1177-71-5

Usage

Uses

Used in Plant Growth Regulation:
Laxogenin is used as a plant growth regulator for promoting growth and development in plants. It enhances various physiological processes, such as cell elongation, cell division, and photosynthesis, leading to improved plant growth and yield.
Used in Synthesis of Brassinosteroid Analogues:
Laxogenin is used as a starting material in the synthesis of brassinosteroid analogues, which are structurally similar to natural brassinosteroids and exhibit similar biological activities. These analogues can be used to study the structure-activity relationship of brassinosteroids and develop new plant growth regulators with improved efficacy and selectivity.
Used in Synthesis of Spirostanic Analogs:
Laxogenin is also used in the synthesis of spirostanic analogs of brassinolide and castasterone, which are important brassinosteroids with potential applications in agriculture and plant biotechnology. These analogs can be used to investigate the biological functions of brassinosteroids and develop new plant growth regulators with novel properties.

InChI:InChI=1/C27H42O4/c1-15-5-10-27(30-14-15)16(2)24-23(31-27)13-20-18-12-22(29)21-11-17(28)6-8-25(21,3)19(18)7-9-26(20,24)4/h15-21,23-24,28H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21-,23+,24+,25-,26+,27?/m1/s1

Upstream product

• 103665-44-7 (25R)-3β-acetoxy-5α-spirostan-6-one 
• 3514-59-8 (25R)-5α-spirostan-3,6-dione 
• 143202-92-0 (25R)-spirostan-3β-ol-6-one-3-O-<β-D-glucopyranosyl(1->4)><α-L-arabinopyranosyl(1->6)>-β-D-glucopyranoside 
• 123941-67-3 laxogenin 3-O-4)-O-<α-L-arabinopyranosyl-(1->6)>-β-D-glucopyranoside> 
• 511-91-1 chlorogenin 
• 41743-71-9 (3β,5α,6β,25R)-spirostan-3,6-diol 
• 210687-07-3 3-O-benzyl laxogenin 
• 146333-24-6 3-O-benzyl diosgenin 
• 512-04-9 diosgenin 
• 123941-66-2 chinenoside I 
• 210687-05-1 3β-O-benzylchlorogenin 
• 4965-78-0 (25R)-3β-O-(p-toluenesulfonyloxy)spirost-5-ene 

Downstream Products

• 1383476-47-8 laxogenin 3-O-(3,6-di-O-benzoyl-2,4-di-O-levulinoyl-β-D-glucopyranoside) 
• 1383476-51-4 laxogenin 3-O-(3,6-di-O-benzoyl-β-D-glucopyranoside) 
• 484002-10-0 laxogenin-3-yl 2,3-di-O-benzoyl-6-O-(2,3,4-tri-O-benzoyl-L-arabinopyranosyl)-D-glucopyranoside 
• 484002-14-4 laxogenin-3-yl 2,3-O-di-benzoyl-4,6-O-benzylidene-D-glucopyranoside 
• 484002-09-7 laxogenin-3-yl 2,3-di-O-benzoyl-D-glucopyranoside 
• 484002-13-3 laxogenin-3-yl 4,6-O-benzylidene-D-glucopyranoside 
• 484002-08-6 laxogenin-3-yl 2,3,4,6-tetra-O-benzoyl-D-glucopyranoside 
• 41743-71-9 (3β,5α,6β,25R)-spirostan-3,6-diol 

Relevant academic research and scientific papers

Synthesis of (22R, 25R)-3β,26-dihydroxy-5α-furostan-6-one

The synthesis of a plant growth promoter furostanol which bears the characteristic functionality of teasterone on rings A and B is described.

SAPOGENINS FROM SOLANUM MERIDENSE

In addition to chlorogenin, chlorogenone, diosgenin, and sitosterol a new sapogenin has been isolated from the green berries of Solanum meridense.Its structure was established by spectral data and chemical degradation as (25R)-3β-acetoxy-5α-spirostan-6-one.Key Word Index-Solanum meridense; Solanaceae; steroidal sapogenins; (25R)-3β-acetoxy-5α-spirostan-6-one; chlorogenone; chlorogenin; diosgenin; sitosterol.

