Lochnericine | CAS#72058-36-7 | alkaloid

MedKoo Cat#: 599140 | Name: Lochnericine

Description:

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

Lochnericine is a alkaloid isolated from elicited cell cultures of Catharanthus roseus.

Chemical Structure

Lochnericine

CAS#72058-36-7

Theoretical Analysis

MedKoo Cat#: 599140

Name: Lochnericine

CAS#: 72058-36-7

Chemical Formula: C21H24N2O3

Exact Mass: 352.1787

Molecular Weight: 352.43

Elemental Analysis: C, 71.57; H, 6.86; N, 7.95; O, 13.62

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

No Data

Synonym

Lochnericine; Lochnericine, (-)-;

IUPAC/Chemical Name

methyl (1aR,2aS,2bS,2b1R,9bS)-2b-ethyl-1a,2a,2b,2b1,3,5,10,11-octahydro-1H-oxireno[2',3':6,7]indolizino[8,1-cd]carbazole-4-carboxylate

InChi Key

AUVZFRDLRJQTQF-MCUYSKAESA-N

InChi Code

InChI=1S/C21H24N2O3/c1-3-20-10-12(18(24)25-2)16-21(13-6-4-5-7-14(13)22-16)8-9-23(19(20)21)11-15-17(20)26-15/h4-7,15,17,19,22H,3,8-11H2,1-2H3/t15-,17-,19+,20-,21-/m1/s1

SMILES Code

CC[C@]1([C@@](O2)([H])[C@@]2([H])CN3CC[C@@]45[C@@]31[H])CC(C(OC)=O)=C5NC6=C4C=CC=C6

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

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 352.43 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.

