Galangal acetate (BioDeep_00001874160)

Main id: BioDeep_00000008086

 

PANOMIX_OTCML-2023 Volatile Flavor Compounds


代谢物信息卡片


D,L-1-Acetoxychavicol acetate

化学式: C13H14O4 (234.0892044)
中文名称: D,L-1-醋酸乙酰氧基甲壳酚, 1’-乙酰氧基乙酸乙酯，（+/-）
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: c1(ccc(cc1)[C@@H](OC(=O)C)C=C)OC(=O)C
InChI: InChI=1S/C13H14O4/c1-4-13(17-10(3)15)11-5-7-12(8-6-11)16-9(2)14/h4-8,13H,1H2,2-3H3/t13-/m0/s1

描述信息

An acetate ester that is chavicol acetate substituted by an acetoxy group at position 1.

同义名列表

6 个代谢物同义名

D,L-1-Acetoxychavicol acetate; 1S-1-Acetoxychavicol acetate; 1-Acetoxychavicol acetate; Galangal acetate; 1'-Acetoxychavicol acetate; 1'-Acetoxychavicol acetate, (+/-)-



数据库引用编号

13 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)

3 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

  • Akiko Kojima-Yuasa, Isao Matsui-Yuasa. Pharmacological Effects of 1'-Acetoxychavicol Acetate, a Major Constituent in the Rhizomes of Alpinia galanga and Alpinia conchigera. Journal of medicinal food. 2020 May; 23(5):465-475. doi: 10.1089/jmf.2019.4490. [PMID: 32069429]
  • Rahul Datta, Amandeep Kaur, Isha Saraf, Inder Pal Singh, Sanehdeep Kaur. Effect of crude extracts and purified compounds of Alpinia galanga on nutritional physiology of a polyphagous lepidopteran pest, Spodoptera litura (Fabricius). Ecotoxicology and environmental safety. 2019 Jan; 168(?):324-329. doi: 10.1016/j.ecoenv.2018.10.065. [PMID: 30390531]
  • A K M Mahmudul Haque, Kok Hoong Leong, Yoke Lin Lo, Khalijah Awang, Noor Hasima Nagoor. In vitro inhibitory mechanisms and molecular docking of 1'-S-1'-acetoxychavicol acetate on human cytochrome P450 enzymes. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2017 Jul; 31(?):1-9. doi: 10.1016/j.phymed.2017.05.002. [PMID: 28606510]
  • R G Baradwaj, M V Rao, T Senthil Kumar. Novel purification of 1'S-1'-Acetoxychavicol acetate from Alpinia galanga and its cytotoxic plus antiproliferative activity in colorectal adenocarcinoma cell line SW480. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2017 Jul; 91(?):485-493. doi: 10.1016/j.biopha.2017.04.114. [PMID: 28477464]
  • Sophia P M Sok, Norhafiza M Arshad, Mohamad Nurul Azmi, Khalijah Awang, Bulent Ozpolat, Noor Hasima Nagoor. The apoptotic effect of 1'S-1'-Acetoxychavicol Acetate (ACA) enhanced by inhibition of non-canonical autophagy in human non-small cell lung cancer cells. PloS one. 2017; 12(2):e0171329. doi: 10.1371/journal.pone.0171329. [PMID: 28158287]
  • Akiko Kojima-Yuasa, Tomiya Yamamoto, Keisuke Yaku, Shiori Hirota, Shigeo Takenaka, Kouichi Kawabe, Isao Matsui-Yuasa. 1'-Acetoxychavicol acetate ameliorates age-related spatial memory deterioration by increasing serum ketone body production as a complementary energy source for neuronal cells. Chemico-biological interactions. 2016 Sep; 257(?):101-9. doi: 10.1016/j.cbi.2016.07.031. [PMID: 27481192]
  • Norhafiza M Arshad, Lionel L A In, Tchen Lin Soh, Mohamad Nurul Azmi, Halijah Ibrahim, Khalijah Awang, Elena Dudich, Eduard Tatulov, Noor Hasima Nagoor. Recombinant human alpha fetoprotein synergistically potentiates the anti-cancer effects of 1'-S-1'-acetoxychavicol acetate when used as a complex against human tumours harbouring AFP-receptors. Oncotarget. 2015 Jun; 6(18):16151-67. doi: 10.18632/oncotarget.3951. [PMID: 26158863]
