Harry Fong - Academia.edu (original) (raw)
Papers by Harry Fong
Evidence-Based Complementary and Alternative Medicine, 2013
As part of our continuing efforts in the search for potential biologically active compounds from ... more As part of our continuing efforts in the search for potential biologically active compounds from medicinal plants, we have isolated 18 compounds including two novel nitrogen containing diterpenes from extracts of the fruits ofVitex agnus-castus. These isolates, along with our previously obtained novel compound vitexlactam A (1), were evaluated for potential biological effects, including cancer chemoprevention. Chemically, the nitrogenous isolates were found to be two labdane diterpene alkaloids, each containing anα,β-unsaturatedγ-lactam moiety. Structurally, they were elucidated to be 9α-hydroxy-13(14)-labden-16,15-amide (2) and 6β-acetoxy-9α-hydroxy-13(14)-labden-15,16-amide (3), which were named vitexlactams B and C, respectively. The 15 known isolates were identified as vitexilactone (4), rotundifuran (5), 8-epi-manoyl oxide (6), vitetrifolin D (7), spathulenol (8),cis-dihydro-dehydro-diconiferylalcohol-9-O-β-D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4′-tetram...
Journal of andrology
(+)-Gossypol was isolated from the bark of Thespesia populnea and tested for its ability to inhib... more (+)-Gossypol was isolated from the bark of Thespesia populnea and tested for its ability to inhibit the fertility of male hamsters. Male hamsters of proven fertility were treated orally for 54 days with 40 mg/kg of (+)-gossypol, 40 mg/kg of racemic gossypol, or 5% gum acacia (vehicle control) and were mated with estrous female hamsters during the fourth and seventh weeks of treatment. Both the control and the (+)-gossypol-treated animals exhibited normal fertility throughout the experiment. The racemic gossypol-treated animals were infertile when evaluated during both the fourth and seventh weeks of treatment. Morphologic examination of the testicular tissue could not explain the loss of fertility. These data demonstrate the inability of (+)gossypol to decrease male fertility and suggest that the activity of racemic gossypol may be due primarily to the presence of the (-) optical isomer.
Tetrahedron Letters, 2000
Three new anthracene derivatives, rubiasins A±C (1±3), were isolated from the combined roots and ... more Three new anthracene derivatives, rubiasins A±C (1±3), were isolated from the combined roots and stems of Rubia cordifolia, and their structures were elucidated by spectroscopic analysis. Their absolute con®gurations were determined by Mosher ester methodology. A known compound, mollugin (4), was obtained as an active antiproliferative principle by bioassay-monitored fractionation using a human colon cancer (Col2) cell line. #
ChemInform, 2002
Polyacetyleneginsenoside-Ro, a Novel Triterpene Saponin from Panax ginseng.
Phytochemistry, 2010
Three new kaempferol glycosides, named palmatosides A (1), B (2) and C (3), together with three k... more Three new kaempferol glycosides, named palmatosides A (1), B (2) and C (3), together with three known kaempferol glycosides, multiflorins A (4) and B (5), and afzelin (6), were isolated from the roots of the fern Neocheiropteris palmatopedata. Palmatosides A (1) and B (2) were determined to be novel kaempferol glycosides, each possessing an unusual sugar moiety containing a 4, 4dimethyl-3-oxo-butoxy substituent group. The isolated compounds were evaluated for their cancer chemopreventive potential based on their ability to inhibit tumor necrosis factor alpha (TNF-α)induced NF-κB activity, nitric oxide (NO) production, aromatase, quinone reductase 2 (QR-2) and COX-1/-2 activities. Palmatosides B (2) and C (3) inhibited TNF-α-induced NF-κB activity with IC 50 values of 15.7 and 24.1 μM, respectively; multiflorin A (4) inhibited aromatase enzyme with an IC 50 value of 15.5 μM; afzelin (6) showed 68.3% inhibition against QR2 at a concentration of 11.5 μg/ml; palmatoside A (1) showed 52 % inhibition against COX-1 enzyme at a concentration of 10 μg/ml; and multiflorin B (5) showed 52 % inhibition against nitric oxide production at a concentration of 20 μg/ml. In addition, compounds 3-6 were shown to bind QR2 enzyme using LC-MS ultrafiltration binding assay.
