Accession Number: pdtdbl00222

Details of the Ligand

Ligand Name : Cubebin
Systematic Names : Cubebin; (-)-Cubebin; (2s,3r,4r)-3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydrofuran-2-ol
Molecular Formula : C20H20O6
Molecular Weight : g/mol
IUPAC Name : (2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
Canonical SMILES : C1C(C(C(O1)O)CC2=CC3=C(C=C2)OCO3)CC4=CC5=C(C=C4)OCO5
Ligand Description :

Cubebin is found in herbs and spices. Cubebin is isolated from unripe fruit of Piper cubeba (cubeb pepper) About 15% of a volatile oil is obtained by distilling cubebs with water. It is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor. After rectification with water, or on keeping, this deposits rhombic crystals of camphor of cubebs. Cubeb (Piper cubeba), or tailed pepper, is a plant in genus Piper, cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubebs consist of the dried berries, similar in appearance to black pepper, but with stalks attached the "tails" in "tailed pepper". The dried pericarp is wrinkled, its color ranges from grayish-brown to black. The seed is hard, white and oily. The odor of cubebs is described as agreeable and aromatic. The taste, pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper.

Cubebin is a crystalline substance existing in cubebs, discovered by Eugene Soubeiran and Capitaine in 1839. It may be prepared from cubebene, or from the pulp left after the distillation of the oil. The drug, along with gum, fatty oils, and malates of magnesium and calcium, contains also about 1% of cubebic acid, and about 6% of a resin. The dose of the fruit is 30 to 60 grains, and the British Pharmacopoeia contains a tincture with a dose of 4 to 1 dram. In Europe, cubeb was one of the valuable spices during the Middle Ages. It was ground as a seasoning for meat or used in sauces. Cubebin is a medieval recipe includes cubeb in making sauce sarcenes, which consists of almond milk and several spices. As an aromatic confectionery, cubeb was often candied and eaten whole. In traditional Chinese medicine cubeb is used for its alleged warming property. In Tibetan medicine, cubeb (ka ko la in Tibetan) is one of bzang po drug, six fine herbs beneficial to specific organs in the body, with cubeb assigned to the spleen. Cubebin has been shown to exhibit anti-pyretic function. Cubebin belongs to the family of Dibenzylbutyrolactols. These are lignan compounds containing a 3,4-dibenzyloxolan-2-ol moiety.

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