ABSTRACT
Ten new dolabrane-type diterpenoids, notolutesins A-J (1-10), were isolated from the Chinese liverwort Notoscyphus lutescens, along with four known compounds. The structures of the new compounds were established on the basis of extensive spectroscopic data, and that of 1 was confirmed by single-crystal X-ray crystallography. The absolute configuration of 1 was determined by comparing its experimental and calculated electronic circular dichroism spectra. All of the isolates were evaluated for their cytotoxicity against a small panel of human cancer cell lines, and compound 1 exhibited an IC50 value of 6.2 µM against the PC3 human prostate cancer cell line.
Subject(s)
Antineoplastic Agents, Phytogenic/isolation & purification , Diterpenes/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Hepatophyta/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Circular Dichroism , Crystallography, X-Ray , Diterpenes/chemistry , Diterpenes/pharmacology , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Drugs, Chinese Herbal/pharmacology , Humans , Inhibitory Concentration 50 , Male , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
Five cis-clerodane diterpenoids, stephanialides A-E, along with seven known cis-clerodanes, scaparvins A-C, parvitexins B and C, 3-chloro-4-hydroxy-parvitexin A, and scapanialide B, were isolated from the Chinese liverwort Scapania stephanii. Their structures were established unequivocally on the basis of spectroscopic data. The absolute configuration of stephanialide A was determined by analysis of CD data using the octant rule. Phytotoxic activity evaluation showed that this type of diterpenoids can significantly inhibit root elongation of the seeds of Arabidopsis thaliana, Lepidium sativum and Brassica pekinensis.
Subject(s)
Diterpenes, Clerodane/isolation & purification , Diterpenes, Clerodane/pharmacology , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Hepatophyta/chemistry , Animals , Arabidopsis/drug effects , Brassica/drug effects , Crystallography, X-Ray , Diterpenes, Clerodane/chemistry , Drugs, Chinese Herbal/chemistry , Lepidium sativum/drug effects , Molecular Structure , Plant Roots/drug effects , Plant Roots/growth & development , Seeds/drug effects , Seeds/growth & development , StereoisomerismABSTRACT
Ten highly oxygenated ent-pimarane-type diterpenoids, pedinophyllols A-J (1-10), were isolated from the Chinese liverwort Pedinophyllum interruptum. Their structures were determined by comprehensive analysis of spectroscopic data together with single-crystal X-ray diffraction analysis. The absolute configurations were elucidated by comparison of experimental and theoretically calculated electronic circular dichroism spectra. Allelopathic testing showed that several new diterpenoids inhibited germination of Arabidopsis thaliana seeds.
Subject(s)
Abietanes/isolation & purification , Abietanes/pharmacology , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Hepatophyta/chemistry , Abietanes/chemistry , Arabidopsis/drug effects , Arabidopsis/growth & development , Circular Dichroism , Crystallography, X-Ray , Drugs, Chinese Herbal/chemistry , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , Oxygen/chemistry , Seeds/drug effects , Seeds/growth & developmentABSTRACT
Sixteen new clerodane diterpenoids, cephaloziellins A-P (1-16), and two known analogues (17 and 18) were isolated from an EtOH extract of the Chinese liverwort Cephaloziella kiaeri. The structures of the new compounds were elucidated from extensive spectroscopic data (IR, UV, HRESIMS, 1D NMR, and 2D NMR), and the structures of 5, 9, and 15 were confirmed by single-crystal X-ray diffraction analyses. The absolute configurations of all new compounds were established by comparing experimental and calculated electronic circular dichroism spectra.
Subject(s)
Diterpenes, Clerodane/isolation & purification , Drugs, Chinese Herbal/isolation & purification , Hepatophyta/chemistry , Circular Dichroism , Crystallography, X-Ray , Diterpenes, Clerodane/chemistry , Drugs, Chinese Herbal/chemistry , Models, Chemical , Molecular Conformation , Molecular Structure , Nuclear Magnetic Resonance, BiomolecularABSTRACT
Three new pimarane-type diterpenoids, 7ß,11α-dihydroxypimara-8(14),15-diene (1), 1ß,11α-dihydroxypimara-8(14),15-diene (2), and 11α-hydroxypimara-8(14),15-diene (3), five 2,3-secoaromadendrane-type sesquiterpenoids, including a new one, ethyoxyplagiochiline A2 (4), and three known fusicoccane-type diterpenoids were isolated from the Chinese liverwort Plagiochila pulcherrima. Their structures were established on the basis of extensive spectroscopic analysis. Compounds 6 and 7 exhibited moderate inhibitory activity on the proliferation of human cancer cell lines Hela, A172, and H460. Moreover, the cytotoxicity of compound 6 to Hela cells was related to apoptotis as confirmed by DAPI nuclear staining and flow cytometry.
Subject(s)
Abietanes/isolation & purification , Abietanes/pharmacology , Drugs, Chinese Herbal/isolation & purification , Drugs, Chinese Herbal/pharmacology , Hepatophyta/chemistry , Abietanes/chemistry , Antineoplastic Agents, Phytogenic/chemistry , Antineoplastic Agents, Phytogenic/pharmacology , Apoptosis/drug effects , Diterpenes , Drug Screening Assays, Antitumor , Drugs, Chinese Herbal/chemistry , Humans , Molecular Structure , Nuclear Magnetic Resonance, Biomolecular , StereoisomerismABSTRACT
A new bakkenolide and a known one were isolated from Petasites tatewakianus. The structure of the new compound was elucidated on the basis of spectroscopic methods including IR, EIMS, HRESIMS, 1D and 2D NMR, and the known compound was established by single crystal X-ray structural analysis. The in vitro cytotoxic activity of these two compounds against cultured human cervical carcinoma (HeLa), human breast cancer (MCF-7) and murine Lewis lung carcinoma (LLC) cell lines was also evaluated.