Ryanoids and related compounds. Identification of five new ryanoids from the plantRyaniaspeciosaVahl. Formal total syntheses of 3-deoxyryanodol (cinnzeylanol), 10-O-acetyl-3-deoxyryanodol (cinnzeylanine), 2-deoxyryanodol, 2-deoxy-2-epiryanodol, 2,3-dideoxy-2,3-dihydroryanodol, 2-deoxy-3-epiryanodol, and 2-deoxy-3-epiryanodine

Abstract

In the course of a preliminary investigation on the relationships between the chemical structure of ryanoids and their affinity to the ryanodine binding site, we have isolated, from the plant Ryarzia speciosn Vahl, four new members of this family of natural insecticidal compounds (ryanoids 3,4,5, and 6) and corrected the reported structure of a fifth one (ryanoid 7). In addition, we have synthesized, from anhydroryanodol (lo), new members of this family having fewer hydroxyl groups in ring A: cinnzeylanol (14) and cinnzeylanine (15). 2,3-dideoxy-2,3-dihydroryanodol (16), 2-deoxy-3-epiryanodol (IS), and 2-deoxy-3-epiryanodine (19), 2-deoxyryanodol (20), and 2-deoxy-2-epiryanodol(21).Key words: ryanoids synthesis, cinnzeylanine, 2-deoxyryanodols, 2-deoxy-3-epiryanodine.Resume : Dans le cadre d'une ttude prCliminaire des relations structures chimiques -activitC biologique des ryanoi'des et de leur affinitC au site rCcepteur de la ryanodine, nous avons isole de la plante Ryania speciosa Vahl, quatre nouveaux membres de cette famille d'insecticides naturels (les ryanoi'des 3 , 4 , 5 et 6) et conigC la structure dCjB rapportCe d'un cinquikme (le ryanoi'de 7). Par ailleurs, B partir de l'anhydroryanodol (lo), nous avons synthCtisC quelques membres de cette famille, moins oxygtnCs au cycle A : le cinnzeylanol(14) et la cinnzeylanine (IS), le 2,3-didCoxy-2,3-dihydroryanodol(16), le 2-dCoxy-3-Cpiryanodol(1S) et la 2-dCoxy-3-Cpiryanodine (19), le 2-dCoxyryanodol(20) et le 2-dCoxy-2-Cpiryanodol (21).

Aromatic and Aliphatic Apiuronides from the Bark of Cinnamomum cassia

“…The bark of C. cassia represents one of the major sources of phenolic compounds, and there are various secondary metabolites such as diterpenoids, − phenylpropanoids, − flavonoids, lignans, , sesquiterpenoids, and other compounds. , …”