Yakuchinone A
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Hodoodo CAT#: H341100

CAS#: 78954-23-1

Description: Yakuchinone-A is a natural product isolated from Alpinia oxyphylla Miquel (Zingiberaceae). Yakuchinone-A has strong inhibitory effects on the synthesis of prostaglandins and leukotrienes in vitro. Yakuchinone A inhibits the expression of cyclooxygenase-2 (COX-2) and of inducible nitric oxide synthase (iNOS) as well as the expression of tumor necrosis factor (TNF)-alpha mRNA in mouse skin treated with the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA).


Chemical Structure

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Yakuchinone A
CAS# 78954-23-1

Theoretical Analysis

Hodoodo Cat#: H341100
Name: Yakuchinone A
CAS#: 78954-23-1
Chemical Formula: C20H24O3
Exact Mass: 312.17
Molecular Weight: 312.409
Elemental Analysis: C, 76.89; H, 7.74; O, 15.36

Price and Availability

Size Price Availability Quantity
100mg USD 450 2 Weeks
200mg USD 750 2 Weeks
500mg USD 1650 2 Weeks
1g USD 2950 2 Weeks
2g USD 5250 2 Weeks
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Synonym: Yakuchinone-A

IUPAC/Chemical Name: 3-Heptanone, 1-(4-hydroxy-3-methoxyphenyl)-7-phenyl-

InChi Key: TXELARZTKDBEKS-UHFFFAOYSA-N

InChi Code: InChI=1S/C20H24O3/c1-23-20-15-17(12-14-19(20)22)11-13-18(21)10-6-5-9-16-7-3-2-4-8-16/h2-4,7-8,12,14-15,22H,5-6,9-11,13H2,1H3

SMILES Code: O=C(CCCCC1=CC=CC=C1)CCC2=CC=C(O)C(OC)=C2

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: Yakuchinone A inhibits the expression of cyclooxygenase-2 (COX-2) and of inducible nitric oxide synthase (iNOS) as well as the expression of tumor necrosis factor (TNF)-alpha mRNA in mouse skin treated with the tumor promoter 12-O-tetradecanoylphorbol-13-acetate (TPA).
In vitro activity: Antioxidant and antitumor characteristics of yakuchinone A in skin cancer cells as well as novel mechanisms for the inhibition of adipocyte differentiation, cestocidal activities against Hymenolepis nana adults, and nematocidal activities against Anisakis simplex larvae were investigated in this study. Yakuchinone A presents the ability of the removal of DPPH·and ABTS+ free radicals and inhibition of lipid peroxidation. Yakuchinone A suppresses intracellular lipid accumulation during adipocyte differentiation in 3 T3-L1 cells and the expressions of leptin and peroxisome proliferator-activated receptor γ (PPARγ). Yakuchinone A induces apoptosis and inhibits cell proliferation in skin cancer cells. The inhibition of cell growth by yakuchinone A is more significant for non-melanoma skin cancer (NMSC) cells than for melanoma (A375 and B16) and noncancerous (HaCaT and BNLCL2) cells. Treatment BCC cells with yakuchinone A shows down-regulation of Bcl-2, up-regulation of Bax, and an increase in cleavage poly (ADP-ribose) polymerase (PARP). This suggests that yakuchinone A induces BCC cells apoptosis through the Bcl-2-mediated signaling pathway. The anthelmintic activities of yakuchinone A for A. simplex are better than for H. nana. Reference: BMC Complement Altern Med. 2013 Sep 26;13:237. https://pubmed.ncbi.nlm.nih.gov/24070160/
In vivo activity: In the present work, the effects of yakuchinone A and yakuchinone B, phenolic diarylheptanoids derived from A. oxyphylla, on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation and epidermal ornithine decarboxylase (ODC) activity as well as on skin tumor promotion in female ICR mice were assessed. Thus, topical application of 2 or 6 micromol of the diarylheptanoids prior to each topical dose of TPA significantly ameliorated 7,12-dimethylbenz[a]anthracene-initiated mouse skin tumor formation. In parallel with suppression of tumor promotion, topically applied yakuchinone A and B markedly inhibited TPA-induced epidermal ODC activity and ODC mRNA expression. In another experiment, yakuchinone A and B reduced production of tumor necrosis factor-alpha in TPA-stimulated mouse skin. Furthermore, both compounds inhibited the TPA-induced expression of cyclooxygenase-2 at both transcriptional and translational levels. These findings indicate that pungent diarylheptanoids from A. oxyphylla Miquel have an antitumor promotional activity that might be related to their anti-inflammatory properties. Reference: Oncol Res. 2002;13(1):37-45. https://pubmed.ncbi.nlm.nih.gov/12201673/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 0.0 0.00

