''Piper cubeba'', cubeb or tailed pepper is a plant in

genus Genus (; : genera ) is a taxonomic rank above species and below family (taxonomy), family as used in the biological classification of extant taxon, living and fossil organisms as well as Virus classification#ICTV classification, viruses. In bino ...

'' Piper'', cultivated for its

fruit In botany, a fruit is the seed-bearing structure in flowering plants (angiosperms) that is formed from the ovary after flowering. Fruits are the means by which angiosperms disseminate their seeds. Edible fruits in particular have long propaga ...

and

essential oil An essential oil is a concentrated hydrophobic liquid containing volatile (easily evaporated at normal temperatures) chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the ...

. It is mostly grown in

Java Java is one of the Greater Sunda Islands in Indonesia. It is bordered by the Indian Ocean to the south and the Java Sea (a part of Pacific Ocean) to the north. With a population of 156.9 million people (including Madura) in mid 2024, proje ...

and

Sumatra Sumatra () is one of the Sunda Islands of western Indonesia. It is the largest island that is fully within Indonesian territory, as well as the list of islands by area, sixth-largest island in the world at 482,286.55 km2 (182,812 mi. ...

, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubeb consists of the dried

berries A berry is a small, pulpy, and often edible fruit. Typically, berries are juicy, rounded, brightly colored, sweet, sour or tart, and do not have a stone fruit, stone or pit (fruit), pit although many wikt:pip#Etymology 2, pips or seeds may be p ...

, similar in appearance to

black pepper Black pepper (''Piper nigrum'') is a flowering vine in the family Piperaceae, cultivated for its fruit (the peppercorn), which is usually dried and used as a spice and seasoning. The fruit is a drupe (stonefruit) which is about in diameter ...

, but with stalks attached – the "tails" in "tailed pepper". The dried pericarp is wrinkled, and its color ranges from grayish brown to black. The

seed In botany, a seed is a plant structure containing an embryo and stored nutrients in a protective coat called a ''testa''. More generally, the term "seed" means anything that can be Sowing, sown, which may include seed and husk or tuber. Seeds ...

is hard, white and oily. The odor of cubeb is described as agreeable and aromatic and the taste as pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper. Cubeb came to Europe via

India India, officially the Republic of India, is a country in South Asia. It is the List of countries and dependencies by area, seventh-largest country by area; the List of countries by population (United Nations), most populous country since ...

through the trade with the Arabs. The name ''cubeb'' comes from

Arabic Arabic (, , or , ) is a Central Semitic languages, Central Semitic language of the Afroasiatic languages, Afroasiatic language family spoken primarily in the Arab world. The International Organization for Standardization (ISO) assigns lang ...

' () by way of

Old French Old French (, , ; ) was the language spoken in most of the northern half of France approximately between the late 8th Cubeb is mentioned in alchemical writings by its Arabic name. In his ''Theatrum Botanicum'', John Parkinson (botanist)">John Parkinson tells that the king of Portugal (Possibly either Philip IV of Spain or John IV of Portugal, as that year was marked by the start of the Portuguese Restoration War) prohibited the sale of cubeb to promote

(''Piper nigrum'') around 1640. It experienced a brief resurgence in 19th-century Europe for medicinal uses, but has practically vanished from the European market since. It continues to be used as a

flavoring agent A flavoring (or flavouring), also known as flavor (or flavour) or flavorant, is a food additive that is used to improve the taste or Sense of smell, smell of food. It changes the perceptual impression of food as determined primarily by the chem ...

for gins and

cigarette A cigarette is a narrow cylinder containing a combustible material, typically tobacco, that is rolled into Rolling paper, thin paper for smoking. The cigarette is ignited at one end, causing it to smolder; the resulting smoke is orally inhale ...

s in the West, and as a seasoning for food in

Indonesia Indonesia, officially the Republic of Indonesia, is a country in Southeast Asia and Oceania, between the Indian Ocean, Indian and Pacific Ocean, Pacific oceans. Comprising over List of islands of Indonesia, 17,000 islands, including Sumatra, ...

