Humulanes, drimanes, ent-kaurane, lupane, cycloartane, flavanone, flavones and quinol derivatives were isolated from Malagasy Cussonia vantsilana, Helichrysum gymnocephalum, Phyllarthron madagascariense, Gomphocarpus fructicosus, Cinnamosma sp. and C. fragrans, and their structures elucidated by using extensive NMR analysis. A mixture of a few flavones and/or lupane triterpene showed antimicrobial activity against Mycobacterium smegmatis and Pseudomonas aeruginosa.
HarinantenainaL, AsakawaY. (2004) Chemical constituents of Malagasy liverworts, Part II: Mastigophoric acid methyl ester of biogenetic interest from Mastigophora diclados (Lepicoleaceae subf. Mastigophoroideae). Chemical and Pharmaceutical Bulletin, 52, 1382–1384.
2.
HarinatenainaL, KurataR, AsakawaY. (2005) Chemical constituents of Malagasy liverworts, Part III: Sesquiterpenoids from Bazzania decrescens and Bazzania madagassa. Chemical and Pharmaceutical Bulletin, 53, 515–518.
3.
HarinatenainaL, KurataR, TakaokaS, AsakawaY. (2006) Chemical constituents of Malagasy liverworts: Cyclomyltaylanoids from Bazzania madagassa. Phytochemistry, 67, 2616–2622.
4.
HarinantenainaL, DangNQ, NashizawaT, HashimotoT, KohchiC, SomaG-I, AsakawaY. (2007) Bioactive compounds from liverworts: inhibition of lipopolysaccharide-induced inducible NOS mRNA in RAW 264.7 cells by herbertenoids and cuparenodis. Phytomedicine, 14, 486–491.
5.
HarinantenainaL, AsakawaY. (2007) Chemical constituents of Malagasy liverworts. 6: A myltaylane caffeate with nitric oxide inhibitory activity from Bazzania nitida. Journal of Natural Products, 70, 856–858.
6.
HarinantenainaL.AsakawaY. (2007) Malagasy liverworts, source of new and biologically active compounds. Natural Product Communications, 2, 701–709.
7.
HarinantenainaL, TakaokaS. (2006) Cinnafragrins A-C, dimeric and trimeric drimane sesquiterpenoids from Cinnamosma fragrans, and structure revision of capsicodendrin. Journal of Natural Products, 69, 1193–1197.
8.
HarinantenainaL, AsakawaY. (2006) Identification of Cinnamosma secondary metablites as α-glucosidase inhibitors and cytostatic compounds. A successful example of the application of ethnobotany in drug discovery. Journal of Pharmaceutical Society of Japan, 126, 96–99.
9.
HarinantenainaL, AsakawaY.De ClercqE. (2007) Cinnamacrins A-D, cinnafragrin D and cytostatic metabolites with α-glucosidase inhibitory activity from Cinnamosma macrocarpa. Journal of Natural Products, 70, 277–282.
10.
HarinantenainaL, MatsunamiK, OtsukaH, KawahataM, YamaguchiK, AsakawaY. (2008) Secondary metabolites of Cinnamosma madagascariensis and their α-glucoidase inhibitory properties. Journal of Natural Products, 71, 123–126.
11.
ReinaM, NoldM, SantanaO, OrihuelaJC, Gonzeálea-ColomaA. (2002) C-5-Substituted antifeedant silphinene sesquiterpenes from Senecio palmensis. Journal of Natural Products, 65, 448–453.
12.
KhomenkoTM, ZenkovetsGA, BarkhashVA. (1997) Transformations of α-humulene and some its monoepoxy derivatives over solid acid catalysts. Epoxidation of α-humulene. Russian Journal of Organic Chemistry, 33, 655–359.
ToshimaH, OikawaH, ToyomasuT, SassaT. (2001) Total synthesis of (+)-albicanol and (+)-albicanyl acetate. Bioscience, Biotechnology, & Biochemistry, 65, 1244–1247.
15.
OhnmachtS, WestR, SimionescuR, AtkinsonJ. (2008) Assignment of the 1H and 13C NMR of tocotrienols. Magnetic Resonance in Chemistry, 46, 287–294.
16.
CoreyEJ, DaigneaultS, DixonBR. (1993) A biomimetic chemical synthesis of humulene from farnesol. Tetrahedron Letters, 34, 3675–3678.
17.
CanonicaL, CorbellaA, GariboldiP, JommiG, KrepinskyJ, FerrariG, CasagrandeC. (1969) Sesquiterpenoids of Cinnamosma fragrans Baillon. Structure of cinnamolide, cinnamosmolide and cinnamodial. Tetrahedron, 25, 3895–3902.
18.
MahmoudI-I, KinghornAD, CordellGA, FarnsworthNR. (1980) Potential anticancer agents. XVI. Isolation of bicyclofarnesane sesquiterpenoids from Capsicodendron dinisii. Journal of Natural Products, 43, 365–371.