Preparing Stock Solutions

The following data is based on the product molecular weight 312.41 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: 1. Lin RJ, Yen CM, Chou TH, Chiang FY, Wang GH, Tseng YP, Wang L, Huang TW, Wang HC, Chan LP, Ding HY, Liang CH. Antioxidant, anti-adipocyte differentiation, antitumor activity and anthelmintic activities against Anisakis simplex and Hymenolepis nana of yakuchinone A from Alpinia oxyphylla. BMC Complement Altern Med. 2013 Sep 26;13:237. doi: 10.1186/1472-6882-13-237. PMID: 24070160; PMCID: PMC3879407. 2. Huang KK, Lin MN, Hsu YL, Lu IH, Pan IH, Yang JL. Alpinia oxyphylla Fruit Extract Ameliorates Experimental Autoimmune Encephalomyelitis through the Regulation of Th1/Th17 Cells. Evid Based Complement Alternat Med. 2019 Mar 14;2019:6797030. doi: 10.1155/2019/6797030. PMID: 31001353; PMCID: PMC6437745. 3. Chun KS, Kang JY, Kim OH, Kang H, Surh YJ. Effects of yakuchinone A and yakuchinone B on the phorbol ester-induced expression of COX-2 and iNOS and activation of NF-kappaB in mouse skin. J Environ Pathol Toxicol Oncol. 2002;21(2):131-9. PMID: 12086399. 4. Chun KS, Park KK, Lee J, Kang M, Surh YJ. Inhibition of mouse skin tumor promotion by anti-inflammatory diarylheptanoids derived from Alpinia oxyphylla Miquel (Zingiberaceae). Oncol Res. 2002;13(1):37-45. doi: 10.3727/096504002108747944. PMID: 12201673.
In vitro protocol: 1. Lin RJ, Yen CM, Chou TH, Chiang FY, Wang GH, Tseng YP, Wang L, Huang TW, Wang HC, Chan LP, Ding HY, Liang CH. Antioxidant, anti-adipocyte differentiation, antitumor activity and anthelmintic activities against Anisakis simplex and Hymenolepis nana of yakuchinone A from Alpinia oxyphylla. BMC Complement Altern Med. 2013 Sep 26;13:237. doi: 10.1186/1472-6882-13-237. PMID: 24070160; PMCID: PMC3879407. 2. Huang KK, Lin MN, Hsu YL, Lu IH, Pan IH, Yang JL. Alpinia oxyphylla Fruit Extract Ameliorates Experimental Autoimmune Encephalomyelitis through the Regulation of Th1/Th17 Cells. Evid Based Complement Alternat Med. 2019 Mar 14;2019:6797030. doi: 10.1155/2019/6797030. PMID: 31001353; PMCID: PMC6437745.
In vivo protocol: 1. Chun KS, Kang JY, Kim OH, Kang H, Surh YJ. Effects of yakuchinone A and yakuchinone B on the phorbol ester-induced expression of COX-2 and iNOS and activation of NF-kappaB in mouse skin. J Environ Pathol Toxicol Oncol. 2002;21(2):131-9. PMID: 12086399. 2. Chun KS, Park KK, Lee J, Kang M, Surh YJ. Inhibition of mouse skin tumor promotion by anti-inflammatory diarylheptanoids derived from Alpinia oxyphylla Miquel (Zingiberaceae). Oncol Res. 2002;13(1):37-45. doi: 10.3727/096504002108747944. PMID: 12201673.

