204
Ligularia myriocephala Y. Ling ex S.W. Liu (sample 21 from Teibei) was
investigated, and the bicyclic eremophilane methyl ester 45, 8β,10βdihydroxyeremophilan- 12,8α-olide (393), and four polyoxygenated eremophilanolides (408, 409, 410 (major constituent), and 411) were isolated [72]. All these
compounds except for 393 have a 1β-angeloyloxy substituent and all except 45 a
hydroxy group at C-10. Sample 22 afforded compounds 410 and 411 [197].
Ligularia platyglossa (Franchet) Handel-Mazzetti (sample 23 from Yunnan
Province) produced the 10-OH lactone 418, two 1(10)-ene compounds (276 and
464), the 9-ene lactone 446 (the major constituent), and a dimeric lactone 611, as
well as a eudesmane, 804 [160]. The dimeric compound, 611, was connected
between the 2- and 8-positions of eremophilatrienolide units. Both compounds
418 and 446 possess a 1-oxo group and compound 464 an enolic hydroxy
group at C-1.
Bohlmann and Knoll reported the chemical constituents of L. schmidtii
(Maximowicz) Makino (sample 24) [20]. Ligularol (161) was found to be a major
constituent, and a furanoeremophilane (160), two 15-oic acids (202 and 204), and a
hydrocarbon (877) were isolated.
3.41 Further Ligularia Species IV: L. brachyphylla
Handel- Mazzetti (= L. latihastata), L. calthifolia
(Maximowicz) Diels, L. clivorum Maximowicz (=
L. dentata), L. sachalinensis Nakai, L. tangutica
(Maximowicz) Bergmans, L. trichocephala (Maximowicz)
Matsumura et Koidzumi, and L. vorobierii Worosh
Bohlmann and his group reported on the chemical composition of some rare
Ligularia species in 1977 (Table 49), and their results may be mentioned here [13].
From L. brachyphylla Handel-Mazzetti (= L. latihastata) [2] (sample 25), humulene
(812) was isolated as a major constituent, and four germacranes (758, 769, 770, and
771), the noraldehyde, liguhodgsonal (125), cis-β-ocimene (875), and the polyacetylene 883 also were identified.
L. calthifolia (Maximowicz) Diels (sample 26) produced two
10H-furanoeremophilan-15,6-olides (212 and 218), bakkenolide A (629), and cis-βocimene (875) (found as the major constituent). These two species were collected at
botanical gardens in Giesen and Munich, Germany, respectively [13].
Liguhodgsonal (125), (−)-germacrene D (758), a germacrane ketone (769)
(major constituent), and cis-β-ocimene (875) were isolated from L. clivorum
Maximowicz (= L. dentata) [2], collected in Nijmegen, The Netherlands (sample
27) [13].
Sample 28 of L. sachalinensis Nakai collected in Munich, Germany, produced
the 10-OH furanoeremophilane 232, four 1,10-epoxyfuranoeremophilanes (290,
291, 293, and 296), (−)-germacrene D (758), and cis-β-ocimene (875) [13].
M. Tori and C. Kuroda
Ligularia myriocephala Y. Ling ex S.W. Liu (sample 21 from Teibei) was
investigated, and the bicyclic eremophilane methyl ester 45, 8β,10βdihydroxyeremophilan- 12,8α-olide (393), and four polyoxygenated eremophilanolides (408, 409, 410 (major constituent), and 411) were isolated [72]. All these
compounds except for 393 have a 1β-angeloyloxy substituent and all except 45 a
hydroxy group at C-10. Sample 22 afforded compounds 410 and 411 [197].
Ligularia platyglossa (Franchet) Handel-Mazzetti (sample 23 from Yunnan
Province) produced the 10-OH lactone 418, two 1(10)-ene compounds (276 and
464), the 9-ene lactone 446 (the major constituent), and a dimeric lactone 611, as
well as a eudesmane, 804 [160]. The dimeric compound, 611, was connected
between the 2- and 8-positions of eremophilatrienolide units. Both compounds
418 and 446 possess a 1-oxo group and compound 464 an enolic hydroxy
group at C-1.
Bohlmann and Knoll reported the chemical constituents of L. schmidtii
(Maximowicz) Makino (sample 24) [20]. Ligularol (161) was found to be a major
constituent, and a furanoeremophilane (160), two 15-oic acids (202 and 204), and a
hydrocarbon (877) were isolated.
3.41 Further Ligularia Species IV: L. brachyphylla
Handel- Mazzetti (= L. latihastata), L. calthifolia
(Maximowicz) Diels, L. clivorum Maximowicz (=
L. dentata), L. sachalinensis Nakai, L. tangutica
(Maximowicz) Bergmans, L. trichocephala (Maximowicz)
Matsumura et Koidzumi, and L. vorobierii Worosh
Bohlmann and his group reported on the chemical composition of some rare
Ligularia species in 1977 (Table 49), and their results may be mentioned here [13].
From L. brachyphylla Handel-Mazzetti (= L. latihastata) [2] (sample 25), humulene
(812) was isolated as a major constituent, and four germacranes (758, 769, 770, and
771), the noraldehyde, liguhodgsonal (125), cis-β-ocimene (875), and the polyacetylene 883 also were identified.
L. calthifolia (Maximowicz) Diels (sample 26) produced two
10H-furanoeremophilan-15,6-olides (212 and 218), bakkenolide A (629), and cis-βocimene (875) (found as the major constituent). These two species were collected at
botanical gardens in Giesen and Munich, Germany, respectively [13].
Liguhodgsonal (125), (−)-germacrene D (758), a germacrane ketone (769)
(major constituent), and cis-β-ocimene (875) were isolated from L. clivorum
Maximowicz (= L. dentata) [2], collected in Nijmegen, The Netherlands (sample
27) [13].
Sample 28 of L. sachalinensis Nakai collected in Munich, Germany, produced
the 10-OH furanoeremophilane 232, four 1,10-epoxyfuranoeremophilanes (290,
291, 293, and 296), (−)-germacrene D (758), and cis-β-ocimene (875) [13].
M. Tori and C. Kuroda