Antimicrobial susceptibility and molecular characteristics of methicillin-resistant Staphylococcus aureus in a Japanese secondary care facility.

Methicillin-resistant Staphylococcus aureus (MRSA) is prevalent in Japan, and the Staphylococcus cassette chromosome mec (SCCmec) type II is common among hospital-acquired MRSA isolates. Information pertaining to MRSA characteristics is limited, including SCCmec types, in primary or secondary care facilities. A total of 128 MRSA isolates (90 skin and soft tissue isolates and 38 blood isolates) were collected at a secondary care facility, Kawatana Medical Center, from 2005 to 2011. Antimicrobial susceptibility testing for anti-MRSA antibiotics and molecular testing for SCCmec and virulence genes (tst, sec, etb, lukS/F-PV) were performed. Strains positive for lukS/F-PV were analyzed by multilocus sequence typing and phage open-reading frame typing. SCCmec typing in skin and soft tissue isolates revealed that 65.6% had type IV, 22.2% had type II, 8.9% had type I, and 3.3% had type III. In blood isolates, 50.0% had type IV, 47.4% had type II, and 2.6% had type III. Minimum inhibitory concentrations, MIC(50)/MIC(90), against vancomycin, teicoplanin, linezolid, and arbekacin increased slightly in SCCmec II isolates from skin and soft tissue. MICs against daptomycin were similar between sites of isolation. SCCmec type II isolates possess tst and sec genes at a greater frequently than SCCmec type IV isolates. Four lukS/F-PV-positive isolates were divided into two clonal patterns and USA300 was not included. In conclusion, SCCmec type IV was dominant in blood, skin, and soft tissue isolates in a secondary care facility in Japan. Because antimicrobial susceptibility varies with the SCCmec type, SCCmec typing of clinical isolates should be monitored in primary or secondary care facilities.

Three new cyclic diarylheptanoids and other phenolic compounds from the bark of Myrica rubra and their melanogenesis inhibitory and radical scavenging activities.

Ten cyclic diarylheptanoids (1-10), including three new compounds: myricanone 5-O-alpha-L-arabinofuranosyl-(1-->6)-beta-D-glucopyranoside (7), myricanone 17-O-beta-D-(6'-O-galloyl)-glucopyranoside (8), and 16-methoxy acerogenin B 9-O-beta-D-apiofuranosyl-(1-->6)-beta-D-glucopyranoside (10), along with two flavonoids (11, 12), were isolated from the extracts of Myrica rubra (Myricaceae) bark. The structures of new compounds were determined on the basis of spectroscopic methods. On evaluation of compounds 1-12 against the melanogenesis in the B16 melanoma cells, six compounds, 3, 5, 7, 8, 10, and 12, exhibited inhibitory effects with 30-56% reduction of melanin content at 25 microg/mL with no or very weak toxicity to the cells (82-103% of cell viability at 25 microg/mL). In addition, upon evaluation of compounds 1-12 against the scavenging activities of free radicals [against the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical], seven compounds, 1, 3, 5, 6, 8, 11, and 12, showed potent scavenging activity [IC(50) 2-21 microM (0.6-7.3 microg/mL)].

Melanogenesis inhibitory activities of iridoid-, hemiterpene-, and fatty acid-glycosides from the fruits of Morinda citrifolia (Noni).

A new iridoid glycoside, 9-epi-6alpha-methoxy geniposidic acid (4), three new hemiterpene glycosides, 3-methylbut-3-enyl 2'-O-(beta-D-glucopyranosyl)-beta-D-glucopyranoside (nonioside K) (6), 3-methylbut-3-enyl 6'-O-(beta-D-xylopyranosyl)-beta-D-glucopyranoside (nonioside L) (8), and 3-methylbut-3-enyl 6'-O-(beta-D-xylofuranosyl)-beta-D-glucopyranoside (nonioside M) (9), and two new saccharide fatty acid esters, 6'-O-(beta-D-glucopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside N) (16) and 6'-O-(beta-D-xylopyranosyl)-1'-O-[(2xi)-2-methylbutanoyl]-beta-D-glucopyranose (nonioside O) (17), were isolated from a methanol extract of the fruits of Morinda citrifolia (noni), along with 11 known compounds, namely, three iridoid glycosides (1-3), two hemiterpene glycosides (5 and 7), and five saccharide fatty acid esters (10-15). Upon evaluation of compounds 1-17 on the melanogenesis in the B16 melanoma cells induced with alpha-melanocyte-stimulating hormone (alpha-MSH), 13 compounds (1, 3, 4, 6-14, and 17) exhibited marked inhibitory effects with 34-49% reduction of melanin content at 100 muM with no or almost no toxicity to the cells (91-116% of cell viability at 100 microM).

