조엽오가피 (Acanthopanax henryi, Araliaceae)의 열매에 대한 식물화학적 연구를 통해 3 개의 신규 화합물 (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-glucopyranoside (1), (2Z,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-gluco -pyranoside (2), (-)-(4R)-4,7-dihydroxy-1-menthene-7-O-β-D-glucopyranoside (3)과 36 개의 기지물질인 5-hydroxymethyl-2-furaldehyde (4), 5-hydroxymaltol (5), protocatechuic acid (6), ...
조엽오가피 (Acanthopanax henryi, Araliaceae)의 열매에 대한 식물화학적 연구를 통해 3 개의 신규 화합물 (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-glucopyranoside (1), (2Z,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-gluco -pyranoside (2), (-)-(4R)-4,7-dihydroxy-1-menthene-7-O-β-D-glucopyranoside (3)과 36 개의 기지물질인 5-hydroxymethyl-2-furaldehyde (4), 5-hydroxymaltol (5), protocatechuic acid (6), 6-methoxy-7-hydroxycoumarin (7), quercetin-3-O-β-D-glucopyranoside (8), quercetin-3-O-β-D-galactopyranoside (9), rutin (10), kaempferol-3-O-β-D-glucoside (11), kaempferol-3-rutinoside (12), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), 3,4-di-O-caffeoyl-quinic acid (16), 3,5-di-O-caffeoyl-quinic acid (17), 4,5-di-O-caffeoyl-quinic acid (18), methyl chlorogenate (19), (-)-pinoresinol-4-O-β-D-glucopyranoside (20), (+)-simplexoside (21), (-)-sesamin (22), (-)-kobusin (23), rosin (24), phenylmethyl-β-D-glucopyranoside-6’-O-acetate (25), 3,4-dihydroxy-p-menth-1-ene (26), (4R)-p-menth-1-en-4,7-diol (27), (2E,6S)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D- glucopyranoside (28), (2Z,6R)-6-hydroxy- 2,6-dimethyl-2,7-octadien-1-yl-β-D- glucopyranoside (29), (2Z, 6R)- 1-hydroxy-2,6-dimethyl-2,7- octadien-6-yl-β-D- glucopyranoside (30), (2E,6R)-2,6-dimethyl-2,7-octadiene-1,6-diol (31), (2E,6R)-6-hydroxy- 2,6-dimethyl-2,7-octadien-1-yl-β-D-glucopyranoside (32), (2E,6R)-1-hydroxy-2,6-dimethyl-2,7- octadien-6-yl-β-D- glucopyranoside (33), (+)-(3S,4S,6R)-3,6- dihydroxy-1-menthene (34), (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene-6-O-β-D-glucopyranoside (35), (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene-3-O-β-D- glucopyranoside (36), oleanolic acid-3-O-β-D-glucuronopyranoside (37), styraxlignolide E (38), styraxlignolide D (39)를 포함한 39 개의 화합물을 발견하였다. 분리된 물질들은 질량분석 및 NMR 등의 분석, 물리 화학적 성질, 문헌과의 비교를 통해 구조동정 하였다. 그 중에서 17개의 화합물에 대한 항염증 활성을 마우스 유래 대식세포인 RAW264.7 세포주와 마우스 유래 미세아교세포인 BV2 세포주에서 검색하였다. (-)-kobusin (23)은 RAW264.7 세포주와 BV2 세포주에서 LPS 자극에 의한 NO의 생성을 유의적으로 억제하였으며, IC50 값으로 각각 36.35 ± 6.27 및 14.25 ± 2.69 μM을 나타내었다. 