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MedKoo Cat#: 592364 | Name: Cauloside C
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Description:

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

Cauloside C, also known as Hederoside D2, is a triterpenoid saponin that induces potassium release and hemolysis in mouse erythrocytes in a pH-dependent manner. Hederoside D2 is cytotoxic to N1E-115 neuroblastoma cells at low pH. It induces proliferation of human embryonic fibroblasts in acidic medium, an effect that can be blocked by the calcium channel blockers verapamil, diltiazem, and nitrendipine.

Chemical Structure

Cauloside C
Cauloside C
CAS#20853-58-1

Theoretical Analysis

MedKoo Cat#: 592364

Name: Cauloside C

CAS#: 20853-58-1

Chemical Formula: C41H66O13

Exact Mass: 766.4503

Molecular Weight: 766.97

Elemental Analysis: C, 64.21; H, 8.67; O, 27.12

Price and Availability

Size Price Availability Quantity
1mg USD 350.00 2 Weeks
5mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Cauloside C; Fatsiaside D1; Hederoside D2
IUPAC/Chemical Name
3-((2-0-beta-D-Glucopyranosyl-alpha-L-arabinopyranosyl)oxy)-23-hydroxyolean-12-en-28-oic acid
InChi Key
RROGHRHLBLVQSG-UUWFFIQNSA-N
InChi Code
InChI=1S/C41H66O13/c1-36(2)13-15-41(35(49)50)16-14-39(5)21(22(41)17-36)7-8-26-37(3)11-10-27(38(4,20-43)25(37)9-12-40(26,39)6)53-34-32(28(45)23(44)19-51-34)54-33-31(48)30(47)29(46)24(18-42)52-33/h7,22-34,42-48H,8-20H2,1-6H3,(H,49,50)/t22-,23-,24+,25+,26+,27-,28-,29+,30-,31+,32+,33-,34-,37-,38-,39+,40+,41-/m0/s1
SMILES Code
CC1(CC[C@]2(C(O)=O)CC[C@@]3(C([C@@H]2C1)=CC[C@@H]4[C@]5(CC[C@@H]([C@@](CO)([C@@H]5CC[C@@]34C)C)O[C@@H]6OC[C@@H]([C@@H]([C@H]6O[C@@H]7O[C@@H]([C@H]([C@@H]([C@H]7O)O)O)CO)O)O)C)C)C
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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 766.97 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
1: Likhatskaya GN, Aminin DL, Agafonova IG, Gnedoi SN, Shentsova EB, Strigina LI, Anisimov MM. The pH-dependent channels formed by cauloside C. Adv Exp Med Biol. 1996;404:239-49. doi: 10.1007/978-1-4899-1367-8_22. PMID: 8957300. 2: Aminin DL, Agafonova IG, Gnedoi SN, Strigina LI, Anisimov MM. The effect of pH on biological activity of plant cytotoxin cauloside C. Comp Biochem Physiol A Mol Integr Physiol. 1999 Jan;122(1):45-51. doi: 10.1016/s1095-6433(98)10138-1. PMID: 10216931. 3: Lü S, Dong S, Xu D, Duan J, Li G, Guo Y, Kuang H, Wang Q. Spectrum-Effect Relationships between Fingerprints of Caulophyllum robustum Maxim and Inhabited Pro-Inflammation Cytokine Effects. Molecules. 2017 Oct 26;22(11):1826. doi: 10.3390/molecules22111826. PMID: 29072610; PMCID: PMC6150361. 4: Avula B, Wang YH, Rumalla CS, Ali Z, Smillie TJ, Khan IA. Analytical methods for determination of magnoflorine and saponins from roots of Caulophyllum thalictroides (L.) Michx. using UPLC, HPLC and HPTLC. J Pharm Biomed Anal. 2011 Dec 15;56(5):895-903. doi: 10.1016/j.jpba.2011.07.028. Epub 2011 Jul 29. PMID: 21872415. 5: Datta S, Mahdi F, Ali Z, Jekabsons MB, Khan IA, Nagle DG, Zhou YD. Toxins in botanical dietary supplements: blue cohosh components disrupt cellular respiration and mitochondrial membrane potential. J Nat Prod. 2014 Jan 24;77(1):111-7. doi: 10.1021/np400758t. Epub 2013 Dec 11. PMID: 24328138; PMCID: PMC3932489. 6: Prokof'eva NG, Likhatskaia GN, Aminin DL, Gafurov IuM, Sasunkevich VA, Strigina LI, Anisimov MM. Mekhanizm vzaimodeĭstviia pH-zavisimogo tsitostatika kaulozida C s memranami opukholevykh kletok i liposom [The mechanism of the interaction of the pH-dependent cytostatic cauloside C with the membranes of tumor cells and liposomes]. Izv Akad Nauk SSSR Biol. 1990 May-Jun;(3):338-42. Russian. PMID: 2401767. 7: Strigina LI, Isakov VV. Struktura sul'fatirovannogo kaulozida C [The structure of sulfated cauloside C]. Bioorg Khim. 2000 May;26(5):387-91. Russian. PMID: 10900510. 8: Kovalchuk SN, Kozhemyako VB, Atopkina LN, Silchenko AS, Avilov SA, Kalinin VI, Rasskazov VA, Aminin DL. Estrogenic activity of triterpene glycosides in yeast two-hybrid assay. J Steroid Biochem Mol Biol. 2006 Nov;101(4-5):226-31. doi: 10.1016/j.jsbmb.2006.06.022. Epub 2006 Sep 12. PMID: 16973351. 