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MedKoo Cat#: 584628 | Name: Secologanin
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Description:

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

Secologanin is a monoterpene that has been found in V. rosea and is an intermediate in the synthesis of monoterpene indole alkaloids from geraniol.

Chemical Structure

Secologanin
Secologanin
CAS#19351-63-4

Theoretical Analysis

MedKoo Cat#: 584628

Name: Secologanin

CAS#: 19351-63-4

Chemical Formula: C17H24O10

Exact Mass: 388.1369

Molecular Weight: 388.37

Elemental Analysis: C, 52.58; H, 6.23; O, 41.20

Price and Availability

Size Price Availability Quantity
1mg USD 250.00 2 weeks
5mg USD 630.00 2 weeks
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Related CAS #
No Data
Synonym
Secologanin; NSC 640525
IUPAC/Chemical Name
(2S,3R,4S)-3-ethenyl-2-(β-D-glucopyranosyloxy)-3,4-dihydro-4-(2-oxoethyl)-2H-pyran-5-carboxylic acid, methyl ester
InChi Key
CSKKDSFETGLMSB-NRZPKYKESA-N
InChi Code
InChI=1S/C17H24O10/c1-3-8-9(4-5-18)10(15(23)24-2)7-25-16(8)27-17-14(22)13(21)12(20)11(6-19)26-17/h3,5,7-9,11-14,16-17,19-22H,1,4,6H2,2H3/t8-,9+,11-,12-,13+,14-,16+,17+/m1/s1
SMILES Code
OC[C@H]1O[C@H]([C@@H]([C@H]([C@@H]1O)O)O)O[C@]2([C@@H]([C@@H](C(C(OC)=O)=CO2)CC=O)C=C)[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
>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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Secologanin is a metabolite of loganin formed by the cytochrome P450 isoform CYP72A1, also known as secologanin synthase.
In vitro activity:
This article reviews the involvement of cytochrome P450 monooxygenases in the biosyntheses of three structurally and biosynthetically interesting compounds, secologanin, cornoside, and shikonin. Reference: Yakugaku Zasshi. 2005 Jan;125(1):31-49. https://pubmed.ncbi.nlm.nih.gov/15635280/
In vivo activity:
To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 388.37 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. Inoue K. [Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites]. Yakugaku Zasshi. 2005 Jan;125(1):31-49. Japanese. doi: 10.1248/yakushi.125.31. PMID: 15635280. 2. Geerlings A, Redondo FJ, Contin A, Memelink J, van der Heijden R, Verpoorte R. Biotransformation of tryptamine and secologanin into plant terpenoid indole alkaloids by transgenic yeast. Appl Microbiol Biotechnol. 2001 Aug;56(3-4):420-4. doi: 10.1007/s002530100663. PMID: 11549013.
In vitro protocol:
1. Inoue K. [Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites]. Yakugaku Zasshi. 2005 Jan;125(1):31-49. Japanese. doi: 10.1248/yakushi.125.31. PMID: 15635280. 2. Geerlings A, Redondo FJ, Contin A, Memelink J, van der Heijden R, Verpoorte R. Biotransformation of tryptamine and secologanin into plant terpenoid indole alkaloids by transgenic yeast. Appl Microbiol Biotechnol. 2001 Aug;56(3-4):420-4. doi: 10.1007/s002530100663. PMID: 11549013.
In vivo protocol:
To be determined
1: Knölker HJ. Preface. Alkaloids Chem Biol. 2019;81:ix-x. doi: 10.1016/S1099-4831(19)30008-2. PMID: 30685051. 2: Zhu H, Cai Y, Ma S, Futamura Y, Li J, Zhong W, Zhang X, Osada H, Zou H. Privileged Biorenewable Secologanin-Based Diversity-Oriented Synthesis for Pseudo-Natural Alkaloids: Uncovering Novel Neuroprotective and Antimalarial Frameworks. ChemSusChem. 2021 Dec 6;14(23):5320-5327. doi: 10.1002/cssc.202101868. Epub 2021 Oct 28. PMID: 34636473. 3: Kidd T, Easson ML, Qu Y, De Luca V. Inter-organ transport of secologanin allows assembly of monoterpenoid indole alkaloids in a Catharanthus roseus mutant. Phytochemistry. 2019 Mar;159:119-126. doi: 10.1016/j.phytochem.2018.12.017. Epub 2019 Jan 3. PMID: 30611871. 