Combretastatin B-1

Last updated
Combretastatin B-1
Combretastatin B-1.svg
Names
Preferred IUPAC name
3-Methoxy-6-[2-(3,4,5-trimethoxyphenyl)ethyl]benzene-1,2-diol
Other names
Combretastatin B1
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C18H22O6/c1-21-13-8-7-12(16(19)17(13)20)6-5-11-9-14(22-2)18(24-4)15(10-11)23-3/h7-10,19-20H,5-6H2,1-4H3
    Key: ZSNYQENLWQYSRK-UHFFFAOYSA-N
  • InChI=1/C18H22O6/c1-21-13-8-7-12(16(19)17(13)20)6-5-11-9-14(22-2)18(24-4)15(10-11)23-3/h7-10,19-20H,5-6H2,1-4H3
    Key: ZSNYQENLWQYSRK-UHFFFAOYAW
  • COC1=C(C(=C(C=C1)CCC2=CC(=C(C(=C2)OC)OC)OC)O)O
  • O(c1cc(cc(OC)c1OC)CCc2ccc(OC)c(O)c2O)C
Properties
C18H22O6
Molar mass 334.368 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Combretastatin B-1 is a combretastatin and a dihydrostilbenoid. It can be found in Combretum caffrum , the Eastern Cape South African bushwillow tree [1] or in Combretum kraussii , the forest bushwillow. [2]

It can be produced by selective hydrogenation of combretastatin A-1. [1]

It is a potent inhibitor of microtubule assembly in vitro . [1]

Related Research Articles

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Combretum imberbe is a characteristic and often impressive bushwillow species of the southern Afrotropics. The medium to large tree has a sparse, semi-deciduous canopy of grey-green leaves. The twigs and leaves are hairless as the name imberbe suggests. Its heartwood is dark brown, close-grained, and very hard and heavy, as suggested by its vernacular name. The durable heartwood is much sought after in the woodcarving industry. The Hereros and Ovambos of Namibia attach special cultural and religious significance to the tree, as to them it is the great ancestor of all animals and people, which must be passed with respect.

<i>Combretum</i> Genus of plants in Combretaecae family

Combretum, the bushwillows or combretums, make up the type genus of the family Combretaceae. The genus comprises about 272 species of trees and shrubs, most of which are native to tropical and southern Africa, about 5 to Madagascar, but there are others that are native to tropical Asia, New Guinea and the Bismarck Archipelago, Australia, and tropical America. Though somewhat reminiscent of willows (Salix) in their habitus, they are not particularly close relatives of these.

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Combretum caffrum, commonly known as Cape bushwillow, is a species of tree native to South Africa. It is endemic to the Cape Provinces.

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

Combretastatin is a dihydrostilbenoid found in Combretum caffrum.

<i>Combretum edwardsii</i> Species of flowering plant

Combretum edwardsii, the Natal combretum or forest climbing bushwillow, is an uncommon forest plant endemic to the mistbelt region of eastern South Africa. It has a climbing habit and the stems may often lie prostrate on the forest floor or on cliff tops. As with some other Combretum species the leaves assume autumn colours before they are shed. The plant flowers in spring and the 4-winged fruits reach maturity in late summer.

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A mitotic inhibitor, microtubule inhibitor, or tubulin inhibitor, is a drug that inhibits mitosis, or cell division, and is used in treating cancer, gout, and nail fungus. These drugs disrupt microtubules, which are structures that pull the chromosomes apart when a cell divides. Mitotic inhibitors are used in cancer treatment, because cancer cells are able to grow through continuous division that eventually spread through the body (metastasize). Thus, cancer cells are more sensitive to inhibition of mitosis than normal cells. Mitotic inhibitors are also used in cytogenetics, where they stop cell division at a stage where chromosomes can be easily examined.

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<span class="mw-page-title-main">Combretastatin A-4</span> Chemical compound

Combretastatin A-4 is a combretastatin and a stilbenoid. It can be isolated from Combretum caffrum, the Eastern Cape South African bushwillow tree or in Combretum leprosum, the mofumbo, a species found in Brazil.

<span class="mw-page-title-main">Combretastatin A-1</span> Chemical compound

Combretastatin A-1 is a combretastatin and a stilbenoid. It can be found in Combretum caffrum, the Eastern Cape South African Bushwillow tree.

<i>Combretum kraussii</i> Species of tree

Combretum kraussii, the forest bushwillow, is a medium-sized to large tree of eastern South Africa, Eswatini and southern Mozambique, which is found within, or in the vicinity of forests. The specific name commemorates Dr. F. Krauss who undertook a collecting trip to South Africa from 1838 to 1840.

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<i>Combretum molle</i> Species of tree

Combretum molle, the velvet bushwillow, is a medium to large tree species in the genus Combretum found in western, eastern and southern Africa.

C. kraussii may refer to:

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Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.

<i>Combretum apiculatum</i> Species of flowering plant

Combretum apiculatum is a species of tree in the family Combretaceae known by the common name red bushwillow. It is native to the mesic to semi-arid savanna regions of Africa, southwards of the equator.

<i>Combretum mkuzense</i> Species of tree

Combretum mkuzense, commonly known as the Maputaland bushwillow, is a deciduous shrub or small tree that is native to a restricted area in the lowlands of eastern South Africa and southern Mozambique. It is similar in appearance to the large-fruited bushwillow.

Photostatins are inhibitors that can be switched on and off in vivo by visible light, to optically control microtubule dynamics. Photostatins are a form of photopharmacology.

<i>Combretum zeyheri</i> Species of plant

Combretum zeyheri, the large-fruited bushwillow or Zeyher's bushwillow, is a species of flowering plant in the family Combretaceae, usually found growing on acidic or sandy soils in tropical African savannas. A small to medium-sized tree, its roots are used as a source of material for making baskets and as a traditional medicine for haemorrhoids.

References

  1. 1 2 3 Pettit, G. R.; Singh, S. B.; Niven, M. L.; Hamel, E.; Schmidt, J. M. (1987). "Isolation, Structure, and Synthesis of Combretastatins A-1 and B-1, Potent New Inhibitors of Microtubule Assembly, Derived from Combretum caffrum". Journal of Natural Products. 50 (1): 119–131. doi:10.1021/np50049a016. PMID   3598594.
  2. Bridget K Brookes, Olga V Doudoukina, Lynn C Katsoulis and Joy H D Veale (1999). "Uteroactive constituents from Combretum kraussii". South African Journal of Chemistry. 52 (4): 127.{{cite journal}}: CS1 maint: multiple names: authors list (link)