Ligustilide

Last updated
Ligustilide
Ligustilide.svg
Names
Other names
3-Butylidene-4,5-dihydrophthalide
Identifiers
3D model (JSmol)
ECHA InfoCard 100.237.128 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
  • O=C1OC(=CCCC)C2=C1C=CCC2
Properties
C12H14O2
Molar mass 190.242 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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]

Contents

Herbal extract

Ligustilide is a volatile compound, found in the essential oil of various herb roots. [3] 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%. [4] In an other report, ligustilide was not mentioned as a component in hydrodistilled essential oil of Angelica archangelica root from Serbia. [5] When dried whole root is used, as in TCM, the pharmacological effect may be ascribed to a range of components, including polysaccharides. [6]

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. [7] A variety of in vitro effects of ligustilide have been reported, including antiinflammatory and neuroprotective effects. [8] However, because of the chemical instability of ligustilide, the relevance of these studies to any effects in humans is uncertain. [9]

Related Research Articles

<i>Angelica</i> Genus of flowering plants

Angelica is a genus of about 90 species of tall biennial and perennial herbs in the family Apiaceae, native to temperate and subarctic regions of the Northern Hemisphere, reaching as far north as Iceland, Lapland, and Greenland. They grow to 1–3 m tall, with large bipinnate leaves and large compound umbels of white or greenish-white flowers. Found mainly in China, its main use was for medicine. It shows variations in fruit anatomy, leaf morphology, and subterranean structures. The genes are extremely polymorphic.

<i>Angelica archangelica</i> Species of plant

Angelica archangelica, commonly known as angelica, garden angelica, wild celery, and Norwegian angelica, is a biennial plant from the family Apiaceae, a subspecies of which is cultivated for its sweetly scented edible stems and roots. Like several other species in Apiaceae, its appearance is similar to several poisonous species, and should not be consumed unless it has been identified with absolute certainty. Synonyms include Archangelica officinalisHoffm. and Angelica officinalisMoench.

<i>Angelica sinensis</i> Species of flowering plant

Angelica sinensis, commonly known as dong quai or female ginseng, is a herb belonging to the family Apiaceae, indigenous to China. Angelica sinensis grows in cool high altitude mountains in East Asia. The yellowish brown root of the plant is harvested in the fall and is a well-known Chinese medicine which has been used for thousands of years.

<span class="mw-page-title-main">Anethole</span> Chemical compound

Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of the aromatic compound allylbenzene and occurs widely in plants in essential oils. It is in the class of phenylpropanoid organic compounds. It contributes a large component of the odor and flavor of anise and fennel, anise myrtle (Myrtaceae), liquorice (Fabaceae), magnolia blossoms, and star anise (Schisandraceae). Closely related to anethole is its isomer estragole, which is abundant in tarragon (Asteraceae) and basil (Lamiaceae), and has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water; this is called the ouzo effect.

<span class="mw-page-title-main">Imperatorin</span> Chemical compound

Imperatorin is a furocoumarin and a phytochemical that has been isolated from Urena lobata L. (Malvaceae), Angelica archangelica, Angelica dahurica, Glehnia littoralis, Saposhnikovia divaricata, Cnidium monnieri, Incarvillea younghusbandii, and Zanthoxylum americanum mill. It is biosynthesized from umbelliferone, a coumarin derivative.

<span class="mw-page-title-main">Sodium ferulate</span> Chemical compound

Sodium ferulate, the sodium salt of ferulic acid, is a compound used in traditional Chinese medicine thought to be useful for treatment of cardiovascular and cerebrovascular diseases and to prevent thrombosis, although there is no high-quality clinical evidence for such effects. It is found in the root of Angelica sinensis. As of 2005, it was under preliminary clinical research in China. Ferulic acid can also be extracted from the root of the Chinese herb Ligusticum chuanxiong.

<span class="mw-page-title-main">Caryophyllene</span> Chemical compound

Caryophyllene, more formally (−)-β-caryophyllene,(BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, copaiba, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

<i>Salvia miltiorrhiza</i> Species of flowering plant

Salvia miltiorrhiza, also known as red sage, redroot sage, Chinese sage, or danshen, is a perennial plant in the genus Salvia, highly valued for its roots in traditional Chinese medicine. Native to China and Japan, it grows at 90 to 1,200 m elevation, preferring grassy places in forests, hillsides, and along stream banks. The specific epithet miltiorrhiza means "red ochre root".

