Sesquiterpenes and Dimers Thereof from Chloranthus fortunei

Abstract

Four new compounds, including one new sesquiterpene dimer, i.e., shizukaol P (1), one new dimeric sesquiterpene glycoside, i.e., 9-O-b-glucopyranosylcycloshizukaol A (2), and two new sesquiterpenes, i.e., shizukanolides G and H (3 and 4, resp.), together with eight known compounds, were isolated from the aerial part of Chloranthus fortunei. The structures and relative configurations were elucidated on the basis of spectroscopic data and by comparison with those of the related compounds reported in the literature.Introduction. [25]. Chloranthus fortunei (A. Gray) Solms-Laub has been used in Chinese folk medicine for the treatment of bone fractures [26]. During our ongoing search for biologically active substances from this plant, 13 compounds have been isolated from the aerial part of it. Four of them were new compounds, including one new sesquiterpene dimer, i.e., shizukaol P (1), one new dimeric sesquiterpene glycoside, i.e., 9-O-b-glucopyranosylcycloshizukaol A (2), and two new sesquiterpenes, i.e., shizukanolides G and H (3 and 4, resp.). The other eight known compounds were identified as shizukaol F (5) [7], and chloranoside A (12) [10]. Their structures and relative configurations were elucidated on the basis of their spectroscopic data and by comparing with the related compounds reported in the literature.

Chlorfortunones A and B, Two Sesquiterpenoid Dimers, Possessing Dispiro[4,2,5,2]pentadecane-6,10,14-tren Moiety from Chloranthus fortunei

“… 7 , 8 In previous phytochemical studies, 26 dilindenane-type and lindeane-eudesmane-type SDs had been isolated from C. fortunei . 1 , 7 − 10 In this paper, we reported two novel SDs, chlorfortunones A ( 1 ) and B ( 2 ), isolated from the roots of C. fortunei ( Figure 1 ). They are a new class of SDs formed by the [4 + 2] cycloaddition of lindenane- and acrane-type sesquiterpenoid monomers and possess an unprecedented 3/5/6/6/6/5 hexacyclic system with a unique dispiro[4,2,5,2]pentadecane-6,10,14-trien moiety.…”

“…It has long been used as a traditional Chinese medicine to treat blood stasis, inflammatory swelling, drainage, and detoxification. , In previous phytochemical studies, 26 dilindenane-type and lindeane-eudesmane-type SDs had been isolated from C. fortunei. ,− In this paper, we reported two novel SDs, chlorfortunones A ( 1 ) and B ( 2 ), isolated from the roots of C. fortunei (Figure ).…”

Chemistry and bioactivity of lindenane sesquiterpenoids and their oligomers

“…In this group, chloranthalactone A ( 64 ), 119 chlojaponilactone B ( 65 ), 114 onoseriolide B ( 66 ), 120,121 sibirolide B ( 67 ) 18 and onoseriolide senecioate ( 68 ) 19 possess Δ 15(4) , Δ 7(11) , and Δ 8(9) double bonds, whereas sarcandralactone D ( 69 ) 116 has an isomerized Δ 4(5) . 15-Hydroxyisoonoseriolide senecioate ( 70 ), 19 chloranthalactone C ( 71 ), 109 shizukanolide C ( 72 ), 122 chloranoside B ( 73 ), 123 chlorajaponol F ( 74 ), 124 chloranthalactone G ( 75 ) with rare and unstable 4,15-epoxide, 125 shizukanolide F ( 76 ), 126 shizukanolide H ( 77 ), 127 shizukanolide E ( 78 ), 126 chloranoside A ( 79 ) 123 and linderaggredin B ( 80 ) 128 with anticonfigurational cyclopropane were isolated as the oxidated derivatives of the Δ 15(4) double bond. Chlorafortulide ( 81 ) 129 and sarglabolide L ( 82 ) 130 possess a rare 18-membered macrolide.…”

“…The epoxidation of the active Δ 8(9) olefinic bond generated a series of 8,9-epoxide LS monomers, such as chloranthalactone B ( 83 ), 119 oxyonoseriolide ( 84 ), 120 chlojaponilactone C ( 85 ), 114 shizukanolide D ( 86 ), 126 shizukanolide G ( 87 ), 127 (+)-chloranthalactone B ( 88 ), 25 13-desoxyisoonoseriolide ( 89 ), 22 8β,9β-epoxyonoseriolide senecioate ( 90 ), 19 and sarcaglaboside F ( 91 ). 131 It is worth mentioning that 88 is an enantiomer of 83 from the marine animal gorgonian Menella sp.…”

Sesquiterpenoids from Chloranthus anhuiensis with Neuroprotective Effects in PC12 Cells

“…In this paper, we describe 32 sesquiterpenes from the whole plants of C. anhuiensis , including a unique 5,6- seco -germacrane-type sesqui­terpenoid ( 1 ), a rare 4,5- seco -cadinane-type sesqui­terpenoid ( 2 ), and four further new sesqui­terpenoids ( 3 – 6 ) (see Chart ). Also isolated were 26 known sesqui­terpenoids, 8,12-epoxy-1α-hydroxy-4 αH ,5 αH -eudesma-7,11-diene-6,9-dione ( 7 ), chlor­antene C ( 8 ), 4α-hydroxy-8,12-epoxy­eudesma-7,11-diene-1,6-dione ( 9 ), 1α-hydroxy-8,12-epoxy­eudesma-4,7,11-triene-6,9-dione ( 10 ), zedoaro­furan ( 11 ), curcolonol ( 12 ), 9α-hydroxy­curcolone ( 13 ), lasianthus­lactone A ( 14 ), atractyl­enolide I ( 15 ), atractyl­enolide III ( 16 ), 6α-hydroxy­eudesma-4(15),7(11),8(9)-trien-12,8-olide ( 17 ), 4β,8β-dihydroxy-5α H -eudesm-7­(11)-en-8,12-olide ( 18 ), codono­lactone ( 19 ), shizuka­furanol ( 20 ), shizukolidol ( 21 ), ent -(3 R )-3-hydroxy­atractyl­enolide III ( 22 ), (7 S ,10 S )-7-hydroxy­eudesma-4-en-6-one ( 23 ), 1β-hydroxy-α-cyperone ( 24 ), shizukanolide C ( 25 ), shizukanolide H ( 26 ), istanbulin B ( 27 ), istanbulin A ( 28 ), isogerma­furenolide ( 29 ), shizuka­acora­dienol ( 30 ), chlomultin C ( 31 ), and curcuzederone ( 32 ) . The neuro­protective activity of these substances was investigated using PC12 cells.…”