79
10H-eremophilanolides (345, 359, 360, 361, and 363), a 10-OH lactone (407), two
1β,10β-epoxides (471 and 481), and three noreremophilanes (98, 103, and 114)
were isolated from sample 38 [87, 184, 196]. Sample 39 produced noreremophilane
104 as well as compound 345 [89].
3.2 Ligularia dentata (A. Gray) H. Hara
Bohlmann and his associates studied the chemical constituents of many Ligularia
species, among which L. dentata afforded isohumulene (812) as a major constituent (sample 1, Table 5) [13]. 3α-Angeloyloxy-9β-hydroxyeremophil-11-en-8-one
(59), liguhodgsonal (125), the hydrocarbon 875, two germacranes (758 and 769),
and the enyne compound 883 were isolated from sample 1 collected at a botanical
garden in Berlin [13]. Naya et al. reported that ligudentatol (118), 2-hydroxyplatyphyllide (121), ligujapone (123), liguhodgsonal (125), ligucyperonol (802), and
caryophyllene (809) were isolated from Japanese sample 2 [95]. Gao et al. published the isolation of chemical constituents from sample 3, collected in Gansu
Province, China. Ligudentatol (118), 2-hydroxyplatyphyllide (121), ligujapone
(123), liguhodgsonal (125), ligudentatin A (126), ligudentatin B (127), three bisabolanes (671, 672, and 673), and a diphenyl ether (1012) were all isolated from
sample 3 [94, 97].
Table 5 Samples 1–5 of L. dentata and their chemical constituents
No.
Collection
year
Collection
place
Bicyclic
eremophilanes Bisabolanes
Aromatics Others Ref.
1
1977
Berlin
(Germany)
59, 125
−
−
758,
769,
812,
875,
883
[13]
2
a
Nagano
(Japan)
118, 121, 123,
125, 802
−
−
809
[95]
3
1992
Zhang (G) 118, 121, 123,
125, 126, 127
671, 672, 673 1012
−
[94,
97]
4
2004
Sendai
(Japan)
−
664, 669, 670,
716, 720, 721,
722, 723, 724
−
803,
890,
894,
896
[102,
234]
5
2004
Sendai
(Japan)
−
−
908, 927,
931, 935,
937
828,
860,
898
[248]
a
Not described
Chemical Constituents of Ligularia Species (Asteraceae) and Their Diversity…
10H-eremophilanolides (345, 359, 360, 361, and 363), a 10-OH lactone (407), two
1β,10β-epoxides (471 and 481), and three noreremophilanes (98, 103, and 114)
were isolated from sample 38 [87, 184, 196]. Sample 39 produced noreremophilane
104 as well as compound 345 [89].
3.2 Ligularia dentata (A. Gray) H. Hara
Bohlmann and his associates studied the chemical constituents of many Ligularia
species, among which L. dentata afforded isohumulene (812) as a major constituent (sample 1, Table 5) [13]. 3α-Angeloyloxy-9β-hydroxyeremophil-11-en-8-one
(59), liguhodgsonal (125), the hydrocarbon 875, two germacranes (758 and 769),
and the enyne compound 883 were isolated from sample 1 collected at a botanical
garden in Berlin [13]. Naya et al. reported that ligudentatol (118), 2-hydroxyplatyphyllide (121), ligujapone (123), liguhodgsonal (125), ligucyperonol (802), and
caryophyllene (809) were isolated from Japanese sample 2 [95]. Gao et al. published the isolation of chemical constituents from sample 3, collected in Gansu
Province, China. Ligudentatol (118), 2-hydroxyplatyphyllide (121), ligujapone
(123), liguhodgsonal (125), ligudentatin A (126), ligudentatin B (127), three bisabolanes (671, 672, and 673), and a diphenyl ether (1012) were all isolated from
sample 3 [94, 97].
Table 5 Samples 1–5 of L. dentata and their chemical constituents
No.
Collection
year
Collection
place
Bicyclic
eremophilanes Bisabolanes
Aromatics Others Ref.
1
1977
Berlin
(Germany)
59, 125
−
−
758,
769,
812,
875,
883
[13]
2
a
Nagano
(Japan)
118, 121, 123,
125, 802
−
−
809
[95]
3
1992
Zhang (G) 118, 121, 123,
125, 126, 127
671, 672, 673 1012
−
[94,
97]
4
2004
Sendai
(Japan)
−
664, 669, 670,
716, 720, 721,
722, 723, 724
−
803,
890,
894,
896
[102,
234]
5
2004
Sendai
(Japan)
−
−
908, 927,
931, 935,
937
828,
860,
898
[248]
a
Not described
Chemical Constituents of Ligularia Species (Asteraceae) and Their Diversity…