이 결과를 통하여 화합물 23이 잠재적인 항염증 및 항뇌염증 효과를 가지고 있음을 확인할 수 있었다. 또한, 조엽오가피의 뿌리에 대한 식물 화학적 연구를 통해 20개의 기지물질 6-methoxy-7-hydroxycoumarin (7), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), (-)-sesamin (22), helioxanthin (40), savinin (41), taiwanin C (42), behenic acid (43), 3-O-caffeoyl-quinic acid (44), 5-O-caffeoyl-quinic acid (45), (+)-threo-(7R,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (46), (+)-erythro-(7S,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (47), ferulic acid (48), caffeic acid (49), stigmasterol (50), β-sitosterol (51), adenosine (52), syringing (53), trans-coniferin (54)을 분리 하였다. 분리된 물질들은 질량분석 및 NMR 등의 분석, 물리 화학적 성질, 문헌과의 비교를 통해 구조동정 하였다. 그 중 savinin (41)은 LPS로 유도한 NO 및 prostaglandin E2 (PGE2) 생성에 대해 유의한 억제 효과를 나타내 었으며 IC50 값은 각각 2.22 ± 0.11 및 2.28 ± 0.23 μM이었다. 화합물 41의 이러한 효과는 inducible nitric oxide synthase (iNOS) 및 cyclooxygenase-2 (COX-2) 단백질의 발현 억제와 관련이 있다. 또한, 화합물 41은 LPS로 자극한 BV2 세포에서 interleukin (IL)-1β 및 tumor necrosis factor (TNF)-α의 분비를 억제하였다. 화합물 41의 이와 같은 항뇌염증 효과는 p38 mitogen-activated protein kinase (MAPK)에 의해서 조절되었다. 또다른 식물 화학적 연구를 통하여 조엽오가피의 줄기에서 총 18개의 기지물질 6-methoxy-7-hydroxycoumarin (7), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), (-)-sesamin (22), 3-O-caffeoyl-quinic acid (44), 5-O-caffeoyl-quinic acid (45), caffeic acid (49), stigmasterol (50), β-sitosterol (51), p-hydroxybenzoic acid (55), trans-p-hydroxycinnamic acid (56), (E)-caffeic acid methyl ester (57), trans-coniferyl aldehyde (58), syringaldehyde (59), vanillin (60), trans-sinapaldehyde (61), undecanedioic acid, monomethyl ester (62)을 분리하였다. 이 중 화합물 57은 마우스 유래 대식세포인 RAW264.7 세포주와 BV2 세포주에서 LPS 자극에 의한 NO의 생성을 유의적으로 억제하였으며, IC50 값으로 각각 1.28 ± 0.11 및 12.18 ± 2.85 μM을 나타내었다. 이 결과를 통하여 화합물 57이 잠재적인 항염증 및 항뇌염증 효과를 가지고 있음을 확인할 수 있었다. 조엽오가피의 꽃에 대한 식물 화학적 연구를 통하여 13 가지 화합물을 얻었으며 화학 구조는quercetin-3-O-β-D-glucopyranoside (8), rutin (10), kaempferol -3-O-β-D-glucoside (11), kaempferol-3-rutinoside (12), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), kaempferol-3-O-α-L-rhamnoside (63), kaempferol (64), dihydrosesamin-9-O-β-D-glucopyranoside (65), eugenol glucoside (66), 3,5-dicaffeoylquinic acid methyl ester (67), 3,4-dicaffeoylquinic acid methyl ester (68)로 확인되었다. 그 중에서 화합물 68은 RAW264.7 세포에서 LPS로 자극한 NO 생성을 억제하였으며, 38.69 ± 2.91 μM의 IC50 값을 나타내었다. 그 결과, 화합물 68은 잠재적인 항염증 활성을 가지고 있음을 확인할 수 있었다.
