Tasumatrols P – T, Five New Taxoids from Taxus sumatrana

Abstract

The phytochemical investigation of the more polar fractions from the leaves and twigs of Taxus sumatrana (Taxaceae) afforded five new taxane diterpene esters, tasumatrols P–T (1–5) possessing an 11(15→1),11(10→9)‐diabeotaxane skeleton. Compounds 1, 4, and 5 contain an α‐hydroxy group at C(14), while 3 has no OH group at either C(13) or C(14). Compound 2 is a natural 4,5‐acetonide derivative, while 4 has an unusual spiro‐connected 2‐hydroxy‐2‐phenyl‐1,3‐dioxolane ring. Ten known taxoids, were also isolated in the course of the chromatographic fractionation. Five additional new O‐acetyl derivatives 3a, 4a, 4b, 5a, and 5b were prepared from the taxanes 3–5. The structures of all new compounds were established on the basis of their spectroscopic analyses. Compound 1 showed mild cytotoxic activity against human Hela and Daoy tumor cells.

Natural Taxanes: Developments Since 1828

“…This group of taxanes are often oxygenated at C-10 and esterified with a C-15-hydroxy group, sometimes with C-19-hydroxy group. Tasumatrol S ( 465 ) has a remarkable spiro-connected 2-hydroxy-2-pheny-1,3-dioxolane ring . This class of taxanes presumably arises from 10-dehydro-10-deacetylabeobaccatin III by benzyl–benzylic acid rearrangement of the α-dioxosystem .…”

“…It should be noted that compound wallifoliol ( 460 ) could isomerize intotasumatrol H ( 455 ) along with the migration of the C-4- O -acetyl to C-5 and hydroxylated at C-20 in CDCl 3 solution (Scheme ), but it was stable in acetone- d 6 solution at ambient temperature . In addition, Tasumatrol P ( 462 ) showed mild cytotoxic activity against human HeLa and Daoy tumor cells …”

Cytotoxic Activity of Taxus Sumatrana (Miq.) De Laub. Bark, Leaves, and Shoots on Hela, T47d, and McF-7/Her2 Cell Lines

“…Wallifoliol, taxuspine F, 13-Oacetyl wallifoliol, and taxumairol Q were from the leaves and twigs [9]. The tasumatrols A-Z were reported isolated from leaves and twigs [10][11][12][13][14][15]. The leaves and twigs also isolated Taiwantaxins A-D isolated [16] and other chemical compounds [17,18].…”

“…Some of the isolated compounds reported have cytotoxic activities. Among them are wallifoliol (KB and Hepa 59 T/VGH), taxuspine F, and 3, 6, 7, 10-deacetylbaccatin III (Hepa cells), tasumatrol F (A-498, NCI-H226, A549, and PC-3 tumor cells), Tasumatrols I and K (Hepa59T/VGH, NCI, HELA, DLD-1, and Med cell lines), tasumatrol P (HELA and Daoy tumor cells), tasumatrol Z (Hep2 cell line), and Taiwantaxin B (PC-3 tumor cells) [9][10][11][12][13][14][15][16][17]. The results of clinical studies also indicated that paclitaxelcontaining regimens on breast cancer patients provided additional benefits [19].…”

Tasumatrols U−Z, Taxane Diterpene Esters from Taxus sumatrana

“…(Taxaceae) growing in Taiwan. [9][10][11] Herein, we report the isolation of six new taxoids, tasumatrols U-Z (1)(2)(3)(4)(5)(6). Tasumatrols U, V, W, Y, and Z (1-3, 5, 6) possess an 11(15f1), 11(10f9)-bis-abeo-taxane skeleton, while tasumatrol X (4) has a 2(3f20)-abeo-taxane skeleton.…”