A thiophene, two furans, a dihydro furan, and two acetylenic benzene derivatives were isolated from the roots of Eupatorium heterophyllum collected in China. Structures were established on the basis of spectroscopic analyses as well as chemical transformations.
SchmidtGJ, SchillingEE. (2000) Phylogeny and biogeography of Eupatorium (Asteraceae: Eupatorieae) based on nuclear ITS sequence data. American Journal of Botany, 87, 716–726.
2.
DolejsL, HeroutV. (1962) Terpenes. CXLV. Constitution of eupatoriopicrin, a germacranolide from Eupatorium cannabinum. Collection of Czechoslovak Chemical Communications, 27, 2654–2661.
3.
DrozdzB, GrabarczykH, SamekZ, HolubM, HeroutV, SŏrrmF. (1972) Terpenes. CCXVI. Sesquiterpenic lactones from Eupatorium cannabinum. Revision of the structure of eupatoriopicrin. Collection of Czechoslovak Chemical Communications, 37, 1546–1554.
4.
KupchanSM, MaruyamaM, HemingwayRJ, HemingwayJC, ShibuyaS, FujitaT, CradwickPD, HardyADU, SimGA. (1971) Tumor inhibitors. LXVII. Eupacunin, a novel antileukemic sesquiterpene lactone from Eupatorium cuneifolium. Journal of the American Chemical Society, 934914–4916;
5.
KupchanSM, FujitaT, MaruyamaM, BrittonRW. (1973) Tumor inhibitors. LXXXIV. Isolation and structural elucidation of eupaserrin and deacetyleupaserrin, new antileukemic sesquiterpene lactones from Eupatorium semiserratum. Journal of Organic Chemistry, 38, 1260–1264.
6.
HerzW, de GrooteR, MurariR, KumarN. (1979) Sesquiterpene lactones of Eupatorium serotinum. Journal of Organic Chemistry, 44, 2784–2788.
7.
BohlmannF, MahantaPK, SuwitaA, SuwitaA, NatuAA, ZderoC, DornerW, EhlersD, GrenzM. (1977) Neue sesquiterpenlactone und andere inhaltsstoffe aus vertretern der Eupatorium-gruppe. Phytochemistry, 16, 1973–1981.
8.
ToriM, TakeichiY, KugaH, NakashimaK, SonoM. (2000) Two New Chlorine-containing Germacranolides, Eupaglehnins E And F from Eupatorium glehni. Heterocycles, 521075–1078;
9.
ToriM, TakeichiY, KugaH, NakashimaK, SonoM. (2002) Seven germacranolides, eupaglehnins A, B, C, D, E, and F, and 2α-acetoxyepitulipinolide from Eupatorium glehni. Chemical & Pharmaceutical Bulletin, 501250–1254;
10.
ToriM, MorishitaN, HirotaN, SaitoY, NakashimaK, SonoM, TanakaM, UtagawaA, HirotaH. (2008) Sesquiterpenoids isolated from Eupatorium glehnii. Isolation of guaiaglehnin A, structure revision of hiyodorilactone B, and genetic comparison. Chemical & Pharmaceutical Bulletin, 56, 677–681.
11.
BohlmannF, KleineKM, BornowskiH. (1962) Polyacetylenverbindungen. XLI. Über zwei Thiophenketone aus Artemisia arborescens L. Chemische Berichte, 952934–2938;
12.
AtkinsonRE, CurtisRF. (1971) A thiophen from Liatris pycnostachya. Phytochemistry, 10, 454–455.
13.
KamthoryB, RobertsonA. (1939) Furano-compounds. Part V. The synthesis of tetrahydroeuparin and the structure of euparin. Jornal of Chemical Society, 933–936;
14.
BohlmannF, ZderoC. (1971) Polyacetylenverbindungen. 193 Notiz über die Inhaltsstoffe von Carelia cistifolia Less. Chemische Berichte, 104, 964–966.
15.
ElsohlyMA, DoorenbosNJ, QuimbyMW, KnappJE, SlatkinDJ, SchiffPLJr. (1974) Euparone, a new benzofuran from Ruscus aculeatus. Journal of Pharmaceutical Sciences, 63, 1623–1624.
16.
BohlmannF, DuttaLN, DornerW, KingRM, RobinsonH. (1979) Zwei neue Guajanolide sowie weitere Longipinenester aus Stevia-arten. Phytochemistry, 18, 673–675.
17.
HusseinNS. (1970) Benzofurans from Senecio desfontainei. Pharmazie, 47, 468–469.
18.
BohlmannF, GrenzM. (1970) Neue Isopentenyl-acetophenon-Derivate aus Helianthella uniflora. Chemische Berichte, 103, 90–96.
19.
BohlmannF, KnollKH, ZderoC, MahantaPK, GrenzM, SuwitaA, EhlersD, VanN L, AbrahamWR, NatuAA. (1977) Terpen-derivate aus Senecio-arten. Phytochemistry, 16, 965–985.
20.
BohlmannF, ZderoC, GuptaRK, KingRM, RobinsonH. (1980) Aromatic esters and terpenoids of the liverworts in the genera Trichocolea, Neotrichocolea and Trichocoleopsis. Phytochemistry, 19, 2695–2699.
21.
BohlmannF, ZderoC. (1976) Natürlich vorkommende Terpen-Derivate, 58: Über Inhaltsstoffe der Gattung Brickellia. Chemische Berichte, 109, 1436–1445.
22.
ToriM, OtoseK, FukuyamaH, MurataJ, ShiotaniY, TakaokaS, NakashimaK, SonoM, TanakaM. (2010) New eremophilanes from Farfugium japonicum. Tetrahedron, 66, 5235–5243 and references cited therein.
23.
BohlmannF, GrenzM. (1977) Über Inhaltsstoffe der Gattung Flourensia. Chemische Berichte, 110, 295–300.
24.
BohlmannF, ZderoC, GrenzM. (1977) Natürlich vorkommende Terpen-Derivate, 81. Weitere Inhaltsstoffe aus Vertretern der Eupatorium-Gruppe. Chemische Berichte, 110, 1034–1041.
25.
ZalkowLH, KeinanE, SteindelS, KalyanaramanAR, BertrandJA. (1972) On the absolute configuration of toxol at C-3. Vicinal H-H coupling constants in 2-alkyl-3-hydroxydihydrobenzofurans. Tetrahedron Letters, 13, 2873–2876.
26.
MertesMP, PowersLJ, ShefterE. (1971) Isolation and identification of the cis-trans stereoisomers of substituted 3-hydroxy-(or acetoxy) 2-methyl-2,3-dihydrobenzofurans. Dihydrobenzofurans which obey the Karplus equation. Journal of Organic Chemistry, 36, 1805–1807.
27.
SiebertzR, ProkschP, WrayV, WitteL. (1989) Accumulation and biosynthesis of benzofurans in root cultures of Eupatorium cannabinum. Phytochemistry, 28789–793;
28.
BohlmannF, ZderoC. (1982) A dehydrofarnesol derivative from Stomanthaes africanus. Phytochemistry, 21, 1155–1156.
29.
HiroyaK, HashimuraK, OgasawaraK. (1994) An alternative route to a benzofuran natural product dehydrotremetone. Heterocycles, 38, 2463–2472.