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MedKoo Cat#: 463171 | Name: Gomisin D
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Description:

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

Gomisin D is a lignan that has been found in S. chinensis and has diverse biological activities, including enzyme inhibitory and antioxidant properties. It inhibits acetylcholinesterase (AChE) with an IC50 value of 7.84 µM. Gomisin D scavenges ABTS and 2,2-diphenyl-1-picrylhydrazyl radicals. It inhibits the UDP-glucuronosyltransferase (UGT) isoforms UGT1A1 and UGT1A3 by 89.9 and 83.1%, respectively, when used at a concentration of 100 µM. It is selective for UGT1A1 and UGT1A3 over other UGT isoforms at 100 µM.

Chemical Structure

Gomisin D
Gomisin D
CAS#60546-10-3

Theoretical Analysis

MedKoo Cat#: 463171

Name: Gomisin D

CAS#: 60546-10-3

Chemical Formula: C28H34O10

Exact Mass: 530.2152

Molecular Weight: 530.57

Elemental Analysis: C, 63.39; H, 6.46; O, 30.15

Price and Availability

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1mg USD 350.00 2 Weeks
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Related CAS #
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Synonym
Gomisin D; Gomisin-D;
IUPAC/Chemical Name
(6R,7R,10S,18S,19S)-7,19-dihydroxy-12,13,14-trimethoxy-6,7,18,19-tetramethyl-6,7-dihydro-10H-10,15-propano[1,3]dioxolo[4',5':5,6]benzo[1,2-g]benzo[i][1,6]dioxacycloundecin-8(5H)-one
InChi Key
VLLFEMVDMFTBHG-KMIFWYFFSA-N
InChi Code
InChI=1S/C28H34O10/c1-13-8-15-9-18-22(37-12-36-18)24-19(15)20-16(10-17(32-5)21(33-6)23(20)34-7)25(27(13,3)30)38-26(29)28(4,31)14(2)11-35-24/h9-10,13-14,25,30-31H,8,11-12H2,1-7H3/t13-,14+,25-,27-,28+/m0/s1
SMILES Code
COC1=CC2=C(C3=C(C[C@@H]([C@](O)([C@]2(OC([C@@]4(O)C)=O)[H])C)C)C=C5C(OCO5)=C3OC[C@H]4C)C(OC)=C1OC
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
>3 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Gomisin D inhibits UDP-Glucuronosyltransferases activity and scavenges ABTS(+) radicals.
In vitro activity:
The results demonstrated that UVA and UVB irradiation markedly promoted LDH release compared with the control group. However, gomisin D significantly reduced LDH release and gomisin J markedly reduced LDH release under UVA or UVB irradiation, compared with the UVA and UVB only groups, respectively (Fig. 1C). Reference: Mol Med Rep. 2022 Jan;25(1):8. https://pubmed.ncbi.nlm.nih.gov/34751410/
In vivo activity:
The AUC(0–t) and AUC(0-∞) were 32,795.6 ± 11,104.6 µg L/h and 35,091.7 ± 8092.8 µg L/h, respectively. The result of apparent volume of distribution (V) indicated that gomisin D was distributed in extracellular rat plasma fluid. The results of t1/2 showed that gomisin D experienced a slow elimination process after i.v. or i.g. administration, thus possibly obtaining a good therapeutic effect. The bioavailability could reach up to 107.6% as calculated by the formula of F = [(AUCi.g.) × (Dosei.v.)]/[(AUCi.v.) × (Dose i.g.)] × 100%, suggesting that gomisin D may become a promising intragastrical medication. Reference: Molecules. 2019 Apr 10;24(7):1403. https://pubmed.ncbi.nlm.nih.gov/30974748/
Solvent mg/mL mM
Solubility
DMSO 100.0 188.48
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 530.57 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. Jeon JS, Kang HM, Park SY, Choi YW. Comparative study of the photo‑protective and anti‑melanogenic properties of gomisin D, J and O. Mol Med Rep. 2022 Jan;25(1):8. doi: 10.3892/mmr.2021.12524. Epub 2021 Nov 9. PMID: 34751410; PMCID: PMC8600414. 2. Zheng X, Feng F, Jiang X, Qiu J, Cai X, Xiang Z. A Rapid UPLC-MS Method for Quantification of Gomisin D in Rat Plasma and Its Application to a Pharmacokinetic and Bioavailability Study. Molecules. 2019 Apr 10;24(7):1403. doi: 10.3390/molecules24071403. PMID: 30974748; PMCID: PMC6479676.
In vitro protocol:
1. Jeon JS, Kang HM, Park SY, Choi YW. Comparative study of the photo‑protective and anti‑melanogenic properties of gomisin D, J and O. Mol Med Rep. 2022 Jan;25(1):8. doi: 10.3892/mmr.2021.12524. Epub 2021 Nov 9. PMID: 34751410; PMCID: PMC8600414.
In vivo protocol:
1. Zheng X, Feng F, Jiang X, Qiu J, Cai X, Xiang Z. A Rapid UPLC-MS Method for Quantification of Gomisin D in Rat Plasma and Its Application to a Pharmacokinetic and Bioavailability Study. Molecules. 2019 Apr 10;24(7):1403. doi: 10.3390/molecules24071403. PMID: 30974748; PMCID: PMC6479676.
