Alpinumisoflavone

Last updated
Alpinumisoflavone
Alpinumisoflavone.svg
Names
IUPAC name
4′,5-Dihydroxy-6′′,6′′-dimethyl-6′′H-pyrano[3′′,2′′:6,7]isoflavone
Systematic IUPAC name
5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethyl-4H,8H-benzo[1,2-b:5,4-b′]dipyran-4-one
Other names
5-Hydroxy-3-(4-hydroxyphenyl)-8,8-dimethylpyrano[3,2-g]chromen-4-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C20H16O5/c1-20(2)8-7-13-15(25-20)9-16-17(18(13)22)19(23)14(10-24-16)11-3-5-12(21)6-4-11/h3-10,21-22H,1-2H3 Yes check.svgY
    Key: RQAMSFTXEFSBPK-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C20H16O5/c1-20(2)8-7-13-15(25-20)9-16-17(18(13)22)19(23)14(10-24-16)11-3-5-12(21)6-4-11/h3-10,21-22H,1-2H3
    Key: RQAMSFTXEFSBPK-UHFFFAOYAG
  • CC1(C=CC2=C(O1)C=C3C(=C2O)C(=O)C(=CO3)C4=CC=C(C=C4)O)C
  • O=C2/C(c1ccc(O)cc1)=C\Oc4c2c(O)c3\C=C/C(Oc3c4)(C)C
Properties
C20H16O5
Molar mass 336.33 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Alpinumisoflavone is a pyranoisoflavone, a type of isoflavone. It can be found in the bark of Rinorea welwitschii . [1] It can also be found in the molluscicide plant Millettia thonningii and is thought to be an antischistosomal agent [2] since it has been shown to kill the snails which transmit the schistosomiasis and also the larvae of the parasite itself. [3]

Related Research Articles

<span class="mw-page-title-main">Fabaceae</span> Family of legume flowering plants

The Fabaceae or Leguminosae, commonly known as the legume, pea, or bean family, are a large and agriculturally important family of flowering plants. It includes trees, shrubs, and perennial or annual herbaceous plants, which are easily recognized by their fruit (legume) and their compound, stipulate leaves. The family is widely distributed, and is the third-largest land plant family in number of species, behind only the Orchidaceae and Asteraceae, with about 765 genera and nearly 20,000 known species.

<span class="mw-page-title-main">Faboideae</span> Subfamily of plants

The Faboideae are a subfamily of the flowering plant family Fabaceae or Leguminosae. An acceptable alternative name for the subfamily is Papilionoideae, or Papilionaceae when this group of plants is treated as a family.

Pongamia oil is derived from the seeds of the Millettia pinnata tree, which is native to tropical and temperate Asia. Millettia pinnata, also known as Pongamia pinnata or Pongamia glabra, is common throughout Asia and thus has many different names in different languages, many of which have come to be used in English to describe the seed oil derived from M. pinnata; Pongamia is often used as the generic name for the tree and is derived from the genus the tree was originally placed in. Other names for this oil include honge oil, kanuga oil, karanja oil, and pungai oil.

<i>Pongamia</i> Species of tree in the family Fabaceae

Pongamia pinnata is a species of tree in the pea family, Fabaceae, native to eastern and tropical Asia, Australia, and the Pacific islands. It is the sole species in genus Pongamia. It is often known by the synonym Millettia pinnata. Its common names include Indian beech and Pongame oiltree.

<i>Tylosema</i> Genus of legumes

The genus Tylosema is in the plant family Fabaceae and encompasses four accepted species of perennial legumes native to southern and central Africa. These are semi-woody viniferous plants broadly distributed from Sudan and Ethiopia south to Angola and South Africa. Coetzer and Ross originally described four Tylosema species:

<i>Millettia</i> Genus of legumes

Millettia is a genus of flowering plants in the family Fabaceae. It consists of about 169 species of shrubs, lianas or trees, which are native to tropical and subtropical regions of sub-Saharan Africa, the Indian subcontinent, Indochina, southern China, Malesia, and New Guinea. Typical habitats include tropical rain forest and seasonally-dry lowland and upland forest and forest margins, woodland, thicket, wooded grassland, and secondary vegetation.

<i>Rinorea</i> Genus of plants

Rinorea is a genus of plant in family Violaceae.

<i>Ficus thonningii</i> Species of fig

Ficus thonningii is a species of Ficus. It is native to Africa. It is commonly known as Mugumo to the Agikuyu or the Strangler Fig in common English. Recent phylogenetic analysis suggests it may be a species complex.

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

Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa, a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying properties, the other three being homoeriodictyol, its sodium salt, and sterubin.

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

Prenylated flavonoids or prenylflavonoids are a sub-class of flavonoids. They are widely distributed throughout the plant kingdom. Some are known to have phytoestrogenic or antioxidant properties. They are given in the list of adaptogens in herbalism. Chemically they have a prenyl group attached to their flavonoid backbone. It is usually assumed that the addition of hydrophobic prenyl groups facilitate attachment to cell membranes. Prenylation may increase the potential activity of its original flavonoid.

<i>Millettia thonningii</i> Species of legume

Millettia thonningii is a species in the genus Millettia. It is a molluscicide plant. It contains the isoflavone alpinumisoflavone that is thought to be an antischistosomal agent.