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: Wang Q, He J, Yan J, Wu D, Li H. Spectroscopy and docking simulations of the interaction between lochnericine and bovine serum albumin. Luminescence. 2015 Mar;30(2):240-6. doi: 10.1002/bio.2724. Epub 2014 Jun 19. PubMed PMID: 24942935. 2: GORMAN M, NEUSS N, SVOBODA GH, BARNES AJ Jr, CONE NJ. A note on the alkaloids of Vinca rosea Linn. (Catharanthus roseus G. Don.). II. Catharanthine, lochnericine, vindolinine, and vindoline. J Am Pharm Assoc Am Pharm Assoc. 1959 Apr;48(4):256-7. PubMed PMID: 13641069. 3: Tikhomiroff C, Allais S, Klvana M, Hisiger S, Jolicoeur M. Continuous selective extraction of secondary metabolites from Catharanthus roseus hairy roots with silicon oil in a two-liquid-phase bioreactor. Biotechnol Prog. 2002 Sep-Oct;18(5):1003-9. PubMed PMID: 12363351. 4: Rijhwani SK, Shanks JV. Effect of elicitor dosage and exposure time on biosynthesis of indole alkaloids by Catharanthus roseus hairy root cultures. Biotechnol Prog. 1998 May-Jun;14(3):442-9. PubMed PMID: 9622525. 5: Furuya T, Sakamoto K, Iida K, Asada Y, Yoshikawa T, Sakai S, Aimi N. Biotransformation of tabersonine in cell suspension cultures of Catharanthus roseus. Phytochemistry. 1992 Sep;31(9):3065-8. PubMed PMID: 1368411. 6: Peebles CA, Sander GW, Hughes EH, Peacock R, Shanks JV, San KY. The expression of 1-deoxy-D-xylulose synthase and geraniol-10-hydroxylase or anthranilate synthase increases terpenoid indole alkaloid accumulation in Catharanthus roseus hairy roots. Metab Eng. 2011 Mar;13(2):234-40. doi: 10.1016/j.ymben.2010.11.005. Epub 2010 Dec 7. PubMed PMID: 21144909. 7: Li M, Peebles CA, Shanks JV, San KY. Effect of sodium nitroprusside on growth and terpenoid indole alkaloid production in Catharanthus roseus hairy root cultures. Biotechnol Prog. 2011 May-Jun;27(3):625-30. doi: 10.1002/btpr.605. Epub 2011 May 12. PubMed PMID: 21567990. 8: Fernández-Pérez F, Almagro L, Pedreño MA, Gómez Ros LV. Synergistic and cytotoxic action of indole alkaloids produced from elicited cell cultures of Catharanthus roseus. Pharm Biol. 2013 Mar;51(3):304-10. doi: 10.3109/13880209.2012.722646. Epub 2012 Nov 8. PubMed PMID: 23137274. 9: Morgan JA, Shanks JV. Inhibitor studies of tabersonine metabolism in C. roseus hairy roots. Phytochemistry. 1999 May;51(1):61-8. PubMed PMID: 10349729. 10: Binder BY, Peebles CA, Shanks JV, San KY. The effects of UV-B stress on the production of terpenoid indole alkaloids in Catharanthus roseus hairy roots. Biotechnol Prog. 2009 May-Jun;25(3):861-5. doi: 10.1002/btpr.97. PubMed PMID: 19479674. 11: Liu HM, Wu B, Zheng QT, Feng XZ. New Indole Alkaloids from Amsonia sinensis. Planta Med. 1991 Dec;57(6):566-8. PubMed PMID: 17226203. 12: Carqueijeiro IT, Brown S, Chung K, Dang TT, Walia M, Besseau S, Dugé de Bernonville T, Oudin A, Lanoue A, Billet K, Munsch T, Koudounas K, Melin C, Godon C, Razafimandimby B, de Craene JO, Glévarec G, Marc J, Giglioli-Guivarc'h N, Clastre M, St-Pierre B, Papon N, Andrade RB, O'Connor S, Courdavault V. Two tabersonine 6,7-epoxidases start synthesis of lochnericine-type alkaloids in Catharanthus roseus. Plant Physiol. 2018 Jun 22. pii: pp.00549.2018. doi: 10.1104/pp.18.00549. [Epub ahead of print] PubMed PMID: 29934299. 13: Sun J, Peebles CA. Engineering overexpression of ORCA3 and strictosidine glucosidase in Catharanthus roseus hairy roots increases alkaloid production. Protoplasma. 2016 Sep;253(5):1255-64. doi: 10.1007/s00709-015-0881-7. Epub 2015 Sep 8. PubMed PMID: 26351111. 14: Morgan JA, Barney CS, Penn AH, Shanks JV. Effects of buffered media upon growth and alkaloid production of Catharanthus roseus hairy roots. Appl Microbiol Biotechnol. 2000 Mar;53(3):262-5. PubMed PMID: 10772463. 15: Eles J, Kalaus G, Greiner I, Kajtár-Peredy M, Szabó P, Keserû GM, Szabó L, Szántay C. Synthesis of vinca alkaloids and related compounds. 100. Stereoselective oxidation reactions of compounds with the aspidospermane and quebrachamine ring system. First synthesis of some alkaloids containing the epoxy ring. J Org Chem. 2002 Oct 18;67(21):7255-60. PubMed PMID: 12375951. 16: Cordell GA, Farnsworth NR. Catharanthus alkaloids XXXII: isolation of alkaloids from Catharanthus trichophyllus roots and structure elucidation of cathaphylline. J Pharm Sci. 1976 Mar;65(3):366-9. PubMed PMID: 1263083. 17: Zhong XZ, Wang GC, Wang Y, Zhang XQ, Ye WC. [Monomeric indole alkaloids from the aerial parts of Catharanthus roseus]. Yao Xue Xue Bao. 2010 Apr;45(4):471-4. Chinese. PubMed PMID: 21355212. 18: Giddings LA, Liscombe DK, Hamilton JP, Childs KL, DellaPenna D, Buell CR, O'Connor SE. A stereoselective hydroxylation step of alkaloid biosynthesis by a unique cytochrome P450 in Catharanthus roseus. J Biol Chem. 2011 May 13;286(19):16751-7. doi: 10.1074/jbc.M111.225383. Epub 2011 Mar 24. PubMed PMID: 21454651; PubMed Central PMCID: PMC3089517. 19: Bhadra R, Morgan JA, Shanks JV. Transient studies of light-adapted cultures of hairy roots of Catharanthus roseus: growth and indole alkaloid accumulation. Biotechnol Bioeng. 1998 Dec 20;60(6):670-8. PubMed PMID: 10099477. 20: Hong SB, Hughes EH, Shanks JV, San KY, Gibson SI. Role of the non-mevalonate pathway in indole alkaloid production by Catharanthus roseus hairy roots. Biotechnol Prog. 2003 May-Jun;19(3):1105-8. PubMed PMID: 12790690.