131929-60-7 Usage
Uses
Spinosyn A is the major component of a complex of unusual, hydrophobic macrocyclic lactones isolated from Saccharopolyspora spinosa in 1991. The 12-membered macrocyclic lactone is fused to form a rare 12-5-6-5 tetracyclic ring system, with the macrocycle and the terminal cyclopentane bearing glycosides. Spinosyn A is a potent insecticide for crop pathogens and ectoparasite control on animals. The spinosyns have a unique mechanism of action involving disruption of nicotinic acetylcholine receptors.
Definition
ChEBI: A spinosyn in which the sugar amino and hydroxy groups are globally methylated. One of the two active ingredients of spinosad.
Biological Activity
spinosyn a is an insect nicotinic acetylcholinesterase receptors (nachrs) agonist and potent insecticide.the spinosyns are a family of macrolide natural products produced by the soil microorganism saccharopolyspora spinosa. spinosyn a is identified as a naturally-occurring macrocyclic lactone that is a potent insecticide.
Veterinary Drugs and Treatments
For the prevention and treatment of fleas for one month on dogs 14 weeks of age and older.
Spinosad is a group 5 nicotinic acetylcholine receptor agonist, that causes involuntary muscle contractions and tremors secondary
to motor neuron activation. Prolonged exposure causes paralysis and flea death. Flea death begins within 30 minutes of dosing and in 4
hours is complete. Spinosad does not interact with bindings sites of other insecticidal agents (GABA-ergic or nicotinic).
in vitro
the mixture of spinosyns a and d, a commercial insecticide tracertm (dowagrosciences), is useful against various crop pests such as tobacco budworm. it was found that the deoxy analogs of spinosyns a were more potent insecticides than their respective parent factor. moreover, the 2’-desmethoxy analogs of spinosyns a showed insecticidal potency against h. virescens greater than that of spinosyns a and d, suggesting that polarity was not well tolerated. furthermore, the activity of 3'-deoxy spinosyn j was about the same as spinosyn a, and the activity of 2'-deoxy spinosyn h was found to be slightly greater than that of spinosyn a [1].
Metabolic pathway
Spinosad consists of two major components, namely
psinosyns A (ca 85%) and D (ca 15%). When either
14C-spinosyn A or -spinosyn D is applied in the soil
under aerobic conditions, the major degradation
product of spinosyn A is spinosyn B, resulting from demethylation on the forosamine sugar. Other
degradation products are hydroxylation products of
psinosyns A and B, probably on the aglycone portion
of the molecule.
Degradation
Spinosad is relatively stable in water with no observed decomposition
between pH 5 and 7. Measured DT50 values at pH 9 were 200 and 259
days, respectively, for spinosyns A and D (Saunders and Bret, 1997).
Aqueous photolysis was very rapid with a DT50 of < 1 day in pH 7 buffered
water at 25 °C (DowElanco, 1996). Spinosad was rapidly dissipated
and degraded in an outdoor mesocosm study and on plant surfaces
(Saunders and Bret, 1997).
Toxicity evaluation
Acute oral LD50 for rats: 2,000-5,000 mg/kg
references
[1] l. c. creemer, h. a. kirst, j. w. paschal, et al. synthesis and insecticidal activity of spinosyn analogs functionally altered at the 2'-,3'- and 4'-positions of the rhamnose moiety. j.antibiot.(tokyo) 53(2), 171-178 (2000).
Check Digit Verification of cas no
The CAS Registry Mumber 131929-60-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,3,1,9,2 and 9 respectively; the second part has 2 digits, 6 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 131929-60:
(8*1)+(7*3)+(6*1)+(5*9)+(4*2)+(3*9)+(2*6)+(1*0)=127
127 % 10 = 7
So 131929-60-7 is a valid CAS Registry Number.
InChI:InChI=1/C41H65NO10/c1-10-26-12-11-13-34(52-36-17-16-33(42(5)6)23(3)48-36)22(2)37(44)32-20-30-28(31(32)21-35(43)50-26)15-14-25-18-27(19-29(25)30)51-41-40(47-9)39(46-8)38(45-7)24(4)49-41/h14-15,20,22-31,33-34,36,38-41H,10-13,16-19,21H2,1-9H3/t22-,23?,24?,25?,26?,27?,28-,29-,30?,31+,33?,34?,36?,38?,39?,40?,41?/m1/s1
131929-60-7Relevant articles and documents
Total Synthesis of (-)-Spinosyn A via Carbonylative Macrolactonization
Bai, Yu,Shen, Xingyu,Li, Yong,Dai, Mingji
, p. 10838 - 10841 (2016/09/12)
Spinosyn A (1), a complex natural product featuring a unique 5,6,5,12-fused tetracyclic core structure, is the major component of spinosad, an organic insecticide and an FDA-approved agent used worldwide. Herein, we report an efficient total synthesis of (-)-spinosyn A with 15 steps in the longest linear sequence and 23 steps total from readily available compounds 14 and 23. The synthetic approach features several important catalytic transformations including a chiral amine-catalyzed intramolecular Diels-Alder reaction to afford 22 in excellent diastereoselectivity, a one-step gold-catalyzed propargylic acetate rearrangement to convert 28 to α-iodoenone 31, an unprecedented palladium-catalyzed carbonylative Heck macrolactonization to form the 5,12-fused macrolactone in one step, and a gold-catalyzed Yu glycosylation to install the challenging β-forosamine. This total synthesis is highly convergent and modular, thus offering opportunities to synthesize spinosyn analogues in order to address the emerging cross-resistance problems.
