Justicidin A

Last updated
Justicidin A
Justicidin A.svg
Names
Preferred IUPAC name
9-(2H-1,3-Benzodioxol-5-yl)-4,6,7-trimethoxynaptho[2,3-c]furan-1(3H)-one
Other names
Diphyllin methyl ether
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1S/C22H18O7/c1-24-16-7-12-13(8-17(16)25-2)21(26-3)14-9-27-22(23)20(14)19(12)11-4-5-15-18(6-11)29-10-28-15/h4-8H,9-10H2,1-3H3
    Key: ANFSXHKDCKWWDB-UHFFFAOYSA-N
  • COC1=C(C=C2C(=C1)C(=C3C(=C2OC)COC3=O)C4=CC5=C(C=C4)OCO5)OC
Properties
C22H18O7
Molar mass 394.379 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Justicidin A is an organic compound isolated from Justicia procumbens . It is classified as a lignan. [1] [2] The compound may possess cytotoxic effects. [3]

Related Research Articles

Cytotoxicity is the quality of being toxic to cells. Examples of toxic agents are toxic metals, toxic chemicals, microbe neurotoxins, radiation particles and even specific neurotransmitters when the system is out of balance. Also some types of drugs, e.g alcohol, and some venom, e.g. from the puff adder or brown recluse spider are toxic to cells.

The lignans are a large group of low molecular weight polyphenols found in plants, particularly seeds, whole grains, and vegetables. The name derives from the Latin word for "wood". Lignans are precursors to phytoestrogens. They may play a role as antifeedants in the defense of seeds and plants against herbivores.

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

Secoisolariciresinol is an organic compound. It is classified as a lignan, i.e., a type of phenylpropanoid. It is present in some cereals, such as rye, and together with matairesinol has attracted much attention for its beneficial nutritional effects.

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

Podophyllotoxin (PPT) is the active ingredient in Podofilox, a medical cream used to treat genital warts and molluscum contagiosum. It is not recommended for HPV infections without external warts. It can be applied either by a healthcare provider or the patient themselves.

<span class="mw-page-title-main">Complex-toothed flying squirrel</span> Species of rodent

The complex-toothed flying squirrel occurs in the southern Chinese provinces Hubei, Hunan, Guizhou, Sichuan, and Yunnan. The common name refers to the teeth, which differ from those of other species of flying squirrels.

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

Honokiol is a lignan isolated from the bark, seed cones, and leaves of trees belonging to the genus Magnolia. It has been identified as one of the chemical compounds in some traditional eastern herbal medicines along with magnolol, 4-O-methylhonokiol, and obovatol.

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

Magnolol is an organic compound that is classified as lignan. It is a bioactive compound found in the bark of the Houpu magnolia and in M. grandiflora. The compound exists at the level of a few percent in the bark of species of magnolia, the extracts of which have been used in traditional Chinese and Japanese medicine. In addition to magnolol, related lignans occur in the extracts including honokiol, which is an isomer of magnolol.

<i>Tabernaemontana corymbosa</i> Species of plant

Tabernaemontana corymbosa is a species of plant in the family Apocynaceae. It is native to Brunei, China, Indonesia, Laos, Malaysia, Myanmar, Singapore, Thailand, and Vietnam. Glossy green leaves and faintly sweet scented flower. Flowers continuously all year. Frost tolerant. Grows to about 2 metres. Likes full sun to part shade. A number of cultivars are available.

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

Herbacetin is a flavonol, a type of flavonoid.

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

Enterolactone is an organic compound classified as an enterolignan. It is formed by the action of intestinal bacteria on plant lignan precursors present in the diet.

<span class="mw-page-title-main">Enterodiol</span> Lignan formed by the action of intestinal bacteria on lignan precursors found in plants.[1]

Enterodiol is an organic compound with the formula [HOC6H4CH2CH(CH2OH)]2.

<i>Justicia gendarussa</i> Species of shrub

Justicia gendarussa, commonly known as Willow-leaved justicia ,Lapsulis in Creole Seychelles; is a small erect, branched shrub. According to Plants of the World Online it is native to the Indian subcontinent, Indochina, Peninsular Malaysia, Sumatra, the Philippines, and New Guinea, and has been introduced to Nepal, the western Himalayas, Pakistan, southern China including Hainan and Taiwan, eastern Africa, and the Mascarene Islands, Comoro Islands, and Seychelles. It has been described as rare and endemic to India, though those claims are at least confusing, in the context of statements that the plant is widely used in various forms for many of its medicinal and insecticidal properties, and that it is a quick-growing, evergreen forest shrub considered to be a native of China and distributed in Sri Lanka, India and Malaysia.

