Alisol A
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MedKoo CAT#: 464796

CAS#: 19885-10-0

Description: Alisol A is a terpenoid that has been found in A. orientale and has diverse biological activities. It inhibits the secretion of hepatitis B virus (HBV) surface antigen in HBV-infected 2.2.15 cells (IC50 = 39 µM).2 Alisol A (20 and 40 µM) induces cell cycle arrest at the G0/G1 phase and autophagy in MDA-MB-231 human breast cancer cells. It reduces hepatic steatosis and increases in plasma triglyceride, total cholesterol, LDL-C, and HDL-C levels in a mouse model of high-fat diet-induced obesity when administered at a dose of 100 mg/kg per day. Alisol A decreases blood glucose and insulin levels in intraperitoneal glucose and insulin tolerance tests, respectively, in the same model.

Chemical Structure

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Alisol A
CAS# 19885-10-0
Instruction

Theoretical Analysis

MedKoo Cat#: 464796
Name: Alisol A
CAS#: 19885-10-0
Chemical Formula: C30H50O5
Exact Mass: 490.37
Molecular Weight: 490.725
Elemental Analysis: C, 73.43; H, 10.27; O, 16.30

Price and Availability

Size Price Availability Quantity
1mg USD 450 2 Weeks
5mg USD 1250 2 Weeks
10mg USD 2150 2 Weeks
Bulk inquiry

Synonym: Alisol A; Alisol-A;

IUPAC/Chemical Name: (5R,8S,9S,10S,11S,14R)-11-hydroxy-4,4,8,10,14-pentamethyl-17-((2R,4S,5R)-4,5,6-trihydroxy-6-methylheptan-2-yl)-1,2,4,5,6,7,8,9,10,11,12,14,15,16-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one

InChi Key: HNOSJVWYGXOFRP-UNPOXIGHSA-N

InChi Code: InChI=1S/C30H50O5/c1-17(15-21(32)25(34)27(4,5)35)18-9-13-29(7)19(18)16-20(31)24-28(6)12-11-23(33)26(2,3)22(28)10-14-30(24,29)8/h17,20-22,24-25,31-32,34-35H,9-16H2,1-8H3/t17-,20+,21+,22+,24+,25-,28+,29+,30+/m1/s1

SMILES Code: C[C@H](C[C@@H]([C@H](C(O)(C)C)O)O)C1=C2C[C@H](O)[C@@]([H])([C@]3(C)[C@@]([H])(CC4)C(C(CC3)=O)(C)C)[C@@]4(C)[C@@]2(C)CC1

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMF 30.0 61.13
DMSO 30.0 61.13
Ethanol 30.0 61.13

Preparing Stock Solutions

The following data is based on the product molecular weight 490.73 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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Lu L, Lu T, Shen J, Lv X, Wei W, Wang H, Xue X. Alisol A 24-acetate protects against brain microvascular endothelial cells injury through inhibiting miR-92a-3p/tight junctions axis. Aging (Albany NY). 2021 Jun 4;13(undefined). doi: 10.18632/aging.203094. Epub ahead of print. PMID: 34086605.

2: Zhou Y, Wei W, Shen J, Lu L, Lu T, Wang H, Xue X. Alisol A 24-acetate protects oxygen-glucose deprivation-induced brain microvascular endothelial cells against apoptosis through miR-92a-3p inhibition by targeting the B-cell lymphoma-2 gene. Pharm Biol. 2021 Dec;59(1):513-524. doi: 10.1080/13880209.2021.1912117. PMID: 33905668; PMCID: PMC8081307.

3: Lou HX, Fu WC, Chen JX, Li TT, Jiang YY, Liu CH, Zhang W. Alisol A 24-acetate stimulates lipolysis in 3 T3-L1 adipocytes. BMC Complement Med Ther. 2021 Apr 22;21(1):128. doi: 10.1186/s12906-021-03296-0. PMID: 33888116; PMCID: PMC8063434.

4: Yang F, Gu L, Han Z, Wang Z. Rapid screening for natural lipase inhibitors from Alisma orientale combining high-performance thin-layer chromatography- bioautography with mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2021 Apr 30;1170:122599. doi: 10.1016/j.jchromb.2021.122599. Epub 2021 Feb 27. PMID: 33713950.

5: Jia XK, Huang JF, Huang XQ, Li XY, Huang MQ, Zhu HC, Li GP, Lan ML, Yu ZW, Xu W, Wu SS. Alismatis Rhizoma Triterpenes Alleviate High-Fat Diet-Induced Insulin Resistance in Skeletal Muscle of Mice. Evid Based Complement Alternat Med. 2021 Feb 2;2021:8857687. doi: 10.1155/2021/8857687. PMID: 33623531; PMCID: PMC7875633.

6: He L, Liu Y, Yang K, Zou Z, Fan C, Yao Z, Dai Y, Li K, Chen J, Yao X. The discovery of Q-markers of Qiliqiangxin Capsule, a traditional Chinese medicine prescription in the treatment of chronic heart failure, based on a novel strategy of multi-dimensional "radar chart" mode evaluation. Phytomedicine. 2021 Feb;82:153443. doi: 10.1016/j.phymed.2020.153443. Epub 2020 Dec 23. PMID: 33429210.

7: Wang K, Zhang B, Song D, Xi J, Hao W, Yuan J, Gao C, Cui Z, Cheng Z. Alisol A Alleviates Arterial Plaque by Activating AMPK/SIRT1 Signaling Pathway in apoE- Deficient Mice. Front Pharmacol. 2020 Nov 2;11:580073. doi: 10.3389/fphar.2020.580073. PMID: 33224034; PMCID: PMC7667245.