Melanogenesis inhibitory, anti-inflammatory, and chemopreventive effects of limonoids from the seeds of Azadirachta indicia A. Juss. (neem).

Thirty-one nortriterpenoids, including 28 limonoids (1-28) and 3 degraded limonoids (29-31), and one diterpenoid (32), were isolated from the seed extract of Azadirachta indica (neem). Among these, six were new compounds and their structures were established to be 15-hydroxyazadiradione (3), 7-benzoyl-17-hydroxynimbocinol (5), 23-deoxyazadironolide (12), limocin E (13), 23-epilimocin E (14), and 7alpha-acetoxy-3-oxoisocopala-1,13-dien-15-oic acid (32). Upon evaluation of compounds 1-32 on the melanogenesis in the B16 melanoma cells, five compounds, 20, 26, 27, 29, and 31, exhibited marked inhibitory effect (74-91% reduction of melanin content at 25 microg/mL) with no or almost no toxicity to the cells. Seven compounds, 1, 6, 9, 10, 18, 20, and 26, on evaluation for their inhibitory effect against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice, exhibited, except for compound 26, marked anti-inflammatory activity (ID(50) values 0.09-0.26 mg/ear). In addition, all of the 32 compounds exhibited moderate or potent inhibitory effects (IC(50) values of 230-501 mol ratio/32 pmol TPA) against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA. Furthermore, on evaluation of azadirachtin B (21) for its anti-tumor-initiating activity on the two-stage carcinogenesis of mouse skin tumor induced by peroxynitrite (ONOO-; PN) as an initiator and TPA as a promoter, this exhibited marked inhibitory activity.

Cucurbitane-type triterpenoids from the fruits of Momordica charantia and their cancer chemopreventive effects.

Thirteen cucurbitane-type triterpene glycosides, including eight new compounds named charantosides I (6), II (7), III (10), IV (11), V (12), VI (13), VII (16), and VIII (17), and five known compounds, 8, 9, 14, 15, and 18, were isolated from a methanol extract of the fruits of Japanese Momordica charantia. The structures of the new compounds were determined on the basis of spectroscopic methods. On evaluation of these triterpene glycosides and five other cucurbitane-type triterpenes, 1-5, also isolated from the extract of M. charantia fruits, for their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, these compounds showed inhibitory effects on EBV-EA induction with IC(50) values of 200-409 mol ratio/32 pmol TPA. In addition, upon evaluation of compounds 1-5 for inhibitory effects against activation of (+/-)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, compounds 1-3 showed moderate inhibitory effects. Compounds 1 and 2 exhibited marked inhibitory effects in both 7,12-dimethylbenz[a]anthracene (DMBA)- and peroxynitrite (ONOO-; PN)-induced mouse skin carcinogenesis tests.

Triterpene acids from Poria cocos and their anti-tumor-promoting effects.

The structures of six new lanostane-type triterpene acids isolated from the epidermis of the sclerotia of Poria cocos were established to be 15alpha-hydroxydehydrotumulosic acid (5), 16alpha,25-dihydroxydehydroeburicoic acid (9), 5alpha,8alpha-peroxydehydrotumulosic acid (10), 25-hydroxyporicoic acid H (11), 16-deoxyporicoic acid B (12), and poricoic acid CM (16) on the basis of spectroscopic methods. On evaluation of these six and 11 other known triterpene acids isolated from the sclerotium, 1-4, 6-8, 13-15, and 17, against the Epstein-Barr virus early antigen (EBV-EA) activation induced by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, all of the compounds except for 1, 3, 4, and 8 exhibited inhibitory effects with IC50 values of 195-340 mol ratio/32 pmol TPA. Compound 12 and poricoic acid C (13) exhibited inhibitory effects on skin tumor promotion in an in vivo two-stage carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter.