  • Jieqiong Wang, Li Zhang, Guoliang Chen, Jing Zhang, Zhenxi Li, Weiqiang Lu, Mingyao Liu, Xiufeng Pang. Small molecule 1'-acetoxychavicol acetate suppresses breast tumor metastasis by regulating the SHP-1/STAT3/MMPs signaling pathway. Breast cancer research and treatment. 2014 Nov; 148(2):279-89. doi: 10.1007/s10549-014-3165-6. [PMID: 25301089]
  • Lionel L A In, Norhafiza M Arshad, Halijah Ibrahim, Mohamad Nurul Azmi, Khalijah Awang, Noor Hasima Nagoor. 1'-Acetoxychavicol acetate inhibits growth of human oral carcinoma xenograft in mice and potentiates cisplatin effect via proinflammatory microenvironment alterations. BMC complementary and alternative medicine. 2012 Oct; 12(?):179. doi: 10.1186/1472-6882-12-179. [PMID: 23043547]
  • Somendu K Roy, Sonika Pahwa, Hemraj Nandanwar, Sanjay M Jachak. Phenylpropanoids of Alpinia galanga as efflux pump inhibitors in Mycobacterium smegmatis mc² 155. Fitoterapia. 2012 Oct; 83(7):1248-55. doi: 10.1016/j.fitote.2012.06.008. [PMID: 22735598]
  • Vinita Batra, Zanobia Syed, Jennifer N Gill, Malari A Coburn, Patrick Adegboyega, John DiGiovanni, J Michael Mathis, Runhua Shi, John L Clifford, Heather E Kleiner-Hancock. Effects of the tropical ginger compound,1'-acetoxychavicol acetate, against tumor promotion in K5.Stat3C transgenic mice. Journal of experimental & clinical cancer research : CR. 2012 Jun; 31(?):57. doi: 10.1186/1756-9966-31-57. [PMID: 22704648]
  • Rie Ohnishi, Isao Matsui-Yuasa, Yohei Deguchi, Keisuke Yaku, Masaki Tabuchi, Hiroshi Munakata, Yasumitsu Akahoshi, Akiko Kojima-Yuasa. 1'-acetoxychavicol acetate inhibits adipogenesis in 3T3-L1 adipocytes and in high fat-fed rats. The American journal of Chinese medicine. 2012; 40(6):1189-204. doi: 10.1142/s0192415x12500887. [PMID: 23227791]
  • Hideki Azuma, Yui Aizawa, Nao Higashitani, Takashi Tsumori, Akiko Kojima-Yuasa, Isao Matsui-Yuasa, Takeshi Nagasaki. Biological activity of water-soluble inclusion complexes of 1'-acetoxychavicol acetate with cyclodextrins. Bioorganic & medicinal chemistry. 2011 Jun; 19(12):3855-63. doi: 10.1016/j.bmc.2011.04.038. [PMID: 21596572]
  • Keisuke Yaku, Isao Matsui-Yuasa, Hideki Azuma, Akiko Kojima-Yuasa. 1'-Acetoxychavicol acetate enhances the phase II enzyme activities via the increase in intranuclear Nrf2 level and cytosolic p21 level. The American journal of Chinese medicine. 2011; 39(4):789-802. doi: 10.1142/s0192415x11009196. [PMID: 21721157]
  • Khalijah Awang, Mohamad Nurul Azmi, Lionel In Lian Aun, Ahmad Nazif Aziz, Halijah Ibrahim, Noor Hasima Nagoor. The apoptotic effect of 1's-1'-acetoxychavicol acetate from Alpinia conchigera on human cancer cells. Molecules (Basel, Switzerland). 2010 Nov; 15(11):8048-59. doi: 10.3390/molecules15118048. [PMID: 21063268]
  • Noor Hasima, Lionel In Lian Aun, Mohamad Nurul Azmi, Ahmad Nazif Aziz, Eswary Thirthagiri, Halijah Ibrahim, Khalijah Awang. 1'S-1'-acetoxyeugenol acetate: a new chemotherapeutic natural compound against MCF-7 human breast cancer cells. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2010 Oct; 17(12):935-9. doi: 10.1016/j.phymed.2010.03.011. [PMID: 20729047]
  • Heather E Kleiner-Hancock, Runhua Shi, Angela Remeika, Delira Robbins, Misty Prince, Jennifer N Gill, Zanobia Syed, Patrick Adegboyega, J Michael Mathis, John L Clifford. Effects of ATRA combined with citrus and ginger-derived compounds in human SCC xenografts. BMC cancer. 2010 Jul; 10(?):394. doi: 10.1186/1471-2407-10-394. [PMID: 20659317]
