Cytotoxic indole alkaloids from Nauclea orientalis

Liu, Yan-Ping; Ju, Peng-Kun; Jiang, Long; Lai, Luhua; Zhao, Wan-Hui; Zhang, Chao; Zhang, Zhijie; Fu, Yan-Hui

doi:10.1080/14786419.2017.1395429

Cited by 12 publications

(3 citation statements)

References 17 publications

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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.…”

mentioning

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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“…The dried stem wood of N. orientalis is used to treat cases of fatigue in Laos, with alkaloid 6 and triterpenoid 8 and their analogues being characterized as active components of this species (Soejarto et al, 2012). Also, several triterpene analogues of 8 were identified as the major components of the hard wood of N. orientalis collected in Japan (Fujita et al, 1967), while a number of indole alkaloid derivatives of 6 were characterized from the leaves and stems of N. orientalis collected in China and in Thailand (Kanchanapoom et al, 2021;Liu et al, 2018). Thus, triterpenoids and indole alkaloids could be the major bioactive constituents of N. orientalis growing in Laos and in other countries in Asia, including China, Japan, and Thailand.…”

Section: Rubiaceae (Nauclea Orientalis (L) L)mentioning

confidence: 99%

Bioactive small-molecule constituents of Lao plants

Ren¹,

Bethany²,

Joshua³

et al. 2021

J. Med. Plants Res.

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Laos has a rich plant diversity, and medicinal plants are used extensively in Lao traditional medicine for the treatment of a variety of human diseases. However, only a relatively small number of these plants have been investigated for their major components with potential antitumor, anti-infective, and other types of bioactivities. These species include Asparagus cochinchinensis, Diospyros quaesita, Gongronema napalense, Marsypopetalum modestum, Nauclea orientalis, Rourea minor, Stemona pierrei, and Stemona tuberosa. Thus far, the bioactive compounds isolated from these Lao plants include alkaloids, glycerol esters, phenolic compounds such as lignans and stilbenoids, steroids, and triterpenoids. Of these, the norlignan, nyasol (1b), the triterpenes, pyracrenic acid [3β-O-transcaffeoylbetulinic acid (3)] and betulinic acid (3b), and the dimeric thiopyridine, dipyrithione (5), were found to show both cancer cell cytotoxicity and anti-infective activity. The present review focuses on examples of promising lead compounds isolated from Lao plants, with their possible development as potential therapeutic agents being discussed. It is hoped that this contribution will provide useful information on higher plants growing in Laos to help stimulate future discoveries of potential agents for the treatment of cancer, infections, and other diseases.

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Cytotoxic indole alkaloids from Nauclea orientalis

Cited by 12 publications

References 17 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

Bioactive small-molecule constituents of Lao plants

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