Anti-inflammatory and potential cancer chemopreventive constituents of the fruits of Morinda citrifolia (Noni).

A new anthraquinone, 1,5,15-tri-O-methylmorindol (1), and two new saccharide fatty acid esters, 2-O-(beta-D-glucopyranosyl)-1-O-hexanoyl-beta-D-gluropyranose (4) and 2-O-(beta-D-glucopyranosyl)-1-O-octanoyl-beta-D-gluropyranose (5), have been isolated from a methanol extract of the fruits of Morinda citrifolia (noni) along with 10 known compounds, namely, two anthraquinones (2, 3), six saccharide fatty acid esters (6-11), an iridoid glycoside (12), and a flavanol glycoside (13). Upon evaluation of six compounds (5-7, 9, 10, and 13) for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice, four saccharide fatty acid esters, 5-7 and 9, exhibited potent anti-inflammatory activity, with ID50 values of 0.46-0.79 mg per ear. In addition, when compounds 1-13 were evaluated against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA, all of the compounds exhibited moderate inhibitory effects (IC50 values of 386-578 mol ratio/32 pmol TPA).

Triterpene glycosides from the flower petals of sunflower (Helianthus annuus) and their anti-inflammatory activity.

Two new oleanane-type triterpene glycosides, named helianthosides 4 (4) and 5 (5), along with four known triterpene glycosides, helianthosides 1 (1), 2 (2), 3 (3), and B (6), were isolated from an n-butanol-soluble fraction of a methanol extract of sunflower (Helianthus annuus) petals. The structures of the two new compounds were determined on the basis of spectroscopic and chemical methods. Upon evaluation of compounds 1-6 for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1.7 nmol/ear) in mice, all of the compounds tested exhibited marked anti-inflammatory activity, with ID50 values in the range 65-262 nmol per ear.

Anti-inflammatory, anti-tumor-promoting, and cytotoxic activities of constituents of marigold (Calendula officinalis) flowers.

Ten oleanane-type triterpene glycosides, 1-10, including four new compounds, calendulaglycoside A 6'-O-methyl ester (2), calendulaglycoside A 6'-O-n-butyl ester (3), calendulaglycoside B 6'-O-n-butyl ester (5), and calendulaglycoside C 6'-O-n-butyl ester (8), along with five known flavonol glycosides, 11-15, were isolated from the flowers of marigold (Calendula officinalis). Upon evaluation of compounds 1-9 for inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice, all of the compounds, except for 1, exhibited marked anti-inflammatory activity, with ID50 values of 0.05-0.20 mg per ear. In addition, when 1-15 were evaluated against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA, compounds 1-10 exhibited moderate inhibitory effects (IC50 values of 471-487 mol ratio/32 pmol TPA). Furthermore, upon evaluation of the cytotoxic activity against human cancer cell lines in vitro in the NCI Developmental Therapeutics Program, two triterpene glycosides, 9 and 10, exhibited their most potent cytotoxic effects against colon cancer, leukemia, and melanoma cells.

Cancer chemopreventive effects and cytotoxic activities of the triterpene acids from the resin of Boswellia carteri.

Fifteen triterpene acids, viz., seven of the beta-boswellic acids (ursane-type) (1-7), two of the alpha-boswellic acids (oleanane-type) (8, 9), two of the lupeolic acids (lupane-type) (10, 11), and four of the tirucallane-type (12-14, 16), and two cembrane-type diterpenes (17, 18), isolated from the MeOH extract of the resin of Boswellia carteri (Burseraceae), together with a triterpene acid 15 (the acetyl derivative of 14), were examined for their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells and on activation of (+/-)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, and cytotoxic activities against three human neuroblastoma cell lines, IMR-32, NB-39, and SK-N-SH in vitro. On evaluation against the EBV-EA activation induced by TPA, seven compounds, 2, 10, 11, and 13-16, showed potent inhibitory effects on EBV-EA induction. Upon evaluation against activation of NOR 1, five compounds, 7, 13, and 14-16, showed potent inhibitory effects. Further, fifteen compounds, 1-7, 9-11, 13-15, 17, and 18, exhibited potent cytotoxic activities with IC(50) values of 4.1-82.4 muM against all of the three human neuroblastoma cells tested.

