Chemical Constituents Of Two Liverworts And Their Biological Activities

Bryophytes are considered as transitional plants in nature,which are taxonomically placed between the algae and the vascular plants,and further divided into three phyla as liverworts,mosses and homworts.Bryophytes have a strong vitality,a wide range of species,widely distributed,which is of great significance to maintain the ecological balance.As early as the 1690s,the medicinal value of bryophytes has been developed.With the improvement of plant extraction,isolation technology and chemical structure identification technology,the chemical constituents of bryophytes have been widely studied.Unlike moss and hornworts,liverworts contain characteristic cell organelles,cellular oil bodies,which can synthesize and store terpenes and aromatic compounds with special structures.These compounds exhibited various biological activities,such as antifungal,anti-tumor,anti-inflammatory,anti-hypertensive,antioxidant,anti-alzheimers disease and so onTwo liverworts collected from Zhejiang Province were chemically investigated,namely,Odontoschisma grosseverrucosum Stephani(Cephaloziaceae)and Trocholejeunea sandvicensis(Gott.)Mizut.53 compounds,which include 24 previously undescribed compounds were isolated and identified based on column chromatography and high performance liquid chromatography,together with high resolution mass spectrum,nuclear magnetic resonance spectrum,infrared spectrum,ultraviolet spectrum,circular dichroism,X ray single crystal diffraction.The biological activities and mechanism of the new compounds were studied.A dilospirane diterpenoid isolated from O.grosseverrucosum displayed moderate anti-virulence activities against Candida albicans,pinguisane sesquiterpenoids isolated from T.sandvicensis exhibited moderate anti-inflammatory activity34 compounds were isolated and identified from the Chinese liverwort Odontoschisma grosseverrucosum Stephani(Cephaloziaceae),including 8 previously undescribed compounds involved two new dilospirane diterpenoids odongrossins A-B(1-2),which was the first dilospirane-type diterpenoid that was isolated from liverworts,a new cadinene sesquiterpenoid odongrossin C(3),three new clerodane diterpenoids odongrossins D-F(4-6),a new vibsane diterpenoid odongrossin G(7),a new dolabrane diterpenoid odongrossin H(8).We evaluated the effects of odongrossins A-H(1-8)on the morphological transitions of C.albicans CDR1-and CDR2-efflux-pump-deficient strain DSY654 and wild-type strain SC5314.The results demonstrated that odongrossin A(1)and odongrossin G(7)exhibited antifungal activity by inhibiting the hyphal formation of DSY654.Between them,odongrossin A(1)displayed the more potent inhibitory effect,which could restrict C.albicans DSY654 in yeast form at the minimum concentration of 16 μg/mL within 6 h.Therefore,we continue investigate the inhibitory performance of odongrossin A(1)inhibit cell adhesion and biofilm formation,the results demonstrated that odongrossin A(1)exhibited dose-dependent inhibitory activity against cell adhesion and biofilm formation of C.albicans DSY654 Meanwhile,odongrossin A(1)likely regulates the transcriptional level of genes that are related to the virulence of C.albicans to retard the yeast-to-hyphae transition.19 compounds were isolated and identified from the Chinese liverwort Trocholejeunea sandvicensis(Gott.)Mizut,including 16 previously undescribed compounds involved ten new pinguisane sesquiterpenoids trocholejeunenols A-J(35-44),six new phytane diterpenoids trocholejeunenols K-P(45-50).We evaluated the anti-inflammatory activity in vitro of isolated pinguisane sesquiterpenoids,the results demonstrated that trocholejeunenols A-B(35-36)and trocholejeunenol J(44)could reduce LPS-induced NO production in RAW 264.7 murine macrophages under the nontoxic tested concentration,and exhibited moderate anti-inflammatory activity in vitro.We continue investigate the anti-inflammatory activity of trocholejeunenols A-B(35-36)in zebrafish vivo.The results demonstrated that trocholejeunenol B(36)could inhibit the inflammatory reaction induced by CuSO4 at the concentration of 25,uM and below,and displayed obvious teratogenicity and lethal effect on zebrafish when the concentration was increased.