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MedKoo Cat#: 412858 | Name: Toosendanin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Toosendanin is a triterpenoid extracted from Melia toosendan Sieb et Zucc, which was used as a digestive tract-parasiticide and agricultural insecticide in ancient China. It is from the bark of Melia toosendan.

Chemical Structure

Toosendanin
CAS#58812-37-6

Theoretical Analysis

MedKoo Cat#: 412858

Name: Toosendanin

CAS#: 58812-37-6

Chemical Formula: C30H38O11

Exact Mass: 574.2414

Molecular Weight: 574.62

Elemental Analysis: C, 62.71; H, 6.67; O, 30.63

Price and Availability

Size Price Availability Quantity
100mg USD 1,355.00 2 Weeks
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Related CAS #
No Data
Synonym
Toosendanin; BRN1674886; BRN-1674886 BRN 1674886
IUPAC/Chemical Name
(1S,2aR,3aS,3bS,4R,5aR,7R,9S,9aS,9bR,11R,11aR,14R)-1-(furan-3-yl)-4,9,14-trihydroxy-3b,6,11a-trimethyl-10-oxotetradecahydro-1H-6,9a-(methanooxymethano)naphtho[1',2':6,7]indeno[1,7a-b]oxirene-7,11-diyl diacetate
InChi Key
NAHTXVIXCMUDLF-SLWGVJJJSA-N
InChi Code
InChI=1S/C30H38O11/c1-13(31)39-20-10-19(34)29-12-38-25(36)26(20,3)17(29)9-18(33)28(5)23(29)22(35)24(40-14(2)32)27(4)16(15-6-7-37-11-15)8-21-30(27,28)41-21/h6-7,11,16-21,23-25,33-34,36H,8-10,12H2,1-5H3/t16-,17-,18+,19-,20+,21+,23-,24-,25+,26?,27+,28+,29+,30+/m0/s1
SMILES Code
CC(O[C@@H]1C[C@@H]([C@@]23CO[C@H](C1([C@@H]2C[C@H]([C@@]4([C@@H]3C([C@@H]([C@]5([C@H](c6ccoc6)C[C@H]7O[C@@]457)C)OC(C)=O)=O)C)O)C)O)O)=O
Appearance
Solid powder
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
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 574.62 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.

