Constituents of the Stem of <i>Nauclea orientalis</i>

Dao, Phan Thi Anh; Quan, Tran Le; Thanh, Nguyễn Thị

doi:10.1177/1934578x1501001122

Cited by 7 publications

(6 citation statements)

References 9 publications

(1 reference statement)

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“…China, Japan, Laos, Papua New Guinea, Thailand, and Vietnam Heartwood; bark; leaves; stems; roots; Noreugenin, Naucleoside [212]; Angustine, 18,19-Dihydroangustine, 10-Hydroxyangustine, 3,14,18,19-Tetrahydroangustine, Parvine, Angustoline [213]; Nauclealines A and B, Naucleosides A and B, Strictosamide, Vincosamide, Pumiloside, Kelampayoside A, β-Sitosterol, Sitosteryl β-D-glucoside [214,215]; Naucleaorals A and B [216]; 10-Hydroxystrictosamide, 6 -O-Acetylstrictosamide [215]; α-Pinene, Loganetin, Loganin, Sweroside, Grandifloroside, Methyl 3,4-dihydroxybenzoate, 4-Hydroxycinnamic acid, 3-(2,4-Dihydroxylphenyl)propanoic acid, Methyl 3-(2,4-dihydroxylphenyl)propanoate, Skimmin, Adicardin, Aloe emodin, Pinoresinol [217]; Naucleaorine, Epimethoxynaucleaorine, Strictosidine lactam, 3,4,5-Trimethoxyphenol, 3α-Hydroxyurs-12-en-28-oic acid methyl ester, 3α,23-Dihydroxyurs-12-en-28-oic acid, 3α,19α,23-Trihydroxyurs-12-en-28-oic acid methyl ester, Oleanolic acid [218]; Nauclorienine, Antirhine, Iso-antirhine, Alangine, Naucline, Neonaucline, Angustidine, Subditine [219].…”

Section: Vietnam Stem Barkmentioning

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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Section: Vietnam Stem Barkmentioning

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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“…The leaf extract of this plant showed potent anthelmintic activity against Pheretima posthuma as compared to albendazole [14]. The alkaloids isolated from this plant also exhibited potent cytotoxic, anti-proliferation, anti-malarial, and antioxidant activities [15][16][17][18]. Our present study is the first report on lipoxygenase inhibitory activity and exact mechanisms of inhibition of the indole alkaloids from N. orientalis.…”

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confidence: 63%

Non-redox Lipoxygenase Inhibitors from Nauclea orientalis

Surapinit

Sichaem

Tip‐pyang

2018

Natural Product Communications

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Eight alkaloids recently isolated from the roots of Nauclea orientalis (L.) L. were obtained to evaluate the lipoxygenase (LOX) inhibitory activity. According to the LOX inhibitory assay, the cis isomer 1 (IC 50 39.2±1.1 µM) was more potent than the trans isomer 2 (IC 50 52.1±1.5 µM) (P < 0.05). Compound 5 (IC 50 57.8±1.8 µM) was more potent than 6 (IC 50 97.6±3.4 µM), 3 (IC 50 112.1±2.6 µM) and 4 (inactive) (P <0.05), respectively. Alkaloid glycosides 7 and 8 were completely inactive in a screening assay. All active indole alkaloids were inactive in DPPH and 13-HPOD scavenging assays at the concentration of 100 µM. Moreover, these compounds did not exhibit the interferential effects on the Fe 2+ /Fe 3+ redox state as indicated by the iron reduction and oxidation assays. The enzyme kinetic study revealed that 1, 2 and 6 inhibited sb-LOX-1 through the mixed inhibition with a set of inhibition constants (K and K) of 9 and 22, 17 and 46, and 16 and 32 µM, respectively. Indole alkaloids 3 and 5 were the uncompetitive and noncompetitive inhibitors with the K of 24 and 8 µM. These findings undoubtedly demonstrated that these active indole alkaloids were non-redox lipoxygenase inhibitors.

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“…These derivatives belong to the polyphenol's family, which are natural molecules of crucial importance in pharmaceutics and dietary, among others (Tresserra‐Rimbaua et al, 2018). Most of them were obtained previously as natural products from different species, such as Sterculia diversifolia ( 11 ), Prunus persica , and Agastache rugosa ( 12 ) (Dahae‐Lee et al, 2021; Seo et al, 2019), Nauclea orientalis ( 16 ) (Dao et al, 2015), Galla rhois ( 17 ) (Choi et al, 2014), Anigozanthos preissii ( 21 ) (Hidalgo et al, 2015), Ipomoea subincana ( 22 ) (Meira et al, 2008). Also found in food sources: green onion ( Allium cepa ) ( 11 , 13 ) (Xiao & Parkin, 2007), oregano ( Origanum vulgare L.) ( 20 ) (Nakatani & Kikuzaki, 1987), riesling wine ( 16, 12 ) (Baderschneider & Winterhalter, 2001), and sausage fruit ( Kigelia africana ) ( 13 ) (Ilmiawati et al, 2020), Moroccan Zantaz honey ( 19 ) (Elamine et al, 2021; Rogério da Nóbrega et al, 2018; Tuberoso et al, 2009).…”

Section: Resultsmentioning

confidence: 99%

Methyl benzoate and cinnamate analogs as modulators of DNA methylation in hepatocellular carcinoma

et al. 2022

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Phenolic acids represent a large collection of phytochemical molecules present in the plant kingdom; they have an important role as epigenetic regulators, particularly as inhibitors of DNA methylation. In the present study, 14 methyl benzoate and cinnamate analogs were synthesized (11–24). Their cytotoxic activity on hepatocellular carcinoma cells (Hep3B) and immortalized human hepatocyte cells was then evaluated. In addition, its effect on the inhibition of global DNA methylation in Hep3B was also determined. Our results showed that the cinnamic derivatives 11–14 and 20–22 were more potent than the free caffeic acid (IC50 109.7–364.2 µM), being methyl 3,4‐dihydroxycinammate (12) the most active with an IC50 = 109.7 ± 0.8 µM. Furthermore, 11–14, 20–23 compounds decreased overall DNA methylation levels by 63% to 97%. The analogs methyl 4‐hydroxycinnamate (11), methyl 3,4,5‐trimethoxycinnamate (14), methyl 4‐methoxycinnamate (21), and methyl 3,4‐dimethoxycinnamate (22) showed relevant activities of both cytotoxicity and global DNA methylation inhibition. The molecular docking of 21 and 14 suggested that they partly bind to the SAH‐binding pocket of DNA methyltransferase 1. These results emphasize the importance of natural products and their analogs as potential sources of DNA methylation modulating agents.

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Constituents of the Stem of Nauclea orientalis

Cited by 7 publications

References 9 publications

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

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

Non-redox Lipoxygenase Inhibitors from Nauclea orientalis

Methyl benzoate and cinnamate analogs as modulators of DNA methylation in hepatocellular carcinoma

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