Sarracenin

Last updated
Sarracenin
Sarracenin.svg
Names
Preferred IUPAC name
Methyl (1S,3S,7R,8R,9R)-9-methyl-2,4,10-trioxatricyclo[5.3.1.03,8]undec-5-ene-6-carboxylate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
  • InChI=1S/C11H14O5/c1-5-9-6-3-8(15-5)16-11(9)14-4-7(6)10(12)13-2/h4-6,8-9,11H,3H2,1-2H3
    Key: QGBCGMGBGAHJIT-UHFFFAOYSA-N
  • CC1C2C3CC(O1)OC2OC=C3C(=O)OC
Properties
C11H14O5
Molar mass 226.228 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Sarracenin is an iridoid found in several plant species in the carnivorous family Sarraceniaceae. [1] It also occurs in other non-carnivorous plants such as Strychnos spinosa (Loganiaceae) [2] and Patrinia heterophylla (Caprifoliaceae). [3]

Contents

History

Sarracenin was first isolated from the roots of Sarracenia flava in 1976. Analysis of S. flava extracts was prompted by their use as a folk remedy by people of the Okefenokee swamp region [4]

Biosynthesis

Sarracenin is believed to be derived from loganin, with either morronoside or secologanin serving as intermediates in the biosynthetic process. [4]

Uses

Sarracenin displays antimicrobial activity against several pathogens including Staphylococcus aureus , Streptococcus pyogenes , Shigella dysenteriae , Klebsiella pneumonia , Candida albicans, Candida tropicalis , Candida thrusei , and Candida stellatoidea [2] . It has also demonstrated cytotoxicity against three tumor cell lines: A375 (human melanoma cell), SGC-7901 (human gastric cancer cell), and HeLa. [3]

Ecology

Sarracenin is the primary volatile present in the insect-attracting spoons of Heliamphora species. When Heliamphora plants were grown in a laboratory setting, sarracenin was rarely present in these spoons. Plants that did produce sarracenin generally attracted more insects than those without, suggesting a role in prey attraction or capture. [5] Sarracenin is also present in the pitchers and lids of Darlingtonia californica and many Sarracenia species, likely serving the same purpose as in Heliamphora. [1]


Related Research Articles

<span class="mw-page-title-main">Pitcher plant</span> Carnivorous plant

Pitcher plants are several different carnivorous plants that have modified leaves known as pitfall traps—a prey-trapping mechanism featuring a deep cavity filled with digestive liquid. The traps of what are considered to be "true" pitcher plants are formed by specialized leaves. The plants attract and drown their prey with nectar.

<span class="mw-page-title-main">Sarraceniaceae</span> Family of carnivorous plants

Sarraceniaceae are a family of pitcher plants, belonging to order Ericales.

<i>Brocchinia reducta</i> Species of carnivorous plant

Brocchinia reducta is a carnivorous plant in the bromeliad family. It is native to southern Venezuela, Brazil, Colombia, and Guyana, and is found in areas with nutrient-poor, high moisture soil. B. reducta is able to grow in sparse conditions, which is evident when it uses its roots as anchors over rocks. Its funnel-like structure and waxy coating, among other characteristics, suggest that this plant is carnivorous.

<i>Sarracenia</i> Genus of carnivorous plants

Sarracenia is a genus comprising 8 to 11 species of North American pitcher plants, commonly called trumpet pitchers. The genus belongs to the family Sarraceniaceae, which also contain the closely allied genera Darlingtonia and Heliamphora.

<i>Heliamphora</i> Genus of carnivorous plants

The genus Heliamphora contains 23 species of pitcher plants endemic to South America. The species are collectively known as sun pitchers, based on the mistaken notion that the heli of Heliamphora is from the Greek helios, meaning "sun". In fact, the name derives from helos, meaning marsh, so a more accurate translation of their scientific name would be marsh pitcher plants. Species in the genus Heliamphora are carnivorous plants that consist of a modified leaf form that is fused into a tubular shape. They have evolved mechanisms to attract, trap, and kill insects; and control the amount of water in the pitcher. At least one species produces its own proteolytic enzymes that allows it to digest its prey without the help of symbiotic bacteria.