<i>Derris taiwaniana</i> Species of legume

Derris taiwaniana is a perennial climbing shrub belonging to the genus Derris. It is known by several synonyms, including Millettia pachycarpa and M. taiwaniana. It is widely used in traditional practices, such as for poisoning fish, agricultural pesticide, blood tonic, and treatments of cancer and infertility. The bark fiber is used for making strong ropes.

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

Barbigerone is one of a few pyranoisoflavones among several groups of isoflavones. It was first isolated from the seed of a leguminous plant Tephrosia barbigera; hence the name "barbigerone". Members of the genus Millettia are now known to be rich in barbigerone, including M. dielsiena, M. ferruginea, M. usaramensis, and M. pachycarpa. It has also been isolated from the medicinal plant Sarcolobus globosus. Barbigerone from S. globosus is validated to have significant antioxidant property. Barbigerone exhibits profound antiplasmodial activity against the malarial parasite Plasmodium falciparum. It is also demonstrated that it has anti-cancer potential as it causes apoptosis of murine lung-cancer cells.

<span class="mw-page-title-main">Sophoreae</span> Tribe of legumes

The tribe Sophoreae is one of the subdivisions of the plant family Fabaceae. Traditionally this tribe has been used as a wastebasket taxon to accommodate genera of Faboideae which exhibit actinomorphic, rather than zygomorphic floral symmetry and/or incompletely differentiated petals and free stamens. Various morphological and molecular analyses indicated that Sophoreae as traditionally circumscribed was polyphyletic. This led to a re-circumscription of Sophoreae, which resulted in the transfer of many genera to other tribes. This also necessitated the inclusion of two former tribes, Euchresteae and Thermopsideae, in the new definition of Sophoreae. Tribe Sophoreae, as currently circumscribed, consistently forms a monophyletic clade in molecular phylogenetic analyses. The Sophoreae arose 40.8 ± 2.4 million years ago.

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

Rotenoids are naturally occurring substances containing a cis-fused tetrahydrochromeno[3,4-b]chromene nucleus. Many have insecticidal and piscicidal activity, such as the prototypical member of the family, rotenone. Rotenoids are related to the isoflavones.

Rinorea welwitschii is a plant species in the genus Rinorea found in Africa.

<span class="mw-page-title-main">Inverted repeat-lacking clade</span> Group of flowering plants

The inverted repeat-lacking clade(IRLC) is a monophyletic clade of the flowering plant subfamily Faboideae (or Papilionaceae). Faboideae includes the majority of agriculturally-cultivated legumes. The name of this clade is informal and is not assumed to have any particular taxonomic rank like the names authorized by the ICBN or the ICPN. The clade is characterized by the loss of one of the two 25-kb inverted repeats in the plastid genome that are found in most land plants. It is consistently resolved in molecular phylogenies. The clade is predicted to have diverged from the other legume lineages 39.0±2.4 million years ago (in the Eocene). It includes several large, temperate genera such as AstragalusL., HedysarumL., MedicagoL., OxytropisDC., SwainsonaSalisb., and TrifoliumL..

<span class="mw-page-title-main">Genistoids</span> Clade of legumes

The Genistoids are one of the major radiations in the plant family Fabaceae. Members of this phylogenetic clade are primarily found in the Southern hemisphere. Some genera are pollinated by birds. The genistoid clade is consistently resolved as monophyletic in molecular phylogenetic analyses. It is estimated to have arisen 56.4 ± 0.2 million years ago. A node-based definition for the genistoids is: "the MRCA of Poecilanthe parviflora and Lupinus argenteus." One morphological synapomorphy has been tentatively identified: production of quinolizidine alkaloids. Some genera also accumulate pyrrolizidine. A new genus, to be segregated from Clathrotropis, has also been proposed to occupy an undetermined position within the genistoid clade.

Villosocallerya bonatiana is a species of flowering plant in the family Fabaceae, native to south-central and southeastern mainland China, Laos and Vietnam. It is the sole species in genus Villosocallerya. The species was first described in 1910 as Millettia bonatiana.

Millettia usaramensis is a tree or shrub belonging to the family Fabaceae. It has two known subspescies namely, Millettia usaramensis subsp. australis and ''Millettia usaramensis subsp. usaramensis.

References

  1. Stewart, M.; Bartholomew, B.; Currie, F.; Abbiw, D.K.; Latif, Z.; Sarker, S.D.; Nash, R.J. (2000). "Pyranoisoflavones from Rinorea welwitschii". Fitoterapia. 71 (5): 595–597. doi:10.1016/S0367-326X(00)00210-0. PMID   11449519.
  2. Perrett, S.; Whitfield, P.J.; Sanderson, L.; Bartlett, A. (1995). "The plant molluscicide Millettia thonningii (Leguminosae) as a topical antischistosomal agent". Journal of Ethnopharmacology. 47 (1): 49–54. doi:10.1016/0378-8741(95)01253-a. PMID   7564421.
  3. Perrett, Sheena; Whitfield, Philip J. (1995). "Aqueous degradation of isoflavonoids in an extract of Millettia thonningii (Leguminosae) which is larvicidal towards schistosomes". Phytotherapy Research. 9 (6): 401–404. doi:10.1002/ptr.2650090603. S2CID   85035592.