201
From the Chinese L. nanchuanica S.W. Liu (sample 9 from Chingqing City,
China) liguhodgsonal (125), ligudentatin A (126), and two tritepenes (828 and 829)
were isolated [104].
Ligularia purdomii (Turrill) Chittenden (sample 10 from Qinghai Province) produced 372 and 491 and 12 aromatic derivatives (904, 909, 919, 926, 930, 940, 952,
959, 989, 1038, 1039, and 1041) as well as lupeol (828) [190]. The dilactone 491
resulted from the cyclization of acid 372.
Ligularia odontomanes Handel-Mazzetti (sample 11 from Sichuan Province)
produced euparin (952), and the other aromatic compounds 907, 954, 957, and 962,
with three triterpenoids (828, 837, and 838), two noreremophilanes (123 and 125),
and a eudesmane derivative (795) [100]. These isolated secondary metabolites were
similar to those obtained from L. veitchiana or L. latihastata (Sects. 3.23 and 3.31).
L. odontomanes is closely related taxonomically to L. latihastata [2].
Three benzofurans (942, 948, and 954), (−)-germacrene D (758), and cis-βocimene (875) were isolated from L. sibirica (Linnaeus) Cassini (sample 12 from
Halle, Germany) [13]. Ishii et al. studied L. sibirica (from Japan) in 1965 and
found ligularol (161) and ligularone (168) [11], although this species was later
revised taxonomically to L. fischeri (Ledebour) Turczaninow (Sect. 3.23,
Table 26) [50].
Ligularia thomsonii (C. B. Clarke) Pojarkova from Pakistan (sample 13) produced 12 aromatic compounds (903, 904, 905, 921, 922, 923, 926, 1015, 1016,
1017, 1018, and 1035), of which five were glucosides [258].
The six species mentioned above may be seen in common to produce aromatic
compounds. Lupeol (828) was isolated from three species listed in Table 46. It is
still not obvious why lupeol (828), among the many triterpenoids biosynthesized in
the plant kingdom, is found so frequently in Ligularia.
3.40 Further Ligularia Species III: L. angusta (Nakai)
Kitamura, L. calthifolia Maximowicz, L. fauriei
(Franchet) Koidzumi, L. hiberniflorum (Makino)
Kitamura, L. kangtingensis S. W. Liu, L. lingiana
S. W. Liu, L. myriocephala Y. Ling ex S. W. Liu,
L. platyglossa (Franchet) Handel-Mazzetti,
and L. schmidtii (Maximowicz) Makino
Furanoeremophilan-15,6-olide (212) was isolated from L. angusta (Nakai) Kitamura
(sample 14 from Tokyo, Japan) (Table 48) [139].
Ligularia calthifolia Maximowicz (sample 15) produced six glucosides of
eremophil- 11-en-2-one derivatives (81, 82, 84, 90, 91, and 92) [83]. Glycosides of
terpenoids have rarely been isolated so far from Ligularia species (Fig. 5).
Takahashi’s group studied the chemical constituents of Japanese L. fauriei
(Franchet) Koidzumi (sample 16 from Iwate Prefecture, Japan). Five lactones, 212,
Chemical Constituents of Ligularia Species (Asteraceae) and Their Diversity…
From the Chinese L. nanchuanica S.W. Liu (sample 9 from Chingqing City,
China) liguhodgsonal (125), ligudentatin A (126), and two tritepenes (828 and 829)
were isolated [104].
Ligularia purdomii (Turrill) Chittenden (sample 10 from Qinghai Province) produced 372 and 491 and 12 aromatic derivatives (904, 909, 919, 926, 930, 940, 952,
959, 989, 1038, 1039, and 1041) as well as lupeol (828) [190]. The dilactone 491
resulted from the cyclization of acid 372.
Ligularia odontomanes Handel-Mazzetti (sample 11 from Sichuan Province)
produced euparin (952), and the other aromatic compounds 907, 954, 957, and 962,
with three triterpenoids (828, 837, and 838), two noreremophilanes (123 and 125),
and a eudesmane derivative (795) [100]. These isolated secondary metabolites were
similar to those obtained from L. veitchiana or L. latihastata (Sects. 3.23 and 3.31).
L. odontomanes is closely related taxonomically to L. latihastata [2].
Three benzofurans (942, 948, and 954), (−)-germacrene D (758), and cis-βocimene (875) were isolated from L. sibirica (Linnaeus) Cassini (sample 12 from
Halle, Germany) [13]. Ishii et al. studied L. sibirica (from Japan) in 1965 and
found ligularol (161) and ligularone (168) [11], although this species was later
revised taxonomically to L. fischeri (Ledebour) Turczaninow (Sect. 3.23,
Table 26) [50].
Ligularia thomsonii (C. B. Clarke) Pojarkova from Pakistan (sample 13) produced 12 aromatic compounds (903, 904, 905, 921, 922, 923, 926, 1015, 1016,
1017, 1018, and 1035), of which five were glucosides [258].
The six species mentioned above may be seen in common to produce aromatic
compounds. Lupeol (828) was isolated from three species listed in Table 46. It is
still not obvious why lupeol (828), among the many triterpenoids biosynthesized in
the plant kingdom, is found so frequently in Ligularia.
3.40 Further Ligularia Species III: L. angusta (Nakai)
Kitamura, L. calthifolia Maximowicz, L. fauriei
(Franchet) Koidzumi, L. hiberniflorum (Makino)
Kitamura, L. kangtingensis S. W. Liu, L. lingiana
S. W. Liu, L. myriocephala Y. Ling ex S. W. Liu,
L. platyglossa (Franchet) Handel-Mazzetti,
and L. schmidtii (Maximowicz) Makino
Furanoeremophilan-15,6-olide (212) was isolated from L. angusta (Nakai) Kitamura
(sample 14 from Tokyo, Japan) (Table 48) [139].
Ligularia calthifolia Maximowicz (sample 15) produced six glucosides of
eremophil- 11-en-2-one derivatives (81, 82, 84, 90, 91, and 92) [83]. Glycosides of
terpenoids have rarely been isolated so far from Ligularia species (Fig. 5).
Takahashi’s group studied the chemical constituents of Japanese L. fauriei
(Franchet) Koidzumi (sample 16 from Iwate Prefecture, Japan). Five lactones, 212,
Chemical Constituents of Ligularia Species (Asteraceae) and Their Diversity…