Hydroxyisogermafurenolide

[Quality evaluation of Curcumae Radix from different origins based on UPLC characteristic chromatogram, multicomponent content, and chemometrics].[Pubmed:35718518]

Zhongguo Zhong Yao Za Zhi. 2022 Jun;47(11):2964-2974.

In this study, UPLC was used to establish the characteristic chromatograms of Curcumae Radix from different origins(LSYJ, WYJ, HSYJ, and GYJ) and the content determination method of 11 chemical components. The evaluation of characteristic chromatogram similarity, cluster analysis(CA), principal component analysis(PCA), and orthogonal partial least square discriminant analysis(OPLS-DA) were combined to evaluate the quality of Curcumae Radix from four origins. LSYJ, WYJ, HSYJ, and GYJ showed 15, 17, 15, and 10 characteristic peaks, respectively, and 8 of the peaks were identified. The characteristic chromatograms of Curcumae Radix samples(except for GYJ07) from the same origin showed the similarity greater than 0.854. The 11 chemical components had different content among the samples from four origins. Curcumenol, furanodienone, and isocurcumenol were rich in LSYJ; Hydroxyisogermafurenolide, curdione, and furanodiene had high content in WYJ; gemacrone, beta-elemene, bisdemethoxycurcumin, demethoxycurcumin, and curcumin were rich in HSYJ; all the components had low content in GYJ. The chemometric analysis showed that CA, PCA, and OPLS-DA could accurately classify the four origins of Curcumae Radix into four categories, and five different quality markers, namely furanodienone, curcumenol, curdione, Hydroxyisogermafurenolide, and furanodiene, were screened out by OPLS-DA. UPLC in combination with multicomponent content determination is simple, rapid, reproducible, and specific, which can provide reference for the quality control and identification of Curcumae Radix from four origins.

[Chemical constituents of sesquiterpenes from Chloranthus multistachys].[Pubmed:34467726]

Zhongguo Zhong Yao Za Zhi. 2021 Aug;46(16):4145-4149.

With repeated silica gel, octadecyl silica(ODS), and Sephadex LH-20 column chromatography, normal-phase and reverse-phase high performance liquid chromatography(HPLC), etc., a pair of new enantiomers and 5 known compounds were separated from the 95% ethanol extract of Chloranthus multistachys. These compounds were identified by the nuclear magnetic resonance spectroscopy(including 1 D-NMR and 2 D-NMR), single-crystal X-ray diffraction, circular dichroism(CD) spectroscopy, mass spectrometry(MS), and some other methods as(1R,4R,5R,8S,10R)-chloraeudolide H(1 a),(1S,4S,5S,8R,10S)-chloraeudolide H(1 b), Hydroxyisogermafurenolide(2), 4alpha-hydroxy-5alpha,8beta(H)-eudesm-7(11)-en-8,12-olide(3), chloraniolide A(4), chlorantene D(5), 4alpha,8beta-dihydroxy-5alpha(H)-eudesm-7(11)-en-8,12-olide(6). Compounds 1 a and 1 b are a pair of new eudesmane-type sesquiterpene enantiomers, and compounds 2-4 were isolated from C. multistachys for the first time.

Investigation of Antiplasmodial Effects of Terpenoid Compounds Isolated from Myrrh.[Pubmed:32365391]

Planta Med. 2020 Jun;86(9):643-654.

