Ophiopogonin D
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MedKoo CAT#: 464986

CAS#: 945619-74-9

Description: Ophiopogonin D is a steroid glycoside that has been found in O. japonicus tubers and has diverse biological activities. It induces apoptosis in, and reduces TGF-β1-induced migration of, MDA-MB-231 human breast cancer cells when used at concentrations of 2.5, 5, or 10 µM. Ophiopogonin D (10 and 100 µM) inhibits hydrogen peroxide-induced production of reactive oxygen species (ROS) in RAW 264.7 cells. It inhibits peritoneal neutrophil infiltration in a mouse model of peritonitis induced by zymosan A when administered at a dose of 1 mg/kg.3 Ophiopogonin D (1 and 2 mg/kg) reduces thrombus weight in a mouse model of venous thrombosis.


Chemical Structure

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Ophiopogonin D
CAS# 945619-74-9

Theoretical Analysis

MedKoo Cat#: 464986
Name: Ophiopogonin D
CAS#: 945619-74-9
Chemical Formula: C44H70O16
Exact Mass: 854.47
Molecular Weight: 855.028
Elemental Analysis: C, 61.81; H, 8.25; O, 29.94

Price and Availability

Size Price Availability Quantity
1mg USD 210 2 Weeks
5mg USD 420 2 Weeks
10mg USD 690 2 Weeks
25mg USD 1040 2 Weeks
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Synonym: Ophiopogonin D; Ophiopogonin-D; Deacetylophiopogonin C; Deacetylophiopogonin-C; OJV-V; OJVV; OJV V;

IUPAC/Chemical Name: (2S,3R,4R,5R,6S)-2-(((2R,3R,4S,5S,6R)-5-hydroxy-2-(((4R,5'R,6R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bS)-4-hydroxy-5',6a,8a,9-tetramethyl-1,3,3',4,4',5,5',6,6a,6b,6',7,8,8a,8b,9,11a,12,12a,12b-icosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-6-yl)oxy)-6-methyl-4-(((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-6-methyltetrahydro-2H-pyran-3,4,5-triol

InChi Key: FHKHGNFKBPFJCB-LYLKFOBISA-N

InChi Code: InChI=1S/C44H70O16/c1-18-9-12-44(54-16-18)19(2)30-28(60-44)15-26-24-8-7-22-13-23(45)14-29(43(22,6)25(24)10-11-42(26,30)5)57-41-38(59-40-36(52)34(50)31(47)20(3)55-40)37(32(48)21(4)56-41)58-39-35(51)33(49)27(46)17-53-39/h7,18-21,23-41,45-52H,8-17H2,1-6H3/t18-,19+,20+,21-,23-,24-,25+,26+,27-,28+,29-,30+,31+,32+,33+,34-,35-,36-,37+,38-,39+,40+,41+,42+,43+,44-/m1/s1

SMILES Code: C[C@@]12[C@@]3([C@]([H])(C[C@]1([C@]4([C@]([H])(CC2)[C@@]5(C)[C@H](O[C@H]6[C@H](O[C@H]7[C@H](O)[C@H](O)[C@@H](O)[C@H](C)O7)[C@@H](O[C@H]8[C@H](O)[C@@H](O)[C@H](O)CO8)[C@@H](O)[C@@H](C)O6)C[C@H](O)CC5=CC4)[H])[H])O[C@@]9([C@H]3C)CC[C@@H](C)CO9)[H]

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 35.09
DMSO 30.0 35.09
Ethanol 15.0 17.54

Preparing Stock Solutions

The following data is based on the product molecular weight 855.03 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: Zhang YX, Qu SS, Zhang LH, Gu YY, Chen YH, Huang ZY, Liu MH, Zou W, Jiang J, Chen JQ, Wang YJ, Zhou FH. The Role of Ophiopogonin D in Atherosclerosis: Impact on Lipid Metabolism and Gut Microbiota. Am J Chin Med. 2021 Jul 14:1-19. doi: 10.1142/S0192415X21500683. Epub ahead of print. PMID: 34263719.

