Two New Antibacterial Sesquiterpenoids from <i>Centipeda minima</i>

He, Liang; Bao, Fukai; Dong, Xiaoping; Zhu, Hua‐Jie; Lu, Xiaojie; Shi, Ming Li; Lü, Qing; Cheng, Yong‐Xian

doi:10.1002/cbdv.200790230

Cited by 21 publications

(5 citation statements)

References 22 publications

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“…[94,96]; Asiaticoside B [93,97]; Isomadecassoside [98]; Quadranoside IV, Quercetin, Astragalin, Isoquercetrin [94]; Centelloside E-G, 11-oxo-Asiaticoside B, 11-oxo-Madecassoside, 11(β)-Methoxy asiaticoside B, 11(β)-Methoxy madecassoside, Centellasaponin A, Isoasiaticoside, Scheffoleoside A [93]; 2α,3β,20,23-Tetrahydroxyurs-28-oic acid [99]; Ursolic acid lactone, Ursolic acid, Pomolic acid, Epi-maslinic acid, Corosolic acid, Rosmarinic acid [95]. [111]; Microhelenalin B and C, Arnicolides B-D, Helenalin-angelate, Helenalin-isovalerate, Helenalin-isobutyrate, Helenalin-3-methyl-2-butanoate, Minimolide E, Minimolide B, 2α-Methoxy-6α-angeloyl-2,3-helenalin [101]; Caloinophyllin A, Nobiletin, Quercetin pentamethyl ether, 3 ,4 5,7-Tetramethoxyflavone, 4 ,5,7-Trimethoxyflavone, 1,5-Dihydroxyxanthone, 1,8-Dimethoxy-2-hydroxyxanthone, 1,6-Dihydroxy-7-methoxyxanthone, 4-Methoxycaffeic acid [112].…”

Section: Canadamentioning

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: Canadamentioning

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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“…This led to our deduction that IF might possess similar apoptotic activity. However, other than a report on the sensitivity Gram-positive bacteria [ 8 ], no other information has reported such activity in IF.…”

Section: Resultsmentioning

confidence: 99%

“…In addition, it is used in the Chinese folk medicine to treat nasopharyngeal carcinoma (NPC) [ 3 , 4 ]. Recent pharmacological interest has focused on its anti-allergy and anti-bacterial effects [ 5 , 6 , 7 , 8 ]. Phytochemical studies of its composition have led to the identification of a number of terpenes, including sesquiterpene lactones and triterpenes [ 5 , 6 , 9 ].…”

Section: Introductionmentioning

confidence: 99%

2β-(Isobutyryloxy)florilenalin, a Sesquiterpene Lactone Isolated from the Medicinal Plant Centipeda minima, Induces Apoptosis in Human Nasopharyngeal Carcinoma CNE Cells

Chung

2009

Molecules

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Centipeda minima is a medicinal plant reputed in China as a remedy for nasopharyngeal carcinoma (NPC). In this study, bioactivity-guided fractionation of the anti-NPC compound(s) from C. minima led to the isolation of 2β-(isobutyryloxy)florilenalin (IF), a sesquiterpene lactone. IF showed significant dose- and time- dependent inhibition on the growth of the human nasopharyngeal carcinoma epithelia cells (CNE). It induced apoptosis in CNE cells, as shown by the accumulation of sub-G1 cell population, DNA fragmentation and nuclear condensation, caspase-3 activation and PARP cleavage. Such induction was associated with the depletion of mitochondrial membrane potential (ΔΨm) and the release of cytochrome c to cytosol to regulate the expression of Bcl-2 family proteins. These activities led to the cleavage of caspases and the trigger of cell death process. Overall, IF in C. minima showed potent antiproliferative effect of C. minima on NPC cells, suggesting that the plant deserves more extensive investigation for its potential medicinal application.

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“…Modern pharmacological research suggests that active compounds isolated from medicinal plants have multiple pharmacological effects [ 2 , 3 , 4 ]. At present, it has been reported that medicinal plants have been proven to have anti-inflammatory [ 5 , 6 ] and antibacterial [ 7 , 8 ] effects, according to traditional Chinese medicine books, and these compounds also have a wide range of antitumor effects, which can inhibit the proliferation of nasopharyngeal cancer [ 9 ], gastric cancer [ 10 ], colon cancer [ 11 ] and other tumors and induce tumor cell apoptosis. Arnicolide C is a sesquiterpene lactone [ 12 ] isolated from C. minima .…”

Section: Introductionmentioning

confidence: 99%

Arnicolide C Suppresses Tumor Progression by Targeting 14-3-3θ in Breast Cancer

Liu,

Lyu,

Chen

et al. 2024

Pharmaceuticals

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Background: Arnicolide C, which is isolated from Centipeda minima, has excellent antitumor effects. However, the potential impacts and related mechanisms of action of arnicolide C in breast cancer remain unknown. Methods: The viability of breast cancer cells was measured using MTT (3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay and colony formation assays. For analysis of apoptosis and the cell cycle, flow cytometry was used. A molecular docking approach was used to explore the possible targets of arnicolide C. Western blot analysis was used to detect changes in the expression of 14-3-3θ and proteins in related pathways after arnicolide C treatment in breast cancer cells. The anti-breast cancer effect of arnicolide C in vivo was evaluated by establishing cell-derived xenograft (CDX) and patient-derived xenograft (PDX) models. Results: Arnicolide C inhibited proliferation, increased apoptosis, and induced G1 arrest. In particular, molecular docking analysis indicated that arnicolide C binds to 14-3-3θ. Arnicolide C reduced 14-3-3θ expression and inhibited its downstream signaling pathways linked to cell proliferation. Similar results were obtained in the CDX and PDX models. Conclusion: Arnicolide C can have an anti-breast cancer effect both in vitro and in vivo and can induce cell cycle arrest and increase apoptosis in vitro. The molecular mechanism may be related to the effect of arnicolide C on the expression level of 14-3-3θ. However, the specific mechanism through which arnicolide C affects 14-3-3θ protein expression still needs to be determined.

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Two New Antibacterial Sesquiterpenoids from Centipeda minima

Cited by 21 publications

References 22 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

2β-(Isobutyryloxy)florilenalin, a Sesquiterpene Lactone Isolated from the Medicinal Plant Centipeda minima, Induces Apoptosis in Human Nasopharyngeal Carcinoma CNE Cells

Arnicolide C Suppresses Tumor Progression by Targeting 14-3-3θ in Breast Cancer

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