Phytochemistry, 2005
Bioassay directed-fractionation led to isolation of 12 compounds from the roots of Bursera tonkin... more Bioassay directed-fractionation led to isolation of 12 compounds from the roots of Bursera tonkinensis Guillaum (Burseraceae), including burselignan, bursephenylpropane, and burseneolignan. Of the 12 compounds, only 4 0 -demethyldesoxypodophyllotoxin exhibited significant cytotoxic activities against KB, Col2 and LNCaP cell lines.
Tetrahedron Letters, 2002
A new oleanolic acid-derived saponin, polyacetyleneginsenoside-Ro (1), was isolated along with th... more A new oleanolic acid-derived saponin, polyacetyleneginsenoside-Ro (1), was isolated along with the known ginsenosides-Ro methyl ester (2), -Rf, -Rg1, -Rg2, and gingerglycolipid B from the roots of Panax ginseng C. A. Meyer. The new saponin was identified as a ginsenoside-Ro derivative containing a polyacetylene side chain by spectroscopic means including 1D and 2D NMR, and was found to inhibit the replication of human immunodeficiency virus type 1 (HIV-1) with an IC 50 value of 13.4 mg/mL (11.1 mM).
Tetrahedron Letters, 2002
Tetrahedron, 2001
AbstractÐFour novel 29-nor-3,4-seco-cycloartanes, (6S)-hydroxy-25-methoxy-29-nor-3,4-seco-cycloar... more AbstractÐFour novel 29-nor-3,4-seco-cycloartanes, (6S)-hydroxy-25-methoxy-29-nor-3,4-seco-cycloart-4(30),23-dien-3-oic acid methyl ester (1), (6S,25)-dihydroxy-29-nor-3,4-seco-cycloart-4(30),23-dien-3-oic acid methyl ester (2), (6S)-hydroxy-24-oxo-29-nor-3,4-secocycloart-4(30),25-dien-3-oic acid methyl ester , and (6S)-hydroxy-(24j )-hydroperoxy-29-nor-3,4-seco-cycloart-4(30),25-dien-3-oic acid methyl ester (4), along with a semi-synthetic acetylated derivative, (6S,24j)-diacetyloxy-29-nor-3,4-seco-cycloart-4(30),25-dien-3oic acid methyl ester (5), were isolated and characterized from the aerial parts of Antirhea acutata (DC.) Urb. (Rubiaceae). Their structures and absolute stereochemistry were elucidated by spectroscopic and chemical methods. Compounds 1±5 are based on the unprecedented 29-nor-3,4-seco-cycloartane skeleton. Compound 4 showed moderate inhibitory activities in cyclooxygenase-1 and -2 assays (IC 50 45.7 and 18.4 mM, respectively), while the other four isolates were inactive. q
Tetrahedron, 2000
(+)-(20S)-20-(Dimethylamino)-3α-(methylbenzoylamino)-11-methylene-5α-pregnane (1), a steroidal al... more (+)-(20S)-20-(Dimethylamino)-3α-(methylbenzoylamino)-11-methylene-5α-pregnane (1), a steroidal alkaloid with a new substitution pattern, was isolated from the entire plant of Pachysandra procumbens, together with four other new steroidal alkaloids,(+)-(20S)-3-( ...
Planta Medica, 2002
Bioassay-directed fractionation of an extract prepared from the dried leaves and stem barks of Fi... more Bioassay-directed fractionation of an extract prepared from the dried leaves and stem barks of Ficus fistulosa Reinw. ex Blume (Moraceae) led to the isolation of verrucarin L acetate (1), together with 3alpha-hydroxyisohop-22(29)-en-24-oic acid, 3beta-gluco-sitosterol, 3,4-dihydro-6,7-dimethoxyisocarbostyril, 3,4,5-trimethoxybenzyl alcohol, alpha-methyl-3,4,5-trimethoxybenzyl alcohol, indole-3-carboxaldehyde, palmanine, and aurantiamide acetate. Roridin E (2) was identified in a subfraction from the dried leaves and stems of Rhaphidophora decursiva Schott (Araceae). Verrucarin L acetate and roridin E were characterized as macrocyclic trichothecene sesquiterpenoids and found to inhibit the growth of Plasmodium falciparum with IC 50 values below 1 ng/ml.