Mimicking natural phytohormones. 26-Hydroxycholestan-22-one derivatives as plant growth promoters

26-Hydroxycholestan-22-one derivatives with oxygenated functions in the rings A and/or B were successfully synthesized from diosgenin. After the modifications of rings A and B, the spiroketal side chain was selectively opened through a Lewis acid mediated

Structure-activity relationships of saponin derivatives: A series of entry inhibitors for highly pathogenic H5N1 influenza virus

The occurrence of highly pathogenic avian influenza virus H5N1 highlights the urgent need for new classes of antiviral drugs. Theoretically, each of steps in influenza viral life cycle can be a target of antiviral therapeutics. However, up to date, no licenced entry inhibitor drug is available for H5N1 or any other influenza viruses. Our strategy for developing new anti-influenza therapeutics is to target the interaction between HA and sialic acid which is influenza viral receptor presented on host cell surface. Here, based on our previously discovered small molecule inhibitor saponin 1, intensive SAR studies around the sugar chain and aglycone were conducted. The results showed that both the chacotriosyl residue and the chlorogenin moiety of active compound 1 are important for the antiviral activity, although several subtle modifications can be made on particular positions.

Glycosyl trifluoroacetimidates. 2. Synthesis of dioscin and Xiebai saponin I

Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin I (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.

Spirostanic analogues of teasterone. Synthesis, characterisation and biological activity of laxogenin, (23S)-hydroxylaxogenin and 23-ketolaxogenin (23-oxolaxogenin)

The synthesis and characterization of the naturally occurring steroid sapogenin laxogenin and its derivatives 23-ketolaxogenin and (23S)-hydroxylaxogenin were described. Compounds reported have shown plant-growth-stimulating activity in tests and field trials. The effect consisted of an increase of the length of the treated hypocotyls compared with that of the non-treated plants. Results showed that when the same solutions were applied to the seeds of orange tree, a strong promotion of the germination was observed.

STEROIDAL SAPONINS FROM tHE RHIZOMES OF SMILAX SIEBOLDII

Six new steroidal saponins were isolated from the rhizomes of Smilax sieboldii.Their structures were determined by spectroscopic analysis and hydrolysis to be 3β-hydroxy-(25R)-5α-spirostan-6-one (laxogenin) 3-O-β-D-glucopyranosyl-(14-O-6)>-β-D-glucopyranoside, laxogenin 3-O-α-L-arabinopyranosyl-(16)-β-D-glucopyranoside, 3β,27-dihydroxy-(25S)-5α-spirostan-6-one 3-O-β-D-glucopyranosyl-(14)-O-6)>-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-3β,22ξ,26-trihydroxy-(25R)-5α-furostan-6-one 3-O-α-L-arabinopyranosyl-(16)-β-D-glucopyranoside, 26-O-β-D-glucopyranosyl-3β,22ξ,26-trihydroxy-(25R)-5α-furostan-6-one 3-O-β-D-glucopyranosyl-(14)-O-6)>-β-D-glucopyranoside and (25R)-5α-spirostan-3β-ol (tigogenin) 3-O-β-D-glucopyranosyl-(14)-O-6)>-β-D-glucopyranoside.The inhibition of cAMP phosphodiesterase by the saponins was evaluated. Key Word Index - Smilax sieboldii; Liliaceae; steroidal saponins; spirostanol glycosides; furostanol glycosides; laxogenin glycosides; tigogenin glycoside; cAMP phosphdiesterase; inhibitory activity.

A FUROSTANOL GLYCOSIDE FROM ALLIUM CHINENSE G. DON

From bulbs of Allium chinense G.DON (Liliaceae), a new furostanol glycoside, named chinenoside I (1), was isolated and the structure was established to be 26-O-β-glucopyranosyl 3β,22,26-trihydroxy-25(R)-5α-furostan-6-one 3-O-β-xylopyranosyl(1->4)-6)>-β-glucopyranoside.Keywords Allium chinense; chinenoside I; furostanol glycoside; laxogenin; Liliaceae; oligoglycoside 13C-NMR