Petiveria

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Petiveria
Petiveria - Ehret.jpg
Status TNC G5.svg
Secure  (NatureServe) [1]
Scientific classification Red Pencil Icon.png
Kingdom: Plantae
Clade: Tracheophytes
Clade: Angiosperms
Clade: Eudicots
Order: Caryophyllales
Family: Petiveriaceae
Genus: Petiveria
L.
Species:
P. alliacea
Binomial name
Petiveria alliacea
L. [2]
Synonyms

Mapa graveolens
Petiveria corrientina
Petiveria foetida
Petiveria graveolens
Petiveria hexandria
Petiveria paraguayensis

Contents

Petiveria is a genus of flowering plants in the pigeonberry family, Petiveriaceae. The sole species it contains, Petiveria alliacea, [3] is native to Florida and the lower Rio Grande Valley of Texas in the United States, [4] Mexico, Central America, the Caribbean, and tropical South America. [2] Introduced populations occur in Benin and Nigeria. [5] It is a deeply rooted herbaceous perennial shrub growing up to 1 m (3.3 ft) in height and has small greenish piccate flowers. The roots and leaves have a strong acrid, garlic-like odor which taints the milk and meat of animals that graze on it. [6]

Common names

It is known by a wide number of common names including: guinea henweed, guiné (pronounced  [giˈnɛ] ) in Brazil, anamu in the Dominican Republic, Puerto Rico and Brazil, apacin in Guatemala, mucura in Peru, and guine in many other parts of Latin America, feuilles ave, herbe aux poules, petevere a odeur ail, and, in Trinidad, as mapurite (pronounced Ma-po-reete) and gully root, [7] and in Jamaica as guinea hen weed [8] and many others.

Description

Petiveria alliacea is a herbaceous shrub. Leaves are simple, alternate, pinnate in the first order and netted the second order. It has determinate inflorescences. Although the plant is capable of reproducing throughout the year, reproductive activity peaks during a portion of the year that is dependent on geography. For example, in Mexico this period is from September to October, while in Central America it is from July to January.

Range and habitat

This plant is native to the United States (southernmost Florida and Texas), the West Indies, Mexico, Central America and South America. In southern Florida it has been reported in disturbed areas, maritime, mesic, prairie and tropical hardwood hammocks and shell mound. [9] In Mexico, P. alliacea is widely present in corn, coffee and apple plantations. [10]

Uses

Petiveria alliacea is used as a bat and insect repellent. [11]

Phytochemistry

Petiveria alliacea has been found to contain a large number of biologically active chemicals including benzaldehyde, benzoic acid, benzyl 2-hydroxyethyl trisulphide, coumarin, isoarborinol, isoarborinol acetate, isoarborinol cinnamate, isothiocyanates, polyphenols, senfol, tannins, and trithiolaniacine. [12]

The plant's roots have also been shown to contain cysteine sulfoxide derivatives that are analogous to, but different from, those found in such plants as garlic and onion. For example, P. alliacea contains S-phenylmethyl-L-cysteine sulfoxides (petiveriins A and B) [13] and S-(2-hydroxyethyl)-L-cysteines (6-hydroxyethiins A and B). These compounds serve as the precursors of several thiosulfinates such as S-(2-hydroxyethyl) 2-hydroxyethane)thiosulfinate, S-(2-hydroxylethyl) phenylmethanethiosulfinate, S-benzyl 2-hydroxyethane)thiosulfinate and S-benzyl phenylmethanethiosulfinate (petivericin). [14] All four of these thiosulfinates have been found to exhibit antimicrobial activity. [15] Petiveriin also serves as precursor to phenylmethanethial S-oxide, a lachrymatory agent structurally similar to syn-propanethial-S-oxide from onion, [16] [17] but whose formation requires novel cysteine sulfoxide lyase and lachrymatory factor synthase enzymes differing from those found in onion. [18] [19] [20]

Domestic animals that consume P. alliacea can pass the garlic-like odor characteristic of the plant to their meat, eggs and milk. In addition, nitrates in the plant can cause toxicosis in cattle. [10]

Related Research Articles

<span class="mw-page-title-main">Onion</span> Bulbous vegetable, grown for food

An onion, also known as the bulb onion or common onion, is a vegetable that is the most widely cultivated species of the genus Allium. The shallot is a botanical variety of the onion which was classified as a separate species until 2011. Its close relatives include garlic, scallion, leek, and chive.

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

Allicin is an organosulfur compound obtained from garlic, a species in the family Alliaceae. It was first isolated and studied in the laboratory by Chester J. Cavallito and John Hays Bailey in 1944. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. The allicin generated is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. Allicin is part of a defense mechanism against attacks by pests on the garlic plant.

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

Alliin is a sulfoxide that is a natural constituent of fresh garlic. It is a derivative of the amino acid cysteine. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. Allicin and other thiosulfinates in garlic are unstable and form a number of other compounds, such as diallyl sulfide (DAS), diallyl disulfide (DADS) and diallyl trisulfide (DAT), dithiins and ajoene. Garlic powder is not a source of alliin, nor is fresh garlic upon maceration, since the enzymatic conversion to allicin takes place in the order of seconds.

