Paspaline

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MedKoo CAT#: 584995

CAS#: 11024-56-9

Description: Paspaline is an indole-diterpene.

Chemical Structure

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Paspaline
CAS# 11024-56-9
Instruction

Theoretical Analysis

MedKoo Cat#: 584995
Name: Paspaline
CAS#: 11024-56-9
Chemical Formula: C28H39NO2
Exact Mass: 421.30
Molecular Weight: 421.625
Elemental Analysis: C, 79.76; H, 9.32; N, 3.32; O, 7.59

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

Request quote for custom synthesis

Synonym: Paspaline

IUPAC/Chemical Name: 2H-1-Benzopyrano(5',6':6,7)indeno(1,2-b)indole-2-methanol, 3,4,4a,4b,5,6,6a,7,12,12b,12c,13,14,14a-tetradecahydro-alpha,alpha,4a,12b,12c-pentamethyl-, (2S-(2alpha,4aalpha,4bbeta,6aalpha,12bbeta,12calpha,14abeta))-

InChi Key: WLAIEIMDXUAGPY-HSECPPETSA-N

InChi Code: InChI=1S/C28H39NO2/c1-25(2,30)22-12-14-26(3)21-11-10-17-16-19-18-8-6-7-9-20(18)29-24(19)28(17,5)27(21,4)15-13-23(26)31-22/h6-9,17,21-23,29-30H,10-16H2,1-5H3/t17-,21-,22-,23-,26-,27-,28+/m0/s1

SMILES Code: OC(C)(C)[C@@H]1CC[C@]([C@]([C@@]2(C)[C@]34C)([H])CC[C@@]3([H])CC5=C4NC6=C5C=CC=C6)(C)[C@@](CC2)([H])O1

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 421.63 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: Sharpe RJ, Johnson JS. Asymmetric Total Synthesis of the Indole Diterpene Alkaloid Paspaline. J Org Chem. 2015 Oct 2;80(19):9740-66. doi: 10.1021/acs.joc.5b01844. PubMed PMID: 26398568; PubMed Central PMCID: PMC4598058.

2: Sharpe RJ, Johnson JS. A global and local desymmetrization approach to the synthesis of steroidal alkaloids: stereocontrolled total synthesis of paspaline. J Am Chem Soc. 2015 Apr 22;137(15):4968-71. doi: 10.1021/jacs.5b02631. Epub 2015 Apr 9. PubMed PMID: 25856767; PubMed Central PMCID: PMC4409926.

3: Saikia S, Parker EJ, Koulman A, Scott B. Four gene products are required for the fungal synthesis of the indole-diterpene, paspaline. FEBS Lett. 2006 Mar 6;580(6):1625-30. Epub 2006 Feb 17. PubMed PMID: 16494875.

4: Kozák L, Szilágyi Z, Tóth L, Pócsi I, Molnár I. Tremorgenic and neurotoxic paspaline-derived indole-diterpenes: biosynthetic diversity, threats and applications. Appl Microbiol Biotechnol. 2019 Feb;103(4):1599-1616. doi: 10.1007/s00253-018-09594-x. Epub 2019 Jan 6. Review. PubMed PMID: 30613899; PubMed Central PMCID: PMC6384164.

5: Kim DE, Zweig JE, Newhouse TR. Total Synthesis of Paspaline A and Emindole PB Enabled by Computational Augmentation of a Transform-Guided Retrosynthetic Strategy. J Am Chem Soc. 2019 Jan 30;141(4):1479-1483. doi: 10.1021/jacs.8b13127. Epub 2019 Jan 14. PubMed PMID: 30626183.

6: Fan Y, Wang Y, Liu P, Fu P, Zhu T, Wang W, Zhu W. Indole-diterpenoids with anti-H1N1 activity from the aciduric fungus Penicillium camemberti OUCMDZ-1492. J Nat Prod. 2013 Jul 26;76(7):1328-36. doi: 10.1021/np400304q. Epub 2013 Jul 2. PubMed PMID: 23886345.

7: Shymanovich T, Saari S, Lovin ME, Jarmusch AK, Jarmusch SA, Musso AM, Charlton ND, Young CA, Cech NB, Faeth SH. Alkaloid variation among epichloid endophytes of sleepygrass (Achnatherum robustum) and consequences for resistance to insect herbivores. J Chem Ecol. 2015 Jan;41(1):93-104. doi: 10.1007/s10886-014-0534-x. Epub 2014 Dec 11. PubMed PMID: 25501262.

8: Kozák L, Szilágyi Z, Vágó B, Kakuk A, Tóth L, Molnár I, Pócsi I. Inactivation of the indole-diterpene biosynthetic gene cluster of Claviceps paspali by Agrobacterium-mediated gene replacement. Appl Microbiol Biotechnol. 2018 Apr;102(7):3255-3266. doi: 10.1007/s00253-018-8807-x. Epub 2018 Feb 19. PubMed PMID: 29457197; PubMed Central PMCID: PMC5854541.

