Chebulinic acid

February 19, 2024
I’m a natural product that promises to ameliorate many medical conditions.
What molecule am I?
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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 “eutannin”. In 2006, Hongxi Xu and co-workers at the Hong Kong Jockey Club Institute of Chinese Medicine reported the preparative isolation 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 safe, potent antiangiogenic agent for treating RA.

Two years later, Bhawna Chopra and colleagues at Guru Gobind Singh College of Pharmacy (Haryana, India) reviewed the pharmacological properties 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 strong inhibition of dengue 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 hazard information*

Hazard class**GHS code and hazard statement
Acute toxicity, oral, category 4H302—Harmful if swallowedChemical Safety Warning
Acute toxicity, dermal, category 4H312—Harmful in contact with skinChemical Safety Warning

Serious eye damage/eye irritation, category 2A

H319—Causes serious eye irritationChemical Safety Warning

Acute toxicity, inhalation, category 4

H332—Harmful if inhaledChemical Safety Warning
Long-term (chronic) aquatic hazard, category 1H410—Very toxic to aquatic life with long lasting effectsChemical Safety Warning

*Compilation of multiple safety data sheets. Some SDS report “not a hazardous substance or mixture”.
**Globally Harmonized System (GHS) of Classification and Labeling of Chemicals. Explanation of pictograms.

Molecule of the Future

Sorangiolide A1 is one of two metabolites2 isolated in 1995 by Gerhard Höfle and co-workers at the German Research Center for Biotechnology3 (Braunschweig) from the bacterium Sorangium cellulosum4. The authors reported that the sorangiolides showed some antibiotic activity against Gram-positive bacteria, including Staphylococcus aureus.

Molecule of the Future

In October 2023, Rajib Kumar Goswami and colleagues at the Indian Association of Cultivation Science (Kolkata) reported a total synthesis of sorangiolide A. The researchers used several key techniques in their synthetic sequence, including a Julia–Kocienski 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 “slime” or “gliding” bacteria.

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Chebulinic acid fast facts

CAS Reg. No.18942-26-2
Empirical formulaC41H32O27
Molar mass956.68 g/mol
AppearanceWhite powder
Melting point234 °C
Water solubilitySlight
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