4429-63-4 Usage
Description
TABERSONINE, also known as (-)-Tabersonine, is a monoterpenoid indole alkaloid derived from the plant Amsonia tabernaemontana. It is a naturally occurring compound with a complex structure, which is difficult to obtain in crystalline form, but its hydrochloride form is readily crystallizable with a melting point of 195-196°C. TABERSONINE exhibits a range of biological activities, including hypotensive, anti-tumor, hypoglycemic, and diuretic properties, making it a promising candidate for various pharmaceutical applications.
Uses
Used in Pharmaceutical Industry:
TABERSONINE is used as a pharmaceutical compound for its cytotoxic activity. It has been found to exhibit anti-tumor properties, making it a potential candidate for the development of cancer treatments. Its hypotensive, hypoglycemic, and diuretic activities also suggest potential applications in the treatment of cardiovascular, metabolic, and renal disorders.
Used in Cancer Research:
TABERSONINE is used as a research tool for studying the mechanisms of cancer cell growth and proliferation. Its cytotoxic activity against cancer cells can provide valuable insights into the development of novel cancer therapies and help identify potential targets for drug development.
Used in Drug Discovery:
TABERSONINE is used as a lead compound in drug discovery efforts, particularly in the search for new cancer treatments. Its unique chemical structure and biological activities make it an attractive starting point for the design and synthesis of new, more potent, and selective anti-cancer agents.
Used in Traditional Medicine:
TABERSONINE is used in traditional medicine, particularly in the treatment of various ailments related to its biological activities. Its hypotensive, hypoglycemic, and diuretic properties may be harnessed to develop natural remedies for conditions such as high blood pressure, diabetes, and fluid retention.
References
lanot, Paourrat, LeMen., Bull. Soc. Chim. Fr., 707 (1954)
Plat et al., Tetrahedron Lett., 271 (1962)
Check Digit Verification of cas no
The CAS Registry Mumber 4429-63-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 4,4,2 and 9 respectively; the second part has 2 digits, 6 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 4429-63:
(6*4)+(5*4)+(4*2)+(3*9)+(2*6)+(1*3)=94
94 % 10 = 4
So 4429-63-4 is a valid CAS Registry Number.
InChI:InChI=1/C21H24N2O2/c1-3-20-9-6-11-23-12-10-21(19(20)23)15-7-4-5-8-16(15)22-17(21)14(13-20)18(24)25-2/h4-9,19,22H,3,10-13H2,1-2H3/t19-,20-,21+/m0/s1
4429-63-4Relevant articles and documents
Alkaloids and other compounds from seeds of Tabernaemontana cymosa
Achenbach, Hans,Benirschke, Monika,Torrenegra, Ruben
, p. 325 - 335 (1997)
From the seeds of Tabernaemontana cymosa (= T. psychotrifolia) 17 indole alkaloids and six lignan glacosides were isolated, besides triacylglycerols, 9,12-octadecadienoic acid, lupeol, (+)-lyoniresinol, obtusifoliol, sweroside and a glucoside of 3-O-methylgallic acid. 9-(β-D-Glucopyranosyloxy)- tetrahydroalstonine, (+)-5,5'-dimethoxy-9-O-(β-D- glucopyranosyl)lariciresinol, (-)-2α-O-(β-D-glucopyranosyl)-lyoniresinol and 3-O-(β-D-glucopyranosyl)-5-O-methylgallic acid are described for the first time. Structural determination is based on spectroscopic studies and/or on comparison with authentic compounds. Some of the isolated substances exhibited significant antifungal and/or cytotoxic effects.
METHOD AND MEANS FOR MANUFACTURING TERPENE INDOLE ALKALOIDS
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Page/Page column 11; 31, (2019/10/04)
The complex chemistry underlying the extensive transformations involved in terpene indole alkaloid synthesis makes identification of the biosynthetic genes challenging. The present invention relates to methods for producing a terpene indole alkaloid derivative, comprising the steps of: (1) providing a terpene indole alkaloid; and (2) providing a first enzyme termed "Precondylocarpine Acetate Synthase" (PAS) or a functional variant or homologue thereof; and/or a second enzyme termed "Dehydroprecondylocarpine Acetate Synthase" (DPAS) or a functional variant or homologue thereof, and optionally providing further identified enzymes involved in this pathway. The invention also encompasses related kits, enzymes, expression vectors, host cells and plants.
Development and Scope of the Arene-Fused Domino Michael/Mannich Reaction: Application to the Total Syntheses of Aspidosperma Alkaloids (-)-Aspidospermidine, (-)-Tabersonine, and (-)-Vincadifformine
Zhao, Senzhi,Andrade, Rodrigo B.
, p. 521 - 531 (2017/04/26)
The development and application of the arene-fused domino Michael/Mannich route to the tetrahydrocarbazole (ABE) core of Aspidosperma alkaloids is described. The scope of this novel transformation was studied in terms of the nucleophilic component (i.e., N-sulfinyl metallodienamine) and the electrophilic component (i.e., Michael acceptor). The successful application of this methodology toward the concise total syntheses of classical indole alkaloids (-)-aspidospermidine, (-)-tabersonine, and (-)-vincadifformine in 10-11 steps, respectively, is also discussed.