cadinane and guaiane

Diverse terpenoids including a novel sesquiterpenoidal lactam, commipholactam A (1), and a structurally related new cadinane sesquiterpenoid, commiphorane H (2), a new eudesmane sesquiterpenoid, commiphorane I (4), a new guaiane sesquiterpenoid, commiphorane J (5), and two new nor-abietane diterpenoids, commiphoranes K1 and K2 (6 and 7) along with two known terpenoids (3 and 8), were isolated from Resina Commiphora. Their structures with absolute configurations were characterized by spectroscopic methods and calculated electronic circular dichroism (ECD). Notably, commipholactam A represents the first example of cadinane sesquiterpene alkaloids isolated from Resina Commiphora. Biological assessment toward human cancer cells showed that the IC

Topics: A549 Cells; Abietanes; Antineoplastic Agents, Phytogenic; China; Commiphora; Hep G2 Cells; Humans; Molecular Structure; Phytochemicals; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Guaiane; Terpenes

Five sesquiterpenoids, 1α,8α-epidioxy-4α-hydroxy- 5αH-guai-7(11),9-dien- 12,8-olide. (1), 8,9-seco-4β-hydroxy-1α,5βH-7(11)-guaen-8,10-olide (2), 8α-hydroxy-1α, 4β,7βH-guai-10(15)-en- 5β,8β-endoxide(3), 7β,8α-dihydroxy-1α,4αH-guai-10(15)-en-5β,8β-endoxide(4) and 7-hydroxy-5(10),6,8-cadinatriene-4-one(5), together with seven known analogs were isolated from the rhizomes of Curcuma wenyujin. Their structures and relative configurations were determined on the basis of spectroscopic methods including 2D NMR techniques, and the structures of 1 and 2 were confirmed by single-crystal X-ray diffraction experiment. Compounds 1-10 and 12 showed significant in vitro antiviral activity against the influenza virus A with IC₅₀ values ranged from 6.80 to 39.97 μM, and SI values ranged from 6.35 to 37.25.

Topics: Animals; Antiviral Agents; Cell Line; Curcuma; Dogs; Humans; Influenza, Human; Magnetic Resonance Spectroscopy; Molecular Structure; Polycyclic Sesquiterpenes; Sesquiterpenes; Sesquiterpenes, Guaiane

Three new cadinane- and guaiane-type sesquiterpenoids, 2-hydroxy-10-epi-zonarene 1, 2, 15-dihydroxycalamenene 2 and guaia-4, 6-dien-3-one 3, were isolated from the wood of Enterospermum madagascariensis (Rubiaceae) grown in Madagascar. Their structures were established from concerted application of 2D NMR techniques including gs-COSY, gs-HMQC, gs-HMBC and NOESY.

Topics: Cycloheptanes; Magnetic Resonance Spectroscopy; Molecular Structure; Polycyclic Sesquiterpenes; Rubiaceae; Sesquiterpenes; Sesquiterpenes, Guaiane