Planta Medica, 2000
A cytotoxic steroidal glycoside was isolated from Chlorophytum malayense Ridley and its structure... more A cytotoxic steroidal glycoside was isolated from Chlorophytum malayense Ridley and its structure was characterized as a known compound, neohecogenin 3-O-beta-D-glucopyranosyl(1-->2)-[beta-D-xylopyranosyl(1-->3)]-beta-D- glucopyranosyl(1-->4)-beta-D-galactopyranoside (chloromaloside A). The structural identification was performed using 2D-NMR and LC/MS/MS analysis. The previous, erroneously assigned 1H-NMR spectral data were revised whereas the published 13C-NMR spectral assignments were confirmed. This compound showed in vitro cytotoxicity against several human cancer cell lines.
Planta Medica, 1998
From the leaves of Isodon megathyrsus, a novel ent-kaurene diterpene, megathyrin B, was isolated ... more From the leaves of Isodon megathyrsus, a novel ent-kaurene diterpene, megathyrin B, was isolated and its structure determined as 1 alpha,7 beta,11 beta,15 beta-tetrahydroxy-ent-7 alpha,20-epoxy-kaur-16-ene by 1D- and 2D-NMR spectral analysis. Additionally, its stereochemistry was unambiguously assigned by X-ray crystallography. This compound was cytotoxic to the KB and KB-V cell lines.
Planta Medica, 2006
A new cyclic 4-hydroxy-dithiosulfonate, bruguiesulfurol (1), as well as two known 4-hydroxydithio... more A new cyclic 4-hydroxy-dithiosulfonate, bruguiesulfurol (1), as well as two known 4-hydroxydithiolane 1-oxides, brugierol (2) and isobrugierol (3) were isolated from the flowers of Bruguiera gymnorrhiza. With stably-transfected HepG2 cells, the three isolates activated antioxidant response element (ARE) luciferase activation with (EC(50)) values of 56.7, 3.7 and 1.8 microM, respectively. Compounds 2 and 3 also inhibited phorbol ester-induced NF-kappaB (nuclear factor-kappaB) luciferase activity with IC (50) values of 85.0 and 14.5 microM, respectively. In addition, compound 2 inhibited enzyme cyclooxygenase-2 (COX-2) activity with an IC(50) value of 6.1 microM. The structures of these isolates were determined by spectral data, and that of compound 1 was confirmed by X-ray crystallographic analysis.
Phytochemistry, 2001
The pregnane steroid, (E)-aglawone, along with four known triterpenes, and a known sterol mixture... more The pregnane steroid, (E)-aglawone, along with four known triterpenes, and a known sterol mixture were isolated from the bark of Aglaia lawii (Wight) Saldanha ex Ramamoorty (Meliaceae). The structural determination/identification was accomplished by a combination of 1D- and 2D-NMR spectroscopic techniques. The relative stereochemistry of the known triterpene, 20S,24S-epoxydammarane-3alpha,25-diol acetate, was also unequivocally determined for the first time by X-ray crystallography. The isolates were not active against various human cancer cell lines.
Phytochemistry, 1988
From the stems of Larrea tridentata two new triterpenoids have been obtained, whose stereo struct... more From the stems of Larrea tridentata two new triterpenoids have been obtained, whose stereo structures have been elucidated on the basis of chemical and physical evidence.
