Naturally Occurring Spinosyns

Saccharopolyspora spinosa produces 23 spinosyns that are designated with letters reflecting the order in which these were identified.12 For the spinosyns produced by S. spinosa, the neutral sugar at C9 is 2,3,4-tri-O-methyl-a-L-rhamnose and

Structure

number

Name

R6a

5,6 bond

Rya

5.1

Spinosyn Ab

H

double

Me

5.2

Spinosyn Dc

Me

double

Me

5.3

Spinosyn J

H

double

H

5.4

Spinosyn L

Me

double

H

5.5

3'-O-ethyl-5,6-dihydro spinosyn Jd

H

single

Et

5.6

3'-O-ethyl spinosyn Le

Me

double

Et

'Major component of spinosad.

'Minor component of spinosad.

dMajor component of spinetoram, also identified as spinetoram-J and as XDE-175-J.

'Minor component of spinetoram, also identified as spinetoram-L and as XDE-175-L.

'Major component of spinosad.

'Minor component of spinosad.

dMajor component of spinetoram, also identified as spinetoram-J and as XDE-175-J.

'Minor component of spinetoram, also identified as spinetoram-L and as XDE-175-L.

Figure 5.2 Spinosyn chemical structure.

the amino sugar at C17 is generally p-D-forosamine. The 23 spinosyns produced by S. spinosa differ primarily in the presence or absence of methyl groups at eight positions (three positions on the tetracycle, three positions on the 2',3',4'-tri-O-methyl rhamnose and two positions on the forosamine). Spinosad is the ISO common name for the mixture of spinosyns that is extracted from the fermentation broth of S. spinosa. Spinosyn A (see Figure 5.2; structure 5.1) is produced in the greatest quantity by S. spinosa, followed by spinosyn D (see Figure 5.2; structure 5.2), which differs from spinosyn A by having a methyl group instead of a hydrogen atom at position C6 on the macrolide. The other 21 spinosyns are produced in very small quantities. Spinosyns A and D have the highest levels of insecticidal activity among the spinosyns produced by S. spinosa, the others are generally much less active.12,14

Saccharopolyspora pogona produces a similar series of secondary metabolites.3 These compounds are referred to as butenyl-spinosyns because a majority of the 31 spinosyns produced by S. pogona have a but-1-enyl group at the C21 position on the tetracycle, instead of the ethyl group typically found in spin-osyns produced by S. spinosa. The spinosyns produced by S. pogona have greater structural diversity than the spinosyns produced by S. spinosa; some have hydroxyl groups instead of methyl groups in several positions, sugars other than forosamine at C17, substituents other than ethyl or but-1-enyl at C21, or a 14-membered macrolide instead of a 12-membered macrolide.3

Several spinosyns produced by S. pogona have high levels of insecticidal

activity.

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