Twelve new grayanoids(1-12)along with five known compounds were isolated from flowers of Rhododendron molle.Their structures were fully characterized using a combination of spectroscopic analyses,computational calcula...Twelve new grayanoids(1-12)along with five known compounds were isolated from flowers of Rhododendron molle.Their structures were fully characterized using a combination of spectroscopic analyses,computational calculations,and single crystal X-ray diffraction.Rhomollone A(1)possesses an unprecedented 5/6/6/5 tetra-cyclic ring system(B-nor grayanane)incorporating a cyclopentene-1,3-dione scaffold.Rhodomollein XLIII(2)is a dimeric grayanoid,containing a novel 14-membered heterocyclic ring with a C2 symmetry axis.The antinociceptive activities of compounds 3,4,6,7,and 12-17 were evaluated by an acetic acid-induced writhing test.Among them,compounds 3,7,12,15 and 16 displayed significant antinociceptive activities at a dose of 20 mg/kg with inhibition rates ranging from41.9%to 91.6%.Compounds 6 and 13 inhibited 46.0%and 39.4%of the acetic acid-induced writhes at a dose of 2 mg/kg,while compound 17 inhibited 34.3%of the writhes at a dose of 0.4 mg/kg.展开更多
Six highly oxygenated dimeric grayanane diterpenoids(1—6)including three new ones,bismollethers A—C(1—3),were isolated from the flowers of Rhododendron molle collected at Qichun,Hubei,China.The structures and relat...Six highly oxygenated dimeric grayanane diterpenoids(1—6)including three new ones,bismollethers A—C(1—3),were isolated from the flowers of Rhododendron molle collected at Qichun,Hubei,China.The structures and relative configurations of 1—6 were determined by comprehensive spectroscopic data analysis and 13C NMR calculation with DP4+analysis.The absolute configurations of bismollethers A—C(1—3)and birhodomollein B(5)were indubitably assigned by single-crystal X-ray diffraction analysis,revealing the head-to-tail linking manner of diterpenoid monomers.Bismollether A(1)is a caged dimeric grayanane diterpenoid linked through two oxygen-bridges of C-2−O−C-14′and C-14−O−C-2′,featuring a unique 1,8-dioxacyclotetradecane motif.The plausible biosynthesis pathways of 1—6 are proposed.All the isolates displayed significant analgesic activities and their structure-activity relationships were discussed.Grayanane diterpenoid dimers were found to be TRPV1 and TRPA1 dual antagonists,and docking studies provide a structural basis to design potent analgesics.展开更多
One new grayanane diterpene glucoside, rhodomoside A 1 was isolated from the roots of Rhododendron molle G. Don (Ericaccae). Its structure was elucidated on the basis of spectral analysis.
Birhodomolleins A-C（1-3）,three novel diterpenoids dimerized from two grayanane diterpenes through an oxygen bridge,were isolated from the flowers of Rhododendron molle.Their structures were elucidated by interpretat...Birhodomolleins A-C（1-3）,three novel diterpenoids dimerized from two grayanane diterpenes through an oxygen bridge,were isolated from the flowers of Rhododendron molle.Their structures were elucidated by interpretation of their 1D and 2D NMR and other spectroscopic data.Birhodomollein A（1） contains a rare chloro-substitution on one of the grayanane moieties.These are the first examples of dimeric diterpenes from the Ericaceae family.展开更多
基金supported by grants from the National Natural Science Foundation of China(Nos.21572274 and 21732008)the CAMS Innovation Fund for Medical Sciences(No.2016-I2M1-010,China)
文摘Twelve new grayanoids(1-12)along with five known compounds were isolated from flowers of Rhododendron molle.Their structures were fully characterized using a combination of spectroscopic analyses,computational calculations,and single crystal X-ray diffraction.Rhomollone A(1)possesses an unprecedented 5/6/6/5 tetra-cyclic ring system(B-nor grayanane)incorporating a cyclopentene-1,3-dione scaffold.Rhodomollein XLIII(2)is a dimeric grayanoid,containing a novel 14-membered heterocyclic ring with a C2 symmetry axis.The antinociceptive activities of compounds 3,4,6,7,and 12-17 were evaluated by an acetic acid-induced writhing test.Among them,compounds 3,7,12,15 and 16 displayed significant antinociceptive activities at a dose of 20 mg/kg with inhibition rates ranging from41.9%to 91.6%.Compounds 6 and 13 inhibited 46.0%and 39.4%of the acetic acid-induced writhes at a dose of 2 mg/kg,while compound 17 inhibited 34.3%of the writhes at a dose of 0.4 mg/kg.
基金This work was supported by the Fund of State Key Laboratory of Phytochemistry and Plant Resources in West China(P2022-KF08)the Fund of Laboratory of Xinjiang Native Medicinal and Edible Plant Resource Chemistry(KSUZDSYS202101)+2 种基金the National Natural Science Foundation of China(22107033 and U1703109)the Traditional Chinese Medicine of Hubei Provincial Health Commission(ZY2021M056)the China Postdoctoral Science Foundation(2021M691152)。
文摘Six highly oxygenated dimeric grayanane diterpenoids(1—6)including three new ones,bismollethers A—C(1—3),were isolated from the flowers of Rhododendron molle collected at Qichun,Hubei,China.The structures and relative configurations of 1—6 were determined by comprehensive spectroscopic data analysis and 13C NMR calculation with DP4+analysis.The absolute configurations of bismollethers A—C(1—3)and birhodomollein B(5)were indubitably assigned by single-crystal X-ray diffraction analysis,revealing the head-to-tail linking manner of diterpenoid monomers.Bismollether A(1)is a caged dimeric grayanane diterpenoid linked through two oxygen-bridges of C-2−O−C-14′and C-14−O−C-2′,featuring a unique 1,8-dioxacyclotetradecane motif.The plausible biosynthesis pathways of 1—6 are proposed.All the isolates displayed significant analgesic activities and their structure-activity relationships were discussed.Grayanane diterpenoid dimers were found to be TRPV1 and TRPA1 dual antagonists,and docking studies provide a structural basis to design potent analgesics.
基金the National Natural Science Foundation of China(Grant No.30170104)
文摘One new grayanane diterpene glucoside, rhodomoside A 1 was isolated from the roots of Rhododendron molle G. Don (Ericaccae). Its structure was elucidated on the basis of spectral analysis.
基金financial support of the National Science & Technology Major Project "Key New Drug Creation and Manufacturing Program"(Nos.2012ZX09301001-001,2015ZX09103002)the National Natural Science Fundation of China(Nos.81302657,81473112,81573305)
文摘Birhodomolleins A-C（1-3）,three novel diterpenoids dimerized from two grayanane diterpenes through an oxygen bridge,were isolated from the flowers of Rhododendron molle.Their structures were elucidated by interpretation of their 1D and 2D NMR and other spectroscopic data.Birhodomollein A（1） contains a rare chloro-substitution on one of the grayanane moieties.These are the first examples of dimeric diterpenes from the Ericaceae family.