Phytochemistry, 1985
Propam for Colhbon~~re Rcsard~ m the Ph-hat .%mox. Colkgc of Phnnry. Halth Snenccs <'enter. Unlve... more Propam for Colhbon~~re Rcsard~ m the Ph-hat .%mox. Colkgc of Phnnry. Halth Snenccs <'enter. Unlvemty of lllinois at CIKmp. Chicago. IL 60612. U.S.A. (Receicrd 25 April 1985) Key Wad la&x -Cocurlpinia pukhewhw Lcpuminorae: dltapmomts vouaapm-5~x4 dcrivatlvu Ahtract-Three new furanoditcrpcnoids of the cacsalpin-type have been isolated from the roots of Caesalpinia pulcherrima The structures of these compounds. vouacapcn-k-al,
Evidence-Based Complementary and Alternative Medicine, 2013
As part of our continuing efforts in the search for potential biologically active compounds from ... more As part of our continuing efforts in the search for potential biologically active compounds from medicinal plants, we have isolated 18 compounds including two novel nitrogen containing diterpenes from extracts of the fruits ofVitex agnus-castus. These isolates, along with our previously obtained novel compound vitexlactam A (1), were evaluated for potential biological effects, including cancer chemoprevention. Chemically, the nitrogenous isolates were found to be two labdane diterpene alkaloids, each containing anα,β-unsaturatedγ-lactam moiety. Structurally, they were elucidated to be 9α-hydroxy-13(14)-labden-16,15-amide (2) and 6β-acetoxy-9α-hydroxy-13(14)-labden-15,16-amide (3), which were named vitexlactams B and C, respectively. The 15 known isolates were identified as vitexilactone (4), rotundifuran (5), 8-epi-manoyl oxide (6), vitetrifolin D (7), spathulenol (8),cis-dihydro-dehydro-diconiferylalcohol-9-O-β-D-glucoside (9), luteolin-7-O-glucoside (10), 5-hydroxy-3,6,7,4′-tetram...
Journal of andrology
(+)-Gossypol was isolated from the bark of Thespesia populnea and tested for its ability to inhib... more (+)-Gossypol was isolated from the bark of Thespesia populnea and tested for its ability to inhibit the fertility of male hamsters. Male hamsters of proven fertility were treated orally for 54 days with 40 mg/kg of (+)-gossypol, 40 mg/kg of racemic gossypol, or 5% gum acacia (vehicle control) and were mated with estrous female hamsters during the fourth and seventh weeks of treatment. Both the control and the (+)-gossypol-treated animals exhibited normal fertility throughout the experiment. The racemic gossypol-treated animals were infertile when evaluated during both the fourth and seventh weeks of treatment. Morphologic examination of the testicular tissue could not explain the loss of fertility. These data demonstrate the inability of (+)gossypol to decrease male fertility and suggest that the activity of racemic gossypol may be due primarily to the presence of the (-) optical isomer.
Tetrahedron Letters, 2000
Three new anthracene derivatives, rubiasins A±C (1±3), were isolated from the combined roots and ... more Three new anthracene derivatives, rubiasins A±C (1±3), were isolated from the combined roots and stems of Rubia cordifolia, and their structures were elucidated by spectroscopic analysis. Their absolute con®gurations were determined by Mosher ester methodology. A known compound, mollugin (4), was obtained as an active antiproliferative principle by bioassay-monitored fractionation using a human colon cancer (Col2) cell line. #
ChemInform, 2002
Polyacetyleneginsenoside-Ro, a Novel Triterpene Saponin from Panax ginseng.
Phytochemistry, 2010
Three new kaempferol glycosides, named palmatosides A (1), B (2) and C (3), together with three k... more Three new kaempferol glycosides, named palmatosides A (1), B (2) and C (3), together with three known kaempferol glycosides, multiflorins A (4) and B (5), and afzelin (6), were isolated from the roots of the fern Neocheiropteris palmatopedata. Palmatosides A (1) and B (2) were determined to be novel kaempferol glycosides, each possessing an unusual sugar moiety containing a 4, 4dimethyl-3-oxo-butoxy substituent group. The isolated compounds were evaluated for their cancer chemopreventive potential based on their ability to inhibit tumor necrosis factor alpha (TNF-α)induced NF-κB activity, nitric oxide (NO) production, aromatase, quinone reductase 2 (QR-2) and COX-1/-2 activities. Palmatosides B (2) and C (3) inhibited TNF-α-induced NF-κB activity with IC 50 values of 15.7 and 24.1 μM, respectively; multiflorin A (4) inhibited aromatase enzyme with an IC 50 value of 15.5 μM; afzelin (6) showed 68.3% inhibition against QR2 at a concentration of 11.5 μg/ml; palmatoside A (1) showed 52 % inhibition against COX-1 enzyme at a concentration of 10 μg/ml; and multiflorin B (5) showed 52 % inhibition against nitric oxide production at a concentration of 20 μg/ml. In addition, compounds 3-6 were shown to bind QR2 enzyme using LC-MS ultrafiltration binding assay.