  • Satoru Tamura, Atsushi Shiomi, Tominori Kimura, Nobutoshi Murakami. Halogenated analogs of 1'-acetoxychavicol acetate, Rev-export inhibitor from Alpinia galanga, designed from mechanism of action. Bioorganic & medicinal chemistry letters. 2010 Apr; 20(7):2082-5. doi: 10.1016/j.bmcl.2010.02.070. [PMID: 20219373]
  • Masataka Narukawa, Kanako Koizumi, Yusaku Iwasaki, Kikue Kubota, Tatsuo Watanabe. Galangal pungent component, 1'-acetoxychavicol acetate, activates TRPA1. Bioscience, biotechnology, and biochemistry. 2010; 74(8):1694-6. doi: 10.1271/bbb.100133. [PMID: 20699565]
  • C Latha, Varsha D Shriram, Sheetal S Jahagirdar, Prashant K Dhakephalkar, Supada R Rojatkar. Antiplasmid activity of 1'-acetoxychavicol acetate from Alpinia galanga against multi-drug resistant bacteria. Journal of ethnopharmacology. 2009 Jun; 123(3):522-5. doi: 10.1016/j.jep.2009.03.028. [PMID: 19501283]
  • Satoru Tamura, Atsushi Shiomi, Masafumi Kaneko, Ying Ye, Minoru Yoshida, Masayuki Yoshikawa, Tominori Kimura, Motomasa Kobayashi, Nobutoshi Murakami. New Rev-export inhibitor from Alpinia galanga and structure-activity relationship. Bioorganic & medicinal chemistry letters. 2009 May; 19(9):2555-7. doi: 10.1016/j.bmcl.2009.03.047. [PMID: 19342232]
  • Akira Murakami, Hajime Ohigashi. Targeting NOX, INOS and COX-2 in inflammatory cells: chemoprevention using food phytochemicals. International journal of cancer. 2007 Dec; 121(11):2357-63. doi: 10.1002/ijc.23161. [PMID: 17893865]
  • Y Unahara, A Kojima-Yuasa, M Higashida, D O Kennedy, A Murakami, H Ohigashi, I Matsui-Yuasa. Cellular thiol status-dependent inhibition of tumor cell growth via modulation of p27(kip1) translocation and retinoblastoma protein phosphorylation by 1'-acetoxychavicol acetate. Amino acids. 2007 Sep; 33(3):469-76. doi: 10.1007/s00726-006-0437-4. [PMID: 17031475]
  • Ying Ye, Baoan Li. 1'S-1'-acetoxychavicol acetate isolated from Alpinia galanga inhibits human immunodeficiency virus type 1 replication by blocking Rev transport. The Journal of general virology. 2006 Jul; 87(Pt 7):2047-2053. doi: 10.1099/vir.0.81685-0. [PMID: 16760408]
  • Keisuke Ito, Tomonori Nakazato, Akira Murakami, Hajime Ohigashi, Yasuo Ikeda, Masahiro Kizaki. 1'-Acetoxychavicol acetate induces apoptosis of myeloma cells via induction of TRAIL. Biochemical and biophysical research communications. 2005 Dec; 338(4):1702-10. doi: 10.1016/j.bbrc.2005.10.153. [PMID: 16289031]
  • Haruyo Ichikawa, Yasunari Takada, Akira Murakami, Bharat B Aggarwal. Identification of a novel blocker of I kappa B alpha kinase that enhances cellular apoptosis and inhibits cellular invasion through suppression of NF-kappa B-regulated gene products. Journal of immunology (Baltimore, Md. : 1950). 2005 Jun; 174(11):7383-92. doi: 10.4049/jimmunol.174.11.7383. [PMID: 15905586]
  • Keisuke Ito, Tomonori Nakazato, Ming Ji Xian, Taketo Yamada, Nobumichi Hozumi, Akira Murakami, Hajime Ohigashi, Yasuo Ikeda, Masahiro Kizaki. 1'-acetoxychavicol acetate is a novel nuclear factor kappaB inhibitor with significant activity against multiple myeloma in vitro and in vivo. Cancer research. 2005 May; 65(10):4417-24. doi: 10.1158/0008-5472.can-05-0072. [PMID: 15899834]
  • Birgit Jaki, Scott Franzblau, Guido F Pauli. An NMR method towards the routine chiral determination of natural products. Phytochemical analysis : PCA. 2004 Jul; 15(4):213-9. doi: 10.1002/pca.760. [PMID: 15311839]
