Synonym
Paspalicine; Paspalicin;
IUPAC/Chemical Name
(3R,5bS,7aS,13bS,13cR,15aS)-5b-hydroxy-2,2,13b,13c-tetramethyl-2,3,5b,6,7,7a,8,13,13b,13c,14,15-dodecahydro-4H-3,15a-epoxyoxepino[2'',3'':5',6']benzo[1',2':6,7]indeno[1,2-b]indol-4-one
InChi Key
BPTIXFRJAOKMRK-SAMRHTEJSA-N
InChi Code
1S/C27H31NO4/c1-23(2)22-19(29)14-20-26(30)10-9-15-13-17-16-7-5-6-8-18(16)28-21(17)25(15,4)24(26,3)11-12-27(20,31-22)32-23/h5-8,14-15,22,28,30H,9-13H2,1-4H3/t15-,22-,24+,25+,26+,27-/m0/s1
SMILES Code
[H][C@]12CC3=C(NC4=CC=CC=C34)[C@]1(C)[C@@]5(C)CC[C@@]67O[C@@H](C(=O)C=C6[C@]5(O)CC2)C(C)(C)O7
Appearance
To be determined
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
433.55
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: Guo LD, Xu Z, Tong R. Asymmetric Total Synthesis of Indole Diterpenes Paspalicine, Paspalinine, and Paspalinine-13-ene. Angew Chem Int Ed Engl. 2022 Jan 17;61(3):e202115384. doi: 10.1002/anie.202115384. Epub 2021 Nov 27. PMID: 34784090.
2: Steyn PS, Vleggaar R. Tremorgenic mycotoxins. Fortschr Chem Org Naturst. 1985;48:1-80. doi: 10.1007/978-3-7091-8815-6_1. PMID: 3912307.
3: Knaus HG, McManus OB, Lee SH, Schmalhofer WA, Garcia-Calvo M, Helms LM, Sanchez M, Giangiacomo K, Reuben JP, Smith AB 3rd, et al. Tremorgenic indole alkaloids potently inhibit smooth muscle high-conductance calcium-activated potassium channels. Biochemistry. 1994 May 17;33(19):5819-28. doi: 10.1021/bi00185a021. PMID: 7514038.
4: Nicholson MJ, Koulman A, Monahan BJ, Pritchard BL, Payne GA, Scott B. Identification of two aflatrem biosynthesis gene loci in Aspergillus flavus and metabolic engineering of Penicillium paxilli to elucidate their function. Appl Environ Microbiol. 2009 Dec;75(23):7469-81. doi: 10.1128/AEM.02146-08. Epub 2009 Oct 2. PMID: 19801473; PMCID: PMC2786402.
5: Sunazuka T. [Synthetic studies of microbial natural products from microorganisms]. Jpn J Antibiot. 2003 Feb;56(1):66-79. Japanese. PMID: 12723401.
