Four eremophil-9-en-8-one derivatives from cremanthodium stenactinium samples collected in China

Molecules

Volumn 16, Issue 12, 2011, Pages 10645-10652

  Saito, Yoshinori ^a   Ichihara, Mayu ^a   Okamoto, Yasuko ^a   Gong, Xun ^b   Kuroda, Chiaki ^c   Tori, Motoo ^a  

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b KUNMING INSTITUTE OF BOTANY   (China)

^c RIKKYO UNIVERSITY   (Japan)

Author keywords

Asteraceae; Cremanthodium stenactinium; Eremophilanes; Sesquiterpenes

Indexed keywords

EREMOPHILANE COMPOUNDS; NAPHTHALENE DERIVATIVE;

ARTICLE; ASTERACEAE; CHEMISTRY; CHINA; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ASTERACEAE; CHINA; MAGNETIC RESONANCE SPECTROSCOPY; NAPHTHALENES;

EID: 84555189762     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules161210645     Document Type: Article

References (26)

1. Liu, J.; Liu, S.; Ho, T.; Lu, A. Karyological studies on the Sino-Himalayan genus, Cremanthodium (Asteraceae: Senecionae). Bot. J. Linn. Soc. 2001, 135, 107-112.
2. Liu, J.Q.; Wang, Y.J.: Wang, A.L.; Ohba, H.; Abbott, R.J. Radiation and diversification within the Ligularia-Cremanthodium-Parasenecio complex (Asteraceae) triggered by uplift of the Qinghai-Tibetan plateau. Mol. Phylogenet. Evol. 2006, 38, 31-49. (Pubitemid 41773272)
3. Yang, L.; Chen, H.; Jia, Z.J. Lignan and a coumarin from Cremanthodium ellisii Kitam. Ind. J. Chem. 1995, 34B, 975-977.
4. Chen, H.; Zhu, T.; Shen, X.M.; Jia, Z.J. Four new sesquiterpene polyol esters from Cremanthodium ellisii. J. Nat. Prod. 1996, 59, 1117-1120. (Pubitemid 27026569)
5. Chen, H.; Jia, Z.J.; Tan, R.X. Two new oplopanol esters from Cremanthodium ellisii. Planta Med. 1997, 63, 245-247. (Pubitemid 27287068)
6. Su, B.N.; Zhu, Q.X.; Jia, Z.J. Nor-lignan and sesquiterpenes from Cremanthodium ellisii. Phytochemistry 2000, 53, 1103-1108.
7. Wang, A.X.; Zhang, Q.; Jia, Z.J. Phenylpropanosides, lignans and other constituents from Cremanthodium ellisii. Pharmazie 2004, 59, 889-892. (Pubitemid 39529770)
8. Zhu, Y.; Yang, L.; Jia, Z.J. Novel highly oxygenated bisabolane sesquiterpenes from Cremanthodium discoideum. J. Nat. Prod. 1999, 62, 1479-1483.
9. Zhu, Y.; Zhu, Q.X.; Jia Z.J. Epoxide sesquiterpenes and steroids from Cremanthodium discoideum. Aust. J. Chem. 2000, 53, 831-834. (Pubitemid 32445633)
10. Cremanthodium potaninii (triterpene): Yang, A.; Zeng, Y.; Yang, Z Isolation and structural elucidation of triterpenes from Cremanthodiium potaninii C. Winkl. Zhongchengyao 2010, 32, 636-639.
11. Tu, Y.; Yang, R.; Shou Q.; Wang, B.; Peng, T. Studies on chemical constituents of essential oils from Cremanthodium pleurocaule. Zhongguo Zhongyao Zazhi 2006, 31, 522-524.
12. Hanai, R.; Gong, X.; Tori, M.; Kondo, S.; Otose, K.; Okamoto, Y.; Nishihama, T.; Murota, A.; Shen, Y.; Wu, S.; Kuroda, C. Chemical and Genetic Study of Ligularia tongolensis, Ligularia cymbulifera, and Ligularia atroviolacea in the Hengduan Mountains of China. Bull. Chem. Soc. Jpn. 2005, 78, 1302-1308. (Pubitemid 41097778)
13. Tori, M.; Honda, K.; Nakamizo, H.; Okamoto, Y.; Sakaoku, M.; Takaoka, S.; Gong, X.; Shen, Y.; Kuroda, C.; Hanai, R. Chemical constituents of Ligularia virgaurea and its diversity in southwestern Sichuan of China. Tetrahedron 2006, 62, 4988-4995.
