Damnacanthal (BioDeep_00000249075)

 

Secondary id: BioDeep_00000177940

PANOMIX_OTCML-2023


代谢物信息卡片


9,10-Dihydroxy-3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarboxaldehyde

化学式: C16H10O5 (282.052821)
中文名称: 丹宁卡
谱图信息: 最多检出来源 Chinese Herbal Medicine(otcml) 1.35%

Reviewed

Last reviewed on 2024-07-09.

Cite this Page

Damnacanthal. BioDeep Database v3. PANOMIX ltd, a top metabolomics service provider from China. https://query.biodeep.cn/s/damnacanthal (retrieved 2024-11-05) (BioDeep RN: BioDeep_00000249075). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

分子结构信息

SMILES: COC1=C2C(=CC(=C1C=O)O)C(=O)C3=CC=CC=C3C2=O
InChI: InChI=1S/C16H10O5/c1-21-16-11(7-17)12(18)6-10-13(16)15(20)9-5-3-2-4-8(9)14(10)19/h2-7,18H,1H3

描述信息

3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarboxaldehyde is a monohydroxyanthraquinone and an aldehyde.
Damnacanthal is a natural product found in Damnacanthus major, Derris brevipes, and other organisms with data available.
Damnacanthal is an alkaloid phytochemical found in the Morinda Citrifolia (Noni) that inhibits the growth of RAS cancer cells. The exact mechanism is unknown but may involve the inhibition of tyrosine kinase. (NCI)

同义名列表

30 个代谢物同义名

9,10-Dihydroxy-3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarboxaldehyde; 9,10-Dihydro-3-hydroxy-1-methoxy-9,10-dioxo-2-anthracenecarboxaldehyde; 3-Hydroxy-1-methoxy-9,10-dioxo-9,10-dihydro-anthracene-2-carbaldehyde; 3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydro-2-anthracenecarbaldehyde; 3-hydroxy-1-methoxy-9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde; 2-Anthraldehyde, 9,10-dihydro-3-hydroxy-1-methoxy-9,10-dioxo-; 3-hydroxy-1-methoxy-9,10-dioxo-anthracene-2-carbaldehyde; 3-hydroxy-1-methoxy-9,10-dioxoanthracene-2-carbaldehyde; 2-Anthraquinonecarboxaldehyde, 3-hydroxy-1-methoxy-; 1-Methoxy-2-formyl-3-hydroxy-9,10-anthraquinone; 3-Hydroxy-1-methoxyanthraquinone-2-aldehyde; BiomolKI2_000030; BCBcMAP01_000230; UNII-WUC3CB63CD; KBio3_000650; KBio2_002893; Damnacanthal; KBio2_000325; KBio3_000649; KBio2_005461; Bio2_000803; Bio1_000654; Bio1_000165; Damnacantal; Bio1_001143; Bio2_000323; QTL1_000028; IDI1_002078; WUC3CB63CD; BMK1-C10



数据库引用编号

10 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

PlantCyc(0)

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

0 个相关的物种来源信息

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

  • PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
  • NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
  • Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
  • Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。