  • Keisuke Ito, Tomonori Nakazato, Akira Murakami, Kenji Yamato, Yoshitaka Miyakawa, Taketo Yamada, Nobumichi Hozumi, Hajime Ohigashi, Yasuo Ikeda, Masahiro Kizaki. Induction of apoptosis in human myeloid leukemic cells by 1'-acetoxychavicol acetate through a mitochondrial- and Fas-mediated dual mechanism. Clinical cancer research : an official journal of the American Association for Cancer Research. 2004 Mar; 10(6):2120-30. doi: 10.1158/1078-0432.ccr-1142-03. [PMID: 15041733]
  • Shinichiro Orita, Masao Hirose, Satoru Takahashi, Katsumi Imaida, Nobuyuki Ito, Koichi Shudo, Hajime Ohigashi, Akira Murakami, Tomoyuki Shirai. Modifying effects of 1'-acetoxychavicol acetate (ACA) and the novel synthetic retinoids Re-80, Am-580 and Am-55P in a two-stage carcinogenesis model in female rats. Toxicologic pathology. 2004 Mar; 32(2):250-7. doi: 10.1080/01926230490274425. [PMID: 15200164]
  • Hisashi Matsuda, Toshio Morikawa, Hiromi Managi, Masayuki Yoshikawa. Antiallergic principles from Alpinia galanga: structural requirements of phenylpropanoids for inhibition of degranulation and release of TNF-alpha and IL-4 in RBL-2H3 cells. Bioorganic & medicinal chemistry letters. 2003 Oct; 13(19):3197-202. doi: 10.1016/s0960-894x(03)00710-8. [PMID: 12951092]
  • Hisashi Matsuda, Yutana Pongpiriyadacha, Toshio Morikawa, Momotaro Ochi, Masayuki Yoshikawa. Gastroprotective effects of phenylpropanoids from the rhizomes of Alpinia galanga in rats: structural requirements and mode of action. European journal of pharmacology. 2003 Jun; 471(1):59-67. doi: 10.1016/s0014-2999(03)01785-0. [PMID: 12809953]
  • A Murakami, K Toyota, S Ohura, K Koshimizu, H Ohigashi. Structure-activity relationships of (1'S)-1'-acetoxychavicol acetate, a major constituent of a southeast Asian condiment plant Languas galanga, on the inhibition of tumor-promoter-induced Epstein-Barr virus activation. Journal of agricultural and food chemistry. 2000 May; 48(5):1518-23. doi: 10.1021/jf990528r. [PMID: 10820053]
  • X Yang, R G Eilerman. Pungent principal of Alpinia galangal (L.) swartz and its applications. Journal of agricultural and food chemistry. 1999 Apr; 47(4):1657-62. doi: 10.1021/jf9808224. [PMID: 10564034]
  • T Tanaka, K Kawabata, M Kakumoto, H Makita, K Matsunaga, H Mori, K Satoh, A Hara, A Murakami, K Koshimizu, H Ohigashi. Chemoprevention of azoxymethane-induced rat colon carcinogenesis by a xanthine oxidase inhibitor, 1'-acetoxychavicol acetate. Japanese journal of cancer research : Gann. 1997 Sep; 88(9):821-30. doi: 10.1111/j.1349-7006.1997.tb00457.x. [PMID: 9369929]
  • T Tanaka, H Makita, T Kawamori, K Kawabata, H Mori, A Murakami, K Satoh, A Hara, H Ohigashi, K Koshimizu. A xanthine oxidase inhibitor 1'-acetoxychavicol acetate inhibits azoxymethane-induced colonic aberrant crypt foci in rats. Carcinogenesis. 1997 May; 18(5):1113-8. doi: 10.1093/carcin/18.5.1113. [PMID: 9163704]
  • A Murakami, S Ohura, Y Nakamura, K Koshimizu, H Ohigashi. 1'-Acetoxychavicol acetate, a superoxide anion generation inhibitor, potently inhibits tumor promotion by 12-O-tetradecanoylphorbol-13-acetate in ICR mouse skin. Oncology. 1996 Sep; 53(5):386-91. doi: 10.1159/000227593. [PMID: 8784473]
  • N Watanabe, T Kataoka, T Tajika, M Uramoto, J Magae, K Nagai. 1'-Acetoxychavicol acetate as an inhibitor of phagocytosis of macrophages. Bioscience, biotechnology, and biochemistry. 1995 Aug; 59(8):1566-7. doi: 10.1271/bbb.59.1566. [PMID: 7549106]
  • A M Janssen, J J Scheffer. Acetoxychavicol acetate, an antifungal component of Alpinia galanga. Planta medica. 1985 Dec; ?(6):507-11. doi: ". [PMID: 3841613]