section: Discussionmentioning

confidence: 94%

“…[38], 4-methoxybenzoic acid(8) [39], 3-hydroxy-1-(3,5-dimethoxy-4-hydroxyphenyl)propan-1-one(9) [40], 3-hydroxy-1-(4-hydroxy-3-ethoxyphenyl) propan-1-one (10)[41], 2,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one (11)[41], and (2S,3R)-4E-dehydrochebulic acid trimethyl ester (12)[42], a mixture of cerebrosides: gynuramides I-IV(13)(14)(15)(16) [43], three coumarins: scopoletin (17)[44], fraxetin (18)[45], and 6-hydroxy-5,7dimethoxycoumarin (19)[46], six coumarinolignans: cleomiscosins A-D (20-23)[47][48][49], malloapelin A (24)[32,33], and malloapelin B (25)[32,33], three diterpenes: ent-11-α-hydroxy-3-oxo-13-epi-manoyl oxide(26)[50], excoecafolin D (27) [15], and agallochin I (28) [51], two flavonoids: (+)-catechin (29) [52] and kaempferol-3-O-β-d-glucoside (30) [53], six steroids: 6 -(stigmast-5-en-7-one-3-O-β-glucopyransidyl) hexadecanoate (31) [54], (6 -O-palmitoyl) sitosterol-3-O-β-d-glucoside (32) [26], a mixture of βsitosterol (33) and stigmasterol (34) [55], a mixture of 3-O-β-d-glucopyranosyl β-sitosterol (35) and 3-O-β-d-glucopyranosyl stigmasterol (36) [56], and eight galloyl glucoses: isopropyl O-β-(6 -O-galloyl) glucopyranoside (37) [57], 4-hydroxy-3-methoxyphenol 1-O-β-d-(2 ,6 -di-O-galloyl)glucoside (38) [58], 3-methoxy-4-hydroxyphenyl 1-O-β-d-(6 -O-galloyl)glucopyranoside (39) [59], 1,2,3,4,6-penta-O-galloylβ-d-glucose (40) [60], corilagin (41) [61], 1,4,6-tri-O-galloyl-β-d-glucose (42) [62], 1,3,6-tri-O-galloyl-β-dglucose (43) [63], and gallic acid 4-O-β-d-(6 -O-galloyl)-glucose (44) [64]. The phytochemical data of known compounds are available in Supplementary Materials.…”

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confidence: 99%

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Chemical Constituents with GNMT-Promoter-Enhancing and NRF2-Reduction Activities from Taiwan Agarwood Excoecaria formosana

Cheng

Yen

et al. 2020

Molecules

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Hepatocellular carcinoma (HCC) is considered to be a silent killer, and was the fourth leading global cause of cancer deaths in 2018. For now, sorafenib is the only approved drug for advanced HCC treatment. The introduction of additional chemopreventive agents and/or adjuvant therapies may be helpful for the treatment of HCC. After screening 3000 methanolic extracts from the Formosan plant extract bank, Excoecaria formosana showed glycine N-methyltransferase (GNMT)-promoter-enhancing and nuclear factor erythroid 2-related factor 2 (NRF2)-suppressing activities. Further, the investigation of the whole plant of E. formosana led to the isolation of a new steroid, 7α-hydroperoxysitosterol-3-O-β-d-(6-O-palmitoyl)glucopyranoside (1); two new coumarinolignans, excoecoumarin A (2) and excoecoumarin B (3); a new diterpene, excoeterpenol A (4); and 40 known compounds (5–44). Among them, Compounds 38 and 40–44 at a 100 μM concentration showed a 2.97 ± 0.27-, 3.17 ± 1.03-, 2.73 ± 0.23-, 2.63 ± 0.14-, 6.57 ± 0.13-, and 2.62 ± 0.05-fold increase in GNMT promoter activity, respectively. In addition, Compounds 40 and 43 could reduce NRF2 activity, a transcription factor associated with drug resistance, in Huh7 cells with relative activity of 33.1 ± 0.2% and 45.2 ± 2.5%. These results provided the basis for the utilization of Taiwan agarwood for the development of anti-HCC agents.

