Goniothalamine

    WARNING: This product is for research use only, not for human or veterinary use.

Hodoodo CAT#: H562504

CAS#: 17303-67-2

Description: Goniothalamine is an inhibitor of TNF-α-induced NF-κB activation.

Chemical Structure

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Goniothalamine
CAS# 17303-67-2
Instruction

Theoretical Analysis

Hodoodo Cat#: H562504
Name: Goniothalamine
CAS#: 17303-67-2
Chemical Formula: C13H12O2
Exact Mass: 200.08
Molecular Weight: 200.230
Elemental Analysis: C, 77.98; H, 6.04; O, 15.98

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @hodoodo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Goniothalamine; (6R)-(+)-Goniothalamin;

IUPAC/Chemical Name: (2R)-2-[(E)-2-Phenylethenyl]-2,3-dihydropyran-6-one

InChi Key: RLGHFVLWYYVMQZ-BZYZDCJZSA-N

InChi Code: InChI=1S/C13H12O2/c14-13-8-4-7-12(15-13)10-9-11-5-2-1-3-6-11/h1-6,8-10,12H,7H2/b10-9+/t12-/m1/s1

SMILES Code: O=C1C=CC[C@H](/C=C/C2=CC=CC=C2)O1

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 200.23 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Silva RS, Kido LA, Montico F, Vendramini-Costa DB, Pilli RA, Cagnon VHA. Steroidal hormone and morphological responses in the prostate anterior lobe in different cancer grades after Celecoxib and Goniothalamin treatments in TRAMP mice. Cell Biol Int. 2018 Mar 30. doi: 10.1002/cbin.10967. [Epub ahead of print] PubMed PMID: 29603508.

2: Tangchirakhaphan S, Innajak S, Nilwarangkoon S, Tanjapatkul N, Mahabusrakum W, Watanapokasin R. Mechanism of apoptosis induction associated with ERK1/2 upregulation via goniothalamin in melanoma cells. Exp Ther Med. 2018 Mar;15(3):3052-3058. doi: 10.3892/etm.2018.5762. Epub 2018 Jan 17. PubMed PMID: 29456710; PubMed Central PMCID: PMC5795534.

3: Pang KL, Vijayaraghavan K, Al Sayed B, Seyed MA. Betulinic acid induced expression of nicotinamide adenine dinucleotide phosphate diaphorase in the immune organs of mice: A possible role of nitric oxide in immunomodulation. Mol Med Rep. 2018 Feb;17(2):3035-3041. doi: 10.3892/mmr.2017.8262. Epub 2017 Dec 12. PubMed PMID: 29257292; PubMed Central PMCID: PMC5783524.

4: Weber A, Döhl K, Sachs J, Nordschild ACM, Schröder D, Kulik A, Fischer T, Schmitt L, Teusch N, Pietruszka J. Synthesis and cytotoxic activities of goniothalamins and derivatives. Bioorg Med Chem. 2017 Nov 15;25(22):6115-6125. doi: 10.1016/j.bmc.2017.02.004. Epub 2017 Feb 6. PubMed PMID: 28214230.

5: Kido LA, Montico F, Vendramini-Costa DB, Pilli RA, Cagnon VHA. Goniothalamin and Celecoxib Effects During Aging: Targeting Pro-Inflammatory Mediators in Chemoprevention of Prostatic Disorders. Prostate. 2017 Jun;77(8):838-848. doi: 10.1002/pros.23324. Epub 2017 Feb 13. PubMed PMID: 28191652.

6: Sophonnithiprasert T, Mahabusarakam W, Nakamura Y, Watanapokasin R. Goniothalamin induces mitochondria-mediated apoptosis associated with endoplasmic reticulum stress-induced activation of JNK in HeLa cells. Oncol Lett. 2017 Jan;13(1):119-128. doi: 10.3892/ol.2016.5381. Epub 2016 Nov 11. PubMed PMID: 28123531; PubMed Central PMCID: PMC5245090.

7: Vendramini-Costa DB, Francescone R, Posocco D, Hou V, Dmitrieva O, Hensley H, de Carvalho JE, Pilli RA, Grivennikov SI. Anti-inflammatory natural product goniothalamin reduces colitis-associated and sporadic colorectal tumorigenesis. Carcinogenesis. 2017 Jan;38(1):51-63. doi: 10.1093/carcin/bgw112. Epub 2016 Oct 24. PubMed PMID: 27797827; PubMed Central PMCID: PMC5219049.

8: Boonmuen N, Thongon N, Chairoungdua A, Suksen K, Pompimon W, Tuchinda P, Reutrakul V, Piyachaturawat P. 5-Acetyl goniothalamin suppresses proliferation of breast cancer cells via Wnt/β-catenin signaling. Eur J Pharmacol. 2016 Nov 15;791:455-464. doi: 10.1016/j.ejphar.2016.09.024. Epub 2016 Sep 16. PubMed PMID: 27640746.