8: Xu X, Li L, Zhang Y, Lu X, Lin W, Wu S, Qin X, Xu R, Lin W. Hypolipidemic effect of Alisma orientale (Sam.) Juzep on gut microecology and liver transcriptome in diabetic rats. PLoS One. 2020 Oct 9;15(10):e0240616. doi: 10.1371/journal.pone.0240616. PMID: 33035272; PMCID: PMC7546448.

9: Shi Y, Wang M, Wang P, Zhang T, Yu J, Shi L, Li M, Wang H, Zhang Q, Zhao H. Alisol A is potentially therapeutic in human breast cancer cells. Oncol Rep. 2020 Sep;44(3):1266-1274. doi: 10.3892/or.2020.7654. Epub 2020 Jun 22. PMID: 32582967.

10: Tian SS, Zhao XM, Liu SS, Feng WH, Chen LM, Yan LH, Wang ZM. [Regional differences analysis of Alismatis Rhizoma based on UPLC characteristic chromatogram and determination of eight terpenoids]. Zhongguo Zhong Yao Za Zhi. 2020 Apr;45(7):1545-1557. Chinese. doi: 10.19540/j.cnki.cjcmm.20200324.201. PMID: 32489033.

11: Xu F, Chen J, Zhang Y, Wu Q, Shen Y, Gu W, Liu S, Lu C, Liao H, Bao K. Molecular insight into the mechanism of lipid regulating effect of Alisma orientalis based on ACAT. Int J Biol Macromol. 2020 May 3;158:1141-1162. doi: 10.1016/j.ijbiomac.2020.04.260. Epub ahead of print. PMID: 32376257.

12: Sun CP, Zhang J, Zhao WY, Yi J, Yan JK, Wang YL, Morisseau C, Liu ZB, Hammock BD, Ma XC. Protostane-type triterpenoids as natural soluble epoxide hydrolase inhibitors: Inhibition potentials and molecular dynamics. Bioorg Chem. 2020 Mar;96:103637. doi: 10.1016/j.bioorg.2020.103637. Epub 2020 Jan 29. PMID: 32032849; PMCID: PMC7233170.

13: Chen JX, Li HY, Li TT, Fu WC, Du X, Liu CH, Zhang W. Alisol A-24-acetate promotes glucose uptake via activation of AMPK in C2C12 myotubes. BMC Complement Med Ther. 2020 Jan 29;20(1):22. doi: 10.1186/s12906-019-2802-3. PMID: 32020870; PMCID: PMC7076831.

14: Tao Y, Jiang E, Yan J, Cai B. A biochemometrics strategy for tracing diuretic components of crude and processed Alisma orientale based on quantitative determination and pharmacological evaluation. Biomed Chromatogr. 2020 Feb;34(2):e4744. doi: 10.1002/bmc.4744. Epub 2019 Dec 29. PMID: 31725908.

15: Xu F, Chen J, Wu Q, Gu W, Shen Y, Lu C, Zhang Y, Liu S, Liao H. The antitumor molecular mechanism of Alisma orientalis with c-myc DNA: multi- spectroscopic analysis and molecular simulation. J Biomol Struct Dyn. 2020 Sep;38(14):4189-4209. doi: 10.1080/07391102.2019.1688687. Epub 2019 Nov 12. PMID: 31684825.

16: Lou C, Xu X, Chen Y, Zhao H. Alisol A Suppresses Proliferation, Migration, and Invasion in Human Breast Cancer MDA-MB-231 Cells. Molecules. 2019 Oct 10;24(20):3651. doi: 10.3390/molecules24203651. PMID: 31658635; PMCID: PMC6833085.

17: Tai YN, Weng YH, Zhang SP, Xu W, Li XY, Lin QQ, Chu KD, Wu SS. [Determination of seven ingredients of different grades Alismatis Rhizoma by QAMS method]. Zhongguo Zhong Yao Za Zhi. 2019 Jun;44(11):2292-2307. Chinese. doi: 10.19540/j.cnki.cjcmm.20190321.205. PMID: 31359656.

18: Choi E, Jang E, Lee JH. Pharmacological Activities of Alisma orientale against Nonalcoholic Fatty Liver Disease and Metabolic Syndrome: Literature Review. Evid Based Complement Alternat Med. 2019 Jun 3;2019:2943162. doi: 10.1155/2019/2943162. PMID: 31275407; PMCID: PMC6582889.

19: Tao Y, Huang S, Yan J, Cai B. Pharmacokinetic study of six triterpenoids of raw and processed Alisma plantago-aquatica in rat plasma by using ultra performance liquid chromatography-tandem mass spectrometry approach. J Chromatogr B Analyt Technol Biomed Life Sci. 2019 Aug 15;1124:323-330. doi: 10.1016/j.jchromb.2019.06.026. Epub 2019 Jun 24. PMID: 31271908.

20: Ho C, Gao Y, Zheng D, Liu Y, Shan S, Fang B, Zhao Y, Song D, Zhang Y, Li Q. Alisol A attenuates high-fat-diet-induced obesity and metabolic disorders via the AMPK/ACC/SREBP-1c pathway. J Cell Mol Med. 2019 Aug;23(8):5108-5118. doi: 10.1111/jcmm.14380. Epub 2019 May 29. PMID: 31144451; PMCID: PMC6653754.