<span class="mw-page-title-main">Dit da jow</span>

Dit da jow is a common Chinese liniment used as traditional medicine in the belief it can reduce the pain from external injuries.

<span class="mw-page-title-main">Angelic acid</span> Chemical compound

Angelic acid is a monocarboxylic unsaturated organic acid, mostly found in the plants of the family Apiaceae. It is a volatile solid with a biting taste and pungent sour odor. It is the cis isomer of 2-methyl-2-butenoic acid, which easily converts to the trans isomer, tiglic acid, upon heating or reaction with inorganic acids. The reverse transformation occurs much less readily. The salts and esters of angelic acid are called angelates. Angelic acid esters are the active components of herbal medicine used against a wide range of various health disturbances including pains, fever, gout, heartburn, etc.

<span class="mw-page-title-main">Higenamine</span> Chemical compound

Higenamine (norcoclaurine) is a chemical compound found in a variety of plants including Nandina domestica (fruit), Aconitum carmichaelii (root), Asarum heterotropioides, Galium divaricatum, Annona squamosa, and Nelumbo nucifera.

<span class="mw-page-title-main">Osthol</span> Chemical compound

Osthol, or osthole, is a chemical compound which is a derivative of coumarin. It is found in a variety of plants including Cnidium monnieri, Angelica archangelica and Angelica pubescens.

Cāng zhú, also known as black atractylodes rhizome or Rhizoma Atractylodes, is a Chinese herbal medicine. It is the dried rhizome of Atractylodes lancea (Thunb.) DC., synonyms Atractylodes chinensis (DC.) Koidz, and Atractylodes japonica Koidz. The medicine is distinguished from bái zhú, which is typically cultivated, whereas cāng zhú more often tends to be collected from the wild. It is believed that the distinction between cāng zhú and bái zhú emerged in relatively modern times; a single drug "zhú" described in the Shen nong ben cao jing probably included many Atractylodes species.

<span class="mw-page-title-main">Butylphthalide</span> Chemical compound

Butylphthalide is one of the chemical constituents in celery oil, along with sedanolide, which is primarily responsible for the aroma and taste of celery.

A bioactive compound is a compound that has an effect on a living organism, tissue or cell, usually demonstrated by basic research in vitro or in vivo in the laboratory. While dietary nutrients are essential to life, bioactive compounds have not been proved to be essential – as the body can function without them – or because their actions are obscured by nutrients fulfilling the function.

α-Cadinol Chemical compound

α-Cadinol or 10α-hydroxy-4-cadinene is an organic compound, a sesquiterpenoid alcohol.

<i>Angelica acutiloba</i> Species of flowering plant

Angelica acutiloba is a perennial herb from the family Apiaceae or Umbelliferous. It is predominately in Japan and perhaps endemic (unique). It is now distributed widely and cultivated in Jilin, China, Korea, Taiwan and Indonesia.

Alpinia nigra is a medium-sized herb belonging to the ginger family. The rhizome is well known in many Asian cultures as a medicinal and culinary item. In many Asian tribal communities it is a part of the diet along with rice.

<span class="mw-page-title-main">ASP-7663</span> Chemical compound

ASP-7663 is a chemical compound which acts as a potent, selective activator of the TRPA1 channel. It has protective effects on cardiac tissue, and is used for research into the function of the TRPA1 receptor.

References

  1. "Ligustilide". Human Metabolome Database.
  2. 1 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.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  3. http://www.entomoljournal.com/archives/2017/vol5issue4/PartH/5-3-275-671.pdf
  4. "Quality evaluation of Angelicae acutilobae radix: individual differences and localization of (Z)-ligustilide in Angelica acutiloba root" PMID 32737689 PMC8924091
  5. www.researchgate.net/publication/313818355_Chemical_Composition_and_Antibacterial_Activity_of_Angelica_archangelica_Root_Essential_Oil
  6. "The structures and biological functions of polysaccharides from traditional Chinese herbs" PMID 31030757 PMC7102684
  7. 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.
  8. 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.
  9. 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.