Seed dormancy breaking diterpenoids from the liverwort Plagiochila sciophila and their differentiation inducing activity in human promyelocytic leukemia HL-60 cells.

Abstract

To obtain the structural diversity of bioactive compounds similar to cotylenins and fusicoccins that modulate 14-3-3 protein-protein interactions in eukaryotes, screening tests were carried out using the lettuce seed dormancy breaking-assay. An acetone extract of the liverwort Plagiochila sciophila exhibited significant activity against the seeds in the presence of the plant hormone abscisic acid. Activity-guided fractionation of the extract afforded the isolation of seven novel fusicoccane-type diterpenoids, named fusicosciophins A-E (1-5), 8-deacetyl (6) and 9-deacetyl fusicosciophin E (7). Their structures were determined by spectroscopic methods and X-ray crystallographic analyses. All the pure isolated compounds (1-7) exhibited moderate lettuce seed dormancy breaking activity. In addition, the differentiation-inducing activity and cytotoxicity of these isolates, together with fusicoccin A (FC-A) and all-trans retinoic acid (ATRA), were evaluated in human promyelocytic leukemia HL-60 cells and human mouth epidermal carcinoma KB cells, respectively. Fusicosciophins (2 and 4) and FC-A exhibited moderate differentiation-inducing activity (EC50 31.2-59.1 microM) compared with ATRA (EC50 0.3 microM), while 2, 4 and ATRA exhibited higher selectivity indices (IC50/EC50 >3.38-667) than FC-A (IC50/EC50 1.05). This is the first report on the isolation of fusicoccane-type diterpenoids from liverworts having seed dormancy breaking activity and differentiation-inducing activity in mammal cells.

• Authors: Hiromichi Kenmoku, Hiroyuki Tada, Megumi Oogushi, Tomoyuki Esumi, Hironobu Takahashi, Masaaki Noji, Takeshi Sassa, Masao Toyota, Yoshinori Asakawa
• Journal: Natural product communications (Nat Prod Commun) Vol. 9 Issue 7 Pg. 915-20 (Jul 2014) ISSN: 1934-578X [Print] United States
• PMID: 25230492 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Antineoplastic Agents, Phytogenic
• Diterpenes
• Polycyclic Compounds

Topics

• Antineoplastic Agents, Phytogenic (chemistry, pharmacology)
• Diterpenes (chemistry, pharmacology)
• Germination (drug effects)
• HL-60 Cells
• Hepatophyta (physiology)
• Humans
• KB Cells
• Lettuce (drug effects)
• Lymphocytes (drug effects)
• Models, Molecular
• Molecular Structure
• Polycyclic Compounds (chemistry, pharmacology)
• Seeds (physiology)