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

Apigenin (4′,5,7-trihydroxyflavone), found in many plants, is a natural product belonging to the flavone class that is the aglycone of several naturally occurring glycosides. It is a yellow crystalline solid that has been used to dye wool.

Tetrahydrothiophene is an organosulfur compound with the formula (CH2)4S. The molecule consists of a five-membered saturated ring with four methylene groups and a sulfur atom. It is the saturated analog of thiophene. It is a volatile, colorless liquid with an intensely unpleasant odor. It is also known as thiophane, thiolane, or THT.

<span class="mw-page-title-main">Sulfenic acid</span> Organosulfur compound of the form R–SOH

In chemistry, a sulfenic acid is an organosulfur compound and oxoacid with the general formula R−S−OH. It is the first member of the family of organosulfur oxoacids, which also include sulfinic acids and sulfonic acids, respectively. The base member of the sulfenic acid series with R = H is hydrogen thioperoxide.

<i>syn</i>-Propanethial-<i>S</i>-oxide Chemical compound

syn-Propanethial S-oxide (or (Z)-propanethial S-oxide), a member of a class of organosulfur compounds known as thiocarbonyl S-oxides (formerly "sulfines"), is a volatile liquid that acts as a lachrymatory agent (triggers tearing and stinging on contact with the eyes). The chemical is released from onions, Allium cepa, as they are sliced. The release is due to the breaking open of the onion cells and their releasing enzymes called alliinases, which then break down amino acid sulfoxides, generating sulfenic acids. A specific sulfenic acid, 1-propenesulfenic acid, formed when onions are cut, is rapidly rearranged by a second enzyme, called the lachrymatory factor synthase or LFS, giving syn-propanethial S-oxide. The gas diffuses through the air and, on contact with the eye, it stimulates sensory neurons creating a stinging, painful sensation. Tears are released from the tear glands to dilute and flush out the irritant. A structurally related lachrymatory compound, syn-butanethial S-oxide, C4H8OS, has been found in another genus Allium plant, Allium siculum.

<span class="mw-page-title-main">Alliinase</span> Class of enzyme

In enzymology, an alliin lyase is an enzyme that catalyzes the chemical reaction

In enzymology, a secologanin synthase (EC 1.14.19.62, was wrongly classified as EC 1.3.3.9 in the past) is an enzyme that catalyzes the chemical reaction

The enzyme (S)-norcoclaurine synthase (EC 4.2.1.78) catalyzes the chemical reaction

In enzymology, an acridone synthase (EC 2.3.1.159) is an enzyme that catalyzes the chemical reaction

In enzymology, a beta-pyrazolylalanine synthase (EC 2.5.1.51) is an enzyme that catalyzes the chemical reaction

In enzymology, an uracilylalanine synthase (EC 2.5.1.53) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Thiosulfinate</span> Functional group

In organosulfur chemistry, thiosulfinate is a functional group consisting of the linkage R-S(O)-S-R (R are organic substituents). Thiolsulfinates are also named as alkanethiosulfinic (or arenethiosulfinic) acid esters. They are the first member of a family of compounds containing an oxidized disulfide bond. Other members of this family include thiosulfonates (R-SO2-S-R), α-disulfoxides (R-S(O)-S(O)-R), sulfinyl sulfones (R-S(O)-SO2-R), and α-disulfones (R-SO2-SO2-R), all of which are known. The thiosulfinate group can occur in cyclic as well as acyclic structures.

<i>Allium stipitatum</i> Species of flowering plant

Allium stipitatum, Persian shallot, is an Asian species of onion native to central and southwestern Asia.

Vinyldithiins, more precisely named 3-vinyl-4H-1,2-dithiin and 2-vinyl-4H-1,3-dithiin, are organosulfur phytochemicals formed in the breakdown of allicin from crushed garlic (Allium sativum). Vinyldithiins are Diels-Alder dimers of thioacrolein, H2C=CHCH=S, formed in turn by decomposition of allicin. In garlic supplements, vinyldithiins are only found in garlic oil macerates that are made by incubation of crushed garlic in oil.

<i>Allium siculum</i> Species of flowering plant

Allium siculum, known as honey garlic, Sicilian honey lily, Sicilian honey garlic, or Mediterranean bells, is a European and Turkish species of plants genus Allium. It is native to the regions around the Mediterranean and Black Seas, and grown in other regions as an ornamental and as a culinary herb.

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

Sulfinyl halide have the general formula R−S(O)−X, where X is a halogen. They are intermediate in oxidation level between sulfenyl halides, R−S−X, and sulfonyl halides, R−SO2−X. The best known examples are sulfinyl chlorides, thermolabile, moisture-sensitive compounds, which are useful intermediates for preparation of other sufinyl derivatives such as sulfinamides, sulfinates, sulfoxides, and thiosulfinates. Unlike the sulfur atom in sulfonyl halides and sulfenyl halides, the sulfur atom in sulfinyl halides is chiral, as shown for methanesulfinyl chloride.