Acerogenin M, a cyclic diarylheptanoid, and other phenolic compounds from Acer nikoense and their anti-inflammatory and anti-tumor-promoting effects.

A new cyclic diarylheptanoid, acerogenin M (1), has been isolated along with nine known diarylheptanoids, 2-10, and two known phenolic compounds, 11 and 12, from a MeOH extract of the stem bark of Acer nikoense MAXIM. (Aceraceae). The structure of 1 was determined on the basis of a spectroscopic method. Upon evaluation of the inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice of nine of the compounds (2-6, 8, 10-12), six (2, 4-6, 8, 10) showed a marked anti-inflammatory effect with a 50% inhibitory dose (ID(50)) of 0.26-0.81 mg per ear. In addition, upon an evaluation against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA for all of the compounds, all exhibited moderate inhibitory effects against EBV-EA induction (IC(50) values of 356-534 mol ratio/32 pmol TPA).

Anti-inflammatory activities of the triterpene acids from the resin of Boswellia carteri.

Boswellic acids are the main well-known active components of the resin of Boswellia carteri (Burseraceae) and these are still dealing with the ethnomedicinal use for the treatment of rheumatoid arthritis and other inflammatory diseases. Although several studies have already been reported on the pharmacological properties, especially on the anti-inflammatory activity, of Boswellia carteri resin and boswellic acids, the ethnomedicinal importance of Boswellia carteri and its components, boswellic acids, prompted us to undertake detailed investigation on the constituents of the resin and their anti-inflammatory activity. Fifteen triterpene acids, viz., seven of the beta-boswellic acids (ursane-type) (1-7), two of the alpha-boswellic acids (oleanane-type) (8, 9), two of the lupeolic acids (lupane-type) (10, 11), and four of the tirucallane-type (12-14, 16), along with two cembrane-type diterpenes (17, 18), were isolated and identified from the methanol extract of the resin of Boswellia carteri. Upon evaluation of 17 compounds, 1-14 and 16-18, and compound 15, semi-synthesized from 14 by acetylation, for their inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice, all of the compounds, except for 18, exhibited marked anti-inflammatory activity with a 50% inhibitory dose (ID(50)) of 0.05-0.49 mg/ear.

Chalcones and other compounds from the exudates of Angelica keiskei and their cancer chemopreventive effects.

Three new chalcones, xanthoangelol I (1), xanthoangelol J (2), and deoxydihydroxanthoangelol H (3), were isolated from an ethyl acetate-soluble fraction of exudates of the stems of Angelica keiskei, and their structures were established on the basis of spectroscopic methods. Nine aromatic compounds of known structure, 4-12, and a diacetylene, 13, were also isolated and identified from this same fraction. On evaluation of these compounds for their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, 1, 2, 4, and 9-12 showed potent inhibitory effects on EBV-EA induction. In addition, upon evaluation of the inhibitory effects against activation of (+/-)-(E)-methyl-2[(E)-hydroxyimino]-5-nitro-6-methoxy-3-hexemide (NOR 1), a nitrogen oxide (NO) donor, six compounds, namely, 1, 2, 4, 9, 11, and 12, exhibited potent inhibitory effects. Further, isobavachalcone (4) exhibited inhibitory effects on skin tumor promotion in an in vivo two-stage mouse skin carcinogenesis test using 7,12-dimethylbenz[a]anthracene (DMBA) as an initiator and TPA as a promoter.

Cucurbitane-type triterpenoids from the fruit of Momordica charantia.