2: Stalin A, Lin D, Senthamarai Kannan B, Feng Y, Wang Y, Zhao W, Ignacimuthu S, Wei DQ, Chen Y. An in-silico approach to identify the potential hot spots in SARS-CoV-2 spike RBD to block the interaction with ACE2 receptor. J Biomol Struct Dyn. 2021 Mar 9:1-16. doi: 10.1080/07391102.2021.1897682. Epub ahead of print. PMID: 33685364.

3: Chiang TY, Wang HJ, Wang YC, Chia-Hui Tan E, Lee IJ, Yun CH, Ueng YF. Effects of Shengmai San on key enzymes involved in hepatic and intestinal drug metabolism in rats. J Ethnopharmacol. 2021 May 10;271:113914. doi: 10.1016/j.jep.2021.113914. Epub 2021 Feb 9. PMID: 33571617.

4: Jin X, Zhang J, Li Y, Wu W, Zhang H, Yao C, Wei W, Yao S, Huang Y, Qu H, Guo DA. Nontargeted metabolomic analysis and multiple criteria decision-making method induced robust quality markers screening for the authentication of herbal medicines from different origins by taking Ophiopogon japonicus (L. f.) Ker- Gawl. as a case study. J Sep Sci. 2021 Apr;44(7):1440-1451. doi: 10.1002/jssc.202000655. Epub 2021 Feb 10. PMID: 33503285.

5: Wang J, You W, Wang N, Zhou W, Ge Y, Ma Z, Tan H, Wang Y, Gao Y. Ophiopogonin D Increases SERCA2a Interaction with Phospholamban by Promoting CYP2J3 Upregulation. Oxid Med Cell Longev. 2020 Dec 31;2020:8857906. doi: 10.1155/2020/8857906. PMID: 33488937; PMCID: PMC7790559.

6: Li W, Ji L, Tian J, Tang W, Shan X, Zhao P, Chen H, Zhang C, Xu M, Lu R, Guo W. Ophiopogonin D alleviates diabetic myocardial injuries by regulating mitochondrial dynamics. J Ethnopharmacol. 2021 May 10;271:113853. doi: 10.1016/j.jep.2021.113853. Epub 2021 Jan 22. PMID: 33485986.

7: Xu HH, Jiang ZH, Huang CS, Sun YT, Xu LL, Tang XL, Tan HL, Ma ZC, Gao Y. Global metabolomic and lipidomic analysis reveals the potential mechanisms of hemolysis effect of Ophiopogonin D and Ophiopogonin D' in vivo. Chin Med. 2021 Jan 6;16(1):3. doi: 10.1186/s13020-020-00412-z. PMID: 33407692; PMCID: PMC7787624.

8: Xu HH, Jiang ZH, Sun YT, Qiu LZ, Xu LL, Tang XL, Ma ZC, Gao Y. Differences in the Hemolytic Behavior of Two Isomers in Ophiopogon japonicus In Vitro and In Vivo and Their Risk Warnings. Oxid Med Cell Longev. 2020 Dec 13;2020:8870656. doi: 10.1155/2020/8870656. PMID: 33381274; PMCID: PMC7755485.

9: Ji X, Ding B, Wu X, Liu F, Yang F. In vitro study on the effect of ophiopogonin D on the activity of cytochrome P450 enzymes. Xenobiotica. 2021 Mar;51(3):262-267. doi: 10.1080/00498254.2020.1842941. Epub 2020 Nov 16. PMID: 33115303.

10: Wang Y, Li D, Song L, Ding H. Ophiopogonin D attenuates PM2.5-induced inflammation via suppressing the AMPK/NF-κB pathway in mouse pulmonary epithelial cells. Exp Ther Med. 2020 Dec;20(6):139. doi: 10.3892/etm.2020.9268. Epub 2020 Oct 5. PMID: 33093877; PMCID: PMC7571316.

11: Zhu X, Wang K, Chen Y. Ophiopogonin D suppresses TGF-β1-mediated metastatic behavior of MDA-MB-231 breast carcinoma cells via regulating ITGB1/FAK/Src/AKT/β-catenin/MMP-9 signaling axis. Toxicol In Vitro. 2020 Dec;69:104973. doi: 10.1016/j.tiv.2020.104973. Epub 2020 Aug 18. PMID: 32818624.