1: Song Y, Shan B, Zeng S, Zhang J, Jin C, Liao Z, Wang T, Zeng Q, He H, Wei F, Ai Z, Su D. Raw and wine processed Schisandra chinensis attenuate anxiety like behavior via modulating gut microbiota and lipid metabolism pathway. J Ethnopharmacol. 2020 Sep 29;266:113426. doi: 10.1016/j.jep.2020.113426. Epub ahead of print. PMID: 33007392. 2: Chen S, Shi J, Zou L, Liu X, Tang R, Ma J, Wang C, Tan M, Chen J. Quality Evaluation of Wild and Cultivated Schisandrae Chinensis Fructus Based on Simultaneous Determination of Multiple Bioactive Constituents Combined with Multivariate Statistical Analysis. Molecules. 2019 Apr 4;24(7):1335. doi: 10.3390/molecules24071335. PMID: 30987393; PMCID: PMC6479832. 3: Zheng X, Feng F, Jiang X, Qiu J, Cai X, Xiang Z. A Rapid UPLC-MS Method for Quantification of Gomisin D in Rat Plasma and Its Application to a Pharmacokinetic and Bioavailability Study. Molecules. 2019 Apr 10;24(7):1403. doi: 10.3390/molecules24071403. PMID: 30974748; PMCID: PMC6479676. 4: Szopa A, Dziurka M, Warzecha A, Kubica P, Klimek-Szczykutowicz M, Ekiert H. Targeted Lignan Profiling and Anti-Inflammatory Properties of Schisandra rubriflora and Schisandra chinensis Extracts. Molecules. 2018 Nov 27;23(12):3103. doi: 10.3390/molecules23123103. PMID: 30486445; PMCID: PMC6321394. 5: Chen SY, Shi JJ, Zou LS, Liu XH, Tang RM, Ma JM, Yan Y, Zhao H. [Simultaneous determination of lignans and organic acids in Schisandrae Chinensis Fructus by UFLC-Q-TRAP-MS/MS]. Zhongguo Zhong Yao Za Zhi. 2018 May;43(10):2104-2111. Chinese. doi: 10.19540/j.cnki.cjcmm.20180115.019. PMID: 29933678. 6: Zhang AH, Yu JB, Sun H, Kong L, Wang XQ, Zhang QY, Wang XJ. Identifying quality-markers from Shengmai San protects against transgenic mouse model of Alzheimer's disease using chinmedomics approach. Phytomedicine. 2018 Jun 1;45:84-92. doi: 10.1016/j.phymed.2018.04.004. Epub 2018 Apr 3. PMID: 29685366. 7: Zhang H, Zhang X, Jiang H, Xu C, Tong S, Yan J. Screening and identification of α-glucosidase inhibitors from Shenqi Jiangtang Granule by ultrafiltration liquid chromatography and mass spectrometry. J Sep Sci. 2018 Feb;41(3):797-805. doi: 10.1002/jssc.201700835. Epub 2017 Dec 27. PMID: 29152897. 8: Li W, Song YG, Liu KY, Yang LJ, Liu YL, Su D, Feng YL. [Rapid identification of the different constituents in Fructus Schisandrae Chinensis before and after processing by UHPLC-QTOF/MS~E combining with metabonomics]. Yao Xue Xue Bao. 2016 Sep;51(9):1445-50. Chinese. PMID: 29924538. 9: Song JH, Cui L, An LB, Li WT, Fang ZZ, Zhang YY, Dong PP, Wu X, Wang LX, Gonzalez FJ, Sun XY, Zhao DW. Inhibition of UDP-Glucuronosyltransferases (UGTs) Activity by constituents of Schisandra chinensis. Phytother Res. 2015 Oct;29(10):1658-64. doi: 10.1002/ptr.5395. Epub 2015 Jun 18. PMID: 26084208; PMCID: PMC6594156. 10: An KL, Li DK, Zhou DZ, Ye ZL, Guo QS. [Influlance of different drying methods on quality of Schisandrae Chinensis Fructus]. Zhongguo Zhong Yao Za Zhi. 2014 Aug;39(15):2900-6. Chinese. PMID: 25423829. 11: Smejkal K, Slapetová T, Krmenčík P, Babula P, Dall'Acqua S, Innocenti G, Vančo J, Casarin E, Carrara M, Kalvarová K, Dvorská M, Slanina J, Kramářová E, Julínek O, Urbanová M. Evaluation of cytotoxic activity of Schisandra chinensis lignans. Planta Med. 2010 Oct;76(15):1672-7. doi: 10.1055/s-0030-1249861. Epub 2010 May 10. PMID: 20458670. 12: Zhang J, Shi LL, Zheng YN. Dibenzocyclooctadiene lignans from Fructus Schisandrae Chinensis improve glucose uptake in vitro. Nat Prod Commun. 2010 Feb;5(2):231-4. PMID: 20334133. 13: Shi P, He Q, Zhang Y, Qu H, Cheng Y. Characterisation and identification of isomeric dibenzocyclooctadiene lignans from Schisandra Chinensis by high- performance liquid chromatography combined with electrospray ionisation tandem mass spectrometry. Phytochem Anal. 2009 May-Jun;20(3):197-206. doi: 10.1002/pca.1115. PMID: 19259942. 14: Hung TM, Na M, Min BS, Ngoc TM, Lee I, Zhang X, Bae K. Acetylcholinesterase inhibitory effect of lignans isolated from Schizandra chinensis. Arch Pharm Res. 2007 Jun;30(6):685-90. doi: 10.1007/BF02977628. PMID: 17679544. 15: Ikeya Y, Taguchi H, Yosioka I, Iitaka Y, Kobayashi H. The constituents of Schizandra chinensis Baill. II. The structure of a new lignan, gomisin D. Chem Pharm Bull (Tokyo). 1979 Jun;27(6):1395-401. doi: 10.1248/cpb.27.1395. PMID: 544052.