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Section: Discussionmentioning

confidence: 94%

mentioning

confidence: 99%

Chemical Constituents with GNMT-Promoter-Enhancing and NRF2-Reduction Activities from Taiwan Agarwood Excoecaria formosana

Cheng

Yen

et al. 2020

Molecules

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“…Flueggether A, Virosinine A [169]; Flueggenines A, B, and D, Norsecurinine [170][171][172]; Flueggines A and B [173]; Fluevirosines A-C [174]; Virosaines A and B [171,175]; 3β,12-Dihydroxy-13-methylpodocarpa-6,8,11,13-tetraene, 3β,12-Dihydroxy-13-methylpodocarpa-8,11,13-triene, Spruceanol, ent-3β,12α-Dihydroxypimara-8( 14),15-diene, 3α-Hydroxy-12-methoxy-13-methyl-entpodocarp-6,8,11,13-tetraene, 3α-Hydroxy-13-hydroxymethyl-12-methoxy-ent-podocarp-6,8,11,13-tetraene, 3β-Hydroxy-13-hydroxymethyl-12-methoxy-ent-podocarp-6,8,11,13-tetraene, 12-Hydroxy-13-methylent-podocarp-6,8,11,13-tetraen-3-one, 12-Methoxy-13-methyl-ent-podocarp-6,8,11,13-tetraen-3-one, 6β,12-Dihydroxy-13-methyl-ent-podocarp-8,11,13-trien-3-one, 7α,20-Epoxy-3α-hydroxy-12-methoxy-13-methyl-ent-podocarp-8,11,13-triene, 3α,20-Epoxy-3β-hydroxy-12-methoxy-13-methyl-ent-podocarp-8,11,13-triene [176,177];…”

Section: China and Taiwan Aerial; Rootsmentioning

confidence: 99%

Indigenous Uses, Phytochemical Analysis, and Anti-Inflammatory Properties of Australian Tropical Medicinal Plants

Yeshi

Turpin

Jamtsho³

et al. 2022

Molecules

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Australian tropical plants have been a rich source of food (bush food) and medicine to the first Australians (Aboriginal people), who are believed to have lived for more than 50,000 years. Plants such as spreading sneezeweed (Centipeda minima), goat’s foot (Ipomoea pes-caprae), and hop bush (Dodonaea viscosa and D. polyandra) are a few popular Aboriginal medicinal plants. Thus far, more than 900 medicinal plants have been recorded in the tropical region alone, and many of them are associated with diverse ethnomedicinal uses that belong to the traditional owners of Aboriginal people. In our effort to find anti-inflammatory lead compounds in collaboration with Aboriginal communities from their medicinal plants, we reviewed 78 medicinal plants used against various inflammation and inflammatory-related conditions by Aboriginal people. Out of those 78 species, we have included only 45 species whose crude extracts or isolated pure compounds showed anti-inflammatory properties. Upon investigating compounds isolated from 40 species (for five species, only crude extracts were studied), 83 compounds were associated with various anti-inflammatory properties. Alphitolic acid, Betulinic acid, Malabaric acid, and Hispidulin reduced proinflammatory cytokines and cyclooxygenase enzymes (COX-1 and 2) with IC50 values ranging from 11.5 to 46.9 uM. Other promising anti-inflammatory compounds are Brevilin A (from Centipeda minima), Eupalestin, and 5′-methoxy nobiletin (from Ageratum conyzoides), Calophyllolide (from Calophyllum inophyllum), and Brusatol (from Brucea javanica). D. polyandra is one example of an Aboriginal medicinal plant from which a novel anti-inflammatory benzoyl ester clerodane diterpenoid compound was obtained (compound name not disclosed), and it is in the development of topical medicines for inflammatory skin diseases. Medicinal plants in the tropics and those associated with indigenous knowledge of Aboriginal people could be a potential alternative source of novel anti-inflammatory therapeutics.