9: Ramesh P, Rao TP. Biosynthesis-Inspired Total Synthesis of Bioactive Styryllactones (+)-Goniodiol, (6S,7S,8S)-Goniodiol, (-)-Parvistone D, and (+)-Parvistone E. J Nat Prod. 2016 Aug 26;79(8):2060-5. doi: 10.1021/acs.jnatprod.6b00386. Epub 2016 Aug 12. PubMed PMID: 27518479.

10: Banjerdpongchai R, Khawon P, Pompimon W. Phytochemicals from Goniothalamus griffithii Induce Human Cancer Cell Apoptosis. Asian Pac J Cancer Prev. 2016;17(7):3281-7. PubMed PMID: 27509964.

11: Vendramini-Costa DB, Alcaide A, Pelizzaro-Rocha KJ, Talero E, Ávila-Román J, Garcia-Mauriño S, Pilli RA, de Carvalho JE, Motilva V. Goniothalamin prevents the development of chemically induced and spontaneous colitis in rodents and induces apoptosis in the HT-29 human colon tumor cell line. Toxicol Appl Pharmacol. 2016 Jun 1;300:1-12. doi: 10.1016/j.taap.2016.03.009. Epub 2016 Mar 22. PubMed PMID: 27016270.

12: Innajak S, Mahabusrakum W, Watanapokasin R. Goniothalamin induces apoptosis associated with autophagy activation through MAPK signaling in SK-BR-3 cells. Oncol Rep. 2016 May;35(5):2851-8. doi: 10.3892/or.2016.4655. Epub 2016 Mar 7. PubMed PMID: 26987063.

13: Sophonnithiprasert T, Mahabusarakam W, Nakamura Y, Watanapokasin R. Antiproliferation and Apoptosis Induction in Colorectal Cancer Cells by Goniothalamin. J Med Assoc Thai. 2015 Oct;98 Suppl 9:S146-51. PubMed PMID: 26817224.

14: Kido LA, Montico F, Sauce R, Macedo AB, Minatel E, Costa DB, Carvalho JE, Pilli RA, Cagnon VH. Anti-inflammatory therapies in TRAMP mice: delay in PCa progression. Endocr Relat Cancer. 2016 Apr;23(4):235-50. doi: 10.1530/ERC-15-0540. Epub 2016 Jan 15. PubMed PMID: 26772819.

15: Li LK, Rola AS, Kaid FA, Ali AM, Alabsi AM. Goniothalamin induces cell cycle arrest and apoptosis in H400 human oral squamous cell carcinoma: A caspase-dependent mitochondrial-mediated pathway with downregulation of NF-κβ. Arch Oral Biol. 2016 Apr;64:28-38. doi: 10.1016/j.archoralbio.2015.12.002. Epub 2015 Dec 23. PubMed PMID: 26752226.

16: Semprebon SC, Marques LA, D'Epiro GF, de Camargo EA, da Silva GN, Niwa AM, Macedo Junior F, Mantovani MS. Antiproliferative activity of goniothalamin enantiomers involves DNA damage, cell cycle arrest and apoptosis induction in MCF-7 and HB4a cells. Toxicol In Vitro. 2015 Dec 25;30(1 Pt B):250-63. doi: 10.1016/j.tiv.2015.10.012. Epub 2015 Oct 29. PubMed PMID: 26522230.

17: Sophonnithiprasert T, Nilwarangkoon S, Nakamura Y, Watanapokasin R. Goniothalamin enhances TRAIL-induced apoptosis in colorectal cancer cells through DR5 upregulation and cFLIP downregulation. Int J Oncol. 2015 Dec;47(6):2188-96. doi: 10.3892/ijo.2015.3204. Epub 2015 Oct 13. PubMed PMID: 26499766.

18: Vendramini-Costa DB, Spindola HM, de Mello GC, Antunes E, Pilli RA, de Carvalho JE. Anti-inflammatory and antinociceptive effects of racemic goniothalamin, a styryl lactone. Life Sci. 2015 Oct 15;139:83-90. doi: 10.1016/j.lfs.2015.08.010. Epub 2015 Aug 19. PubMed PMID: 26297443.

19: Wasano N, Takemura T, Ismil R, Bakar B, Fujii Y. Transcriptomic evaluation of plant growth inhibitory activity of goniothalamin from the Malaysian medicinal plant Goniothalamus andersonii. Nat Prod Commun. 2015 May;10(5):725-7. PubMed PMID: 26058144.

20: Peng YT, Wu WR, Chen LR, Kuo KK, Tsai CH, Huang YT, Lan YH, Chang FR, Wu YC, Shiue YL. Upregulation of cyclin-dependent kinase inhibitors CDKN1B and CDKN1C in hepatocellular carcinoma-derived cells via goniothalamin-mediated protein stabilization and epigenetic modifications. Toxicol Rep. 2015 Jan 25;2:322-332. doi: 10.1016/j.toxrep.2015.01.010. eCollection 2015. PubMed PMID: 28962365; PubMed Central PMCID: PMC5598353.