As part of our ongoing search for antiprotozoal natural products from plants, we examined different resins from the Burseraceae family. The dichloromethane extract obtained from myrrh, the oleo-gum-resin of Commiphora species, showed promising in vitro activity against Plasmodium falciparum with an IC(50) value of 1 microg/mL. Bioactivity-guided fractionation led to the isolation and characterization of 18 sesquiterpenoids, namely, beta-elemene (1: ), elemyl acetate (2: ), curzerenone (3: ), 8-Hydroxyisogermafurenolide (4: ), 2-methoxyisogermafurenolide (5: ), 8-epi-2-methoxyisogermafurenolide (6: ), furanodienone (7: ), 1(10)Z,4Z-furanodien-6-one (8: ), rel-2R-methyl-5S-acetoxy-4R-furanogermacr-1(10)Z-en-6-one (9: ), (1(10)E)-2-methoxy-8,12-epoxygermacra-1(10),7,11-trien-6-one (10: ), 2R-methoxyfuranodiene (11: ), 2-acetyloxyglechomanolide (12: ), 8-epi-2-acetyloxyglechomanolide (13: ), (1R,2R,4S)-1,2-epoxyfuranogermacr-10(15)-en-6-one (14: ), hydroxylindestrenolide (15: ), isohydroxylindestrenolide (16: ), myrrhone (17: ), and myrrhterpenoid O (18: ). Moreover, nine (nor-)triterpenoids were isolated: mansumbinol (19: ), mansumbinol epoxide (20: ), mansumbinone (21: ), mansumbin-13(17)-en-3,16-dione (22: ), 3,4-seco-mansumbinoic acid (23: ), rel-20S-hydroxy-dammar-24-en-3,16-dione (24: ), rel-(16S,20S)-dihydroxydammar-24-en-3-one (25: ), cycloart-24-en-1alpha,2alpha,3beta-triol (26: ), and 3beta-isovaleroyloxycycloart-24-en-1alpha,2alpha-diol (27: ). All compounds were identified by MS and NMR spectroscopic analyses. To the best of our knowledge, compounds 5, 6, 12, 13, 16, 18: , and 20: are reported for the first time. All isolated compounds were tested in vitro for activity against P. falciparum and cytotoxicity. The sesquiterpene 7: and the triterpene 25: were the most active compounds found in this study with IC(50) values of 7.4 and 2.8 microM, respectively.

Total synthesis, structural revision and biological evaluation of gamma-elemene-type sesquiterpenes.[Pubmed:30303229]

Org Biomol Chem. 2018 Oct 31;16(42):7843-7850.

Total synthesis and absolute configuration confirmation of gamma-elemene-type sesquiterpenes, which possess vast potential for biological activities, was investigated based on a convergent synthetic strategy. A key intermediate with all functional groups of this family of natural products was accessed by an intermolecular aldol reaction and then an acetylation of a known ketone (12) derived from commercially available verbenone. The versatile intermediate can be easily transformed into structurally different gamma-elemene-type sesquiterpenes based on control of base-promoted cyclization manipulation in different solvents. The utility of this robust approach is illustrated by the first syntheses of elema-1,3,7(11),8-tetraen-8,12-lactam (4') and 8beta-methoxy-isogermafurenolide (6a), as well as the syntheses of elem-1,3,7,8-tetraen-8,12-olide (3) and Hydroxyisogermafurenolide (5) in only 6 or 7 steps. In addition, the structure of the reported 5betaH-elem-1,3,7,8-tetraen-8,12-olide (1) was revised as elem-1,3,7,8-tetraen-8,12-olide (3) by comparison of their identified datum, and the absolute configuration of elema-1,3,7(11),8-tetraen-8,12-lactam was confirmed as 4'. Furthermore, the inhibitory effect of all synthesized natural compounds and their natural analogues on cancer cell proliferation was evaluated. Among them compounds 3, 4 and 4' were found to possess potent inhibitory activity against Kasumi-1 and Pfeiffer. Meanwhile, preliminary structure-activity relationships for these compounds are discussed.

Sesquiterpene lactones from the root tubers of Lindera aggregata.[Pubmed:19639966]

J Nat Prod. 2009 Aug;72(8):1497-501.

Phytochemical investigation of the root tubers of Lindera aggregata resulted in the isolation of five new sesquiterpene lactones, linderagalactones A-E (1-5), along with eight known sesquiterpenoids, 3-eudesmene-1beta,11-diol, hydroxylindestenolide, strychnistenolide, Hydroxyisogermafurenolide, atractylenolide III, linderane, neolinderalactone, and linderalactone. The structures and relative configurations of 1-5 were determined by spectroscopic methods, especially HRESIMS and 2D NMR techniques. The absolute configurations of 1-4 were defined by comparison of quantum chemical TDDFT calculated and experimental ECD spectra. Linderagalactone A (1) is a halogenated sesquiterpene lactone possessing a unique rearranged carbon skeleton. Linderagalactone E (5), linderane, hydroxylindestenolide, and linderalactone showed hepatoprotective activity against H2O2-induced oxidative damages on HepG2 cells with EC(50) values of 67.5, 167.0, 42.4, and 98.0 microM, respectively.