Phytochemistry (v.53, #8)

Index (vii-viii).

Peniamidienone and penidilamine, plant growth regulators produced by the fungus Penicillium sp. No. 13 by Yasuo Kimura; Takashi Mizuno; Tsuyoshi Kawano; Katsuhide Okada; Atsumi Shimada (829-831).
Peniamidienone and penidilamine were isolated from cultures of the fungus Penicillium sp. No. 13 as new plant growth regulators and their structures were established by NMR spectroscopic studies. Peniamidienone showed weak inhibition of lettuce seedling growth.
Keywords: Penicillium sp.; Fungus; Peniamidienone; Penidilamine; Growth regulator; Lettuce;

Anti-platelet aggregation constituents from Gynura elliptica by Wei-Yu Lin; Che-Ming Teng; Ian-Lih Tsai; Ih-Sheng Chen (833-836).
A p-hydroxyacetophenone-like derivative, (+)-gynunone, and a chromane, together with six known compounds were isolated from the CHCl3 fraction of the roots of Gynura elliptica. Their structures were determined by means of spectral analyses. Among the isolates, 6-acetyl-2,2-dimethylchroman-4-one and vanillin showed anti-platelet aggregation activity induced by arachidonic acid in vitro.
Keywords: Gynura elliptica; Compositae; Root; p-Hydroxyacetophenone; Chromane; Chroman-4-ol; (+)-Gynunone; Gynunol; Anti-platelet aggregation activity;

Iridoids from Dunnia sinensis by Xiaoyi Wei; Haihui Xie; Xuejun Ge; Fengxian Zhang (837-840).
A plumieride type iridoid glucoside, dunnisinoside, and a non-glucosidic iridoid, dunnisinin, were isolated from the leaves of Dunnia sinensis. Their structures were established by 1D and 2D NMR and FABMS experiments.
Keywords: Dunnia sinensis; Rubiaceae; Iridoids; Dunnisinoside; Dunnisinin;

Cassane diterpenoid from Caesalpinia major by Sophon Roengsumran; Supassara Limsuwankesorn; Nattaya Ngamrojnavanich; Amorn Petsom; Chaiyo Chaichantipyuth; Tsutomu Ishikawa (841-844).
A new cassane diterpenoid, 14-deoxy-ε-caesalpin was isolated from the seed kernels of Caesalpinia major and its structure was determined by spectroscopic data.
Keywords: Caesalpinia major; Caesalpiniaceae; Diterpenoid; Cassane;

Sesquiterpenoids and diterpenoids from the Chilean liverwort Lepicolea ochroleuca by Huei-Ju Liu; Chia-Li Wu; Hans Becker; Josef Zapp (845-849).
The ether extract of the Chilean liverwort Lepicolea ochroleuca yielded three sesquiterpenoids, ent-4β-Hydroxy-10α-methoxyaromadendrane, ent-3β-Hydroxyspathulenol, and 1,10-Dioxotayloriane, as minor components.The major components were ledol and 13-epi-neoverrucosan-5β-ol, four other minor fusicoccanoids were identified.
Keywords: Lepicolea ochroleuca; Lepicoleaceae; Liverwort; Isolation; Aromadendrane; Neoverrucosane; Fusicoccane; ent-4β-hydroxy-10α-methoxyaromadendrane; ent-3β-hydroxyspathulenol; 1,10-dioxotayloriane;

Synthesis of methyl dihydrohardwickiate and its C-4 epimer. by Marta Costa; Elaine C. Perles; Fred Y. Fujiwara; Paulo M. Imamura (851-854).
Reduction of the α,β-unsaturated ester moiety of (+)-methyl hardwickiate with magnesium in methanol afforded methyl (4aS,6S,8aS,1R,5R)-5,6,8a-trimethyl-5-[2′-(3″-oxoyl)-ethyl-perhydro-1-naphthalenyl]-carboxaylate, while reduction with sodium in n-propanol, followed by esterification with diazomethane, furnished its C-4 epimer. After comparison of the 1 H - and 13 C -NMR data of these compounds with those reported for crolechinic acid isolated from Croton lechleri, a stereochemical revision for the natural product is suggested.
Keywords: Reduction; (+)-Methyl hardwickiate; Stereochemistry; Crolechinic acid;

ent-Kaurene diterpenoids from Isodon rubescens by Bao Lin Li; Shao Nong Chen; Zhi Xian Shi; Yao Zu Chen (855-859).
Two kaurenoids, taibairubescensins A and B, were isolated from the ethanol extract of the leaves and branches of Isodon rubescens. Their structures are designated as 2β,3β-diacetoxy-11β,13α-dihydroxy-ent-kaur-16-en-15-one and 3β,11β-diacetoxy-2β,6α-dihydroxy-ent-kaur-16-en-15-one, respectively, on the basis of detailed spectroscopic analyses.
Keywords: Isodon rubescens; Labiatae; Taibairubescensins A and B; ent-Kaurene diterpeniods;