文献列表

  • Saiful Yazan Latifah, Banulata Gopalsamy, Raha Abdul Rahim, Abdul Manaf Ali, Nordin Haji Lajis. Ultrastructural and Morphological Effects in T-Lymphoblastic Leukemia CEM-SS Cells Following Treatment with Nordamnacanthal and Damnacanthal from Roots of Morinda elliptica. Molecules (Basel, Switzerland). 2022 Jun; 27(13):. doi: 10.3390/molecules27134136. [PMID: 35807381]
  • Mark J Henderson, Kathleen A Trychta, Shyh-Ming Yang, Susanne Bäck, Adam Yasgar, Emily S Wires, Carina Danchik, Xiaokang Yan, Hideaki Yano, Lei Shi, Kuo-Jen Wu, Amy Q Wang, Dingyin Tao, Gergely Zahoránszky-Kőhalmi, Xin Hu, Xin Xu, David Maloney, Alexey V Zakharov, Ganesha Rai, Fumihiko Urano, Mikko Airavaara, Oksana Gavrilova, Ajit Jadhav, Yun Wang, Anton Simeonov, Brandon K Harvey. A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome. Cell reports. 2021 04; 35(4):109040. doi: 10.1016/j.celrep.2021.109040. [PMID: 33910017]
  • Saiful Yazan Latifah, Banulata Gopalsamy, Raha Abdul Rahim, Abdul Manaf Ali, Nordin Haji Lajis. Anticancer Potential of Damnacanthal and Nordamnacanthal from Morinda elliptica Roots on T-lymphoblastic Leukemia Cells. Molecules (Basel, Switzerland). 2021 Mar; 26(6):. doi: 10.3390/molecules26061554. [PMID: 33808969]
  • Mokhlesur Rahman Mohd, Tengku Mohd Ariff, Nasir Mohamad, Ahmad Zubaidi Abdul Latif, Wan Mohd Norsani Wan Nik, Awang Mohamed, Izzat Fahim Mohd Suffian. Development of biodegradable sustained-release damnacanthal nanocapsules for potential application in in-vitro breast cancer studies. Pakistan journal of pharmaceutical sciences. 2019 Sep; 32(5):2155-2162. doi: ". [PMID: 31813882]
  • Gohar Shaghayegh, Aied M Alabsi, Rola Ali-Saeed, Abdul Manaf Ali, Vui King Vincent-Chong, Nor Hadiani Ismail, Y F Choon, Rosnah Binti Zain. Effects of Damnacanthal and Nordamnacanthal on Proliferation, Apoptosis, and Migration of Oral Squamous Cell Carcinoma Cells. Asian Pacific journal of cancer prevention : APJCP. 2017 Dec; 18(12):3333-3341. doi: 10.22034/apjcp.2017.18.12.3333. [PMID: 29286228]
  • Na-Ra Han, Phil-Dong Moon, Sun-Young Nam, Ka-Jung Ryu, Myoung-Schook Yoou, Jung-Hye Choi, Sung-Yeoun Hwang, Hyung-Min Kim, Hyun-Ja Jeong. Inhibitory effects of atractylone on mast cell-mediated allergic reactions. Chemico-biological interactions. 2016 Oct; 258(?):59-68. doi: 10.1016/j.cbi.2016.08.015. [PMID: 27553716]
  • Nwet Nwet Win, Takuya Ito, Yi Yi Win, Hla Ngwe, Takeshi Kodama, Ikuro Abe, Hiroyuki Morita. Quassinoids: Viral protein R inhibitors from Picrasma javanica bark collected in Myanmar for HIV infection. Bioorganic & medicinal chemistry letters. 2016 10; 26(19):4620-4624. doi: 10.1016/j.bmcl.2016.08.055. [PMID: 27575477]
  • Negera Abdissa, Fangfang Pan, Amra Gruhonjic, Jürgen Gräfenstein, Paul A Fitzpatrick, Göran Landberg, Kari Rissanen, Abiy Yenesew, Máté Erdélyi. Naphthalene Derivatives from the Roots of Pentas parvifolia and Pentas bussei. Journal of natural products. 2016 09; 79(9):2181-7. doi: 10.1021/acs.jnatprod.6b00178. [PMID: 27518587]
  • Louis P Sandjo, Milene H de Moraes, Victor Kuete, Blaise C Kamdoum, Bonaventure T Ngadjui, Mario Steindel. Individual and combined antiparasitic effect of six plant metabolites against Leishmania amazonensis and Trypanosoma cruzi. Bioorganic & medicinal chemistry letters. 2016 Apr; 26(7):1772-5. doi: 10.1016/j.bmcl.2016.02.044. [PMID: 26906638]
  • Min-Ho Kim, Hyun-Ja Jeong. Damnacanthal inhibits the NF-κB/RIP-2/caspase-1 signal pathway by inhibiting p56lck tyrosine kinase. Immunopharmacology and immunotoxicology. 2014 Oct; 36(5):355-63. doi: 10.3109/08923973.2014.952819. [PMID: 25139491]
  • Nadiah Abu, Norlaily Mohd Ali, Wan Yong Ho, Swee Keong Yeap, Muhammad Yusran Abdul Aziz, Noorjahan Banu Alitheen. Damnacanthal: a promising compound as a medicinal anthraquinone. Anti-cancer agents in medicinal chemistry. 2014 Jun; 14(5):750-5. doi: 10.2174/18715206113136660366. [PMID: 24164045]
  • Dya Fita Dibwe, Suresh Awale, Shigetoshi Kadota, Yasuhiro Tezuka. Damnacanthal from the Congolese medicinal plant Garcinia huillensis has a potent preferential cytotoxicity against human pancreatic cancer PANC-1 cells. Phytotherapy research : PTR. 2012 Dec; 26(12):1920-6. doi: 10.1002/ptr.4672. [PMID: 22447631]
  • Thararat Nualsanit, Pleumchitt Rojanapanthu, Wandee Gritsanapan, Thiwanporn Kwankitpraniti, Kyung-Won Min, Seung Joon Baek. Damnacanthal-induced anti-inflammation is associated with inhibition of NF-κB activity. Inflammation & allergy drug targets. 2011 Dec; 10(6):455-63. doi: 10.2174/187152811798104908. [PMID: 21999179]