The structures of three new cucurbitane-type triterpenoids isolated from the methanol extract of the fruit of Japanese Momordica charantia were established as (19R,23E)-5beta,19-epoxy-19-methoxycucurbita-6,23,25-trien-3beta-ol (1), (23E)-3beta-hydroxy-7beta-methoxycucurbita-5,23,25-trien-19-al (2), and (23E)-3beta-hydroxy-7beta,25-dimethoxycucurbita-5,23-dien-19-al (3) on the basis of spectroscopic methods. These compounds were accompanied by the known (19R,23E)-5beta,19-epoxy-19,25-dimethoxycucurbita-6,23-dien-3beta-ol (4) and (19R,23E)-5beta,19-epoxy-19-methoxycucurbita-6,23-diene-3beta,25-diol (5). This is the first report of the isolation of tetracyclic triterpenoids possessing a delta23,25-conjugated diene system, viz., 1 and 2, from a natural source.

Antitubercular activity of triterpenoids from Asteraceae flowers.

Twenty-eight 3-hydroxy triterpenoids of taraxastane- (1-7), oleanane- (8-12), ursane- (13-15), lupane- (16,18,19), taraxane- (20), cycloartane- (21-25), tirucallane- (26-28), and dammarane-types (29) isolated from the non-saponifiable lipid fraction of the flower extract of chrysanthemum (Chrysanthemum morifolium) and one lupane-type 3alpha-hydroxy triterpenoid (17) derived from 16 were tested for their antitubercular activity against Mycobacterium tuberculosis strain H37Rv using the Microplate Alamar Blue Assay (MABA). Fifteen compounds showed a minimum inhibitory concentration (MIC) in the range of 4-64 microg/ml, among which maniladiol (9; MIC 4 microg/ml), 3-epilupeol (17; 4 microg/ml), and 4,5alpha-epoxyhelianol (27; 6 microg/ml) exhibited the highest activity. Cytotoxicity of compound 17 against Vero cells gave an IC50 value of over 62.5 microg/ml, suggesting some degree of selectivity for M. tuberculosis.

Anti-tumor-initiating effects of monascin, an azaphilonoid pigment from the extract of Monascus pilosus fermented rice (red-mold rice).

Monascin (1) constitutes one of the azaphilonoid pigments in the extracts of Monascus pilosus-fermented rice (red-mold rice). Compound 1 was evaluated for its anti-tumor-initiating activity via oral administration on the two-stage carcinogenesis of mouse skin tumor induced by peroxynitrite (ONOO-; PN) or by ultraviolet light B (UVB) as an initiator and 12-O-tetradecanoylphorbol-13-acetate (TPA) as a promoter. Compound 1 exhibited marked inhibitory activity on both PN- and UVB-induced mouse skin carcinogenesis tests. These findings suggest that compound 1 may be valuable as potential cancer chemopreventive agent in chemical and environmental carcinogenesis.

Triterpene acids from the leaves of Perilla frutescens and their anti-inflammatory and antitumor-promoting effects.

Nine triterpene acids, viz., six of the ursane type, ursolic acid (1), corosolic acid (2), 3-epicorosolic acid (3), pomolic acid (4), tormentic acid (5) and hyptadienic acid (6), and three of the oleanane type, oleanolic acid (7), augustic acid (8) and 3-epimaslinic acid (9), among which 1 constituted the most predominant triterpene acid, were isolated and identified from ethanol extracts of the leaves of red perilla [Perilla frutescens (L.) Britton var. acuta Kudo] and green perilla [P. frutescens (L.) Britton var. acuta Kudo forma viridis Makino]. These eight compounds, 1, 2, 4-9, were evaluated for their inhibitory effects on 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced inflammation (1 microg/ear) in mice. All the compounds tested showed a marked anti-inflammatory effect, with a 50% inhibitory dose (ID50) of 0.09-0.3 mg per ear. In addition, an evaluation against the Epstein-Barr virus early antigen (EBV-EA) activation induced by TPA showed five compounds, 1-3, 5 and 9, with a potent inhibitory effect on EBV-EA induction (91-93% inhibition at 1x10(3) mol ratio/TPA). Furthermore, compound 5 exhibited strong antitumor-promoting activity in an in vivo two-stage carcinogenesis test of mouse tumor by using 7,12-dimethylbenz(a)anthracene (DMBA) as an initiator and TPA as a promoter.