History

In the fourth century BC,

Theophrastus Theophrastus (; ; c. 371 – c. 287 BC) was an ancient Greek Philosophy, philosopher and Natural history, naturalist. A native of Eresos in Lesbos, he was Aristotle's close colleague and successor as head of the Lyceum (classical), Lyceum, the ...

mentioned ''komakon'', including it with

cinnamon Cinnamon is a spice obtained from the inner bark of several tree species from the genus ''Cinnamomum''. Cinnamon is used mainly as an aromatic condiment and flavouring additive in a wide variety of cuisines, sweet and savoury dishes, biscuits, b ...

and cassia as an ingredient in aromatic confections. Guillaume Budé and Claudius Salmasius have identified ''komakon'' with cubeb, probably due to the resemblance which the word bears to the Javanese name of cubeb, ''kumukus''. This is seen as a curious evidence of Greek trade with Java in a time earlier than that of Theophrastus. Chapter XXV. It is unlikely Greeks acquired them from somewhere else, since Javanese growers protected their

monopoly A monopoly (from Greek language, Greek and ) is a market in which one person or company is the only supplier of a particular good or service. A monopoly is characterized by a lack of economic Competition (economics), competition to produce ...

of the trade by sterilizing the berries by scalding, ensuring that the vines were unable to be cultivated elsewhere. In the

Tang dynasty The Tang dynasty (, ; zh, c=唐朝), or the Tang Empire, was an Dynasties of China, imperial dynasty of China that ruled from 618 to 907, with an Wu Zhou, interregnum between 690 and 705. It was preceded by the Sui dynasty and followed ...

, cubeb was brought to China from

Srivijaya Srivijaya (), also spelled Sri Vijaya, was a Hinduism, Hindu-Buddhism, Buddhist thalassocracy, thalassocratic empire based on the island of Sumatra (in modern-day Indonesia) that influenced much of Southeast Asia. Srivijaya was an important ...

. In India, the spice came to be called ''kabab chini'', that is, "Chinese cubeb", possibly because the Chinese had a hand in its trade, but more likely because it was an important item in the trade with China. In China, this pepper was called both ''vilenga'' and ''viḍaṅga'' (the cognate Sanskrit word), which had denoted embelia ribes before being used to denote the Malayan cubeb ( zh, , t=蓽澄茄, s= 荜澄茄, p=bì chéng qié). Li Hsun thought it grew on the same tree as black pepper. Tang physicians administered it to restore appetite, cure "demon vapors", darken the hair, and perfume the body. However, there is no evidence showing that cubeb was used as a condiment in China. In his 1827 dictionary, ''Nhật dụng thường đàm'' (; ), Vietnamese

scholar-official The scholar-officials, also known as literati, scholar-gentlemen or scholar-bureaucrats (), were government officials and prestigious scholars in Chinese society, forming a distinct social class. Scholar-officials were politicians and governmen ...

Phạm Đình Hổ glossed "cubeb" ( Sino-Vietnamese: ''tất đăng gia'') as 乙 ', which currently denotes chilli pepper from the

Americas The Americas, sometimes collectively called America, are a landmass comprising the totality of North America and South America.''Webster's New World College Dictionary'', 2010 by Wiley Publishing, Inc., Cleveland, Ohio. When viewed as a sing ...

. '' The Book of One Thousand and One Nights'', compiled in the 9th century, mentions cubeb as a remedy for infertility, showing it was already used by Arabs for medicinal purposes. Cubeb was introduced to Arabic cuisine around the 10th century. '' The Travels of Marco Polo'', written in late 13th century, describes Java as a producer of cubeb, along with other valuable spices. In the 14th century, cubeb was imported into Europe from the

Grain Coast The Pepper Coast or Grain Coast was a coastal area of western Africa, between Cape Mesurado and Cape Palmas. It encloses the present republic of Liberia. The name was given by European traders. Origin of the name The Pepper Coast got its name f ...

, under the name of pepper, by merchants of

Rouen Rouen (, ; or ) is a city on the River Seine, in northwestern France. It is in the prefecture of Regions of France, region of Normandy (administrative region), Normandy and the Departments of France, department of Seine-Maritime. Formerly one ...

and

Lippe Lippe () is a ''Kreis'' (district) in the east of North Rhine-Westphalia, Germany. Neighboring districts are Herford, Minden-Lübbecke, Höxter, Paderborn, Gütersloh, and district-free Bielefeld, which forms the region Ostwestfalen-Lippe. ...

. Cubeb eventually came to be thought of as repulsive to demons by the people of Europe. Ludovico Maria Sinistrari, a

Roman Catholic priest The priesthood is the office of the ministers of religion, who have been commissioned ("ordained") with the holy orders of the Catholic Church. Technically, bishops are a priestly order as well; however, in common English usage ''priest'' re ...

who wrote about methods of

exorcism Exorcism () is the religious or spiritual practice of evicting demons, jinns, or other malevolent spiritual entities from a person, or an area, that is believed to be possessed. Depending on the spiritual beliefs of the exorcist, this may be do ...