<i>Darlingtonia californica</i> Species of carnivorous plant

Darlingtonia californica, also called the California pitcher plant, cobra lily, or cobra plant, is a species of carnivorous plant. It is the sole member of the genus Darlingtonia in the family Sarraceniaceae. This pitcher plant is native to Northern California and Oregon, US, growing in bogs and seeps with cold running water usually on serpentine soils. This plant is designated as uncommon due to its rarity in the field.

<i>Sarracenia flava</i> Species of carnivorous plant

Sarracenia flava, the yellow pitcherplant, is a carnivorous plant in the family Sarraceniaceae. Like all the Sarraceniaceae, it is native to the New World. Its range extends from southern Alabama, through Florida and Georgia, to the coastal plains of southern Virginia, North Carolina and South Carolina. Populations also exist in the Piedmont, Mendocino County, California and mountains of North Carolina.

<i>Sarracenia purpurea</i> Species of carnivorous plant

Sarracenia purpurea, the purple pitcher plant, northern pitcher plant, turtle socks, or side-saddle flower, is a carnivorous plant in the family Sarraceniaceae.

<i>Carnivorous Plant Newsletter</i> Academic journal

The Carnivorous Plant Newsletter is the official publication of the International Carnivorous Plant Society (ICPS), the largest such organization in the world. It is headquartered in Walnut Creek, California.

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

Andreas Wistuba is a German taxonomist and botanist specialising in the carnivorous plant genera Heliamphora and Nepenthes. More than half of all known Heliamphora species have been described by Wistuba.

<i>Heliamphora heterodoxa</i> Species of Marsh Pitcher Plant native to Gran Sabana, Venezuela

Heliamphora heterodoxa is a species of marsh pitcher plant native to Venezuela and adjacent Guyana. It was first discovered in 1944 on the slopes interlinking Ptari-tepui and Sororopan-tepui and formally described in 1951.

<i>Heliamphora minor</i> Species of carnivorous plant

Heliamphora minor is a species of marsh pitcher plant endemic to Auyán-tepui in Venezuela. As the name suggests, it is one of the smallest species in the genus. It is closely related to H. ciliata and H. pulchella.

<i>Heliamphora neblinae</i> Species of carnivorous plant

Heliamphora neblinae is a species of marsh pitcher plant endemic to Cerro de la Neblina, Cerro Aracamuni and Cerro Avispa in Venezuela. It is one of the most variable species in the genus and was once considered to be a variety of H. tatei. It is unclear whether or not there is a consensus regarding its status as a species, with at least a few researchers supporting the taxonomic revision that would elevate both H. tatei var. neblinae and H. tatei f. macdonaldae to full species status.

<i>Heliamphora nutans</i> Species of carnivorous plant

Heliamphora nutans is a species of marsh pitcher plant native to the border area between Venezuela, Brazil and Guyana, where it grows on several tepuis, including Roraima, Kukenán, Yuruaní, Maringma, and Wei Assipu. Heliamphora nutans was the first Heliamphora to be described and is the best known species.

<i>Heliamphora tatei</i> Species of carnivorous plant

Heliamphora tatei is a species of marsh pitcher plant endemic to Cerro Duida, Cerro Huachamacari and Cerro Marahuaca in Venezuela. It is closely related to H. macdonaldae, H. neblinae, and H. parva, and all three have in the past been considered forms or varieties of H. tatei. Like H. tatei, these species are noted for their stem-forming growth habit.

<i>Archaeamphora</i> Fossil species of Cretaceous-aged flowering plant

Archaeamphora longicervia is a fossil plant species, the only member of the hypothetical genus Archaeamphora. Fossil material assigned to this taxon originates from the Yixian Formation of northeastern China, dated to the Early Cretaceous.