Triterpenoid saponins containing an acetylated branched D-fucosyl residue from Quillaja saponaria Molina by Shengjun Guo; Elisabet Falk; Lennart Kenne; Bengt Rönnberg; Bo G. Sundquist (861-868).
Seven novel saponins were isolated from a bark extract of Quillaja saponaria Molina. the compounds were characterized, using mainly NMR spectroscopy, mass spectrometry and chemical methods, as quillaic acid substituted at C-3 with oligosaccharides consisting of various compositions of D-glucuronic acid D-galactose, D-xylose, and L-rhamnose and at C-28 with complex oligosaccharide structures consisting of various compositions of D-xylose, L-rhamnose, D-apiose and a branched 4-O-acetyl-D-fucose residue.
Keywords: Quillaja saponaria Molina; Structural analysis; Saponins; Quillaic acid; Acetyl group;

Cyclopentene dialdehydes from Tabebuia impetiginosa by Junko Koyama; Izumi Morita; Kiyoshi Tagahara; Kei-Ichi Hirai (869-872).
The isolation of two cyclopentene dialdehydes, 2-formyl-5-(4′-methoxybenzoyloxy)-3-methyl-2-cyclopentene-1-acetaldehyde and 2-formyl-5-(3′,4′-dimethoxybenzoyloxy)-3-methyl-2-cyclopentene-1-acetaldehyde, from the bark of Tabebuia impetiginosa is reported. The structures were established by analysis of spectroscopic data. These compounds showed anti-inflammatory activity.
Keywords: Tabebuia impetiginosa; Bignoniaceae; Cyclopentene dialdehyde; Anti-inflammatory activity;

A glycosidic eudesmanolide from Hyaloseris salicifolia by Elmira C. de Riscala; Silvia Turbay; César A.N. Catalán; Luis R. Hernández; Pedro Joseph-Nathan (873-876).
The flowers of Hyaloseris salicifolia afforded known ivasperin, while the leaves afforded ivasperin and 2-O-(6′-O-acetyl-β-D-glucopyranosyl)-ivasperin, whose structure was determined by spectroscopic methods.
Keywords: Dinoseris salicifolia; Hyaloseris salicifolia; Mutisieae; Compositae; Eudesmanolide; Sesquiterpene lactone; Glucoside;

A cytotoxic diterpene from Alomia myriadenia by Carlos L. Zani; Tânia M.A. Alves; Rogério Queiróz; Elita S. Fontes; Young Geun Shin; Geoffrey A. Cordell (877-880).
An extract of the aerial parts from Alomia myriadenia Schultz-Bip. ex Baker (Asteraceae) showed significant cytotoxicity against a panel of human cancer cell lines in a screening of extracts from Brazilian Atlantic Forest plant species. Employing a bioassay-linked HPLC-electrospray/MS method, followed by semi-preparative HPLC, the active component was isolated and characterized as a mixture of epimers of the labdane diterpene 12S,16-dihydroxy-ent-labda-7,13-dien-15,16-olide.
Keywords: Alomia myriadenia; Asteraceae; 12S,16-dihydroxy-ent-labda-7,13-dien-15,16-olide; Diterpene; Cytotoxicity;

Sesterterpenoid from Gentianella alborosea by Nobuo Kawahara; Masato Nozawa; Diana Flores; Pablo Bonilla; Setsuko Sekita; Motoyoshi Satake (881-884).
The structure of a new type of sesterterpenoid, designated as alborosin, isolated from Gentianella alborosea, has been deduced from a spectroscopic investigation.
Keywords: Gentianella alborosea; Gentianaceae; Hercampuri; Alborosin; Sesterterpenoid;

Triterpenoid saponins and sapogenin lactones from Albizia gummifera by Asfaw Debella; Ernst Haslinger; Martin G. Schmid; Franz Bucar; Günter Michl; Dawit Abebe; Olaf Kunert (885-892).
The structures of two new monodesmosidic and bisdesmosidic triterpenoid saponins (1 and 2) and the known compound Δ5-stigmasterol-3-O-β-D-glucopyranoside (3) as well as two new oleanane type triterpene lactone glycosides 4, 5 and a new sapogenin lactone 6 isolated from the stem bark of Albizia gummifera C.A. Smith (Mimosaceae) have been elucidated as 3-O-{β-D-glucopyranosyl(1→2)-[α-L-arabinopyranosyl(1→6)]-β-D-glucopyranosyl}-oleanolic acid (1), β-D-glucopyranosyl(1→2)-β-D-glucopyranosyl 3-O-{β-D-glucopyra-nosyl(1→2)-[α-L-arabinopyranosyl(1→6)]-β-D-glucopyranosyl}-oleanolate (2), 3β-{O-D-glucopyranosyl-(1→2)-[O-α-L-arabinopyranosyl(1→6)]β-D-glucopyranosyloxy}-machaerinic acid γ-lactone (4), 3β-O-β-D-glucopyranosiduronic acid (1→2)-β-D-glucopyranosyloxy]-machaerinic acid γ-lactone (5), and A-homo-3a-oxa-5β-olean-12-en-3-one-28-oic acid (6), respectively. The complete assignment of the 1 H and 13 C resonances of 1, 2, 4 and 6 and of the peracetate of 5 were achieved by means of 2D-NMR studies.
Keywords: Albizia gummifera (C.A. Smith); Mimosaceae; Machaerinic acid lactone glycosides; A-homo-3a-oxa-olean-12-en-28-oic acid; Oleanolic acid glycosides; Stigmasterol glycoside; Stem bark;

