Ligustilide

Ligustilide

Names
Other names 3-Butylidene-4,5-dihydrophthalide
Identifiers
CAS Number	4431-01-0
3D model (JSmol)	Interactive image
ChemSpider	461606
ECHA InfoCard	100.237.128
EC Number	809-243-4
PubChem CID	529865
InChI InChI=1S/C12H14O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h5,7-8H,2-4,6H2,1H3 Key: IQVQXVFMNOFTMU-UHFFFAOYSA-N
SMILES O=C1OC(=CCCC)C2=C1C=CCC2
Properties
Chemical formula	C12H14O2
Molar mass	190.242 g·mol−1
Hazards
GHS labelling:
Pictograms
Signal word	Danger
Hazard statements	H301
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Ligustilide is a natural chemical compound of the dihydrophthalide class. Ligustilide is found in the highest concentration in wild celeries (Apium graveolens). ^{[1] [2]} It has also been found in Angelica sinensis and a variety of other plants including Todaroa montana . ^[2]

Potential pharmacology

Because of the traditional use of Angelica sinesis in herbal medicine, particularly traditional Chinese medicine where it is known as dong quai, there has been interest in identifying chemical compounds responsible for its putative pharmacological effects. Ligustilide is typically identified as the principal bioactive component. ^[3] A variety of in vitro effects of ligustilide have been reported, including antiinflammatory and neuroprotective effects. ^[4] However, because of the chemical instability of ligustilide, the relevance of these studies to any effects in humans is uncertain. ^[5]

Herbal extract

Ligustilide is a volatile compound, found in the essential oil of various herb roots. ^[6] The oil is obtained by distillation or supercritical CO₂ extraction of the dried root. In one report, total (Z)-ligustilide content in Angelica acutiloba root samples ranged from 0.08% to 0.22%. ^[7] In an other report, ligustilide was not mentioned as a component in hydrodistilled essential oil of Angelica archangelica root from Serbia. ^[8] When dried whole root is used, as in traditional Chinese medicine, the pharmacological effect may be ascribed to a range of components, including polysaccharides. ^[9]

References

1. "Ligustilide". Human Metabolome Database.
2. Gijbels, M.J.M., Fischer, F.C., Scheffer, J.J.C.; et al. (1983). "Phthalides in roots of Anethum graveolens and Todaroa montana". Scientia Pharmaceutica. 51 (4): 414–417.
3. Yang, F.; Lin, Z. W.; Huang, T. Y.; Chen, T. T.; Cui, J.; Li, M. Y.; Hua, Y. Q. (2019). "Ligustilide, a major bioactive component of Angelica sinensis, promotes bone formation via the GPR30/EGFR pathway". Scientific Reports. 9 (1): 6991. Bibcode:2019NatSR...9.6991Y. doi:10.1038/s41598-019-43518-7. PMC   6502875 . PMID   31061445.
4. Xie, Qingxuan; Zhang, Linlin; Xie, Long; Zheng, Yu; Liu, Kai; Tang, Hailong; Liao, Yanmei; Li, Xiaofang (2020). "Z-ligustilide: A review of its pharmacokinetics and pharmacology". Phytotherapy Research. 34 (8): 1966–1991. doi:10.1002/ptr.6662. PMID   32135035. S2CID   212567563.
5. Duric, Kemal; Liu, Yang; Chen, Shao-Nong; Lankin, David C.; Nikolic, Dejan; McAlpine, James B.; Friesen, J. Brent; Pauli, Guido F. (2019). "Studying Mass Balance and the Stability of (Z)-Ligustilide from Angelica sinensis Helps to Bridge a Botanical Instability–Bioactivity Chasm". Journal of Natural Products. 82 (9): 2400–2408. doi:10.1021/acs.jnatprod.8b00962. PMC   6930006 . PMID   31478376.
6. Mahmoud Osanloo, Amir Amani, Hassan Sereshti, Mansoureh Shayeghi, and Mohammad Mehdi Sedaghat (2017). "Extraction and chemical composition essential oil of Kelussia odoratissima and comparison its larvicidal activity with Z-ligustilide (Major Constituent) against Anopheles stephensi" (PDF). Journal of Entomology and Zoology Studies. 5 (4): 611–616.
7. Kudo, Y.; Ando, H.; Sasaki, Y. (2021). "Quality evaluation of Angelicae acutilobae radix: Individual differences and localization of (Z)-ligustilide in Angelica acutiloba root". Journal of Natural Medicines. 75 (1): 1–10. doi:10.1007/s11418-020-01438-1. PMC   8924091 . PMID   32737689.
8. Aćimović, Milica G.; Pavlović, Snežana Đ.; Varga, Ana O.; Filipović, Vladimir M.; Cvetković, Mirjana T.; Stanković, Jovana M.; Čabarkapa, Ivana S. (2017). "Chemical Composition and Antibacterial Activity of Angelica archangelica Root Essential Oil". Natural Product Communications. 12 (2): 205–206. doi:10.1177/1934578X1701200216. PMID   30428212.
9. Zeng, P.; Li, J.; Chen, Y.; Zhang, L. (2019). "The structures and biological functions of polysaccharides from traditional Chinese herbs". Progress in Molecular Biology and Translational Science. 163: 423–444. doi:10.1016/bs.pmbts.2019.03.003. ISBN   978-0-12-817740-2. PMC   7102684 . PMID   31030757.