176
terpenoids in a limited number of the samples scrutinized (types 1 and 2) may be the
result of introgression from other species [36].
3.28 Ligularia hodgsonii J. D. Hooker
Ligularia hodgsonii is considered to be one of the oldest species within the genus
Ligularia and is distributed widely in China, Far Eastern Russia, Korea, and Japan
(Plate 21) [2]. An initial study on a Japanese sample was conducted by Takahashi’s
group, which led to the isolation of the furanoeremophilanes 160 and 212, the eremophilanolide 343, and bakkenolide A (629) (sample 2) [123–125] (Table 35). We
compared the chemical compositions of plant samples acquired in both Japan and
China. From Japanese samples collected in Hokkaido (samples 4 and 5) and Iwate
(sample 6), the 15-oxygenated furanoeremophilanes 199 and 212 were isolated [136].
From the workup of Chinese samples collected in Yunnan Province (samples 3
and 9), the furanoeremophilan-10-ols 244 and 246 were produced [136, 153].
Eremophilanolides 121, 390, 432, and 442 and the eremophilan-8-one 112 were also
isolated by Xu et al. from a sample collected in Yunnan Province (sample 11) [91]. In
contrast, eremophilanes were absent in samples collected in Sichuan Province, and
only the bisabolane 663 and γ-humulene (811) were detected (samples 7 and 8) [153].
Eremophilanes were isolated from L. hodgsonii samples collected in other locations.
From an Anhui sample (samples 13), compounds 374, 376, 377, 495, 496, 497, and
512 were obtained [191]. However, the structures proposed for compounds 377 and
495 are questionable, because unexpected NOEs inconsistent with the conformation
assigned were described. An eremophilane dimer 614 (biliguhodgsonolide), a
Table 33 Samples 1–9 of L. konkalingensis and their chemical constituents
No.
Specimen
number
Collection
place
Elevation
(m)
Aromatics Oplopanes Others Chemotype Ref.
1
2005-65
Luding (S) 3500
−
729, 730,
731, 732
−
2
[36]
2
2007-110 Xiangcheng
(S)
4600
959, 988,
989, 993
−
828
3
[36]
3
2007-70
Kangding
(S)
3700
979, 988,
989, 993
−
−
3
[36]
4
2007-75
Kangding
(S)
4300
979, 988,
989, 993
−
−
3
[36]
5
2009-54
Ganzi (S)
3700
989
−
828
3
[36]
6
2009-74
Dege (S)
4000
−
−
828
4
[36]
7
2009-93
Maerkang
(S)
3700
989
−
828
3
[36]
8
2011-82
Xinlong (S) 2900
988, 989
−
−
3
[126]
9
2012-10
Kangding
(S)
3800
−
−
828
4
[126]
M. Tori and C. Kuroda
terpenoids in a limited number of the samples scrutinized (types 1 and 2) may be the
result of introgression from other species [36].
3.28 Ligularia hodgsonii J. D. Hooker
Ligularia hodgsonii is considered to be one of the oldest species within the genus
Ligularia and is distributed widely in China, Far Eastern Russia, Korea, and Japan
(Plate 21) [2]. An initial study on a Japanese sample was conducted by Takahashi’s
group, which led to the isolation of the furanoeremophilanes 160 and 212, the eremophilanolide 343, and bakkenolide A (629) (sample 2) [123–125] (Table 35). We
compared the chemical compositions of plant samples acquired in both Japan and
China. From Japanese samples collected in Hokkaido (samples 4 and 5) and Iwate
(sample 6), the 15-oxygenated furanoeremophilanes 199 and 212 were isolated [136].
From the workup of Chinese samples collected in Yunnan Province (samples 3
and 9), the furanoeremophilan-10-ols 244 and 246 were produced [136, 153].
Eremophilanolides 121, 390, 432, and 442 and the eremophilan-8-one 112 were also
isolated by Xu et al. from a sample collected in Yunnan Province (sample 11) [91]. In
contrast, eremophilanes were absent in samples collected in Sichuan Province, and
only the bisabolane 663 and γ-humulene (811) were detected (samples 7 and 8) [153].
Eremophilanes were isolated from L. hodgsonii samples collected in other locations.
From an Anhui sample (samples 13), compounds 374, 376, 377, 495, 496, 497, and
512 were obtained [191]. However, the structures proposed for compounds 377 and
495 are questionable, because unexpected NOEs inconsistent with the conformation
assigned were described. An eremophilane dimer 614 (biliguhodgsonolide), a
Table 33 Samples 1–9 of L. konkalingensis and their chemical constituents
No.
Specimen
number
Collection
place
Elevation
(m)
Aromatics Oplopanes Others Chemotype Ref.
1
2005-65
Luding (S) 3500
−
729, 730,
731, 732
−
2
[36]
2
2007-110 Xiangcheng
(S)
4600
959, 988,
989, 993
−
828
3
[36]
3
2007-70
Kangding
(S)
3700
979, 988,
989, 993
−
−
3
[36]
4
2007-75
Kangding
(S)
4300
979, 988,
989, 993
−
−
3
[36]
5
2009-54
Ganzi (S)
3700
989
−
828
3
[36]
6
2009-74
Dege (S)
4000
−
−
828
4
[36]
7
2009-93
Maerkang
(S)
3700
989
−
828
3
[36]
8
2011-82
Xinlong (S) 2900
988, 989
−
−
3
[126]
9
2012-10
Kangding
(S)
3800
−
−
828
4
[126]
M. Tori and C. Kuroda