Oleanane saponins from Gymnema sylvestre by Wen-Cai Ye; Qing-Wen Zhang; Xin Liu; Chun-Tao Che; Shou-Xun Zhao (893-899).
Six oleanane-type saponins, along with two known triterpene saponins, were isolated from the leaves of Gymnema sylvestre. The structures of the oleanane triterpene glycosides were characterized as longispinogenin 3-O-β-D-glucuronopyranoside, 21β-benzoylsitakisogenin 3-O-β-D-glucuronopyranoside, 3-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester, oleanolic acid 3-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl(1→6)-β-D-glucopyranoside, 3-O-β-D-xylopyranosyl(1→6)-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl ester and 3-O-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl oleanolic acid 28-β-D-glucopyranosyl(1→6)-β-D-glucopyranosyl ester on the basis of hydrolysis and spectral evidence, including 1D- and 2D-NMR (TOCSY, ROESY, HMQC and HMBC) and FABMS analyses.
Keywords: Gymnema sylvestre; Asclepiadaceae; Oleanane saponins;

Triterpenoid glycosides and a triterpene from Ilex brevicuspis by Alexandre T.Cardoso Taketa; Tatjana Schmittmann-Schlager; Dominique Guillaume; Grace Gosmann; Eloir Paulo Schenkel (901-904).
Two saponins and a sapogenin were isolated from the leaves of Ilex brevicuspis. Their structures were established by means of spectroscopic methods as brevicuspisaponin 1 (3-O-α-L-arabinopyranosyl-20(S)-19α,24-dihydroxyursolic acid), brevicuspisaponin 2 (3-O-α-L-arabinopyranosyl-20(S)-19α,23,24-trihydroxyursolic acid) and 23-methylester of 20(S)-3β,19α,24-trihydroxyurs-12-en-23,28-dioic acid.
Keywords: Ilex brevicuspis; Aquifoliaceae; Saponin; Sapogenin; Brevicuspisaponin 1 and 2, 20(S)-rotungenic acid, 20(S)-rotundioic acid; Ursolic acid;

Triterpene saponins from the fruits of Hedera helix by E. Bedir; H. Kırmızıpekmez; O. Sticher; İ. Çalış (905-909).
Six triterpene saponins, including two new compounds, were isolated from the fruits of Hedera helix L. (Araliaceae). The structures of the new compounds, named helixosides A and B, were established as 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl hederagenin 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, and 3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranosyl oleanolic acid 28-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, respectively, on the basis of chemical and spectral data.
Keywords: Hedera helix; Araliaceae; Triterpenoid saponins; Helixosides A and B;

Icetexane and abietane diterpenoids from Salvia gilliessi by Matı́as Nieto; Eduardo E. Garcı́a; Oscar S. Giordano; Carlos E. Tonn (911-915).
One icetexane and two abietane diterpenes were isolated from the aerial parts of Salvia gilliesii, and characterized as 5-epi-icetexone; 12-hydroxy-11,14-diketo-6,8,12-abietatrien-19,20-olide and 6α,12,19-trihydroxy-11,14-diketo-8,12-abietadien-20,7β-olide, respectively. The structures were established by analysis of their 1 H and 13 C NMR spectra with the aid of 2D experiments. The triterpene oleanolic acid was isolated from the same source.
Keywords: Salvia gilliessi Benth; Labiatae; Tomentellae; Diterpenoids; Abietane; Icetexane;

A cleistanthane diterpene lactone from Vellozia compacta by Carlos A.S. Riehl; Angelo C. Pinto (917-919).
8,11,13-cleistanthatrien-7-one-19,20β-olide and six other previously described diterpenes were isolated by silica gel chromatography of the ethyl alcohol extract of Vellozia compacta. The structure of the cleistanthane lactone was deduced on the basis of spectral data analysis.
Keywords: Vellozia compacta; Velloziaceae; Structural elucidation; Cleistanthane type diterpene;

Highly oxygenated ecdysteroids from Vitex canescens root bark by A. Suksamrarn; N. Promrangsan; A. Jintasirikul (921-924).
Highly oxygenated ecdysteroids, (24R)-11α,20,24-trihydroxyecdysone and 11α,20,26-trihydroxyecdysone, have been isolated from the polar fraction of Vitex canescens root bark. The latter exists as two C-25 epimers which could be separated by reversed-phase HPLC.
Keywords: Vitex canescens; Verbenaceae; Root bark; Ecdysteroids; (24R)-11α,20,24-Trihydroxyecdysone; 11α,20,26-Trihydroxyecdysone;

Iridals from Iris tectorum and Belamcanda chinensis by Kunihiko Takahashfi; Yoji Hoshino; Sumiko Suzuki; Yoshio Hano; Taro Nomura (925-929).
Three iridals, iridotectorals A and B, and iridobelamal A, were isolated from rhizomes of Iris tectorum and Belamcanda chinensis, respectively, along with five known iridals. Their structures were elucidated on the basis of spectral evidence. The human promyelocytic leukemia (HL-60) cell-adhesion activity of the eight iridals is also discussed.
Keywords: Iris tectorum; Belamcanda chinensis; Iridaceae; Iridal; Iridotectorals A, B; Iridobelamal A;