in the late 17th century, includes cubeb as an ingredient in an incense to ward off an incubus.. "...Incubus none the less persisted in appearing to her constantly, in the shape of an exceptionally handsome young man. At last, among other learned men, whose advice had been taken on the subject, was a very profound Theologian who, observing that the maiden was of a thoroughly phlegmatic temperament, surmised that that Incubus was an aqueous Demon (there are in fact, as is testified by Guazzo (''Compendium Maleficarum, I. 19''), igneous, aerial, phlegmatic, earthly, and subterranean demons who avoid the light of day), and so he prescribed a continual suffumigation in the room. A new vessel, made of earthenware and glass, was accordingly introduced, and filled with sweet calamus, cubeb seed, roots of both aristolochies, great and small cardamom, ginger, long-pepper, caryophylleae, cinnamon, cloves, mace, nutmegs, calamite storax, benzoin, aloes-wood and roots, one ounce of fragrant sandal, and three quarts of half brandy and water; the vessel was then set on hot ashes in order to force forth and upwards the fumigating vapour, and the cell was kept closed. As soon as the suffumigation was done, the Incubus came, but never dared enter the cell." After the prohibition of its sale in Portugal in 1640, culinary use of cubeb decreased dramatically in Europe, and only its medicinal application continued to the 19th century. In the early 20th century, cubeb was regularly shipped from Indonesia to Europe and the United States. The trade gradually diminished to an average of annually, and practically ceased after 1940..

Chemistry

The dried cubeb berries contain essential oil comprising

monoterpene Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen func ...

s ( sabinene 50%, α- thujene, and carene) and

sesquiterpene Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many combinations. Biochemical modifications s ...

s (

caryophyllene Caryophyllene (), more formally (−)-β-caryophyllene (BCP), is a natural bicyclic sesquiterpene that occurs widely in nature. Caryophyllene is notable for having a cyclobutane ring, as well as a ''trans''-double bond in a 9-membered ring, both ...

, copaene, α- and β-cubebene, δ- cadinene, germacrene), the oxides 1,4- and 1,8- cineole and the alcohol cubebol. About 15% of a volatile oil is obtained by distilling cubeb with water. Cubebene, the liquid portion, has the formula C₁₅H₂₄ and comes in two forms, α- and β-. They differ only in the position of the

alkene In organic chemistry, an alkene, or olefin, is a hydrocarbon containing a carbon–carbon double bond. The double bond may be internal or at the terminal position. Terminal alkenes are also known as Alpha-olefin, α-olefins. The Internationa ...

moiety, with the double-bond being endocyclic (part of the five-membered ring) in α-cubebene, as shown, but

exocyclic In organic chemistry, an alicyclic compound contains one or more all-carbon rings which may be either saturated or unsaturated, but do not have aromatic character. Alicyclic compounds may have one or more aliphatic side chains attached. Cyc ...

in β-cubebene. It is a pale green viscous liquid with a warm woody, slightly camphoraceous odor. After rectification with water, or on keeping, this deposits rhombic crystals of camphor of cubeb. Cubebin (C₂₀H₂₀O₆) is a crystalline organic compound isolated from cubeb oilcake, and can be chemically synthesized from cubebene. It was discovered by Eugène Soubeiran and Hyacinthe Capitaine in 1839, and irritates the

mucous membrane A mucous membrane or mucosa is a membrane that lines various cavities in the body of an organism and covers the surface of internal organs. It consists of one or more layers of epithelial cells overlying a layer of loose connective tissue. It ...

Uses

History in folk medicine

Physicians in the

Islamic Golden Age The Islamic Golden Age was a period of scientific, economic, and cultural flourishing in the history of Islam, traditionally dated from the 8th century to the 13th century. This period is traditionally understood to have begun during the reign o ...

distilled "water of ''al butm''" (

turpentine Turpentine (which is also called spirit of turpentine, oil of turpentine, terebenthine, terebenthene, terebinthine and, colloquially, turps) is a fluid obtainable by the distillation of resin harvested from living trees, mainly pines. Principall ...

) from a mixture of herbal products, including cubeb. In Victorian and Edwardian England, cubeb was an antiseptic for gonorrhea treatment. William Wyatt Squire wrote in 1908 that cubeb berries "act specifically on the genitourinary

. (They are) given in all stages of gonorrhea" and ''The National Botanic Pharmacopoeia'' printed in 1921 stated that cubeb was "an excellent remedy for flour albus or whites". A

tincture A tincture is typically an extract of plant or animal material dissolved in ethanol (ethyl alcohol). Solvent concentrations of 25–60% are common, but may run as high as 90%.Groot Handboek Geneeskrachtige Planten by Geert Verhelst In chemistr ...

of the compound appeared in the '' British Pharmacopoeia'', and a gum with 1% cubebin, roughly equivalent to 30-60

grains A grain is a small, hard, dry fruit ( caryopsis) – with or without an attached hull layer – harvested for human or animal consumption. A grain crop is a grain-producing plant. The two main types of commercial grain crops are cereals and le ...

of cubeb fruit, had become standardized as a

drug A drug is any chemical substance other than a nutrient or an essential dietary ingredient, which, when administered to a living organism, produces a biological effect. Consumption of drugs can be via insufflation (medicine), inhalation, drug i ...

