Anwuweizonic acid and manwuweizic acid, the putative anticancer active principle of Schisandra propinqua

Abstract

The structures of two new triterpenoid acids, anwuweizonic acid (1) and manwuweizic acid (2), from Schisandra propinqua are elucidated by spectroscopic evidence and chemical correlation. Compound 2 shows significant inhibitory activity against Lewis lung cancer, brain tumor-22, and solid hepatoma in mice, and exhibits no cytotoxic action in vitro.

Inhibition of Tumor-Promoting Effects by Poricoic Acids G and H and Other Lanostane-Type Triterpenes and Cytotoxic Activity of Poricoic Acids A and G from Poria cocos

“…Thus far, only two 3,4-seco-lanost-8-enes have been reported as natural products: manwuweizic acid from Schisandra propinqua 19 and Kadsura heteroclita, 20 and schisanlactone F from K. longipeduaculata. 21 The inhibitory effects of nine lanostane-type triterpenes, 1-9, and one abietane-type diterpene, 10, on EBV-EA activation induced by TPA were examined as a preliminary evaluation of their potential to inhibit tumor-promoting activities, and the results are shown in Table 2.…”

Lignans and Triterpenoids from the Stems of Kadsura induta

“…The 1 H-NMR spectrum ( Table 3) showed an angelic acid unit (d(H) 6.10, t, J ¼ 7.4, HÀC(24); d(H) 1.92, s, Me(27)), two secondary Me groups (d(H) 1.12, d, J ¼ 6.8; d(H) 0.95, d, J ¼ 6.3), four tertiary Me groups (d(H) 0.97, 0.94, 1.05, and 1.10, each s). These features resembled those of anwuweizonic acid (5) [16], suggesting that 3 was also a lanostane triterpenoid acid.…”

“…1) with CH 2 (1) at d(H) 2.35 and 2.65 (dd, J ¼ 5.5, 17.2, 1 H each), was assigned to HÀC (8). The aromatic H-atom signal at d(H) 6.23 (s, 1 H), which showed a HMBC cross-peak with C(4) at d(C) 47.2 and a ROESY cross-peak with MeOÀC(15) at d(H) 3.86 (s, 3 H), was assigned to HÀC (16). The third aromatic H-atom signal at d(H) 6.11 was due to HÀC(12) on the basis of a HMBC with C(4).…”

“…HMBC of Me (19) at d(H) 0.97 with C(9) at d(C) 134.2, HÀC(7) at d(H) 2.08 -2.14 and 2.00 -2.06, HÀC(11) at d(H) 1.72 -1.76 and 2.16 -2.20 with C(8) at d(C) 135.7 and C(9) suggested a C(8)¼C(9) bond, as in anwuweizonic acid. Comparison of the 1 H-NMR spectra of 3 and anwuweizonic acid showed that the C(13) tertiary Me signal present in the latter at d(H) 0.71 (Me (18) The known compounds were identified as kadsuphilin B [18], anwuweizonic acid [16], epianwuweizic acid [19] and (24Z)-12a-hydroxy-3-oxolanosta-8,24-dien-26-oic acid [20] by comparison of the CD, UV, IR, and NMR data with those reported. All the known compounds were isolated from K. induta for the first time.…”

Cytotoxic and potential anticancer constituents from the stems ofSchisandra pubescens

“…Structures of compounds 1-9. DOI: 10.3109/13880209.2013.818039 five known triterpenoids: micranoic acid B (5) (Li et al, 2003), lancifodilactone H (6) , coccinic acid (7) (Li & Xue, 1986), schisanlactone B (8) (Liu et al, 1983) and anwuweizonic acid (9) (Liu et al, 1988a). Their structures are shown in Figure 1.…”