Phlorigidosides A–C, iridoid glucosides from Phlomis rigida by Yoshio Takeda; Hiroyuki Matsumura; Toshiya Masuda; Gisho Honda; Hideaki Otsuka; Yoshihisa Takaishi; Ekrem Sezik; Erdem Yesilada (931-935).
From the aerial parts of Phlomis rigida, three iridoid glucosides, phlorigidoside A (2-O-acetyllamiridoside), B (8-O-acetyl-6-β-hydroxyipolamide) and C (5-deoxysesamoside), were isolated together with the known iridoid glucosides, shanzhiside methyl ester, 8-O-acetylshanzhiside methyl ester, deoxypulcheloside I, lamiridoside, and 6-β-hydroxyipolamide. The structures of the new compounds were elucidated based on spectral and chemical evidence.
Keywords: Phlomis rigida; Labiatae; Phlorigidosides A, B and C; Iridoid glucosides;

Monoterpene and pregnane glucosides from Solenostemma argel by M.S. Kamel; K. Ohtani; H.A. Hasanain; M.H. Mohamed; R. Kasai; K. Yamasaki (937-940).
From the aerial parts of Solenostemma argel, two monoterpene glucosides have been isolated and identified as 6,7-dihydroxy-dihydrolinalool 3-O-β-glucopyranoside and 6,7-dihydroxy-dihydrolinalool 7-O-β- glucopyranoside. A pregnane glucoside was also isolated and assigned as pregn-5-ene-3,14-β-dihydroxy-7,20-dione 3-O-β-glucopyranoside together with the known compounds benzyl alcohol O-β-apiofuranosyl-(1→6)-β- glucopyranoside, 2-phenylethyl O-α-arabinopyranosyl-(1→6)-β-glucopyranoside, astragalin and kaempferol-3-O-α-rhamnopyranosyl-(1→2)-β-glucopyranoside.
Keywords: Solenostemma argel; Asclepiadaceae; Monoterpene; Preganane glucosides;

Triterpenoid saponins from the roots of tea plant (Camellia sinensis var. assamica) by Yi Lu; Tatsuya Umeda; Akihito Yagi; Kanzo Sakata; Tirthankar Chaudhuri; D.K. Ganguly; Scion Sarma (941-946).
Keywords: Camellia sinensis var. assamica; Tea root; Triterpenoid saponin; Olean-12-ene;

Constituents and bioactivity of the tubers of Euphorbia sessiliflora by Somyote Sutthivaiyakit; Monnapa Thapsut; Virapong Prachayasittikul (947-950).
The diterpene ent-12-hydroxy-12[R]-abieta-8(14),13(15)-dien-16,12-olide was isolated from the tubers of Euphorbia sessiliflora Roxb., together with four known ent-abietadienolides, four known cycloartane triterpenes and ellagic acid-β-D-glucopyranoside. Two of these metabolates displayed moderate antibacterial activities.
Keywords: Euphorbia sessiliflora; Euphorbiaceae; ent-Abietadienolide; ent-12-Hydroxy-12[R]-abieta-8(14),13(15)-dien-16,12-olide; Antibacterial activity;

Diterpenoids from Salvia miltiorrhiza by Hang-Ching Lin; Wen-Liang Chang (951-953).
The abietane diterpenoid, neocryptotanshinone II, and the known 6,12-dihydroxyabieta-5,8,11,13-tetraen-7-one were isolated as minor components from the roots of Salvia miltiorrhiza. Their structures were established on the basis of spectral evidence.
Keywords: Salvia miltiorrhiza; Labiatae; Abietane diterpenoid; Neocryptotanshinone II; 6,12-Dihydroxyabieta-5,8,11,13-tetraen-7-one;

Diterpenoids from Humirianthera ampla by Ilmar B. Graebner; Marco A. Mostardeiro; Eduardo M. Ethur; Robert A. Burrow; Emı́la C.S. Dessoy; Ademir F. Morel (955-959).
Two diterpenoids, humirianthol and acrenol, as well as the known annonalide, were isolated from Humirianthera ampla. Humirianthol and acrenol were determined by 1D and 2D NMR spectroscopic techniques to be 3β,20:14β,16-diepoxy-3α,15α-dihydroxy-7-pimaren-19,6β-olide and 3β,20-epoxy-3α,15,16-trihydroxy-7-pimaren-19,6β-olide, respectively.
Keywords: Humirianthera ampla; Icacinaceae; Diterpenoids; Humirianthol; Acrenol;

Mulinane-type diterpenoids from Laretia acaulis by Luis A. Loyola; Jorge Bórquez; Glauco Morales; Aurelio San-Martı́n (961-963).
In addition to the known mulinolic acid and mulin-11, 13-dien-20-oic acid, 13-epimulinolic acid has been isolated from the aerial parts of Laretia acaulis (Cav.) Gill et Hook (Umbelliferae). Its structure was based on spectroscopic comparison with mulinolic acid and by chemical characterization.
Keywords: Laretia acaulis; Umbelliferae; Diterpenoid; Mulinane derivatives; Mulinolic acid; Mulin-11, 13-dien -20-oic acid; 13-epimulinolic acid;

