Prenylated C6–C3 compounds from the roots of Illicium henryi

“…Several sesquiterpene lactones, lignans, and flavonoids from this plant were reported [17][18][19][20][21][22][23]. In our studies, novel prenylated C 6 -C 3 compounds with antioxidant activities were isolated from the roots of this plant [24]. As a part of our ongoing search for structurally unique and biologically interesting Illicium sesquiterpenes, the MeOH-soluble fraction of the respective EtOH extracts were carefully investigated and led to the isolation of one thapsan-type, illihenlactoneoside A (1), two capnellanetype, illihenlactoneosides B and C (2 and 3), four floridanolide sesquiterpene glycosides, illihenlactoneosides D-G (4-7), one azulene sesquiterpene, illihenazulene A (8) (l " Fig.…”

mentioning

confidence: 86%

“…The absolute configuration of 8 was extrapolated by comparing its experimental and calculated ECD spectra, the latter performed using time-dependent density functional theory. Their optimized geometries were obtained by system conformational analysis with the MMFF94 force field, and then the ECD spectra were calculated at the B3LYP/6-31+G (d) level with the PCM in methanol (See Supporting Information) [24]. The results showed that experimental and calculated spectra for the 6S,7S,10S-isomer were in good agreement (l " Fig.…”

mentioning

confidence: 92%

Novel Sesquiterpenoid Glycosides and Sesquiterpenes from the Roots of Illicium henryi

et al. 2013

Self Cite

View full text Add to dashboard Cite

Seven new sesquiterpenoid glycosides, consisting of one thapsan-type (1), two capnellane-type (2 and 3), four floridanolide sesquiterpene glycosides (4-7), and one new azulene-type sesquiterpene (8), along with six known sesquiterpenes (9-14) were isolated from the roots of Illicium henryi. The structures of 1-8 were elucidated by extensive spectroscopic analyses and chemical methods. The absolute configurations of 1, 2, and 8 were determined based on Rh2(OCOCF3)4-induced CD, Mo2(OAc)4-induced CD data, and calculated electronic circular dichroism (ECD), respectively. Compound 1 was found to exhibit weak neurotoxicant activity.

show abstract

“…2 The Illicium genus has been widely studied and numerous compounds isolated from the various species. Previous studies have revealed the occurrence of monoterpenoids, sesquiterpenoids, diterpenoids and phenylpropanoids from the essential oil, [3][4][5] sesquiterpenoids, diterpenoids, triterpenoids from fruits and pericarps, 6 and phenylpropanoids, prenylated phenylpropanoids, 7 lignans, neolignans, sesquineolignans, terpenesesquineolignans 8 and benzoquinones from barks and roots of genus Illicium plants. Among them, prenylated C6-C3 compounds, sesquineolignans and secoprezizaane-type sesquiterpenoids are considered to be characteristic chemical markers of Illicium species.…”

Section: Introductionmentioning

confidence: 99%