19.
MikolajczakKL, SmithCRJr. (1967) Pentacyclic triterpenes of Jurinea anatolic Boiss. and Jurinea consanguinea DC. fruit. Lipids, 2, 127–132;
20.
SholichinM, YamasakiK, KasaiR, TanakaO. (1980) 13C Nuclear magnetic resonance of lupane-type triterpenes, lupeol, betulin and betulinic acid. Chemical and Pharmaceutical Bulletin, 28, 1006–1008.
21.
BaddeleyGV, JefferiesPR, RetallackRW. (1964) Chemistry of the Euphorbiaceae-IX. Further constituents of Beyeria leschenaultii. Tetrahedron, 20, 1983–1985;
IuY-L, HoD, CassadyJM, CookV, BairdW. (1992) Isolation of potential cancer chemo preventive agents from Eriodictyon californicvm. Journal of Natural Products, 55, 357–363.
26.
AliE, BagchiD, PakrashiSC. (1979) Studies on Indian medicinal plants. Part 49. New flavonoids from Anaphalis araneosa. Phytochemistry, 18, 356–357;
27.
HorieT, KitouT, KawamuraY, YamashitaK. (1996) Studies of the selective O-alkylation and dealkylation of flavonoids. XXI. A convenient method for synthesizing 3,5,7-trihydroxy-6,8-dimethoxyflavones and 5,7-dihydroxy-3,6,8-trimethoxyflavones. Bulletin of the Chemical Society of Japan, 69, 1033–1041.
28.
GaffieldW. (1970) Circular dichroism, optical rotatory dispersion and absolute configuration of flavanones, 3-hydroxyflavanones and their glycosides. Determination of aglycone chirality in flavanone glycosides. Tetrahedron, 26, 4093–4108.
29.
WijeratneDBT, KumarV, SultanbawaMU. (1981) 3-Oxolup-20(29)-en-30-al, a new lupane from Gymnosporia emarginata (Celastraceae). Journal of the Chemical Society, Perkin Transactions 1, 2724–2726;
30.
TintoWF, BlairLC, AlliA, ReynoldsWF, McLeanS. (1992) Lupane triterpenoids of Salacia cordata. Journal of Natural Products, 55, 395–398.
31.
TakahashiK, TakaniM. (1975) Studies on constituents of medicinal plants. XIV. Constituents of Schizandra nigra Max. (1). Chemical and Pharmaceutical Bulletin, 23, 538–542;
32.
SyL-K, SaundersRMK, BrownGD. (1997) Phytochemistry of Illicium donnianum and the systematic position of the Illiciaceae. Phytochemistry, 44, 1099–1108.
33.
HerzW, GibajaS. (1972) 5-Hydroxy-6,7,4′-trimethoxyflavone from Ageratina gilbertii. Phytochemistry, 11, 2625.
34.
HorieT, OhtsuruY, ShibataK, YamashitaK, TsukayamaM, KawamuraY. (1998) 13C NMR spectral assignment of the A-ring of polyoxygenated flavones. Phytochemistry, 47, 865–874.
35.
BohlmannF, SuwitaA. (1976) Naturally occurring terpene derivatives, 62. On the constituents of Senecio abrotanifolius L. Chemische Berichte, 109, 2014–2020.
36.
JoY, SuhJ, ShinMH, JungJH, ImKS. (2005) Jacaranone and related compounds from the fresh fruits of Ternstroemia japonica and their antioxidative activity. Archives of Pharmacal Research, 28, 885–888.
37.
GelbaumLT, ZalkowLH, HamiltonD. (1982) Cytotoxic agent from Senecio anonymus wood. Journal of Natural Products, 45, 370–372;
38.
KawakamiJ, NakamotoK, NuwaS, HandaS, MikiS. (2006) Regioselective reaction of quinones with reformatsky reagent: (BrZnCH2CO2Et • THF)2. Tetrahedron Letters, 47, 1201–1203.
39.
HarinantenainaL, KasaiR, YamasakiK. (2008) ent-Kaurene diterpenoid glycoside from a Malagasy endemic plant, Cussonia vantsilana. Phytochemistry, 61, 367–372.
40.
HarinantenainaL, KasaiR, RakotovaoM, YamasakiK. (2001) New iridoid and phenethyl glycosides from Malagasy medicinal plant, Phyllarthron madagascariense. Natural Medicines, 55, 187–192.
41.
AfoulousS, FerhoutH, RaoelisonEG, ValentinA, MoukarzelB, CoudercF, BouajilaJ. (2011) Helichrysum gymnocephalum essential oil: chemical composition and cytotoxic, antimalarial and antioxidant activities, attribution of the activity origin by correlations. Molecules, 16, 8273–8291.
42.
GodinP. (1954) A new spray reagent for paper chromatography of polyols and cetoses. Nature (London), 174, 134.