6-Hydroxyluteolin-7-O-(1′′-α-rhamnoside) from Vriesea sanguinolenta Cogn. and Marchal (Bromeliaceae) by Gerhard Bringmann; Michael Ochse; Gerhard Zotz; Karl Peters; Eva-Maria Peters; Reto Brun; Jan Schlauer (965-969).
The isolation of 6-hydroxyluteolin-7-O-(1′′-α-rhamnoside) from the Central American epiphyte Vriesea sanguinolenta Cogn. and Marchal (Bromeliaceae) is described here. Its stereostructure was established by spectroscopic methods and an X-ray structure analysis of its hepta-O-acetyl derivative. This flavonoid glycoside had previously been reported from some Teucrium species (Labiatae), yet without sufficient physical data and spectroscopic evidence.
Keywords: Vriesea sanguinolenta; Bromeliaceae; Structural elucidation; X-ray crystallography; 6-Hydroxyluteolin-7-O-(1′′-α-rhamnoside); 5,6,3′,4′-Tetra-O-acetyl-6-hydroxyluteolin-7-O-(1′′-α-2′′,3′′,4′′-tri-O-acetylrhamnoside); Antimalarial activity;

Minor diarylheptanoid glycosides of Alnus rubra bark by Jie Chen; Ruben F. Gonzalez-Laredo; Joseph J. Karchesy (971-973).
The diarylheptanoid (S)-1,7-bis-(4-hydroxyphenyl)-heptan-3-one-5-O-β-D-xylopyranoside, and two known compounds, 1,7-bis-(3,4-dihydroxyphenyl)-heptan-3-one-5-O-β-D-glucopyranoside and platyphylloside were isolated from Alnus rubra bark. Structures were established by application of spectrometric techniques.
Keywords: Alnus rubra; Betulaceae; Diarylheptanoids; Bark;

Two chromene derivatives from Calyptranthes tricona by C. Menut; J.M. Bessiere; H. Ntalani; P. Verin; A.T. Henriques; R. Limberger (975-979).
Two α-monomethyl chromene derivatives were isolated from the leaf essential oil of Calyptranthes tricona from Brazil which were characterized by 1 H - and 13 C -NMR. Besides these components, which represent about half of the oil, classical terpenoid structures could be identified, among which cis-β-farnesene is the most abundant (26.6%). A biosynthetic pathway could be proposed to explain the formation of the chromene derivatives in the plant.
Keywords: Calyptranthes tricona; Myrtaceae; 5,7-dimethoxy-2-methyl-2H-benzopyran; 5,7-dimethoxy-2,8-dimethyl-2H-benzopyran;

Indicanines B and C, two isoflavonoid derivatives from the root bark of Erythrina indica by Alain K. Waffo; Guy A. Azebaze; Augustin E. Nkengfack; Zacharias T. Fomum; Michele Meyer; Bernard Bodo; Fanie R. van Heerden (981-985).
In addition to two known compounds, 5,4′-di-O-methylalpinumisoflavone and cajanin, a new 3-phenylcoumarin metabolite, named indicanine B, and a new isoflavone derivative, named indicanine C, were isolated from the root bark of Erythrina indica. By means of spectroscopic analysis, the structures of the new compounds were characterized as 4-hydroxy-3-(4′-hydroxyphenyl)-5-methoxy-2″,2″-dimethylpyrano [5″,6″:6,7] coumarin and 4′-hydroxy-5-methoxy-2″,2″-dimethylpyrano [5″,6″:6,7] isoflavone, respectively. The 13 C -NMR data of cajanin and the in vitro antimicrobial spectrum and potencies of the isolated compounds are also reported.
Keywords: Erythrina indica; Papilionaceae; Leguminosae; Root bark; Indicanines B and C; 5,4′-di-O-methylalpinumisoflavone; Cajanin; Phenylcoumarin; Isoflavones; Antibacterial activity;

Phenanthrenes from Dendrobium plicatile by Chie Honda; Masae Yamaki (987-990).
From Dendrobium plicatile stems, three phenanthrenes were isolated. The structures are 2,5-dihydroxy-4,9,10-trimethoxyphenanthrene, 2,5-dihydroxy-4-methoxyphenanthrene and 2,5,9-trihydroxy-4-methoxy-9,10-dihydrophenanthrene.
Keywords: Dendrobium plicatile; Orchidaceae; Phenanthrene; Plicatol A, B and C;

Chalconoids from Fissistigma bracteolatum by Trinh Phuong Lien; Andrea Porzel; Jürgen Schmidt; Tran Van Sung; Günter Adam (991-995).
Phytochemical studies on the leaves of Fissistigma bracteolatum yielded besides the two known compounds 2-hydroxy-3,4,6-trimethoxychalcone (1) and 5,7,8-trimethoxyflav-3-ene (2), five new chalconoids 2-hydroxy-3,4,6-trimethoxychalcene (3), 2-hydroxy-3,4,6-trimethoxydihydrochalcone (4), 2′-hydroxy-3′,4′,6′-trimethoxydihydrochalcone (5), 2′-hydroxy-3′,4′,6′-trimethoxy-β′-methoxychalcane (6) and 2′-hydroxy-3′,4′,6′-trimethoxy-β′-ethoxychalcane (7). The structures of these compounds were determined by mass and NMR spectroscopic methods.
Keywords: Fissistigma bracteolatum; Annonaceae; Leaves; Chalconoids; 2-Hydroxy-3,4,6-trimethoxychalcene; 2-Hydroxy-3,4,6-trimethoxydihydro-chalcone; 2′-Hydroxy-3′,4′,6′-trimethoxydihydrochalcone; 2′-Hydroxy-3′,4′,6′-trimethoxy-β′-methoxychalcane; 2′-Hydroxy-3′,4′,6′-trimethoxy-β′-ethoxychalcane;