조엽오가피 (Acanthopanax henryi, Araliaceae)의 열매에 대한 식물화학적 연구를 통해 3 개의 신규 화합물 (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-glucopyranoside (1), (2Z,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-gluco -pyranoside (2), (-)-(4R)-4,7-dihydroxy-1-menthene-7-O-β-D-glucopyranoside (3)과 36 개의 기지물질인 5-hydroxymethyl-2-furaldehyde (4), 5-hydroxymaltol (5), protocatechuic acid (6), 6-methoxy-7-hydroxycoumarin (7), quercetin-3-O-β-D-glucopyranoside (8), quercetin-3-O-β-D-galactopyranoside (9), rutin (10), kaempferol-3-O-β-D-glucoside (11), kaempferol-3-rutinoside (12), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), 3,4-di-O-caffeoyl-quinic acid (16), 3,5-di-O-caffeoyl-quinic acid (17), 4,5-di-O-caffeoyl-quinic acid (18), methyl chlorogenate (19), (-)-pinoresinol-4-O-β-D-glucopyranoside (20), (+)-simplexoside (21), (-)-sesamin (22), (-)-kobusin (23), rosin (24), phenylmethyl-β-D-glucopyranoside-6’-O-acetate (25), 3,4-dihydroxy-p-menth-1-ene (26), (4R)-p-menth-1-en-4,7-diol (27), (2E,6S)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D- glucopyranoside (28), (2Z,6R)-6-hydroxy- 2,6-dimethyl-2,7-octadien-1-yl-β-D- glucopyranoside (29), (2Z, 6R)- 1-hydroxy-2,6-dimethyl-2,7- octadien-6-yl-β-D- glucopyranoside (30), (2E,6R)-2,6-dimethyl-2,7-octadiene-1,6-diol (31), (2E,6R)-6-hydroxy- 2,6-dimethyl-2,7-octadien-1-yl-β-D-glucopyranoside (32), (2E,6R)-1-hydroxy-2,6-dimethyl-2,7- octadien-6-yl-β-D- glucopyranoside (33), (+)-(3S,4S,6R)-3,6- dihydroxy-1-menthene (34), (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene-6-O-β-D-glucopyranoside (35), (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene-3-O-β-D- glucopyranoside (36), oleanolic acid-3-O-β-D-glucuronopyranoside (37), styraxlignolide E (38), styraxlignolide D (39)를 포함한 39 개의 화합물을 발견하였다. 분리된 물질들은 질량분석 및 NMR 등의 분석, 물리 화학적 성질, 문헌과의 비교를 통해 구조동정 하였다. 그 중에서 17개의 화합물에 대한 항염증 활성을 마우스 유래 대식세포인 RAW264.7 세포주와 마우스 유래 미세아교세포인 BV2 세포주에서 검색하였다. (-)-kobusin (23)은 RAW264.7 세포주와 BV2 세포주에서 LPS 자극에 의한 NO의 생성을 유의적으로 억제하였으며, IC50 값으로 각각 36.35 ± 6.27 및 14.25 ± 2.69 μM을 나타내었다. 이 결과를 통하여 화합물 23이 잠재적인 항염증 및 항뇌염증 효과를 가지고 있음을 확인할 수 있었다. 또한, 조엽오가피의 뿌리에 대한 식물 화학적 연구를 통해 20개의 기지물질 6-methoxy-7-hydroxycoumarin (7), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), (-)-sesamin (22), helioxanthin (40), savinin (41), taiwanin C (42), behenic acid (43), 3-O-caffeoyl-quinic acid (44), 5-O-caffeoyl-quinic acid (45), (+)-threo-(7R,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (46), (+)-erythro-(7S,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (47), ferulic acid (48), caffeic acid (49), stigmasterol (50), β-sitosterol (51), adenosine (52), syringing (53), trans-coniferin (54)을 분리 하였다. 분리된 물질들은 질량분석 및 NMR 등의 분석, 물리 화학적 성질, 문헌과의 비교를 통해 구조동정 하였다. 그 중 savinin (41)은 LPS로 유도한 NO 및 prostaglandin E2 (PGE2) 생성에 대해 유의한 억제 효과를 나타내 었으며 IC50 값은 각각 2.22 ± 0.11 및 2.28 ± 0.23 μM이었다. 화합물 41의 이러한 효과는 inducible nitric oxide synthase (iNOS) 및 cyclooxygenase-2 (COX-2) 단백질의 발현 억제와 관련이 있다. 또한, 화합물 41은 LPS로 자극한 BV2 세포에서 interleukin (IL)-1β 및 tumor necrosis factor (TNF)-α의 분비를 억제하였다. 화합물 41의 이와 같은 항뇌염증 효과는 p38 mitogen-activated protein kinase (MAPK)에 의해서 조절되었다. 또다른 식물 화학적 연구를 통하여 조엽오가피의 줄기에서 총 18개의 기지물질 6-methoxy-7-hydroxycoumarin (7), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), (-)-sesamin (22), 3-O-caffeoyl-quinic acid (44), 5-O-caffeoyl-quinic acid (45), caffeic acid (49), stigmasterol (50), β-sitosterol (51), p-hydroxybenzoic acid (55), trans-p-hydroxycinnamic acid (56), (E)-caffeic acid methyl ester (57), trans-coniferyl aldehyde (58), syringaldehyde (59), vanillin (60), trans-sinapaldehyde (61), undecanedioic acid, monomethyl ester (62)을 분리하였다. 