4: Abou-Hamdan H, Guillot R, Kouklovsky C, Vincent G. Synthesis of a Seco iso-Secologanin Aglycone Analogue of Interest toward Secoiridoids and Monoterpene Indole Alkaloids. J Org Chem. 2021 Jul 2;86(13):9244-9252. doi: 10.1021/acs.joc.1c00916. Epub 2021 Jun 15. PMID: 34129330. 5: Pizarro-Osilla C. Introducing… Kratom. J Emerg Nurs. 2017 Jul;43(4):373-374. doi: 10.1016/j.jen.2017.03.016. PMID: 28683875. 6: Kim HK, Choi YH, Luijendijk TJ, Rocha RA, Verpoorte R. Comparison of extraction methods for secologanin and the quantitative analysis of secologanin from Symphoricarpos albus using 1H-NMR. Phytochem Anal. 2004 Jul- Aug;15(4):257-61. doi: 10.1002/pca.776. PMID: 15311846. 7: Contin A, van der Heijden R, Lefeber AW, Verpoorte R. The iridoid glucoside secologanin is derived from the novel triose phosphate/pyruvate pathway in a Catharanthus roseus cell culture. FEBS Lett. 1998 Sep 4;434(3):413-6. doi: 10.1016/s0014-5793(98)01022-9. PMID: 9742965. 8: Asada K, Salim V, Masada-Atsumi S, Edmunds E, Nagatoshi M, Terasaka K, Mizukami H, De Luca V. A 7-deoxyloganetic acid glucosyltransferase contributes a key step in secologanin biosynthesis in Madagascar periwinkle. Plant Cell. 2013 Oct;25(10):4123-34. doi: 10.1105/tpc.113.115154. Epub 2013 Oct 8. PMID: 24104568; PMCID: PMC3877786. 9: Berger A, Kostyan MK, Klose SI, Gastegger M, Lorbeer E, Brecker L, Schinnerl J. Loganin and secologanin derived tryptamine-iridoid alkaloids from Palicourea crocea and Palicourea padifolia (Rubiaceae). Phytochemistry. 2015 Aug;116:162-169. doi: 10.1016/j.phytochem.2015.05.013. Epub 2015 Jun 1. PMID: 26043882. 10: Zarembo JE, Douglas B, Valenta J, Weisbach JA. Metabolites of mitragynine. J Pharm Sci. 1974 Sep;63(9):1407-15. doi: 10.1002/jps.2600630916. PMID: 4473532. 11: Wang FY, Jiao L. Total Synthesis of (-)-Arborisidine. Angew Chem Int Ed Engl. 2021 Jun 1;60(23):12732-12736. doi: 10.1002/anie.202101161. Epub 2021 Apr 28. PMID: 33779034. 12: Awakawa T, Abe I. Biosynthesis of the teleocidin-type terpenoid indole alkaloids. Org Biomol Chem. 2018 Jul 4;16(26):4746-4752. doi: 10.1039/c8ob00803e. PMID: 29774913. 13: Mason JD, Weinreb SM. The Alstoscholarisine Alkaloids: Isolation, Structure Determination, Biogenesis, Biological Evaluation, and Synthesis. Alkaloids Chem Biol. 2019;81:115-150. doi: 10.1016/bs.alkal.2018.09.001. Epub 2018 Nov 15. PMID: 30685049. 14: Takayama H. Total Syntheses of Lycopodium and Monoterpenoid Indole Alkaloids Based on Biosynthesis-Inspired Strategies. Chem Pharm Bull (Tokyo). 2020;68(2):103-116. doi: 10.1248/cpb.c19-00872. PMID: 32009077. 15: Raffa RB, Beckett JR, Brahmbhatt VN, Ebinger TM, Fabian CA, Nixon JR, Orlando ST, Rana CA, Tejani AH, Tomazic RJ. Orally active opioid compounds from a non-poppy source. J Med Chem. 2013 Jun 27;56(12):4840-8. doi: 10.1021/jm400143z. Epub 2013 Apr 8. PMID: 23517479. 16: WALDROP FN. Reserpine. Med Ann Dist Columbia. 1956 May;25(5):256-8. PMID: 13321176. 17: Zhao S, Sirasani G, Vaddypally S, Zdilla MJ, Andrade RB. Total synthesis of (-)-melotenine A. Angew Chem Int Ed Engl. 2013 Aug 5;52(32):8309-11. doi: 10.1002/anie.201302517. Epub 2013 Jun 19. PMID: 23784890. 18: Inoue K. [Cytochrome P450 enzymes in biosyntheses of some plant secondary metabolites]. Yakugaku Zasshi. 2005 Jan;125(1):31-49. Japanese. doi: 10.1248/yakushi.125.31. PMID: 15635280. 19: Pan X, Yang C, Cleveland JL, Bannister TD. Synthesis and Cytoxicity of Sempervirine and Analogues. J Org Chem. 2016 Mar 4;81(5):2194-200. doi: 10.1021/acs.joc.6b00022. Epub 2016 Feb 10. PMID: 26828413; PMCID: PMC5573167. 20: Wan AS, Macko E, Douglas B. Pharmacology of pelirine. Planta Med. 1971 Feb;19(3):203-7. doi: 10.1055/s-0028-1099632. PMID: 5546259.

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