12: Qiao Y, Jiao H, Wang F, Niu H. Ophiopogonin D of Ophiopogon japonicus ameliorates renal function by suppressing oxidative stress and inflammatory response in streptozotocin-induced diabetic nephropathy rats. Braz J Med Biol Res. 2020 Jun 3;53(7):e9628. doi: 10.1590/1414-431X20209628. PMID: 32520209; PMCID: PMC7279694.

13: You WT, Zhou T, Ma ZC, Liang QD, Xiao CR, Tang XL, Tan HL, Zhang BL, Wang YG, Gao Y. Author Correction: Ophiopogonin D maintains Ca2+ homeostasis in rat cardiomyocytes in vitro by upregulating CYP2J3/ EETs and suppressing ER stress. Acta Pharmacol Sin. 2020 Dec;41(12):1622. doi: 10.1038/s41401-020-0428-0. Erratum for: Acta Pharmacol Sin. 2016 Mar;37(3):368-81. PMID: 32457415; PMCID: PMC7921441.

14: Yang M, Li CJ, Xiao Y, Guo Q, Huang Y, Su T, Luo XH, Jiang TJ. Ophiopogonin D promotes bone regeneration by stimulating CD31hi EMCNhi vessel formation. Cell Prolif. 2020 Mar;53(3):e12784. doi: 10.1111/cpr.12784. Epub 2020 Feb 20. PMID: 32080957; PMCID: PMC7106967.

15: Lu Z, Wu C, Zhu M, Song W, Wang H, Wang J, Guo J, Li N, Liu J, Li Y, Xu H. Ophiopogonin D' induces RIPK1‑dependent necroptosis in androgen‑dependent LNCaP prostate cancer cells. Int J Oncol. 2020 Feb;56(2):439-447. doi: 10.3892/ijo.2019.4945. Epub 2019 Dec 17. PMID: 31894265; PMCID: PMC6959467.

16: An EJ, Kim Y, Lee SH, Choi SH, Chung WS, Jang HJ. Ophiopogonin D ameliorates DNCB-induced atopic dermatitis-like lesions in BALB/c mice and TNF-α- inflamed HaCaT cell. Biochem Biophys Res Commun. 2020 Jan 29;522(1):40-46. doi: 10.1016/j.bbrc.2019.10.190. Epub 2019 Nov 15. PMID: 31735336.

17: Zhang L, Luo Z, Cui S, Xie L, Yu J, Tang D, Ma X, Mou Y. Residue of Paclobutrazol and Its Regulatory Effects on the Secondary Metabolites of Ophiopogon japonicas. Molecules. 2019 Sep 27;24(19):3504. doi: 10.3390/molecules24193504. PMID: 31569613; PMCID: PMC6804066.

18: Li Y, Wang H, Wang R, Lu X, Wang Y, Duan M, Li H, Fan X, Wang S. Pharmacokinetics, tissue distribution and excretion of saponins after intravenous administration of ShenMai Injection in rats. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Oct 1;1128:121777. doi: 10.1016/j.jchromb.2019.121777. Epub 2019 Aug 26. PMID: 31487566.

19: Wang HY, Guo SC, Peng ZT, Wang C, Duan R, Dong TTX, Tsim KWK. Ophiopogon Polysaccharide Promotes the In Vitro Metabolism of Ophiopogonins by Human Gut Microbiota. Molecules. 2019 Aug 8;24(16):2886. doi: 10.3390/molecules24162886. PMID: 31398918; PMCID: PMC6719028.

20: Wang J, Wang NN, Ge YX, Tan HL, Ma ZC, Wang YG, Gao Y. [Ophiopogonin D protects cardiomyocytes against ophiopogonin D'-induced injury through suppressing endoplasmic reticulum stress]. Zhongguo Zhong Yao Za Zhi. 2019 May;44(9):1876-1881. Chinese. doi: 10.19540/j.cnki.cjcmm.20190102.003. PMID: 31342716.