Recalculate based on batch purity %
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: Mao X, Wang C, Tang H, Liu X, Wei C, Yin F, Fu T, Fang Y, Yu K, Zhang Z, Wu C, Liu H, Le A. Toosendanin alleviates acute lung injury by reducing pulmonary vascular barrier dysfunction mediated by endoplasmic reticulum stress through mTOR. Phytomedicine. 2024 Nov 24;136:156277. doi: 10.1016/j.phymed.2024.156277. Epub ahead of print. PMID: 39615214. 2: Du X, Tao Q, Fan S, Ren J, Dong Y, Li G, He S, Cao X, Zhu Y. Traditional Mongolian medicine Wu-Lan thirteen-flavor decoction protects rat from hypertension-induced renal injury via aryl hydrocarbon receptor-mediated pathway. Drug Dev Ind Pharm. 2024 Nov;50(11):952-967. doi: 10.1080/03639045.2024.2432596. Epub 2024 Nov 26. PMID: 39565140. 3: Li S, Xiong Q, Shen Y, Lin J, Zhang L, Wu Y, Jin J, Luan X. Toosendanin: upgrade of an old agent in cancer treatment. Chin J Nat Med. 2024 Oct;22(10):887-899. doi: 10.1016/S1875-5364(24)60693-X. PMID: 39428181. 4: Zhi XY, Liu Y, Liang J, Yuan X, Shi HC, Duan JQ, He MT, Wang Y, Cao H, Yang C. Novel Pesticide Candidates Inspired by Natural Neolignan: Preparation and Insecticidal Investigation of Honokiol Analogs Containing 2-Aminobenzoxazole- Fused Core Scaffold. J Agric Food Chem. 2024 Sep 25;72(38):20805-20815. doi: 10.1021/acs.jafc.4c03080. Epub 2024 Sep 12. PMID: 39263791. 5: Lu X, Yu L, Zheng J, Li A, Li J, Lou H, Zhang W, Guo H, Wang Y, Li X, Gao Y, Fan X, Borlak J. miR-106b-5p protects against drug-induced liver injury by targeting vimentin to stimulate liver regeneration. MedComm (2020). 2024 Aug 21;5(9):e692. doi: 10.1002/mco2.692. PMID: 39170945; PMCID: PMC11337467. 6: Hao M, Jiang L, Lv M, Ding H, Zhou Y, Xu H. Plant natural product-based pesticides in crop protection: semi-synthesis, mono-crystal structures and agrochemical activities of osthole ester derivatives, and study of their toxicology against Tetranychus cinnabarinus (Boisduval). Pest Manag Sci. 2024 Dec;80(12):6356-6365. doi: 10.1002/ps.8364. Epub 2024 Aug 8. PMID: 39118390. 7: Wang J, Qiu Y, Yang L, Wang J, He J, Tang C, Yang Z, Hong W, Yang B, He Q, Weng Q. Preserving mitochondrial homeostasis protects against drug-induced liver injury via inducing OPTN (optineurin)-dependent Mitophagy. Autophagy. 2024 Dec;20(12):2677-2696. doi: 10.1080/15548627.2024.2384348. Epub 2024 Aug 4. PMID: 39099169; PMCID: PMC11587843. 8: Guo Y, Han M, Zhong Y, Li X, Hu S, Yang R. Discovery of Novel (+)-Nootkatone- Based Amine Derivatives as Potential Insecticide Candidates. J Agric Food Chem. 2024 Aug 7;72(31):17240-17247. doi: 10.1021/acs.jafc.4c02697. Epub 2024 Jun 24. PMID: 38912665. 9: Liu F, Wang G, Zhao L, Chen G, Dong L, Li Q, Zhu D. Toosendanin Induces Lung Squamous Cell Carcinoma Cell Apoptosis and Inhibits Tumor Progression via the BNIP3/AMPK Signaling Pathway. Adv Biol (Weinh). 2024 Sep;8(9):e2300610. doi: 10.1002/adbi.202300610. Epub 2024 May 21. PMID: 38773915. 10: Yang L, Yuan Y, Xiong L, Zhao Q, Yang M, Suo X, Hao Z. Study on the effects of toosendanin against Eimeria tenella and its impact on the apoptosis of cecal cells in chicks. Vet Parasitol. 2024 Jul;329:110194. doi: 10.1016/j.vetpar.2024.110194. Epub 2024 May 3. PMID: 38749123. 11: Luo L, Lin J, Chen S, Ni J, Peng H, Shen F, Huang Z. Rosmarinic acid alleviates toosendanin-induced liver injury through restoration of autophagic flux and lysosomal function by activating JAK2/STAT3/CTSC pathway. J Ethnopharmacol. 2024 Aug 10;330:118196. doi: 10.1016/j.jep.2024.118196. Epub 2024 Apr 15. PMID: 38631488. 12: Zhang T, Luo X, Jing L, Mo C, Guo H, Yang S, Wang Y, Zhao K, Lai Y, Liu Y. Toosendanin inhibits T-cell proliferation through the P38 MAPK signalling pathway. Eur J Pharmacol. 2024 Jun 15;973:176562. doi: 10.1016/j.ejphar.2024.176562. Epub 2024 Apr 6. PMID: 38588767. 13: Chen S, Ni J, Luo L, Lin J, Peng H, Shen F, Huang Z. Toosendanin induces hepatotoxicity via disrupting LXRα/Lipin1/SREBP1 mediated lipid metabolism. Food Chem Toxicol. 2024 May;187:114631. doi: 10.1016/j.fct.2024.114631. Epub 2024 Apr 1. PMID: 38570025. 14: Luo L, Ni J, Zhang J, Lin J, Chen S, Shen F, Huang Z. Toosendanin induces hepatotoxicity by restraining autophagy and lysosomal function through inhibiting STAT3/CTSC axis. Toxicol Lett. 2024 Apr;394:102-113. doi: 10.1016/j.toxlet.2024.03.002. Epub 2024 Mar 7. PMID: 38460807. 15: Pak SW, Lee IS, Kim WI, Lee SJ, Yang YG, Shin IS, Kim T. Melia azedarach L. reduces pulmonary inflammation and mucus hypersecretion on a murine model of ovalbumin exposed asthma. J Ethnopharmacol. 2024 Feb 10;320:117426. doi: 10.1016/j.jep.2023.117426. Epub 2023 Nov 17. PMID: 37979816. 16: Wu Y, Chen L, Feng C, Wang T, He S, Zheng D, Lin L. Antitumor effect of toosendanin on oral squamous cell carcinoma via suppression of p-STAT3. BMC Oral Health. 2023 Nov 9;23(1):846. doi: 10.1186/s12903-023-03602-x. PMID: 37946196; PMCID: PMC10634166. 17: Shu B, Lin Y, Huang Y, Liu L, Cai X, Lin J, Zhang J. Characterization and transcriptomic analyses of the toxicity induced by toosendanin in Spodoptera frugipreda. Gene. 2024 Jan 30;893:147928. doi: 10.1016/j.gene.2023.147928. Epub 2023 Oct 28. PMID: 37898452. 18: Kim SC, Gu DR, Yang H, Lee SJ, Ryuk JA, Ha H. Isolation and Characterization of an Anti-Osteoporotic Compound from Melia toosendan Fructus. Pharmaceutics. 2023 Oct 13;15(10):2454. doi: 10.3390/pharmaceutics15102454. PMID: 37896213; PMCID: PMC10609846. 19: Hu M, Xu M, Chen Y, Ye Z, Zhu S, Cai J, Zhang M, Zhang C, Huang R, Ye Q, Ao H. Therapeutic potential of toosendanin: Novel applications of an old ascaris repellent as a drug candidate. Biomed Pharmacother. 2023 Nov;167:115541. doi: 10.1016/j.biopha.2023.115541. Epub 2023 Sep 20. PMID: 37738795. 20: Lin Y, Huang Y, Liu J, Liu L, Cai X, Lin J, Shu B. Characterization of the physiological, histopathological, and gene expression alterations in Spodoptera frugiperda larval midguts affected by toosendanin exposure. Pestic Biochem Physiol. 2023 Sep;195:105537. doi: 10.1016/j.pestbp.2023.105537. Epub 2023 Jul 15. PMID: 37666609.

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