이 중 화합물 57은 마우스 유래 대식세포인 RAW264.7 세포주와 BV2 세포주에서 LPS 자극에 의한 NO의 생성을 유의적으로 억제하였으며, IC50 값으로 각각 1.28 ± 0.11 및 12.18 ± 2.85 μM을 나타내었다. 이 결과를 통하여 화합물 57이 잠재적인 항염증 및 항뇌염증 효과를 가지고 있음을 확인할 수 있었다. 조엽오가피의 꽃에 대한 식물 화학적 연구를 통하여 13 가지 화합물을 얻었으며 화학 구조는quercetin-3-O-β-D-glucopyranoside (8), rutin (10), kaempferol -3-O-β-D-glucoside (11), kaempferol-3-rutinoside (12), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), kaempferol-3-O-α-L-rhamnoside (63), kaempferol (64), dihydrosesamin-9-O-β-D-glucopyranoside (65), eugenol glucoside (66), 3,5-dicaffeoylquinic acid methyl ester (67), 3,4-dicaffeoylquinic acid methyl ester (68)로 확인되었다. 그 중에서 화합물 68은 RAW264.7 세포에서 LPS로 자극한 NO 생성을 억제하였으며, 38.69 ± 2.91 μM의 IC50 값을 나타내었다. 그 결과, 화합물 68은 잠재적인 항염증 활성을 가지고 있음을 확인할 수 있었다.
The phytochemical investigation on the fruits of Acanthopanax henryi (Araliaceae) resulted in the discovery of thirty-nine compounds including 3 novel ones and 36 known ones, their chemical structures were elucidated by the analysis of 1D-, 2D-NMR, mass data and other physicochemical properties, as ...
The phytochemical investigation on the fruits of Acanthopanax henryi (Araliaceae) resulted in the discovery of thirty-nine compounds including 3 novel ones and 36 known ones, their chemical structures were elucidated by the analysis of 1D-, 2D-NMR, mass data and other physicochemical properties, as well as by comparison of the spectral data with the literature. They were identified as (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-glucopyranoside (1), (2Z,6R) -6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-glucopyranoside (2), (-)-(4R)-4,7-dihydroxy-1-menthene 7-O-β-D-glucopyranoside (3), 5-hydroxymethyl-2-furaldehyde (4), 5-hydroxymaltol (5), protocatechuic acid (6), 6-methoxy-7-hydroxycoumarin (7), quercetin-3-O-β-D-glucopyranoside (8), quercetin-3-O-β-D-galactopyranoside (9), rutin (10), kaempferol-3-O-β-D-glucoside (11), kaempferol-3-rutinoside (12), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), 3,4-di-O-caffeoyl-quinic acid (16), 3,5-di-O-caffeoyl-quinic acid (17), 4,5-di-O-caffeoyl-quinic acid (18), methyl chlorogenate (19), (-)-pinoresinol 4-O-β-D-glucopyranoside (20), (+)-simplexoside (21), (-)-sesamin (22), (-)-kobusin (23), rosin (24), phenylmethyl-β-D-glucopyranoside-6'-O-acetate (25), 3,4-dihydroxy-p-menth-1-ene (26), (4R)-p-menth-1-en-4,7-diol (27), (2E,6S)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D-glucopyranoside (28), (2Z,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-β-D-glucopyranoside (29), (2Z,6R)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D-glucopyranoside (30), (2E,6R)-2,6-dimethyl-2,7-octadiene-1,6-diol (31), (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-β-D-glucopyranoside (32), (2E,6R)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D-glucopyranoside (33), (+)-(3S,4S,6R)-3,6-dihydroxy-1-menthene (34), (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 6-O-β-D-glucopyranoside (35), (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 3-O-β-D-glucopyranoside (36), oleanolic acid-3-O-β-D-glucuronopyranoside (37), styraxlignolide E (38), and styraxlignolide D (39), respectively. Among them, the inhibitory effects of 17 selected compounds on LPS-stimulated NO production in BV2 and RAW264.7 cells were investigated. Compound 23 showed significant inhibitory effect against LPS-induced NO production in BV2 and RAW264.7 cells with IC50 values of 14.25 ± 2.69 and 36.35 ± 6.27 μM, respectively. The results showed that (-)-kobusin (23) has the potential anti-neuroinflammatory and anti-inflammatory activities. In addition, the phytochemical study on the roots of A. henryi led to the discovery of twenty compounds, also, their chemical