Lupeol synthase is an enzyme with systematic name (3S)-2,3-epoxy-2,3-dihydrosqualene mutase . This enzyme catalyses the following chemical reaction

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

Juncusol is a 9,10-dihydrophrenathrene found in Juncus species such as J. acutus, J. effusus or J. roemerianus.

References

  1. ↑ "NatureServe Explorer 2.0". explorer.natureserve.org. Retrieved 6 May 2022.
  2. 1 2 "Petiveria". Germplasm Resources Information Network (GRIN). Agricultural Research Service (ARS), United States Department of Agriculture (USDA). Retrieved 2010-04-05.
  3. ↑ Carlquist, Sherwin (1998). "Wood and Stem Anatomy of Petiveria and Rivina (Caryophyllales); Systematic Implications". IAWA Journal. 19 (4): 383–391. doi:10.1163/22941932-90000659.
  4. ↑ Mild, C (2004-06-26). "Smelly Weed Is Strong Medicine" (PDF). Rio Delta Wild. Retrieved 2010-04-05.
  5. ↑ Schmelzer, GH; Gurib-Fakim, A (2008). Medicinal Plants. Plant Resources of Tropical Africa. pp. 412–415. ISBN   978-90-5782-204-9.
  6. ↑ Johnson, L. 1999. Anamu: Petiveria Alliacea. 14 pages (paperback). Woodland Publishing. ISBN   1-58054-038-4 (In Spanish).
  7. ↑ Mendes J. 1986. Cote ce Cote la: Trinidad & Tobago Dictionary, Arima, Trinidad, p. 95.
  8. ↑ "New anti-cancer discovery from Guinea Hen Weed". Jamaica Observer. 2014-03-09.
  9. ↑ "Petiveria alliacea L. Guinea hen weed". Floristic Inventory of South Florida Database Online. The Institute for Regional Conservation. Retrieved 2017-01-06.
  10. 1 2 "Petiveria alliacea (guinea hen weed)". Invasive Species Compendium. CABI. Retrieved 2017-01-06.
  11. ↑ Pérez-Leal, R.; García-Mateos, M. R.; Martínez-Vásquez, M.; Soto-Hernández, M. (2006). "Cytotoxic and antioxidant activity of Petiveria alliacea L.". Revista Chapingo. Serie Horticultura. 12 (1): 51–56.
  12. ↑ "Petiveria alliacea". Medicinal Plants for Livestock. Cornell University Department of Animal Science. Retrieved 2010-04-04.
  13. ↑ Kubec, R; Musah, RA (2001). "Cysteine sulfoxide derivatives in Petiveria alliacea" (PDF). Phytochemistry. 58: 981985. doi:10.1016/s0031-9422(01)00304-1.
  14. ↑ Kubec, R; Kim, S; Musah, RA (2002). "S-Substituted cysteine derivatives and thiosulfinate formation in Petiveria alliacea--Part II" (PDF). Phytochemistry. 61: 675–680. doi:10.1016/S0031-9422(02)00328-X.
  15. ↑ Kim, S; Kubec, R; Musah, RA (2006). "Antibacterial and antifungal activity of sulfur-containing compounds from Petiveria alliacea" (PDF). Journal of Ethnopharmacology. 104: 188–192. doi:10.1016/j.jep.2005.08.072. PMID   16229980.
  16. ↑ Kubec R, Kim S, Musah RA (2003). "The lachrymatory principle of Petiveria alliacea". Phytochemistry. 63 (1): 37–40. doi:10.1016/S0031-9422(02)00759-8. PMID   12657295.
  17. ↑ Kubec R, Cody RB, Dane AJ, Musah RA, Schraml J, Vattekkatte A, Block E (2010). "Applications of DART Mass Spectrometry in Allium Chemistry. (Z)-Butanethial S-Oxide and 1-Butenyl Thiosulfinates and their S-(E)-1-Butenylcysteine S-Oxide Precursor from Allium siculum". Journal of Agricultural and Food Chemistry. 58 (2): 1121–1128. doi:10.1021/jf903733e. PMID   20047275.
  18. ↑ Musah RA, He Q, Kubec R (2009). "Discovery and characterization of a novel lachrymatory factor synthase in Petiveria alliacea and its influence on alliinase-mediated formation of biologically active organosulfur compounds". Plant Physiology. 151 (3): 1294–1303. doi:10.1104/pp.109.142539. PMC   2773066 . PMID   19692535.
  19. ↑ Musah RA, He Q, Kubec R, Jadhav A (2009). "Studies of a novel cysteine sulfoxide lyase from Petiveria alliacea: the first heteromeric alliinase". Plant Physiology. 151 (3): 1304–1316. doi:10.1104/pp.109.142430. PMC   2773092 . PMID   19789290.
  20. ↑ He Q, Kubec R, Jadhav AP, Musah RA (2011). "First insights into the mode of action of a "lachrymatory factor synthase"--implications for the mechanism of lachrymator formation in Petiveria alliacea, Allium cepa and Nectaroscordum species". Phytochemistry. 72 (16): 1939–1946. doi:10.1016/j.phytochem.2011.07.013. PMID   21840558.

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