Sunpollenol and five other rearranged 3,4-seco-tirucallane-type triterpenoids from sunflower pollen and their inhibitory effects on Epstein-Barr virus activation.

Six new rearranged 3,4-seco-tirucallane-type triterpenoids (1-6) have been isolated from the diethyl ether extract of the pollen grains of sunflower (Helianthus annuus). These compounds were evaluated with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) induced by the tumor promoter 12-O-tetradecanoylphorbol 13-acetate (TPA) in Raji cells. All of the compounds tested showed potent inhibitory effects on EBV-EA activation (97-100% inhibition at 1 x 10(3) mol ratio/TPA).

Sterol ferulates, sterols, and 5-alk(en)ylresorcinols from wheat, rye, and corn bran oils and their inhibitory effects on Epstein-Barr virus activation.

Sterol ferulate, free sterol, and 5-alk(en)ylresorcinol constituents of wheat, rye, and corn bran oils were studied. Among the sterol ferulates, one novel compound, 24-methylenecholestanol ferulate (7), along with six known compounds, namely, 24-methylcholestanol ferulate (1), 24-methylcholesterol ferulate (2), 2-methyllathosterol ferulate (3), stigmastanol ferulate (4), sitosterol ferulate (5), and schottenol ferulate (6), were isolated and characterized. Five known free sterols, namely, 24-methylcholesterol (8), stigmastanol (9), sitosterol (10), schottenol (11), and stigmasterol (12), were isolated and identified. 5-Alk(en)ylresorcinols were found in wheat and rye bran oils but not in corn bran oil. Of these, one new compound, 5-n-(2'-oxo-14'-Z-heneicosenyl) resorcinol (19), and seven known compounds, namely, 5-n-heptadecyl- (13), 5-n-nonadecyl- (14), 5-n-heneicosyl- (15), 5-n-tricosyl- (16), 5-n-pentacosyl- (17), 5-n-(14'-Z-nonadecenyl)- (18), and 5-n-(2'-oxoheneicosyl)resorcinols (20), were isolated and characterized. These compounds were evaluated with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) by 12-O-tetradecanoylphorbol-13-acetate (TPA) in Raji cells, which is known to be a primary screening test for antitumor promoters. Four compounds, 1, 2, 4, and 11, showed potent inhibitory effects on EBV-EA induction.

Isolation, structural elucidation, and inhibitory effects of terpenoid and lipid constituents from sunflower pollen on Epstein-Barr virus early antigen induced by tumor promoter, TPA.

Eight fatty acid esters of triterpene alcohols (1-8), four free triterpene alcohols (9, 12, 17, and 18), four diterpene acids (19-22), two tocopherol-related compounds (23 and 24), four estolides (25-28), three syn-alkane-4,6-diols (29-31), one 1,3-dioxoalkanoic acid (32), and one aliphatic ketone (33), along with the mixture of free fatty acids, were isolated from the diethyl ether extract of the pollen grains of sunflower (Helianthus annuus). Among these compounds, 14 (2-8, 12, 23, 25-28, and 33) were new naturally occurring compounds, and their structures were determined on the basis of spectroscopic methods. Twenty-four terpenoids and lipids (1-4, 6-9, 12, and 19-33) and six free triterpene triols (10, 11, and 13-16), derived from their fatty acid esters (2, 3, and 5-8) by alkaline hydrolysis, were evaluated with respect to their inhibitory effects on the induction of Epstein-Barr virus early antigen (EBV-EA) induced by the tumor promoter, 12-O-tetradecanoylphorbol-13-acetate (TPA), in Raji cells, which is known to be a primary screening test for antitumor promoters. Among the 30 compounds tested, 21 compounds possessing a di- or a polycyclic ring system in the molecule (1-4, 6-16, and 19-24) showed potent inhibitory effects on EBV-EA induction (91-100% inhibition at 1 x 10(3) mol ratio/TPA).