9: Guo Y, Lü S, Yang B, Li G, Ma W, Guo Q, Wang Q, Kuang H. HPLC-MS/MS method for the determination and pharmacokinetic study of six compounds against rheumatoid arthritis in rat plasma after oral administration of the extract of Caulophyllum robustum Maxim. J Pharm Biomed Anal. 2020 Mar 20;181:112923. doi: 10.1016/j.jpba.2019.112923. Epub 2019 Oct 21. PMID: 32029347. 10: Lü S, Zhao S, Zhao M, Guo Y, Li G, Yang B, Wang Q, Kuang H. Systematic screening and characterization of prototype constituents and metabolites of triterpenoid saponins of Caulopphyllum robustum Maxim using UPLC-LTQ Orbitrap MS after oral administration in rats. J Pharm Biomed Anal. 2019 May 10;168:75-82. doi: 10.1016/j.jpba.2019.02.005. Epub 2019 Feb 6. PMID: 30798208. 11: Duan JX, Li GY, Jian JP, Lü SW, Su H, Xu D, Guo YY, Kuang HX, Wang QH. Analysis of bioactive components and pharmacokinetics of Caulophyllum robustum in rat plasma after oral administration by UPLC-ESI-MS/MS. J Asian Nat Prod Res. 2021 Mar;23(3):258-270. doi: 10.1080/10286020.2018.1529029. Epub 2019 Sep 9. PMID: 31496278. 12: Anisimov MM, Shcheglov VV, Dzizenko SN. Bliianie nekotorykh triterpenovykh glikozidov na biosintez sterinov i zhirnykh kislot drozhzheĭ Saccharmyces carlsvergensis [Effect of triterpene glycosides on the biosynthesis of sterols and fatty acids by the yeast Saccharomyces carlsbergensis]. Prikl Biokhim Mikrobiol. 1978 Jul-Aug;14(4):573-82. Russian. PMID: 724665. 13: Shcheglov VV, Anisimov MM, Popov AM, Sebko IG. Vliianie nekotorykh triterpenovykh glikozidov na pronitsaemost' plazmaticheskikh membran dlia UF- pogloshchaiushchikh veshchestv v drozhzhevykh kletkakh Saccharomyces carlsbergensis [Effect of triterpene glycosides on plasma membrane permeability for UV-absorbing substances in Saccharomyces carlsbergensis yeast cells]. Antibiotiki. 1979 Jan;24(1):49-55. Russian. PMID: 34359. 14: Anisimov MM, Baranova SI, Strigina LI, Chetyrina NS, Sokol'skiĭ IN. Vliianie nekotorykh triterpenovykh glikozidov na biosintez RNK v kul'ture drozhzhevykh kletok Saccharomyces carlsbergensis [Effect of triterpene glycosides on RNA biosynthesis in a yeast cell culture of Saccharomyces carlsbergensis]. Antibiotiki. 1977 Sep;22(9):837-41. Russian. PMID: 911157. 15: Popov AM, Rovin IuG, Anisimov MM, Likhatskaia GN, Strigina LI. Vliianie triterpenovykh glikozidov na stabil'nost' bisloĭnykh lipidnykh membran, soderzhashchikh razlichnye steriny [Effect of triterpene glycosides on the stability of bilayer lipid membranes, containing different sterols]. Biofizika. 1982 Sep-Oct;27(5):827-31. Russian. PMID: 7138933. 16: Anisimov MM, Ivanova AS, Popov AM, Kiseleva MI, Sebko IG. Vliianie nekotorykh triterpenovykh glikozidov i polienovykh antibiotikov na pronitsaemost' kletochnykh membran dklia ionov K+ i UF-pogloshchaiushchikh veshchestv [Effect of triterpene glycosides and polyene antibiotics on cell membrane permeability for K+ ions and UV-absorbing substances]. Prikl Biokhim Mikrobiol. 1981 Nov-Dec;17(6):890-5. Russian. PMID: 7198783. 17: Anisimov MM, Shcheglov VV, Kiseleva MI. Vliianie nekotorykh triterpenovykh glikozidov na pronitsaemost' plazmaticheskikh membran dlia aminokislot v drozhzhevykh kletakh Saccharomyces carlsbergensis [Effect of triterpene glycosides on the plasma membrane permeability for amino acids in Saccharomyces carlsbergensis yeast cells]. Antibiotiki. 1978 Jan;23(1):66-9. Russian. PMID: 623450. 18: Popov AM, Anisimov MM, Ivanov AS, Korepanova EA, Antonov VF. Osobennosti membrannoĭ aktivnosti nekotorykh triterpenovykh glikozidov [Characteristics of membrane activity of triterpene glycosides]. Antibiotiki. 1982 Apr;27(4):276-80. Russian. PMID: 7092199. 19: Prokof'eva NG, Loenko IuN, Anisimov MM. Vliianie nekotorykh triterpenovykh glikozidov na vkliuchenie 14C-alanina v kletki kostnogo mozga krys [Effect of triterpene glycosides on 14C-alanine incorporation into rat bone marrow cells]. Izv Akad Nauk SSSR Biol. 1981 Sep-Oct;(5):794-7. Russian. PMID: 7298990.

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