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1: Zhang Q, Cui C, Chen CQ, Hu XL, Liu YH, Fan YH, Meng WH, Zhao QC. Anti-proliferative and pro-apoptotic activities of Alpinia oxyphylla on HepG2 cells through ROS-mediated signaling pathway. J Ethnopharmacol. 2015 Jul 1;169:99-108. doi: 10.1016/j.jep.2015.03.073. Epub 2015 Apr 16. PubMed PMID: 25891473.

2: Yuan Y, Tan YF, Xu P, Li H, Li YH, Chen WY, Zhang JQ, Chen F, Huang GJ. Izalpinin from fruits of Alpinia oxyphylla with antagonistic activity against the rat bladder contractility. Afr J Tradit Complement Altern Med. 2014 Jun 4;11(4):120-5. eCollection 2014. PubMed PMID: 25392590; PubMed Central PMCID: PMC4202406.

3: Chen F, Li HL, Tan YF, Li YH, Lai WY, Guan WW, Zhang JQ, Zhao YS, Qin ZM. Identification of known chemicals and their metabolites from Alpinia oxyphylla fruit extract in rat plasma using liquid chromatography/tandem mass spectrometry (LC-MS/MS) with selected reaction monitoring. J Pharm Biomed Anal. 2014 Aug;97:166-77. doi: 10.1016/j.jpba.2014.04.037. Epub 2014 May 10. PubMed PMID: 24879483.

4: Chen F, Li HL, Tan YF, Guan WW, Zhang JQ, Li YH, Zhao YS, Qin ZM. Different accumulation profiles of multiple components between pericarp and seed of Alpinia oxyphylla capsular fruit as determined by UFLC-MS/MS. Molecules. 2014 Apr 10;19(4):4510-23. doi: 10.3390/molecules19044510. PubMed PMID: 24727421.

5: Chen F, Li HL, Tan YF, Guan WW, Li YH, Zhang JQ. Validated method to measure yakuchinone A in plasma by LC-MS/MS and its application to a pharmacokinetic study in rats. Chem Cent J. 2014 Jan 14;8(1):2. doi: 10.1186/1752-153X-8-2. PubMed PMID: 24422995; PubMed Central PMCID: PMC3896807.

6: Lin RJ, Yen CM, Chou TH, Chiang FY, Wang GH, Tseng YP, Wang L, Huang TW, Wang HC, Chan LP, Ding HY, Liang CH. Antioxidant, anti-adipocyte differentiation, antitumor activity and anthelmintic activities against Anisakis simplex and Hymenolepis nana of yakuchinone A from Alpinia oxyphylla. BMC Complement Altern Med. 2013 Sep 26;13:237. doi: 10.1186/1472-6882-13-237. PubMed PMID: 24070160; PubMed Central PMCID: PMC3879407.

7: Chen F, Li HL, Li YH, Tan YF, Zhang JQ. Quantitative analysis of the major constituents in Chinese medicinal preparation SuoQuan formulae by ultra fast high performance liquid chromatography/quadrupole tandem mass spectrometry. Chem Cent J. 2013 Jul 30;7(1):131. doi: 10.1186/1752-153X-7-131. PubMed PMID: 23899222; PubMed Central PMCID: PMC3733971.

8: Bian QY, Wang SY, Xu LJ, Chan CO, Mok DK, Chen SB. Two new antioxidant diarylheptanoids from the fruits of Alpinia oxyphylla. J Asian Nat Prod Res. 2013;15(10):1094-9. doi: 10.1080/10286020.2013.816297. Epub 2013 Jul 22. PubMed PMID: 23869536.

