What molecule am I?
Chebulinic acid1 is a natural product in the family of ellagitannins, or hydrolyzable tannins, which consist of polyphenols surrounding a glucose center. The compound is found in plants such as Euphoria longana and Terminalia chebula (both tropical Asian fruit trees) and T. macroptera (a central African flowering tree).
Chebulinic acid has been known since 1911, when German scientist W. Richter described it under the name 鈥渆utannin鈥�. In 2006, Hongxi Xu and co-workers at the Hong Kong Jockey Club Institute of Chinese Medicine reported the of it and the similar molecule chebulagic acid2.
Hydrolyzable tannins from the fruits and leaves of plants that contain chebulinic acid are used in traditional Chinese medicine. Consequently, the acid has been widely studied for its pharmacological properties.
In 2020, Sujit Basu and collaborators at Ohio State University (Columbus) and KPC Medical College (Kolkata, India) described how chebulinic acid can help reduce the pain of rheumatoid arthritis (RA). They noted that vascular endothelial growth factor-A (VEGF) induces angiogenesis in RA patients and that then-current anti-VEGF agents cause hypertension and other cardiovascular complications. They investigated reports that chebulinic acid can inhibit VEGF activity and found that it is a for treating RA.
Two years later, Bhawna Chopra and colleagues at Guru Gobind Singh College of Pharmacy (Haryana, India) of chebulinic acid and related ellagitannins. They examined biological properties, including antitumor activity and antiatherogenic, antifibrotic, anti-inflammatory, antiulcer, antioxidant, hepatoprotective, antidiabetic, and antiviral effects attributable to ellagitannins and recommended further studies in these pathology areas.
Also in 2022, Suman Tapryal and fellow investigators at the Central University of Rajasthan (Ajmer) and the National Institute of Virology (Pune, both in India) reported other benefits of chebulinic acid. Noting that the acid had showed the ability to inhibit herpes simplex virus-2 infections, they used in vitro and in silico methods to determine whether it is active against the dengue and chikungunya viruses. Their results indicated that chebulinic acid was ineffective against chikungunya but showed in the early stage of its infection cycle.
1. SciFinder: 7,11-methanopyrano[4,3,2-kl][2,5,8]benzotrioxacyclotridecin-4-acetic acid, 2,3,3a,4,5,7,8,10,11,13-decahydro-3,15,16-trihydroxy-2,5,13-trioxo-10,17-bis[(3,4,5-trihydroxybenzoyl)oxy]-8-[[(3,4,5-trihydroxybenzoyl)oxy]methyl]-, (3S,3aS,4S,7R,8R,10S,11R,17S)-.
2. CAS Reg. No. 23094-71-5.
Chebulinic acid听hazard information*
| Hazard class** | GHS code and hazard statement | |
|---|---|---|
| Acute toxicity, oral, category 4 | H302鈥擧armful if swallowed |  |
| Acute toxicity, dermal, category 4 | H312鈥擧armful in contact with skin | |
Serious eye damage/eye irritation, category 2A | H319鈥擟auses serious eye irritation | |
Acute toxicity, inhalation, category 4 | H332鈥擧armful if inhaled | |
| Long-term (chronic) aquatic hazard, category 1 | H410鈥擵ery toxic to aquatic life with long lasting effects |  |
*Compilation of multiple safety data sheets. Some SDS report 鈥渘ot a hazardous substance or mixture鈥�.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals.听.
Molecule of the Future
Sorangiolide A1 is one of two metabolites2 isolated in 1995 by Gerhard H枚fle and co-workers at the German Research Center for Biotechnology3 (Braunschweig) 4. The authors reported that the sorangiolides showed some antibiotic activity against Gram-positive bacteria, including Staphylococcus aureus.
In October 2023, Rajib Kumar Goswami and colleagues at the Indian Association of Cultivation Science (Kolkata) reported a . The researchers used several key techniques in their synthetic sequence, including a Julia鈥揔ocienski olefination. They plan to use a similar process to make sorangiolide B, as well as structurally simpler analogues of the sorangiolides, to be used in medical research.
1. CAS Reg. No. 164177-51-9.
2. The other is sorangiolide B, CAS Reg. No. 164177-52-0.
3. Now named the Helmholtz Center for Infection Research.
4. S. cellulosum is a type of myxobacterium, a group of 鈥渟lime鈥� or 鈥済liding鈥� bacteria.
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Chebulinic acid fast facts
| CAS Reg. No. | 18942-26-2 |
| Empirical formula | C41H32O27 |
| Molar mass | 956.68 g/mol |
| Appearance | White powder |
| Melting point | 234 掳C |
| Water solubility | Slight |
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