Flavonoids from Goodyera schlechtendaliana by Xiao-Ming Du; Ning-Yi Sun; Yukihiro Shoyama (997-1000).
A flavonol glycoside, 3-[[6-O-(6-deoxy-α-L-mannopyranosyl)-β-D-glucopyranosyl]oxi]-5,7-dihydroxy-8-[(4-hydroxy-3,5-dimethoxyphenyl)methyl]-2-(3,4-dihydroxypheny)-4H-1-benzopyran-4-one, trivially named goodyerin, was isolated from the whole plant of Goodyera schlechtendaliana, along with three known flavonoids, rutin, kaempferol-3-O-rutinoside and isorhamnetin-3-O-rutinoside. The structures were established by spectroscopic analysis.
Keywords: Goodyera schlechtendaliana; Orchidaceae; Flavonoids; Goodyerin;

Two glycosides from the stem bark of Tetracentron sinense by Jin-hai Yi; Guo-lin Zhang; Bo-gang Li; Yao-zu Chen (1001-1003).
Two glycosides, tetracentronsides A and B, were isolated from the stem bark of Tetracentron sinense Oliv., along with ten known compounds, β-sitosterol, lupeol, betulinic acid, oleanolic acid, vanillic aldehyde, vanillic acid, maslinic acid, huazhongilexin, daucosterol and catechin. On the basis of spectral and chemical evidence, tetracentronside A and B were identified as 3,4,5-trimethoxyphenyl-O-6′-O-vanilloyl-β-D-glucopyranoside and (8R, 8′R) 9-β-D-glucopyranosyl dihydrocubebin, respectively.
Keywords: Tetracentron sinense; Magnoliaceae; Tetracentronside A; Tetracentronside B;

A bichalcone from the twigs of Rhus pyroides by Ishmael B. Masesane; Samuel O. Yeboah; Jürgen Liebscher; Clemens Mügge; Berhanu M. Abegaz (1005-1008).
The twigs of Rhus pyroides yielded a novel bichalcone 2′,4″,2‴-trihydroxy-4′,4‴-dimethoxy-4-O-5‴-bichalcone. It was identified on the basis of spectroscopic data including 1D and 2D NMR spectroscopy. The name rhuschalcone-1 is proposed.
Keywords: Rhus pyroides; Anacardiaceae; Biflavonoid; Bichalcone; Rhuschalcone-1;

Stilbene oligomers in roots of Sophora davidii by T. Tanaka; T. Ito; M. Iinuma; M. Ohyama; M. Ichise; Y. Tateishi (1009-1014).
Three stilbene oligomers, davidiols A–C were isolated from the roots of Sophora davidii in addition to the seven known phenols, leachianone A, sophoraflavanones G, H and I, miyabenol C, α-viniferin and ε-viniferin. Their structures and relative configurations were established by means of 2D-NMR spectroscopy including COLOC and PSNOESY.
Keywords: Sophora davidii; Leguminosae; Stilbene Oligomer; Davidiol A; Davidiol B; Davidiol C;

Stilbenoids in the stem bark of Hopea parviflora by T. Tanaka; T. Ito; Y. Ido; T.-K. Son; K. Nakaya; M. Iinuma; M. Ohyama; V. Chelladurai (1015-1019).
From the bark of Hopea parviflora, two stilbenoids, named (+)-parviflorol and (−)-ampelopsin A, were isolated in addition to three known compounds: (+)-balanocarpol, (−)-ε-viniferin and (−)-hopeaphenol. Their structures were determined by analysis of spectral data, including 2D NMR and NOE experiments, respectively.
Keywords: Hopea parviflora; Dipterocarpaceae; Stilbenoids; (+)-Parviflorol; (−)-Ampelopsin A; (+)-Balanocarpol; (−)-ε-Viniferin; (−)-Hopeaphenol;

Xanthones from Calophyllum teysmannii var. inophylloide by Anake Kijjoa; Maria José Gonzalez; Carlos M. Afonso; Madalena M.M. Pinto; Choojit Anantachoke; Werner Herz (1021-1024).
Further study of the wood of Calophyllum teysmannii Miq. var. inophylloide from Thailand yielded the xanthones 1,2,8-trimethoxyxanthone, 6-hydroxy-1,2,5,7-tetramethoxyxanthone and 3-(3′-carboxybutyl)-4-methoxyxanthone (teysmannic acid) in addition to scriblitifolic acid, 1,7-dihydroxyxanthone and the benzoic acid derivative leiocarpic acid.
Keywords: Calophyllum teysmannii var. inophylloide; Guttiferae; Xanthones; 1,2,8-Trimethoxyxanthone; 6-Hydroxy-1,3,5,7-tetramethoxyxanthone; 6-(3′-carboxybutyl)-5-methoxyxanthone; Scriblitifolic acid; Leiocarpic acid;