9: Zhang J, Wang S, Li Y, Xu P, Chen F, Tan Y, Duan J. Anti-diarrheal constituents of Alpinia oxyphylla. Fitoterapia. 2013 Sep;89:149-56. doi: 10.1016/j.fitote.2013.04.001. Epub 2013 Apr 12. PubMed PMID: 23583435.

10: Qing ZJ, Yong W, Hui LY, Yong LW, Long LH, Ao DJ, Xia PL. Two new natural products from the fruits of Alpinia oxyphylla with inhibitory effects on nitric oxide production in lipopolysaccharide-activated RAW264.7 macrophage cells. Arch Pharm Res. 2012 Dec;35(12):2143-6. doi: 10.1007/s12272-012-1211-7. Epub 2012 Dec 21. PubMed PMID: 23263808.

11: Xu J, Tan N, Zeng G, Han H, Huang H, Ji C, Zhu M, Zhang Y. [Studies on chemical constituents in fruit of Alpinia oxyphylla]. Zhongguo Zhong Yao Za Zhi. 2009 Apr;34(8):990-3. Chinese. PubMed PMID: 19639783.

12: Chun KS, Park KK, Lee J, Kang M, Surh YJ. Inhibition of mouse skin tumor promotion by anti-inflammatory diarylheptanoids derived from Alpinia oxyphylla Miquel (Zingiberaceae). Oncol Res. 2002;13(1):37-45. PubMed PMID: 12201673.

13: Chun KS, Kang JY, Kim OH, Kang H, Surh YJ. Effects of yakuchinone A and yakuchinone B on the phorbol ester-induced expression of COX-2 and iNOS and activation of NF-kappaB in mouse skin. J Environ Pathol Toxicol Oncol. 2002;21(2):131-9. PubMed PMID: 12086399.

14: Miyazawa M, Nakamura Y, Ishikawa Y. Insecticidal diarylheptanoid from Alpinia oxyphylla against larvae of Drosophila melanogaster. Nat Prod Lett. 2001;15(1):75-9. PubMed PMID: 11547427.

15: Surh Y. Molecular mechanisms of chemopreventive effects of selected dietary and medicinal phenolic substances. Mutat Res. 1999 Jul 16;428(1-2):305-27. Review. PubMed PMID: 10518003.

16: Chun KS, Sohn Y, Kim HS, Kim OH, Park KK, Lee JM, Moon A, Lee SS, Surh YJ. Anti-tumor promoting potential of naturally occurring diarylheptanoids structurally related to curcumin. Mutat Res. 1999 Jul 16;428(1-2):49-57. PubMed PMID: 10517978.

17: Shirota S, Miyazaki K, Aiyama R, Ichioka M, Yokokura T. Tyrosinase inhibitors from crude drugs. Biol Pharm Bull. 1994 Feb;17(2):266-9. PubMed PMID: 8205125.

18: Kiuchi F, Iwakami S, Shibuya M, Hanaoka F, Sankawa U. Inhibition of prostaglandin and leukotriene biosynthesis by gingerols and diarylheptanoids. Chem Pharm Bull (Tokyo). 1992 Feb;40(2):387-91. PubMed PMID: 1606634.

19: Kimura I, Pancho LR, Shiori T, Kimura M. Suppression of spontaneous calcium spikes and contraction in isolated portal veins of mice by gingerols and chemically related compounds. Jpn J Pharmacol. 1988 Oct;48(2):257-62. PubMed PMID: 3210448.

20: Flynn DL, Rafferty MF, Boctor AM. Inhibition of 5-hydroxy-eicosatetraenoic acid (5-HETE) formation in intact human neutrophils by naturally-occurring diarylheptanoids: inhibitory activities of curcuminoids and yakuchinones. Prostaglandins Leukot Med. 1986 Jun;22(3):357-60. PubMed PMID: 3460103.