Cytotoxic quinones from the aerial parts of Morinda umbellata L.

Li, Changkang; Su, Xiuqin; Li, Fenghua; Fu, Jiahui; Wang, Hongqing; Li, Baoming; Chen, Ruo-Yun; Kang, Jie

doi:10.1016/j.phytochem.2019.112096

Cited by 12 publications

(5 citation statements)

References 15 publications

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“…Morinda umbellata (Yangjiaoteng), as a succedaneum of Bajitian, can effectively alleviate symptoms of rheumatic diseases, such as rheumatoid arthritis, gouty arthritis, and rheumatic low back pain. Li et al extracted 1,6-dihydroxy-2-methoxymethylanthraquinone, and several other anthraquinones with similar chemical structures from Yangjiaoteng ( Li et al, 2019 ).…”

Section: Traditional Chinese Herbs Associated With Melanosis Colimentioning

confidence: 99%

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Review on melanosis coli and anthraquinone-containing traditional Chinese herbs that cause melanosis coli

et al. 2023

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Backgrounds: The incidence of melanosis coli (MC) has gradually increased annually, attracting significant attention and efforts into this field. A potential risk for MC is the long-term use of anthraquinone laxatives in patients with constipation. Most traditional cathartic drugs are made from herbs containing anthraquinone compounds. This review aims to provide guidance for the application of traditional Chinese herbs containing anthraquinones for physicians and researchers.Materials and methods: We reviewed risk factors and pathogenesis of MC, and natural anthraquinones isolated from TCM herbs. We searched Pubmed and CNKI databases for literature related to MC with keywords such as“traditional Chinese medicine”, “Chinese herbs”, “anthraquinones”, and “melanosis coli”. The literature is current to January 2023 when the searches were last completed. After the literature retrieval, the TCM herbs containing anthraquinones (including component identification and anthraquinone content determination) applied in clinical were selected. According to the collected evidence, we provide a list of herbs containing anthraquinones that could cause MC.Results: We identified 20 herbs belonging to 7 families represented by Polygonaceae, Fabaceae, Rhamnaceae, and Rubiaceae, which may play a role in the pathogenesis of MC. Among these, the herbs most commonly used include Dahuang (Rhei Radix et Rhizome), Heshouwu (Radix Polygoni Multiflori), Huzhang (Rhizoma Polygoni Cuspidati), Juemingzi (Semen Cassiae), Luhui (Aloe) and Qiancao (Rubiae Radix et Rhizoma).Conclusion: Due to a lack of awareness of the chemical composition of TCM herbs, many patients with constipation and even some TCM physicians take cathartic herbal remedies containing abundant anthraquinones to relieve defecation disturbances, resulting in long-term dependence on these herbs, which is potentially associated with most cases of MC. When such treatments are prescribed, TCM physicians should avoid long-term use in large doses to reduce their harm on colonic health. Individuals who take healthcare products containing these herbs should also be under the supervision of a doctor.

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Section: Traditional Chinese Herbs Associated With Melanosis Colimentioning

confidence: 99%

“…Li et al extracted 1,6-dihydroxy-2methoxymethylanthraquinone, and several other anthraquinones with similar chemical structures from Yangjiaoteng (Li et al, 2019).…”

Section: Radix Morindae Officinalis (Bajitian)mentioning

confidence: 99%

Review on melanosis coli and anthraquinone-containing traditional Chinese herbs that cause melanosis coli

et al. 2023

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“…5-Hydroxybenzo[ d ]oxazole-4-carboxylic acid ( E ) could be used as the routiennocin and displays potent activity against Gram-positive and anaerobic bacteria . In addition, the derivatives F were used as folk medicines for the treatment of fever, coughing, stomach ache, and acute hepatitis …”

Section: Introductionmentioning

confidence: 99%

La(OTf)₃-Catalyzed [3+2] Cycloaddition Reactions for the Synthesis of Benzo[d]oxazoles/Benzofurans

Li,

Zhang,

Sun

et al. 2024

J. Org. Chem.

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The La(OTf)3-catalyzed [3+2] cycloaddition reactions for the synthesis of benzo[d]oxazoles/benzofurans via quinones and 1,2-di-tert-butyl-3-(cyanimino)diaziridine (1,3-di-tert-butyl-2-cyanoguanidine)/vinyl azides have been explored. A series of 5-hydroxybenzofuran-4-carboxylic acid derivatives and 5-hydroxybenzo[d]oxazole-4-carboxylic acid derivatives were conveniently obtained with high yields and good stereoselectivities, which could be used for further transformations to valuable compounds.

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“…The molecular design of new heterocyclic compounds with high biological activity is an urgent task of synthetic organic chemistry. 1,2-Benzoquinones represent a prospective class of precursors that possess bioactivity [ 1 , 2 ] and can act as building blocks of molecules of biologically important compounds [ 3 , 4 ], particularly those formed in o -quinone ring expansion reactions providing the formation of hardly accessible 2-hetaryl-1,3-tropolones [ 5 , 6 ] possessing high antibacterial [ 7 ] and antitumor activities [ 8 ]. We have recently shown [ 8 ] that 2-quinolyl-1,3-tropolones with electron-withdrawing groups on the periphery of the tropolone ring (NO 2 or Cl) exhibit high activity (<5 μM) in relation to several cancer cell lines (human ovarian cancer - OVCAR-8, OVCAR-3; human lung cancer - H441, A549; human colon cancer - HCT 116; human pancreatic cancer - Panc-1).…”

Section: Introductionmentioning

confidence: 99%

Reaction of quinaldine with 4,6-di(tert-butyl)-3-nitro-1,2-benzoquinone. Dependence of the outcome on the reaction conditions and a deeper insight into the mechanism

Krasnikova

Sayapin

Tupaeva

et al. 2023

Heliyon

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Cytotoxic quinones from the aerial parts of Morinda umbellata L.

Cited by 12 publications

References 15 publications

Review on melanosis coli and anthraquinone-containing traditional Chinese herbs that cause melanosis coli

Review on melanosis coli and anthraquinone-containing traditional Chinese herbs that cause melanosis coli

La(OTf)₃-Catalyzed [3+2] Cycloaddition Reactions for the Synthesis of Benzo[d]oxazoles/Benzofurans

Reaction of quinaldine with 4,6-di(tert-butyl)-3-nitro-1,2-benzoquinone. Dependence of the outcome on the reaction conditions and a deeper insight into the mechanism

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Cytotoxic quinones from the aerial parts of Morinda umbellata L.

Cited by 12 publications

References 15 publications

Review on melanosis coli and anthraquinone-containing traditional Chinese herbs that cause melanosis coli

Review on melanosis coli and anthraquinone-containing traditional Chinese herbs that cause melanosis coli

La(OTf)3-Catalyzed [3+2] Cycloaddition Reactions for the Synthesis of Benzo[d]oxazoles/Benzofurans

Reaction of quinaldine with 4,6-di(tert-butyl)-3-nitro-1,2-benzoquinone. Dependence of the outcome on the reaction conditions and a deeper insight into the mechanism

Contact Info

Product

Resources

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La(OTf)₃-Catalyzed [3+2] Cycloaddition Reactions for the Synthesis of Benzo[d]oxazoles/Benzofurans