Coumarins from Ferulago capillaris and F. brachyloba by Benedicto Jiménez; Marı́a Concepción Grande; Josefa Anaya; Pascual Torres; Manuel Grande (1025-1031).
Four new coumarins, (+)-senecioylprangol, (−)-3′-senecioyloxymarmesin, (+)-3′-hydroxyprantschimgin and (+)-2″-senecioyloxymarmesin, besides 12 known coumarins have been isolated from two Ferulago species. Their structures have been established by spectroscopic methods and partial synthesis. New synthetic 3′-oxocoumarins are also described. There is a remarkable difference in the contents of the most abundant coumarins found in the roots of both species: osthol and aurapten are specific to F. capillaris and F. brachyloba, respectively.
Keywords: Ferulago capillaris; Ferulago brachyloba; Ferulago granatensis; Umbelliferae; Peucedaneae; Furanocoumarins; Marmesin; Prantschimgin; Prandiol; Chemotaxonomy;

7-Caffeoylsedoheptulose from Nyssa sylvatica by Xing-Cong Li; Hala N. ElSohly; Alice M. Clark (1033-1037).
7-Caffeoylsedoheptulose has been isolated from the wood of Nyssa sylvatica, along with two ellagic acid derivatives and scopoletin. Its structure was established by chemical and spectral evidence.
Keywords: Nyssa sylvatica; Nyssaceae; 7-caffeoylsedoheptulose;

Structure elucidation of clavilactone D: an inhibitor of protein tyrosine kinases by Lucio Merlini; Gianluca Nasini; Leonardo Scaglioni; Giuliana Cassinelli; Cinzia Lanzi (1039-1041).
Clavilactones D and E were isolated from an agar culture of the Basidiomycetous fungus Clitocybe clavipes, and their structure was elucidated by 1 H - and 13 C -NMR studies. Clavilactone D is an inhibitor of tyrosine kinases.
Keywords: Clitocybe clavipes; Basidiomycetes; Structural elucidation; NMR; Tyrosine kinases;

Xanthone and dihydroisocoumarin from Montrouziera sphaeroidea by Chihiro Ito; Yoshitaka Mishina; Marc Litaudon; Jean-Pierre Cosson; Hiroshi Furukawa (1043-1046).
A xanthone, montrouxanthone and a dihydroisocoumarin, montroumarin were isolated from the stem bark of Montrouziera sphaeroidea Pancher Ex Planchon et Triana [Guttiferae], along with two known compounds. Their structures were elucidated on the basis of spectroscopic analyses. This is the first report of the analysis of chemical constituents of Montrouziera species.
Keywords: Montrouziera sphaeroidea; Guttiferae; Xanthone; Dihydroisocoumarin; Lignan; Montrouxanthone; Montroumarin;

Flavonoids from Brosimum acutifolium by Sérgio Luiz Torres; Mara Silvia P. Arruda; Alberto C. Arruda; Adolfo H. Müller; Sebastião C. Silva (1047-1050).
4′-Hydroxy-7,8-[2-(2-hydroxyisopropyl)dihydrofuran]flavan and 4′,7-dihydroxy-8-(3,3-dimethylallyl)flavan, together with 10 known plant constituents, were obtained from the trunk bark of Brosimum acutifolium. Their structures were elucidated by spectroscopic methods, including 2D NMR spectroscopic techniques.
Keywords: Brosimum acutifolium; Moraceae; Flavans; Chalcones; Brosimine A and B;

Phenylpropanoid glycosides from Smilax glabra by Ting Chen; Jian-Xin Li; Qiang Xu (1051-1055).
Five phenylpropanoid esters of sucrose glycosides, trivially named smiglasides A–E, were isolated from the rhizomes of Smilax glabra. Their structures were elucidated on the basis of spectroscopic studies.
Keywords: Smilax glabra; Liliaceae; Phenylpropanoid glycosides; Sucrose ester; Smiglaside;

Quaternary indole alkaloids from the stem bark of Strychnos guianensis by Jacques Penelle; Monique Tits; Philippe Christen; Jordi Molgo; Viviane Brandt; Michel Frédérich; Luc Angenot (1057-1066).
Two new quaternary alkaloids, 9-methoxy-N b-methylgeissoschizol and guiachrysine together with the known compounds C-alkaloid O, fluorocurine, mavacurine, macusine B and C-profluorocurine, were isolated from Strychnos guianensis stembark. The structures of the compounds were elucidated on the basis of spectroscopic studies
Keywords: Strychnos guianensis; Loganiaceae; Quaternary alkaloids; 9-Methoxy-N b-methylgeissoschizol; Guiachrysine; C-alkaloid O; Fluorocurine; Mavacurine; Macusine B; C-profluorocurine; 2D-NMR;

