Helvolic Acid
1. Core Information
English Name: Helvolic acid
Chinese Name: Helvolic acid (Yan Qumei Suan)
CAS No.: 29400-42-8
Molecular Formula: C33H44O8
Molecular Weight: 568.7 g/mol
SMILE:CC1C2C(C(=O)C3(C(C2(C=CC1=O)C)CCC4C3(CC(C4=C(CCC=C(C)C)C(=O)O)OC(=O)C)C)C)OC(=O)C
2. International Nomenclature & Identifiers
2.1 IUPAC Name
(2Z)-2-[(4S,5S,6S,8S,9S,10R,13R,14S,16S)-6,16-diacetyloxy-4,8,10,14-tetramethyl-3,7-dioxo-5,6,9,11,12,13,15,16-octahydro-4H-cyclopenta[a]phenanthren-17-ylidene]-6-methylhept-5-enoic acid
2.2 InChI
InChI=1S/C33H44O8/c1-17(2)10-9-11-21(30(38)39)26-22-12-13-25-31(6)15-14-23(36)18(3)27(31)28(41-20(5)35)29(37)33(25,8)32(22,7)16-24(26)40-19(4)34/h10,14-15,18,22,24-25,27-28H,9,11-13,16H2,1-8H3,(H,38,39)/b26-21-/t18-,22+,24+,25+,27-,28+,31-,32+,33-/m1/s1
2.3 InChlKey
MDFZYGLOIJNNRM-OAJDADRGSA-N
2.4 Canonical SMILES
CC1C2C(C(=O)C3(C(C2(C=CC1=O)C)CCC4C3(CC(C4=C(CCC=C(C)C)C(=O)O)OC(=O)C)C)C)OC(=O)C
2.5 Isomeric SMILES
C[C@H]1[C@@H]2[C@@H](C(=O)[C@]3([C@H]([C@]2(C=CC1=O)C)CC[C@@H]\4[C@@]3(C[C@@H](/C4=C(/CCC=C(C)C)\C(=O)O)OC(=O)C)C)C)OC(=O)C
3. Spectroscopic Data
3.1 13C Nuclear Magnetic Resonance (13C NMR)
3.2 1H Nuclear Magnetic Resonance (1H NMR)
4. Research Progress on Helvolic Acid
Helvolic acid is a tetracyclic triterpenoid. It crystallizes as needles from methanol, has a melting point of 215 °C, and exhibits a specific rotation of −121° (c=1, chloroform). The compound is nearly insoluble in water, slightly soluble in petroleum ether, methanol, and ethanol, and readily soluble in chloroform, acetone, ethyl acetate, pyridine, and glacial acetic acid. Initially isolated from the fermentation broth of Aspergillus fumigatus and related fungi, Helvolic acid displays broad-spectrum antimicrobial activity, underscoring its therapeutic potential.
4.1 Chemistry and Source
The distinctive tetracyclic triterpenoid scaffold underpins Helvolic acid’s antimicrobial potency. It is typically obtained from fungal cultures—especially Aspergillus fumigatus—and serves as a natural antibiotic. Its stability profile and solvent compatibility facilitate laboratory studies and scale-up.
4.2 Antimicrobial Activity & Applications
Helvolic acid demonstrates notable activity against diverse bacteria and fungi, including strong inhibition of Staphylococcus aureus. Evidence suggests potential efficacy against drug-resistant strains, making it relevant for confronting antimicrobial resistance. In practice, Helvolic acid derivatives have been used as leads for anti-infective agents. Combination studies with existing antibiotics reveal synergistic effects, reducing required antibiotic doses and mitigating associated side effects.
4.3 Biosynthesis & Engineering
Advances in biotechnology have illuminated the biosynthetic pathway of Helvolic acid. Using an Aspergillus oryzae heterologous expression system, researchers mapped the route, paving the way for combinatorial biosynthesis of more potent fusidane-type antibiotics. Enzymology and gene-editing studies have identified key catalysts such as the short-chain dehydrogenase HelC, highlighting that C-3 carbonyl substitutions enhance activity relative to β-C3 hydroxyl substitutions. These insights inform future engineering of next-generation fusidane antibiotics.
4.4 Future Outlook & Challenges
Despite its promise, several hurdles remain. Improving yields and purity, expanding therapeutic indications, and integrating Helvolic acid into broader antibiotic pipelines are active areas of investigation. With antimicrobial resistance escalating worldwide, molecules such as Helvolic acid—capable of tackling resistant strains—will attract increasing attention and investment.
In summary, Helvolic acid is a highly promising natural product with compelling antimicrobial profiles and increasingly well-understood biosynthesis. Continued advances in biotechnology and pharmaceutical science are expected to unlock its full value across more therapeutic contexts.
References
[1] http://www.kehuaai.com/productInfo/174958
[2] https://baike.baidu.com/item/%E7%83%9F%E6%9B%B2%E9%9C%89%E9%85%B8/8069498
[3] Infection Frontline—ISHAM-Asia 2024 briefing on invasive fungal disease epidemiology and treatment advances.
[4] Qin Ling, Guan Jiafa, Li Bogang, et al. New applications of Helvolic acid in developing anti–drug-resistant agents. 28 April 2010.