  • Celia X-J Chen, Ileana Soto, Ya-Lan Guo, Yuan Liu. Control of secondary granule release in neutrophils by Ral GTPase. The Journal of biological chemistry. 2011 Apr; 286(13):11724-33. doi: 10.1074/jbc.m110.154203. [PMID: 21282111]
  • Kanako Okusada, Kazuo Nakamoto, Mikako Nishida, Wakako Fujita-Hamabe, Kohei Kamiya, Yoshiyuki Mizushina, Toshiko Satake, Shogo Tokuyama. The antinociceptive and anti-inflammatory action of the CHCl3-soluble phase and its main active component, damnacanthal, isolated from the root of Morinda citrifolia. Biological & pharmaceutical bulletin. 2011; 34(1):103-7. doi: 10.1248/bpb.34.103. [PMID: 21212526]
  • Che Puteh Osman, Nor Hadiani Ismail, Rohaya Ahmad, Norizan Ahmat, Khalijah Awang, Faridahanim Mohd Jaafar. Anthraquinones with antiplasmodial activity from the roots of Rennellia elliptica Korth. (Rubiaceae). Molecules (Basel, Switzerland). 2010 Oct; 15(10):7218-26. doi: 10.3390/molecules15107218. [PMID: 20966871]
  • E Jeffrey North, Angela L Howard, Irene W Wanjala, Truc Chi T Pham, Daniel L Baker, Abby L Parrill. Pharmacophore development and application toward the identification of novel, small-molecule autotaxin inhibitors. Journal of medicinal chemistry. 2010 Apr; 53(8):3095-105. doi: 10.1021/jm901718z. [PMID: 20349977]
  • Noorjahan B Alitheen, A Abdul Manaf, S K Yeap, M Shuhaimi, L Nordin, A R Mashitoh. Immunomodulatory effects of damnacanthal isolated from roots of Morinda elliptica. Pharmaceutical biology. 2010 Apr; 48(4):446-52. doi: 10.3109/13880200903168031. [PMID: 20645725]
  • Wasina Thani, Omboon Vallisuta, Pongpan Siripong, Nongluck Ruangwises. Anti-proliferative and antioxidative activities of Thai noni/Yor (Morinda citrifolia Linn.) leaf extract. The Southeast Asian journal of tropical medicine and public health. 2010 Mar; 41(2):482-9. doi: NULL. [PMID: 20578533]
  • B Shivananda Nayak, Steve Sandiford, Anderson Maxwell. Evaluation of the Wound-healing Activity of Ethanolic Extract of Morinda citrifolia L. Leaf. Evidence-based complementary and alternative medicine : eCAM. 2009 Sep; 6(3):351-6. doi: 10.1093/ecam/nem127. [PMID: 18955257]
  • G C L Ee, Y P Wen, M A Sukari, R Go, H L Lee. A new anthraquinone from Morinda citrifolia roots. Natural product research. 2009; 23(14):1322-9. doi: 10.1080/14786410902753138. [PMID: 19735047]
  • Joseph Ngoupayo, Turibio Kuiate Tabopda, Muhammad Shaiq Ali, Etienne Tsamo. alpha-glucosidase inhibitors from Garcinia brevipedicellata (Clusiaceae). Chemical & pharmaceutical bulletin. 2008 Oct; 56(10):1466-9. doi: 10.1248/cpb.56.1466. [PMID: 18827392]
  • Pittaya Tuntiwachwuttikul, Yuttapon Butsuri, Piyanut Sukkoet, Uma Prawat, Walter Charles Taylor. Anthraquinones from the roots of Prismatomeris malayana. Natural product research. 2008; 22(11):962-8. doi: 10.1080/14786410701650261. [PMID: 18629711]
  • Afa K Palu, Brett J West, Jarakae Jensen, Leland White. Knowing your noni tree and traditional usage eliminates confusion. Biochemical and biophysical research communications. 2006 Dec; 351(3):577. doi: 10.1016/j.bbrc.2006.10.162. [PMID: 17101308]
  • D N Singh, N Verma, S Raghuwanshi, P K Shukla, D K Kulshreshtha. Antifungal anthraquinones from Saprosma fragrans. Bioorganic & medicinal chemistry letters. 2006 Sep; 16(17):4512-4. doi: 10.1016/j.bmcl.2006.06.027. [PMID: 16824761]
  • Kwanjai Kanokmedhakul, Somdej Kanokmedhakul, Ruchanee Phatchana. Biological activity of Anthraquinones and Triterpenoids from Prismatomeris fragrans. Journal of ethnopharmacology. 2005 Sep; 100(3):284-8. doi: 10.1016/j.jep.2005.03.018. [PMID: 15885942]
  • S C Nuñez Montoya, A M Agnese, C Pérez, I N Tiraboschi, J L Cabrera. Pharmacological and toxicological activity of Heterophyllaea pustulata anthraquinone extracts. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2003; 10(6-7):569-74. doi: 10.1078/094471103322331854. [PMID: 13678245]
  • T Ohse, S Ohba, T Yamamoto, T Koyano, K Umezawa. Cyclopentabenzofuran lignan protein synthesis inhibitors from Aglaia odorata. Journal of natural products. 1996 Jul; 59(7):650-2. doi: 10.1021/np960346g. [PMID: 8759160]
  • C R Faltynek, J Schroeder, P Mauvais, D Miller, S Wang, D Murphy, R Lehr, M Kelley, A Maycock, W Michne. Damnacanthal is a highly potent, selective inhibitor of p56lck tyrosine kinase activity. Biochemistry. 1995 Sep; 34(38):12404-10. doi: 10.1021/bi00038a038. [PMID: 7547985]
  • T Hiramatsu, M Imoto, T Koyano, K Umezawa. Induction of normal phenotypes in ras-transformed cells by damnacanthal from Morinda citrifolia. Cancer letters. 1993 Sep; 73(2-3):161-6. doi: 10.1016/0304-3835(93)90259-c. [PMID: 7693328]