Aporphinoid alkaloids and other constituents from Lettowianthus stellatus by Mayunga H.H. Nkunya; Stephan A. Jonker; John J. Makangara; Reiner Waibel; Hans Achenbach (1067-1073).
Two new aporphinoid alkaloids, lettowianthine and 11-methoxylettowianthine were isolated from the root bark of Lettowianthus stellatus, together with the new sesquiterpene 11-hydroxyguaia-4,6-diene and the known compounds liriodenine, (Z)-7-octadecen-9-ynoic acid, methyl (2E,6E,10R)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate, methyl (2E,6E,10R)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoate, and 3,4,5-trimethoxyphenol. The structure elucidation was achieved by spectroscopic methods.
Keywords: Lettowianthus stellatus; Annonaceae; Aporphinoid alkaloids; Lettowianthine; 11-Methoxylettowianthine; 11-Hydroxyguaia-4,6-diene; (Z)-7-Octadecen-9-ynoic acid; Methyl (2E,6E,10R)-10,11-epoxy-3,7,11-trimethyl-2,6-dodecadienoate; Methyl (2E,6E,10R)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoate;

Alkaloids and phenylpropanoids from Peganum nigellastrum by Zhong-Ze Ma; Yoshio Hano; Taro Nomura; Ying-Jie Chen (1075-1078).
Two canthin-6-one alkaloids, luotonins C and D, and two phenylpropanoids, dihydrosinapyl ferulate and dihydroconiferyl ferulate, were isolated from the aerial parts of Peganum nigellastrum along with four known alkaloids, harmine, 3-phenylquinoline, 3-(4-hydroxyphenyl)quinoline and 3-(1H-indol-3-yl)quinoline. Their structures were elucidated by spectroscopic techniques. The structures of luotonins C and D were also confirmed by chemical synthesis.
Keywords: Peganum nigellastrum; Zygophyllaceae; Alkaloids; Canthin-6-one; Luotonins C and D; Harmine; Quinoline; Phenylpropanoids;

An azaanthracene alkaloid from Polyalthia suberosa by Patoomratana Tuchinda; Manat Pohmakotr; Bamroong Munyoo; Vichai Reutrakul; Thawatchai Santisuk (1079-1082).
An azaanthracene alkaloid, 1-aza-9,10-dimethoxy-4-methyl-2-oxo-1,2-dihydroanthracene (kalasinamide) has been isolated from the stems of Polyalthia suberosa. In addition, the known N-trans-feruloyltyramine and N-trans-coumaroyltyramine are also reported from the same source. The structures were elucidated by spectroscopic methods.
Keywords: Polyalthia suberosa; Annonaceae; Alkaloid; Azaanthracene;

Volatile constituents in juice and oil of Australian wild lime (Microcitrus inodora) by Philip E. Shaw; Manuel G. Moshonas; Kim D. Bowman (1083-1086).
Fifty-three volatile constituents from the juice and twenty from the peel oil of Microcitrus inodora have been identified by gas chromatographic and mass spectral analysis. All except seven had been reported earlier as citrus constituents. Since M. inodora is used as a parent for production of new citrus hybrids, this information will be useful to horticulturists, plant breeders and phytochemists.
Keywords: Microcitrus inodora; Rutaceae; Volatiles; Gas chromatography; Mass spectrometry; Citrus; Hybridization;

Investigations of the extracts of a culture of Clitocybe catinus gave rise to the isolation of new acetylenic diols 13. Their structure was determined on the basis of 1 H - and 13 C -NMR evidence and the absolute configuration elucidated by means of the modified Mosher’s method.
Keywords: Clitocybe catinus; Basidiomycetes; Acetylene diols; Structural elucidation; Absolute configuration;

Three putrescine bisamides from the leaves of Aglaia grandis by Akira Inada; Kazuhiro Shono; Hiroko Murata; Yuka Inatomi; Dedy Darnaedi; Tsutomu Nakanishi (1091-1095).
Three putrescine (i.e. 1,4-butanediamine) bisamides were isolated from the leaves of Aglaia grandis. Their structures were elucidated by interpretation of spectral data.
Keywords: Aglaia grandis; Meliaceae; Leaf; Putrescine bisamide;

Procyanidins from the seeds of Vitis amurensis by Jiang-Nong Wang; Yoshio Hano; Taro Nomura; Ying-Jie Chen (1097-1102).
Three procyanidins, procyanidin B-5 3′-O-gallate, vitisinol, and amurensisin, were isolated from the seeds of Vitis amurensis, whose structures were elucidated on the basis of spectral and chemical evidence. Vitisinol and amurensisin contain a spiro-type biflavanyl linkage and a biphenyl-lactone partial structure, respectively.
Keywords: Vitis amurensis; Vitaceae; Procyanidins; Procyanidin B-5 3′-O-gallate; Vitisinol; Amurensisin;

Nor-lignan and sesquiterpenes from Cremanthodium ellisii by Bao-Ning Su; Qi-Xiu Zhu; Zhong-Jian Jia (1103-1108).
A nor-lignan and two sesquiterpenes, along with six known compounds, have been isolated from the medicinal plant Cremanthodium ellisii. Their structures were determined on the basis of spectral evidence, especially 2D NMR ( 1 H – 1 H COSY, HMQC, HMBC).
Keywords: Cremanthodium ellisii; Compositae; Nor-lignan; Sesquiterpene;