Illilanceolide A, a unique seco-prezizaane sesquiterpenoid with 5/5/6 tricyclic scaffold from the fruits of Illicium lanceolatum A. C. Smith

Four Highly Oxygenated Sesquiterpenoids from the Fruits of Illicium micranthum Dunn

“…The neurotrophic effect of 1–5 on PC12 cells were conducted by the previously described procedure in the literature with 5 ng/ml NGF as the negative control and 50 ng/ml NGF as the positive control [27] …”

“…[22,23] To date, monoterpenoids, [24] highly oxygenated sesquiterpenoids, [20,22,25,26] phenylpropanoids, [20] prenylated C 6 -C 3 compounds have been reported from this species. [21] Following an interest in the discovery of structurally unique and biologically components from I. species, [8,27] phytochemical research on the fruits of I. micranthum led to the isolation of four highly oxygenated sesquiterpenoids, illimicranolides A (1) and B (2), and illicinolides E (3) and F (4), along with one known compound, illicinolide B (5) (Figure 1). Among them, compound 1 was a unique sesquiterpenoid with a 5/5/6/5 fused tetracyclic ring system and was the first seco-prezizaane sesquiterpenoid having a 11,8-γ-lactone ring.…”

seco‐Prezizanne Sesquiterpenes and Prenylated C6‐C3 Compounds from the Fruits of Illicium lanceolatum A. C. Smith

“…[5,6,9 -14] Illicium lanceolatum A. C. Smith (Illiciaceae), with Chinese name 'Honduhui', is used in Chinese folk medicine for treating rheumatoid arthritis. [2,15] Previous phytochemical investigations of this species have disclosed the occurrence of monoterpenes, [16] Illicium sesquiterpenes, [17,18] phenylpropanoids, [19] and hexalactone derivatives. [20] Recently, we reported a new type of seco-prezeaane sesquiterpene with an unusual 5/5/6 tricyclic core, illilanceolide A, from the fruits of I. lanceolatum.…”

“…[20] Recently, we reported a new type of seco-prezeaane sesquiterpene with an unusual 5/5/6 tricyclic core, illilanceolide A, from the fruits of I. lanceolatum. [17] In a continued effort to discover bioactive chemical ingredients from this plant, two new seco-prezizaane type sesquiterpenes, 2β-hydroxy-6-deoxyneoanisatin (1) and 3,4-anhydro-2-oxo-1αhydroxy-6-deoxyneoanisatin (2), and two new prenylated C 6 -C 3 compounds, illilanceofunones A (3) and B (4), as well as four known prenylated C 6 -C 3 compounds (5 -8), were further isolated from the dry fruits of I. lanceolatum. In this article, we describe the isolation and structure identification of 1-8 (Figure 1) and their anti-inflammatory and neuroprotective properties.…”

Total Synthesis of Illisimonin A and Merrilactone A

“…Unlike 38, in which the configuration of the C6 position was different, the hemiketal was not formed in 47. [22] Removal of TES with pyridine hydrofluoride (HF•py) afforded the α-hydroxyketone for the proposed oxidative cleavage/aldol reaction sequence. The configuration of the C10 stereogenic center was unambiguously confirmed by X-ray crystallographic analysis of 48.…”