<span class="mw-page-title-main">Protocarnivorous plant</span> Carnivorous plant that can not digest prey

A protocarnivorous plant, according to some definitions, traps and kills insects or other animals but lacks the ability to either directly digest or absorb nutrients from its prey like a carnivorous plant. The morphological adaptations such as sticky trichomes or pitfall traps of protocarnivorous plants parallel the trap structures of confirmed carnivorous plants.

<span class="mw-page-title-main">Carnivorous plant</span> Plants that consume animals

Carnivorous plants are plants that derive some or most of their nutrients from trapping and consuming animals or protozoans, typically insects and other arthropods, and occasionally small mammals and birds. They still generate all of their energy from photosynthesis. They have adapted to grow in places where the soil is thin or poor in nutrients, especially nitrogen, such as acidic bogs. They can be found on all continents except Antarctica, as well as many Pacific islands. In 1875, Charles Darwin published Insectivorous Plants, the first treatise to recognize the significance of carnivory in plants, describing years of painstaking research.

Heliamphora uncinata is a species of Marsh Pitcher Plant endemic to Venezuela. This species of carnivorous plant is known as a pitcher plant. Individuals use tube like leaves to trap insects that slip into the bottom. At the bottom of the "pitcher" there are digestive juices which slowly digest the prey item to give the plant additional nutrients. The pitchers of this species are around 25–35 cm long, and are 8–10 cm wide at the opening. The pitcher mouth is circular in shape and the back is raised to form the lid. It is known only from the type collection, which was made in a narrow canyon on Amurí-tepui. There it grows at an elevation of approximately 1850 m on sandstone cliff faces in shady conditions. It is also found in humus pockets and cracks at this location. The only other species in the genus known to have a similar growth habit is H. exappendiculata. These two taxa also share a number of morphological features and appear to be closely related. These shared morphological features include: the shape of pitchers, the general growth pattern, and appearance of nectaries.

<i>Sarraceniaceae of South America</i>

Sarraceniaceae of South America is a monograph on the pitcher plants of the genus Heliamphora by Stewart McPherson, Andreas Wistuba, Andreas Fleischmann, and Joachim Nerz. It was published in September 2011 by Redfern Natural History Productions and covered all species known at the time.

References

  1. 1 2 Hotti H, Gopalacharyulu P, Seppänen-Laakso T, Rischer H (2017-02-21). "Metabolite profiling of the carnivorous pitcher plants Darlingtonia and Sarracenia". PLOS ONE. 12 (2): e0171078. Bibcode:2017PLoSO..1271078H. doi: 10.1371/journal.pone.0171078 . PMC   5319649 . PMID   28222171.
  2. 1 2 Tor-Anyiin TA, Igoli JO, Anyam JV, Anyam JN (2015). "Isolation and Antimicrobial Activity of Sarracenin From Root Bark of Strychnos Spinosa". Journal of Chemical Society of Nigeria. 40 (1). S2CID   55620516.
  3. 1 2 Sheng L, Yang Y, Zhang Y, Li N (May 2019). "Chemical constituents of Patrinia heterophylla Bunge and selective cytotoxicity against six human tumor cells". Journal of Ethnopharmacology. 236: 129–135. doi:10.1016/j.jep.2019.03.005. PMID   30853646. S2CID   73727478.
  4. 1 2 Miles DH, Kokpol U, Bhattacharyya J, Atwood JL, Stone KE, Bryson TA, Wilson C (March 1976). "Structure of sarracenin. An unusual enol diacetal monoterpene from the insectivorous plant Sarracenia flava". Journal of the American Chemical Society. 98 (6): 1569–1573. doi:10.1021/ja00422a048.
  5. Jaffé K, Blum MS, Fales HM, Mason RT, Cabrera A (March 1995). "On insect attractants from pitcher plants of the genusHeliamphora (sarraceniaceae)". Journal of Chemical Ecology. 21 (3): 379–384. Bibcode:1995JCEco..21..379J. doi:10.1007/BF02036725. PMID   24234068. S2CID   12537352.