Phytochemistry, 2005
Bioassay directed-fractionation led to isolation of 12 compounds from the roots of Bursera tonkin... more Bioassay directed-fractionation led to isolation of 12 compounds from the roots of Bursera tonkinensis Guillaum (Burseraceae), including burselignan, bursephenylpropane, and burseneolignan. Of the 12 compounds, only 4 0 -demethyldesoxypodophyllotoxin exhibited significant cytotoxic activities against KB, Col2 and LNCaP cell lines.
Tetrahedron Letters, 2002
A new oleanolic acid-derived saponin, polyacetyleneginsenoside-Ro (1), was isolated along with th... more A new oleanolic acid-derived saponin, polyacetyleneginsenoside-Ro (1), was isolated along with the known ginsenosides-Ro methyl ester (2), -Rf, -Rg1, -Rg2, and gingerglycolipid B from the roots of Panax ginseng C. A. Meyer. The new saponin was identified as a ginsenoside-Ro derivative containing a polyacetylene side chain by spectroscopic means including 1D and 2D NMR, and was found to inhibit the replication of human immunodeficiency virus type 1 (HIV-1) with an IC 50 value of 13.4 mg/mL (11.1 mM).
Tetrahedron Letters, 2002
Tetrahedron, 2001
AbstractÐFour novel 29-nor-3,4-seco-cycloartanes, (6S)-hydroxy-25-methoxy-29-nor-3,4-seco-cycloar... more AbstractÐFour novel 29-nor-3,4-seco-cycloartanes, (6S)-hydroxy-25-methoxy-29-nor-3,4-seco-cycloart-4(30),23-dien-3-oic acid methyl ester (1), (6S,25)-dihydroxy-29-nor-3,4-seco-cycloart-4(30),23-dien-3-oic acid methyl ester (2), (6S)-hydroxy-24-oxo-29-nor-3,4-secocycloart-4(30),25-dien-3-oic acid methyl ester , and (6S)-hydroxy-(24j )-hydroperoxy-29-nor-3,4-seco-cycloart-4(30),25-dien-3-oic acid methyl ester (4), along with a semi-synthetic acetylated derivative, (6S,24j)-diacetyloxy-29-nor-3,4-seco-cycloart-4(30),25-dien-3oic acid methyl ester (5), were isolated and characterized from the aerial parts of Antirhea acutata (DC.) Urb. (Rubiaceae). Their structures and absolute stereochemistry were elucidated by spectroscopic and chemical methods. Compounds 1±5 are based on the unprecedented 29-nor-3,4-seco-cycloartane skeleton. Compound 4 showed moderate inhibitory activities in cyclooxygenase-1 and -2 assays (IC 50 45.7 and 18.4 mM, respectively), while the other four isolates were inactive. q
Tetrahedron, 2000
(+)-(20S)-20-(Dimethylamino)-3α-(methylbenzoylamino)-11-methylene-5α-pregnane (1), a steroidal al... more (+)-(20S)-20-(Dimethylamino)-3α-(methylbenzoylamino)-11-methylene-5α-pregnane (1), a steroidal alkaloid with a new substitution pattern, was isolated from the entire plant of Pachysandra procumbens, together with four other new steroidal alkaloids,(+)-(20S)-3-( ...
Planta Medica, 2002
Bioassay-directed fractionation of an extract prepared from the dried leaves and stem barks of Fi... more Bioassay-directed fractionation of an extract prepared from the dried leaves and stem barks of Ficus fistulosa Reinw. ex Blume (Moraceae) led to the isolation of verrucarin L acetate (1), together with 3alpha-hydroxyisohop-22(29)-en-24-oic acid, 3beta-gluco-sitosterol, 3,4-dihydro-6,7-dimethoxyisocarbostyril, 3,4,5-trimethoxybenzyl alcohol, alpha-methyl-3,4,5-trimethoxybenzyl alcohol, indole-3-carboxaldehyde, palmanine, and aurantiamide acetate. Roridin E (2) was identified in a subfraction from the dried leaves and stems of Rhaphidophora decursiva Schott (Araceae). Verrucarin L acetate and roridin E were characterized as macrocyclic trichothecene sesquiterpenoids and found to inhibit the growth of Plasmodium falciparum with IC 50 values below 1 ng/ml.