14. Tori, M.; Fujiwara, M.; Okamoto, Y.; Tanaka, M.; Gong, X.; Shen, Y.; Hanai, R.; Kuroda, C. New Oplopane-type Sesquiterpenoids from Ligularia duciformis. Nat. Prod. Commun. 2007, 2, 357-360.
15. Tori, M.; Watanabe, A.; Matsuo, S.; Okamoto, Y.; Tachikawa, K.; Takaoka, S.; Gong, X.; Kuroda, C.; Hanai, R. Diversity of Ligularia kanaitzensis in sesquiterpenoid composition and neutral DNA sequences. Tetrahedron 2008, 64, 4486-4495.
16. Tori, M.; Okamoto, Y.; Tachikawa, K.; Mihara, K.; Watanabe, A.; Sakaoku, M.; Takaoka, S.; Tanaka, M.; Gong, X.; Kuroda, C.; Hattori, M.; Hanai, R. Isolation of new eremophilane-type sesquiterpenoids, subspicatins A-D and subspicatolide from Ligularia subspicata, and chemical and genetic diversity of the species. Tetrahedron 2008, 64, 9136-9142.
17. Nagano, H.; Torihata, A.; Matsushima, M,.; Hanai, R.; Saito, Y.; Baba, M.; Tanio, Y.; Okamoto, Y.; Takashima, Y.; Ichihara, M.; Gong, X.; Kuroda, C.; Tori, M. Chemical and Genetic Study of Ligularia cyathiceps in Yunnan Province of China. Helv. Chim. Acta 2009, 92, 2071-2081.
18. Saito, Y.; Hattori, M.; Iwamoto, Y.; Takashima, Y.; Mihara, K.; Sasaki, Y.; Fujiwara, M.; Sakaoku, M.; Shimizu, A.; Chao, X.; Kuroda, C.; Gong, X.; Hanai, R.; Tori, M. Overlapping chemical and genetic diversity in Ligularia lamarum and Ligularia subspicata. Isolation of ten new eremophilanes and a new seco-bakkane compound. Tetrahedron 2011, 67, 2220-2231.
19. Djerassi, C.; Rbcords, R.; Bunnenberg, E.; Mislow, K.; Moscowitz, A. Inherently dissymmetric chromophores. Optical rotatory dispersion of a,b-unsaturated ketones and conformational analysis of cyclohexenones. J. Am. Chem. Soc. 1962, 84, 870-872.
20. Paquette, L.A.; Wang, T.Z.; Philippo, M.G.; Wang, S. Total synthesis of the cembranoid diterpene lactone (+)-cleomeolide. Some remarkable conformational features of nine-membered belts linked in 2,6-fashion to a methylenecyclohexanone core. J. Am. Chem. Soc. 1994, 116, 3367-3374. (Pubitemid 24980893)
21. Guerriero, A.; D'Ambrosio, M.; Cuomo, V.; Vanzanella, F.; Pietra, F. Dendrophiellin A, the first fungal trinor-eremophilane. Isolation from the marine deuteromycete Dendryphiella salina (SUTHERLAND) PUGH et NICOT. Helv. Chim. Acta 1988, 71, 57-61.
22. Maurer, B.; Frachenboud, M.; Grieder, A.; Ohloff, G. Zur Kenntnis der sesquiterpenoiden C12- Ketone des ätherichen Öls von Vetiveria zizanioides (L.) Nash. Helv. Chim. Acta 1972, 55, 2371-2382.
23. Hikino, H.; Hikino, Y.; Koakutsu, S.; Takemoto, T. Structure and absolute configuration of narchinol A. Phytochemistry 1972, 11, 2097-2099.
24. Bohlmann, F.; Kramp, W.; Robinson, H.; King, R.M. A norsequiterpene from Senecio humillimus. Phytochemistry 1981, 20, 1739-1740.
25. Zdero, C.; Bohlmann, F. Eremophilanolides, eudesmanolides, guaianolides and other constituents from Ondetia linearis. Phytochemistry 1989, 28, 1653-1660.
26. Saito, Y.; Ichihara, M.; Okamoto, Y.; Gong, X.; Kuroda, C.; Tori, M. Five new subspicatins and noreremophilane from Parasenecio petasitoides collected in China. Tetrahedron Lett. 2011, 52, 6388-6391 and references cited therein.