9: Bauer JI, Gross M, Cramer B, Wegner S, Hausmann H, Hamscher G, Usleber E. Detection of the tremorgenic mycotoxin paxilline and its desoxy analog in ergot of rye and barley: a new class of mycotoxins added to an old problem. Anal Bioanal Chem. 2017 Aug;409(21):5101-5112. doi: 10.1007/s00216-017-0455-y. Epub 2017 Jul 4. PubMed PMID: 28674820.

10: Saikia S, Parker EJ, Koulman A, Scott B. Defining paxilline biosynthesis in Penicillium paxilli: functional characterization of two cytochrome P450 monooxygenases. J Biol Chem. 2007 Jun 8;282(23):16829-37. Epub 2007 Apr 11. PubMed PMID: 17428785.

11: van Dolleweerd CJ, Kessans SA, Van de Bittner KC, Bustamante LY, Bundela R, Scott B, Nicholson MJ, Parker EJ. MIDAS: A Modular DNA Assembly System for Synthetic Biology. ACS Synth Biol. 2018 Apr 20;7(4):1018-1029. doi: 10.1021/acssynbio.7b00363. Epub 2018 Apr 12. PubMed PMID: 29620866.

12: Reddy P, Guthridge K, Vassiliadis S, Hemsworth J, Hettiarachchige I, Spangenberg G, Rochfort S. Tremorgenic Mycotoxins: Structure Diversity and Biological Activity. Toxins (Basel). 2019 May 27;11(5). pii: E302. doi: 10.3390/toxins11050302. Review. PubMed PMID: 31137882; PubMed Central PMCID: PMC6563255.

13: Sallam AA, Houssen WE, Gissendanner CR, Orabi KY, Foudah AI, El Sayed KA. Bioguided discovery and pharmacophore modeling of the mycotoxic indole diterpene alkaloids penitrems as breast cancer proliferation, migration, and invasion inhibitors. Medchemcomm. 2013 Oct;4(10). doi: 10.1039/C3MD00198A. PubMed PMID: 24273638; PubMed Central PMCID: PMC3835464.

14: Sallam AA, Ayoub NM, Foudah AI, Gissendanner CR, Meyer SA, El Sayed KA. Indole diterpene alkaloids as novel inhibitors of the Wnt/β-catenin pathway in breast cancer cells. Eur J Med Chem. 2013;70:594-606. doi: 10.1016/j.ejmech.2013.09.045. Epub 2013 Oct 8. PubMed PMID: 24211635; PubMed Central PMCID: PMC3884952.

15: Nicholson MJ, Eaton CJ, Stärkel C, Tapper BA, Cox MP, Scott B. Molecular Cloning and Functional Analysis of Gene Clusters for the Biosynthesis of Indole-Diterpenes in Penicillium crustosum and P. janthinellum. Toxins (Basel). 2015 Jul 23;7(8):2701-22. doi: 10.3390/toxins7082701. PubMed PMID: 26213965; PubMed Central PMCID: PMC4549719.

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17: Liu C, Minami A, Noike M, Toshima H, Oikawa H, Dairi T. Regiospecificities and prenylation mode specificities of the fungal indole diterpene prenyltransferases AtmD and PaxD. Appl Environ Microbiol. 2013 Dec;79(23):7298-304. doi: 10.1128/AEM.02496-13. Epub 2013 Sep 13. PubMed PMID: 24038699; PubMed Central PMCID: PMC3837767.

18: Zhang YH, Huang SD, Pan HQ, Bian XQ, Wang ZY, Han AH, Bai J. Structure determination of two new indole-diterpenoids from Penicillium sp. CM-7 by NMR spectroscopy. Magn Reson Chem. 2014 Jun;52(6):306-9. doi: 10.1002/mrc.4065. Epub 2014 Apr 2. PubMed PMID: 24700676.

19: Tagami K, Liu C, Minami A, Noike M, Isaka T, Fueki S, Shichijo Y, Toshima H, Gomi K, Dairi T, Oikawa H. Reconstitution of biosynthetic machinery for indole-diterpene paxilline in Aspergillus oryzae. J Am Chem Soc. 2013 Jan 30;135(4):1260-3. doi: 10.1021/ja3116636. Epub 2013 Jan 15. PubMed PMID: 23311903.

20: Motoyama T, Hayashi T, Hirota H, Ueki M, Osada H. Terpendole E, a kinesin Eg5 inhibitor, is a key biosynthetic intermediate of indole-diterpenes in the producing fungus Chaunopycnis alba. Chem Biol. 2012 Dec 21;19(12):1611-9. doi: 10.1016/j.chembiol.2012.10.010. PubMed PMID: 23261604.