, also called ''cubeb''.

Culinary

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. A medieval recipe includes cubeb in making ''sauce sarcenes'', which consists of almond milk and several spices. "Make a thykke mylke of almondys, do hit in a pot with floure of rys, safron, gynger, macys, ''quibibis'', canel, sygure: and rynse the bottom of the disch with fat broth. Boyle the sewe byfore, and messe hit forth." As an aromatic confectionery, cubeb was often candied and eaten whole. Ocet Kubebowy, a vinegar infused with cubeb, cumin and garlic, was used for meat marinades in

Poland Poland, officially the Republic of Poland, is a country in Central Europe. It extends from the Baltic Sea in the north to the Sudetes and Carpathian Mountains in the south, bordered by Lithuania and Russia to the northeast, Belarus and Ukrai ...

during the 14th century . Cubeb can be used to enhance the flavor of savory soups. Cubeb reached Africa by way of the Arabs. In Moroccan cuisine, cubeb is used in savory dishes and in pastries like ''makrouts'', little diamonds of

semolina Semolina is the name given to roughly milled durum wheat mainly used in making pasta and sweet puddings. The term ''semolina'' is also used to designate coarse millings of other varieties of wheat, and sometimes other grains (such as rice or ma ...

with honey and dates. It also appears occasionally in the list of ingredients for the famed spice mixture '' Ras el hanout''. In

Indonesian cuisine Indonesian cuisine is a collection of various regional culinary traditions by various ethnic groups that formed in the archipelagic nation of Indonesia. There are a wide variety of recipes and cuisines in part because Indonesia is composed ...

, especially in Indonesian gulés (curries), cubeb is frequently used.

Cigarettes and spirits

Cubeb, combined with stramonium,

eucalyptus ''Eucalyptus'' () is a genus of more than 700 species of flowering plants in the family Myrtaceae. Most species of ''Eucalyptus'' are trees, often Mallee (habit), mallees, and a few are shrubs. Along with several other genera in the tribe Eucalyp ...

, and other plant extracts, was once, beginning in the 1880s, frequently used in the form of

s for

asthma Asthma is a common long-term inflammatory disease of the airways of the lungs. It is characterized by variable and recurring symptoms, reversible airflow obstruction, and easily triggered bronchospasms. Symptoms include episodes of wh ...

, chronic pharyngitis, and

hay fever Allergic rhinitis, of which the seasonal type is called hay fever, is a type of rhinitis, inflammation in the nose that occurs when the immune system overreacts to allergens in the air. It is classified as a Allergy, type I hypersensitivity re ...

Edgar Rice Burroughs Edgar Rice Burroughs (September 1, 1875 – March 19, 1950) was an American writer, best known for his prolific output in the adventure, science fiction, and fantasy genres. Best known for creating the characters Tarzan (who appeared in ...

, being fond of smoking cubeb cigarettes, said humorously that if he had not smoked so many, there might never have been ''

Tarzan Tarzan (John Clayton, Viscount Greystoke) is a fictional character, a feral child raised in the African jungle by the Mangani great apes; he later experiences civilization, only to reject it and return to the wild as a heroic adventurer. Creat ...

''. Marshall's Prepared Cubeb Cigarettes was a popular brand, with enough sales to still be made during World War II.. In 2000, cubeb oil was included in the list of ingredients found in cigarettes, published by the Tobacco Prevention and Control Branch of

North Carolina North Carolina ( ) is a U.S. state, state in the Southeastern United States, Southeastern region of the United States. It is bordered by Virginia to the north, the Atlantic Ocean to the east, South Carolina to the south, Georgia (U.S. stat ...

's Department of Health and Human Services. Bombay Sapphire gin is flavored with botanicals including cubeb and grains of paradise. The brand was launched in 1987, but its maker claims that it is based on a secret recipe dating to 1761. Pertsivka, a dark brown Ukrainian pepper-flavoured horilka with a burning taste, is prepared by infusion with cubeb and chiles.

Other

Cubeb is sometimes used to adulterate the

of patchouli, which requires caution for patchouli users. In turn, cubeb is adulterated by '' Piper baccatum'' (also known as the "climbing pepper of Java") and '' Piper caninum''.

References

Notes

Works cited

* . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . * . Attribution * {{Taxonbar, from=Q161927 African cuisine Arab spices Edible nuts and seeds Flora of the Lesser Sunda Islands Indonesian cuisine Medicinal plants of Asia Medieval cuisine Spices cubeba Austronesian agriculture