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

Acetosyringone is a phenolic natural product and a chemical compound related to acetophenone and 2,6-dimethoxyphenol. It was first described in relation to lignan/phenylpropanoid-type phytochemicals, with isolation from a variety of plant sources, in particular, in relation to wounding and other physiologic changes.

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

Pinoresinol is a tetrahydrofuran lignan found in Styrax sp., Forsythia suspensa, and in Forsythia koreana. It is also found in the caterpillar of the cabbage butterfly, Pieris rapae where it serves as a defence against ants.

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

Stictic acid is an aromatic organic compound, a product of secondary metabolism in some species of lichens.

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

Cerevisterol (5α-ergosta-7,22-diene-3β,5,6β-triol) is a sterol. Originally described in the 1930s from the yeast Saccharomyces cerevisiae, it has since been found in several other fungi and, recently, in deep water coral. Cerevisterol has some in vitro bioactive properties, including cytotoxicity to some mammalian cell lines.

<span class="mw-page-title-main">Coumarinolignoid</span>

Coumarinolignoids are a class of phenolic compounds. They are a subset of lignans in which one of the two phenylpropanoids is found in the form of a coumarin.

Droplet countercurrent chromatography was introduced in 1970 by Tanimura, Pisano, Ito, and Bowman. DCCC is considered to be a form of liquid-liquid separation, which includes countercurrent distribution and countercurrent chromatography, that employs a liquid stationary phase held in a collection of vertical glass columns connected in series. The mobile phase passes through the columns in the form of droplets. The DCCC apparatus may be run with the lower phase stationary and the upper phase being introduced to the bottom of each column. Or it may be run with the upper phase stationary and the lower phase being introduced from the top of the column. In both cases, the work of gravity is allowed influence the two immiscible liquids of different densities to form the signature droplets that rise or descend through the column. The mobile phase is pumped at a rate that will allow droplets to form that maximize the mass transfer of a compound between the upper and lower phases. Compounds that are more soluble in the upper phase will travel quickly through the column, while compounds that are more soluble in the stationary phase will linger. Separation occurs because different compounds distribute differently, in a ratio called the partition coefficient, between the two phases.

<span class="mw-page-title-main">Dichapetalins</span> Small class of triterpenoid compounds

Dichapetalins are a small class of triterpenoid compounds found primarily in the Dichapetalaceae family but also reportedly in Phyllanthus (Euphorbiaceae). They are structural derivatives of dammarene characterized by a C6C2 unit connected to a dammarene or a 13,30-cyclodammarane skeleton with variable C-17 side chains containing actone, spirolactone, lactol, acetal, or furan moieties. They have been found to display cytotoxicity against several cancer cell lines.

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

Hinokinin is a dibenzylbutyrolactone lignan, derived from various species of plants. It is a potential antichagonistic agent. In vitro, it has been shown to have potential neuroprotective effects as well as anti-inflammatory, anti-tumor, antiviral and antifungal properties.

References

  1. Umezawa, Toshiaki (2003). "Diversity in lignan biosynthesis". Phytochemistry Reviews. 2 (3): 371–390. Bibcode:2003PChRv...2..371U. doi:10.1023/B:PHYT.0000045487.02836.32. S2CID   6276953.
  2. Xiong, Lu; Bi, Ming-Gang; Wu, Song; Tong, Yuan-Feng (2012). "Total synthesis of 6′-hydroxyjusticidin A". Journal of Asian Natural Products Research. 14 (4): 322–6. doi:10.1080/10286020.2011.653561. PMID   22375869. S2CID   26689006.
  3. Fukamiya, Narihiko; Lee, Kuo-Hsiung (1986). "Antitumor Agents, 81. Justicidin-A and Diphyllin, Two Cytotoxic Principles from Justicia procumbens". Journal of Natural Products. 49 (2): 348–50. doi:10.1021/np50044a030. PMID   3734816.