Taxacin

A comparative optical aggregometry study of antiplatelet activity of taxanes from Taxus cuspidata.[Pubmed:20170941]

Thromb Res. 2010 Jun;125(6):e281-4.

Platelets are highly reactive components of the circulatory system. The cytoskeleton of a platelet is an important structure for platelet aggregation as stimulated by several agonists. An anticancer agent, taxol, has been suggested to exert platelet anti-aggregating activity by stabilizing microtubules during the aggregation process. An activity-guided fractionation was performed with a methanol extract of the leaves and twigs of Taxus cuspidata to isolate taxanes with platelet anti-aggregating effects. Compounds 1 to 7 - taxinine (1), taxinine A (2), taxinine B (3), 2-deacetoxytaxinine B (4), Taxacin (5), taxchinin B (6), and taxol (7) - were obtained as the antiplatelet components of this plant. These taxane compounds present the possibility of securing new antiplatelet compounds which differ from currently available antiplatelet agents in chemical structure and possibly in mechanisms of action. All compounds showed stronger inhibitory effects than acetylsalicylic acid (ASA) on platelet aggregation induced by arachidonic acid (AA) (IC(50): 14.4, 64.5, 35.5, 16.0, 21.9, 28.6 and 48.2 versus 63.0microM) or U46619 (IC(50): 34.8, 24.9, 36.2, 35.0, 46.9, 71.9 and 68.7 versus 340microM). Compounds 1, 3, 4 and 5, with a cinnamoyl group at the C(5) position, showed strong inhibitory effects against AA-induced aggregation compared to compound 2 (with an -OH group at C(5)) or compounds with an oxetane ring at C(4),(5), such as compounds 6 and 7. All of the seven compounds were 5-13-fold more strongly inhibitory than ASA against U46619-induced aggregation.

New taxoids from the seeds of taxus chinensis[Pubmed:9917305]

J Nat Prod. 1999 Jan;62(1):149-51.

Two new taxoids, 2alpha-acetoxy-2',7-dideacetoxyaustrospicatine (1) and decinnamoyltaxinine E (2), have been isolated from the extracts of the seeds of the Chinese yew Taxus chinensis (Pilg.) Rehd. in addition to taxuspine Z (3), taxin B (4), taxezopidine G (5), 7, 2'-bisdeacetoxyaustropicatine (6), 5alpha-cinnamoyl-9alpha,10beta, 13alpha-triacetoxytaxa-4(20),11-diene (7), taxachitriene A, 20-deacetyltaxachitriene A, 13-O-acetylbrevifoliol, taxinines A and J, and Taxacin. The structures of these compounds were elucidated on the basis of spectral analysis and chemical derivatizations.

Effect of seven tricyclic diterpenoids from needles of Taxus media var. Hicksii on stimulus-induced superoxide generation, tyrosyl or serine/threonine phosphorylation and translocation of cytosolic compounds to the cell membrane in human neutrophils.[Pubmed:19288401]

Planta Med. 2009 Jun;75(8):814-22.

Taxol has been widely used as an anticancer drug for ovarian, breast, lung and prostate cancer. Some kinds of Taxus plants are widely distributed in the Northeast Asia region. We have isolated seven tricyclic diterpenoids, taxinine, taxagifine, 5-O-cinnamoylTaxacin I triacetate, 5-decinnamoyltaxinine J, 5-cinnamoyl-9-acetyltaxicin I, Taxacin and taxol from the needles of Taxus media var. Hicksii, and investigated their effects on stimulus-induced superoxide generation and translocation of cytosolic compounds to the cell membrane in human neutrophils. Six tricyclic diterpenoids used in this experiment suppressed the superoxide generation induced by N-formyl-methionyl-leucyl-phenylalanine (fMLP) and arachidonic acid (AA) in a concentration-dependent manner. Taxinine significantly suppressed the superoxide generation induced by phorbol 12-myristate 13-acetate (PMA). The compounds also suppressed fMLP- and AA-induced tyrosyl or PMA-induced serine/threonine phosphorylation, and translocation of cytosolic compounds, p47 (phox), p67 (phox) and Rac to the cell membrane in parallel with the suppression of the stimulus-induced superoxide generation.