Planta Medica, 2000
A cytotoxic steroidal glycoside was isolated from Chlorophytum malayense Ridley and its structure... more A cytotoxic steroidal glycoside was isolated from Chlorophytum malayense Ridley and its structure was characterized as a known compound, neohecogenin 3-O-beta-D-glucopyranosyl(1-->2)-[beta-D-xylopyranosyl(1-->3)]-beta-D- glucopyranosyl(1-->4)-beta-D-galactopyranoside (chloromaloside A). The structural identification was performed using 2D-NMR and LC/MS/MS analysis. The previous, erroneously assigned 1H-NMR spectral data were revised whereas the published 13C-NMR spectral assignments were confirmed. This compound showed in vitro cytotoxicity against several human cancer cell lines.
Planta Medica, 1998
From the leaves of Isodon megathyrsus, a novel ent-kaurene diterpene, megathyrin B, was isolated ... more From the leaves of Isodon megathyrsus, a novel ent-kaurene diterpene, megathyrin B, was isolated and its structure determined as 1 alpha,7 beta,11 beta,15 beta-tetrahydroxy-ent-7 alpha,20-epoxy-kaur-16-ene by 1D- and 2D-NMR spectral analysis. Additionally, its stereochemistry was unambiguously assigned by X-ray crystallography. This compound was cytotoxic to the KB and KB-V cell lines.
Planta Medica, 2006
A new cyclic 4-hydroxy-dithiosulfonate, bruguiesulfurol (1), as well as two known 4-hydroxydithio... more A new cyclic 4-hydroxy-dithiosulfonate, bruguiesulfurol (1), as well as two known 4-hydroxydithiolane 1-oxides, brugierol (2) and isobrugierol (3) were isolated from the flowers of Bruguiera gymnorrhiza. With stably-transfected HepG2 cells, the three isolates activated antioxidant response element (ARE) luciferase activation with (EC(50)) values of 56.7, 3.7 and 1.8 microM, respectively. Compounds 2 and 3 also inhibited phorbol ester-induced NF-kappaB (nuclear factor-kappaB) luciferase activity with IC (50) values of 85.0 and 14.5 microM, respectively. In addition, compound 2 inhibited enzyme cyclooxygenase-2 (COX-2) activity with an IC(50) value of 6.1 microM. The structures of these isolates were determined by spectral data, and that of compound 1 was confirmed by X-ray crystallographic analysis.
Phytochemistry, 2001
The pregnane steroid, (E)-aglawone, along with four known triterpenes, and a known sterol mixture... more The pregnane steroid, (E)-aglawone, along with four known triterpenes, and a known sterol mixture were isolated from the bark of Aglaia lawii (Wight) Saldanha ex Ramamoorty (Meliaceae). The structural determination/identification was accomplished by a combination of 1D- and 2D-NMR spectroscopic techniques. The relative stereochemistry of the known triterpene, 20S,24S-epoxydammarane-3alpha,25-diol acetate, was also unequivocally determined for the first time by X-ray crystallography. The isolates were not active against various human cancer cell lines.
Phytochemistry, 1988
From the stems of Larrea tridentata two new triterpenoids have been obtained, whose stereo struct... more From the stems of Larrea tridentata two new triterpenoids have been obtained, whose stereo structures have been elucidated on the basis of chemical and physical evidence.
Phytochemistry, 1985
Propam for Colhbon~~re Rcsard~ m the Ph-hat .%mox. Colkgc of Phnnry. Halth Snenccs <'enter. Unlve... more Propam for Colhbon~~re Rcsard~ m the Ph-hat .%mox. Colkgc of Phnnry. Halth Snenccs <'enter. Unlvemty of lllinois at CIKmp. Chicago. IL 60612. U.S.A. (Receicrd 25 April 1985) Key Wad la&x -Cocurlpinia pukhewhw Lcpuminorae: dltapmomts vouaapm-5~x4 dcrivatlvu Ahtract-Three new furanoditcrpcnoids of the cacsalpin-type have been isolated from the roots of Caesalpinia pulcherrima The structures of these compounds. vouacapcn-k-al,