Terpenoids and Sterols from Saussurea cauloptera

Abstract

A total of 27 natural products were isolated from Saussurea cauloptera, including two new eudesmane-type sesquiterpenoids, the gerin derivatives 2 and 3, and one new ent-labdane diterpenoid, compound 9. The known compounds included six sesquiterpenoids, eleven triterpenoids, six sterols, and one lignan. Their structures were elucidated on the basis of extensive spectroscopic and mass-spectrometric analyses, as well as by X-ray crystallography in the case of gerin (1). The structurally related compounds 1-4 were found to exhibit strong inhibitory activities against human gastric carcinoma (SGC-7901) cells.

Di- and Triterpenoids from the Rhizomes of Isodon amethystoides and Their Anti-inflammatory Activities

“…The EtOAc part (75.9 g) was separated by silica gel column chromatography and further purified by repeated MPLC and HPLC to obtain a novel triterpenoid ( 1 ), six new diterpenoids ( 2 – 7 ), and 31 known terpenoids ( 8 – 38 ). Based on the NMR and MS data analysis, 21 known diterpenoids, eubotriol ( 8 ), 3α,7α,15β-trihydroxy- ent -kaur-16-ene ( 9 ), ent -16-kauren-3,15-dione ( 10 ), sugiol ( 11 ), 19-hydroxyferruginol ( 12 ), sugikurojin A ( 13 ), hinokiol ( 14 ), 12-methoxy-dehydro-abietic acid ( 15 ), macrophynin E ( 16 ), isodopene A ( 17 ), 8(17),13- ent -labdadien-15 → 16-lactone-19-oic acid ( 18 ), andrograpanin ( 19 ), 3α-hydroxy- ent -labda-8­(20),13-dien-16,15-olide ( 20 ), 7-keto-sempervirol ( 21 ), 3β-hydroxysempervirol ( 22 ), trogopteroid F ( 23 ), 18-hydroxysempervirol ( 24 ), inumakiol B ( 25 ), totarol-19-carboxylic acid ( 26 ), totarolone ( 27 ), and totaradiol ( 28 ), and 10 known triterpenoids, camaldulenic acid ( 29 ), maslinic acid ( 30 ), 2α,3α-dihydroxy-12-en-28-oic acid ( 31 ), 2α,3β-dihydroxyolean-13(18)-en-28-oic acid ( 32 ), 3β- O -( trans - p -coumaroyl) maslinic acid ( 33 ), eucalyptolic acid ( 34 ), 3β- O - trans -feruloyl-2α-hydroxyurs-12-en-28-oic acid ( 35 ), alpinic acid ( 36 ), hyptadienic acid ( 37 ), and maquatic acid ( 38 ), were identified. All compounds were isolated from I. amethystoides for the first time.…”

Sesquiterpenoids with Various Carbocyclic Skeletons from the Flowers of Chrysanthemum indicum

“…On the basis of the literature and spectroscopic data, the known sesquiterpenoids were defined as 11(7→6)­abeo-14-norcarbrane-4,7-dione ( 11 ), 6,8-cycloeudesm-4(15)-en-1-ol ( 12 ), (4 R ,5 R )-4,5-dihydroxycaryophyll-8­(13)-ene ( 13 ), 11-hydroxy-1-oxo-4α,5α,7β,10β-eremophilane ( 14 ), spathulenol ( 15 ), chrysanthediol A ( 16 ), 1β-hydroxy-4(15),5 E ,10­(14)-germacratriene ( 17 ), 5α-hydroxy-β-eudesmol ( 18 ), ligucyperonol ( 19 ), intermedeol ( 20 ), eudesm-4(15)-ene-1β,6α-diol ( 21 ), angeloylcumambrin B ( 22 ), cumambrin A ( 23 ), 11,13-dehydrodesacetylmatricarin ( 24 ), and matricarin ( 25 ) …”

Structurally Diverse Terpenoids from the Rhizomes ofCyperus rotundusL.

“…However, the OH-3 was determined as equatorially β-oriented based on the coupling patterns, but without the NOE difference correlation or NOESY experiment, which was dubitable according to our study. Besides the above chemical constituents, based on the ESIMS, NMR, optical rotation data, and comparison with data from the literature, the other compounds were elucidated as 3,4-O-isopropylideneshikimic acid (1) [22], dehydrocostuslactone (4) [23], (+)-alismoxide (5) [24], sugetriol triacetate (6) [1], 2β-hydroxyα-cyperone (7) [25,26], eudesma-4 (14),11(13)-diene-7α,8α,12triol (8) [27], and 3,4-seco-mansumbinoic acid (10) [28]. The sesquiterpenoid 6 possessed the patchoulane-type skeleton.…”