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“…The fragment ions at m / z 363 and 319 were identified as a result of the elimination of methanol and carbon dioxide from molecular ion, respectively. Due to the lack of sufficient data compound 33 was assigned as dehydrochebulic acid trimethyl ester, previously reported by Geethangili and Ding [ 37 ] in Phyllantus urinaria and in the twigs and leaves extracts of African medicinal plant, Flueggea virosa by Chao, et al [ 47 ].…”

Section: Resultsmentioning

confidence: 99%

LC-ESI-QTOF-MS/MS Analysis, Cytotoxic, Antiviral, Antioxidant, and Enzyme Inhibitory Properties of Four Extracts of Geranium pyrenaicum Burm. f.: A Good Gift from the Natural Treasure

Świątek

Sieniawska

Sinan

et al. 2021

IJMS

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This study focused on the biological evaluation and chemical characterization of Geranium pyrenaicum Burm. f. Different solvent extracts (hexane, ethyl acetate, methanol, and water extracts) were prepared. The phytochemical profile, antioxidant, and enzyme inhibitory activity were investigated. Cytotoxicity was assessed using VERO, FaDu, HeLa and RKO cells. The antiviral activity was carried out against HSV-1 (Herpes simplex virus 1) propagated in VERO cell line. The aqueous extract, possessing high phenolic content (170.50 mg gallic acid equivalent/g extract), showed the highest reducing capacity (613.27 and 364.10 mg Trolox equivalent/g extract, for cupric reducing antioxidant capacity and ferric reducing antioxidant power, respectively), radical scavenging potential (469.82 mg Trolox equivalent/g extract, against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid)), metal chelating ability (52.39 mg ethylenediaminetetraacetic acid equivalent/g extract) and total antioxidant capacity (3.15 mmol Trolox equivalent/g extract). Liquid chromatography-electrospray ionization-quadrupole time-of-flight-mass spectrometry (LC-ESI-QTOF-MS/MS) alloved to tentatively identify a total of 56 compounds in the extracts, including ellagitannins, gallic acid and galloyl derivatives amongst others. The ethyl acetate extracts substantially depressed cholinesterase enzymes (4.49 and 12.26 mg galantamine equivalent/g extract against AChE and BChE, respectively) and α-amylase enzyme (1.04 mmol acarbose equivalent/g extract). On the other hand, the methanolic extract inhibited tyrosinase (121.42 mg kojic acid equivalent/g extract) and α-glucosidase (2.39 mmol acarbose equivalent/g extract) activities. The highest selectivity towards all cancer cell lines (SI 4.5–10.8) was observed with aqueous extract with the FaDu cells being the most sensitive (CC50 40.22 µg/mL). It can be concluded that the presence of certain bioactive antiviral molecules may be related to the high anti HSV-1 activity of the methanolic extract. This work has generated vital scientific data on this medicinal plant, which is a prospective candidate for the creation of innovative phyto-pharmaceuticals.

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Chemical Constituents from Flueggea virosa and the Structural Revision of Dehydrochebulic Acid Trimethyl Ester

Cited by 13 publications

References 16 publications

Chemical Constituents with GNMT-Promoter-Enhancing and NRF2-Reduction Activities from Taiwan Agarwood Excoecaria formosana

Chemical Constituents with GNMT-Promoter-Enhancing and NRF2-Reduction Activities from Taiwan Agarwood Excoecaria formosana

Indigenous Uses, Phytochemical Analysis, and Anti-Inflammatory Properties of Australian Tropical Medicinal Plants

LC-ESI-QTOF-MS/MS Analysis, Cytotoxic, Antiviral, Antioxidant, and Enzyme Inhibitory Properties of Four Extracts of Geranium pyrenaicum Burm. f.: A Good Gift from the Natural Treasure

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