14.3.8 Phytochemistry and Pharmacological Activities
of A. Rupestris
14.3.8.1 Cytotoxicity Activity
Wang et al. isolated 10 alkaloids (288–297) from the ethanolic extract of A.
rupestris leaves (Fig. 14.52) and evaluated its cytotoxicity potentials (Wang et al.
2013). Cytotoxicity effects were evaluated in various cell lines, such as A-549,
HepG2, SMMC-7721, MCF-7, HL-60, BGC-823, and SW-480. Doxorubicin was
used as a positive control. (E)-16-formyl-5a-methoxystrictamine (296), scholarisin
I (288), and scholarisin VI (293) possessed significant cytotoxicity (IC 50
values < 30 µM) against all the tested tumor cell lines. Scholarisin IV (291) and
scholarisin V (292) were found to be non-cytotoxic (IC 50 > 80 µM). Structural
analysis indicated that these compounds lack a linkage between C-5 and N-4, hence
it is speculated that these bonds are essential for cytotoxicity. The remaining
compounds demonstrated moderate cytotoxicity (IC 50 values = 30–80 µM).
Zhang et al. isolated 6 monoterpenoid indole alkaloids (256, 261, 298–301) from
the ethanolic extract of A rupestris aerial parts (Fig. 14.53) and evaluated its cytotoxic
potential (Zhang et al. 2014a). Cytotoxic activity was evaluated in seven head and
neck squamous cell carcinomas (CAL-27, Detroit-562, Hep-2, SCL-1, SCC-PKU,
TCA-83, and UMSCC-1). Doxorubicin was used as positive control (IC 50 values in
the range of 14.7–35.4 nM). Among the screened compounds, 11-hydroxy-6,7epoxy-8-oxovincadifformine (256) 6,7-epoxy-8-oxo-vincadifformine (298), and
11-acetyl-6,7-epoxy-8-oxo-vincadifformine (299) exhibited significant cytotoxicity
(3R,5S,7R,15R,16R,19E)Scholarisine F (295)
N
O
N
O
O
O
H
(E)-16-Formyl-5 -
methoxystrictamine (296)
3-Epidihydrocorymine (297)
N
OH
O
O
OH
N
Scholarisin I (288); R = CHO
Scholarisin II (289); R = CH 2 OH
Scholarisin III (290); R = OCOCH 3
N
N
R
O
O
O
O
H
Scholarisin IV (291)
O
NH
N
H
O
O
O
O
Scholarisin V (292)
O
NH
N
H
O
O
O
O
Scholarisin VI (293)
N
O
O
O
OH
N
Scholarisin VII (294)
N
N
O
OH
O
O
N
N
H
COOMe
OHC
OMe
Fig. 14.52 Chemical structures of various alkaloids from A. rupestris (288–297)
14 Pharmaceutical Application of Bio-actives …
513
of A. Rupestris
14.3.8.1 Cytotoxicity Activity
Wang et al. isolated 10 alkaloids (288–297) from the ethanolic extract of A.
rupestris leaves (Fig. 14.52) and evaluated its cytotoxicity potentials (Wang et al.
2013). Cytotoxicity effects were evaluated in various cell lines, such as A-549,
HepG2, SMMC-7721, MCF-7, HL-60, BGC-823, and SW-480. Doxorubicin was
used as a positive control. (E)-16-formyl-5a-methoxystrictamine (296), scholarisin
I (288), and scholarisin VI (293) possessed significant cytotoxicity (IC 50
values < 30 µM) against all the tested tumor cell lines. Scholarisin IV (291) and
scholarisin V (292) were found to be non-cytotoxic (IC 50 > 80 µM). Structural
analysis indicated that these compounds lack a linkage between C-5 and N-4, hence
it is speculated that these bonds are essential for cytotoxicity. The remaining
compounds demonstrated moderate cytotoxicity (IC 50 values = 30–80 µM).
Zhang et al. isolated 6 monoterpenoid indole alkaloids (256, 261, 298–301) from
the ethanolic extract of A rupestris aerial parts (Fig. 14.53) and evaluated its cytotoxic
potential (Zhang et al. 2014a). Cytotoxic activity was evaluated in seven head and
neck squamous cell carcinomas (CAL-27, Detroit-562, Hep-2, SCL-1, SCC-PKU,
TCA-83, and UMSCC-1). Doxorubicin was used as positive control (IC 50 values in
the range of 14.7–35.4 nM). Among the screened compounds, 11-hydroxy-6,7epoxy-8-oxovincadifformine (256) 6,7-epoxy-8-oxo-vincadifformine (298), and
11-acetyl-6,7-epoxy-8-oxo-vincadifformine (299) exhibited significant cytotoxicity
(3R,5S,7R,15R,16R,19E)Scholarisine F (295)
N
O
N
O
O
O
H
(E)-16-Formyl-5 -
methoxystrictamine (296)
3-Epidihydrocorymine (297)
N
OH
O
O
OH
N
Scholarisin I (288); R = CHO
Scholarisin II (289); R = CH 2 OH
Scholarisin III (290); R = OCOCH 3
N
N
R
O
O
O
O
H
Scholarisin IV (291)
O
NH
N
H
O
O
O
O
Scholarisin V (292)
O
NH
N
H
O
O
O
O
Scholarisin VI (293)
N
O
O
O
OH
N
Scholarisin VII (294)
N
N
O
OH
O
O
N
N
H
COOMe
OHC
OMe
Fig. 14.52 Chemical structures of various alkaloids from A. rupestris (288–297)
14 Pharmaceutical Application of Bio-actives …
513