Bioactive Sesquiterpenoids and Diterpenoids from the Liverwort Bazzania albifolia

One undescribed 6,7‐secofusicoccane‐type diterpene, albifolione (1), and one new aromadendrane‐type sesquiterpenoid ketone, methyl 2‐oxoaromadendra‐1(10),3‐dien‐12‐oate (2), along with four known compounds, δ‐cuparenol (3), fusicoauritone (4), chiloscyphenols A and B (5 and 6, resp.), were isolated from the liverwort Bazzania albifolia Horik. The structures and relative configurations of 1 and 2 were established unequivocally on the basis of spectroscopic data analysis. Preliminary bioassay revealed that compound 5 showed quite strong cytotoxicity against the human tumor cell line MCF‐7, with an IC50 value of 5.6 μM.

[1]  H. Lou,et al.  Scaparvin A, a novel caged cis-clerodane with an unprecedented C-6/C-11 bond, and related diterpenoids from the liverwort Scapania parva. , 2010, Organic letters.

[2]  D. Tantillo,et al.  Consequences of conformational preorganization in sesquiterpene biosynthesis: theoretical studies on the formation of the bisabolene, curcumene, acoradiene, zizaene, cedrene, duprezianene, and sesquithuriferol sesquiterpenes. , 2009, Journal of the American Chemical Society.

[3]  M. Toyota,et al.  BRYOPHYTES : BIO-AND CHEMICAL DIVERSITY, BIOACTIVITY AND CHEMOSYSTEMATICS , 2009 .

[4]  Y. Asakawa Liverworts-potential source of medicinal compounds. , 2008, Current pharmaceutical design.

[5]  H. Lou,et al.  ent-kaurane diterpenoids from the liverwort Jungermannia atrobrunnea. , 2008, Journal of natural products.

[6]  Wen-tao Yu,et al.  Antifungal dibenzofuran bis(bibenzyl)s from the liverwort Asterella angusta. , 2007, Phytochemistry.

[7]  Y. Asakawa,et al.  Chemical constituents of malagasy Liverworts. 6. A myltaylane caffeate with nitric oxide inhibitory activity from Bazzania nitida. , 2007, Journal of natural products.

[8]  Y. Asakawa Biologically active compounds from bryophytes , 2007 .

[9]  H. Lou,et al.  Rearranged Calamenene and Eudesmane Sesquiterpenoids from two Chinese Liverworts , 2007 .

[10]  Y. Asakawa,et al.  Chemical constituents of Malagasy liverworts: cyclomyltaylanoids from Bazzania madagassa. , 2006, Phytochemistry.

[11]  J. Zapp,et al.  Bioactivity guided isolation of antifungal compounds from the liverwort Bazzania trilobata (L.) S.F. Gray. , 2004, Phytochemistry.

[12]  Y. Asakawa Chemosystematics of the hepaticae. , 2004, Phytochemistry.

[13]  J. Zapp,et al.  Lignan derivatives from the liverwort Bazzania trilobata. , 2003, Phytochemistry.

[14]  J. Scher,et al.  A cytotoxic sesquiterpene and unprecedented sesquiterpene-bisbibenzyl compounds from the liverwort Schistochila glaucescens , 2002 .

[15]  Y. Asakawa,et al.  Herbertane-type sesquiterpenoids from the liverwort Herbertus sakuraii. , 2000, Phytochemistry.

[16]  W. König,et al.  Sesquiterpene constituents of the liverwort Bazzania trilobata , 1999 .

[17]  Y. Asakawa,et al.  Sesquiterpenoids from the liverworts Bazzania trilobata and Porella canariensis , 1996 .

[18]  J. Zapp,et al.  SPHENOLOBANE AND FUSICOCCANE DITERPENOIDS FROM THE LIVERWORT ANASTROPHYLLUM AURITUM , 1994 .

[19]  T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. , 1983, Journal of immunological methods.

[20]  M. Toyota,et al.  Sesquiterpenes from Japanese liverworts , 1981 .

[21]  A. Matsuo,et al.  δ-CUPARENOL, A NEW SESQUITERPENE PHENOL FROM THE LIVERWORT, BAZZANIA POMPEANA , 1972 .