structures were elucidated by the analysis of 1D-, 2D-NMR, mass data and other physicochemical properties, as well as by comparison of the spectral data with the literature. They were identified as 6-methoxy-7-hydroxycoumarin (7), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), (-)-sesamin (22), helioxanthin (40), savinin (41), taiwanin C (42), behenic acid (43), 3-O-caffeoyl-quinic acid (44), 5-O-caffeoyl-quinic acid (45), (+)-threo-(7R,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (46), (+)-erythro-(7S,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (47), ferulic acid (48), caffeic acid (49), stigmasterol (50), β-sitosterol (51), adenosine (52), syringin (53), and trans-coniferin (54), respectively. Among these isolates, compound 41 showed significant inhibitory effect against lipopolysaccharide (LPS)-induced nitric oxide and prostaglandin E2 production with IC50 values of 2.22 ± 0.11 and 2.28 ± 0.23 μM, respectively. These effects of compound 41 were associated with the suppression of LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein. Furthermore, compound 41 negatively regulated the production of interleukin (IL)-1β and tumor-necrosis factor (TNF)-α at the transcriptional level in LPS-stimulated BV2 microglial cells. These anti-neuroinflammatory effects of compound 41 was mediated by p38 mitogen-activated protein kinase (MAPK). The phytochemical investigation on the stems of A. henryi based on LPS-induced macrophages RAW264.7 and microglia BV2 as the bioactivity guided model resulted in eighteen compounds were obtained and their chemical structures were identified as 6-methoxy-7-hydroxycoumarin (7), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), (-)-sesamin (22), 3-O-caffeoyl-quinic acid (44), 5-O-caffeoyl-quinic acid (45), caffeic acid (49), stigmasterol (50), β-sitosterol (51), p-hydroxybenzoic acid (55), trans-p-hydroxycinnamic acid (56), (E)-caffeic acid methyl ester (57), trans-coniferyl aldehyde (58), syringaldehyde (59), vanillin (60), trans-sinapaldehyde (61), and undecanedioic acid, monomethyl ester (62), respectively. Among them, the inhibitory effects of selected compounds on lipopolysaccharide (LPS)-stimulated NO production in RAW264.7 and BV2 cells were investigated. Compound 57 showed significant inhibitory effect against LPS-induced NO production in RAW264.7 and BV2 cells with IC50 values of 1.28 ± 0.11 and 12.18 ± 2.85 μM, respectively. The results showed that isolate 57 has the potential anti-inflammatory and anti-neuroinflammatory activities. The phytochemical investigation on the flowers of A. henryi led to thirteen compounds were obtained, and the chemical structures were identified as quercetin-3-O-β-D-glucopyranoside (8), rutin (10), kaempferol-3-O-β-D-glucoside (11), kaempferol-3-rutinoside (12), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), kaempferol-3-O-α-L-rhamnoside (63), kaempferol (64), dihydrosesamin-9-O-β-D-glucopyranoside (65), eugenol glucoside (66), 3,5-dicaffeoylquinic acid methyl ester (67), and 3,4-dicaffeoylquinic acid methyl ester (68), respectively. Among them, the inhibitory effects of selected compounds on LPS-stimulated NO production in RAW264.7 and BV2 cells were investigated. Compound 68 showed significant inhibitory effect against LPS-induced NO production in RAW264.7 cells with IC50 value of 38.69 ± 2.91 μM. The results showed that compound 68 possess the potential anti-inflammatory activity.
The phytochemical investigation on the fruits of Acanthopanax henryi (Araliaceae) resulted in the discovery of thirty-nine compounds including 3 novel ones and 36 known ones, their chemical structures were elucidated by the analysis of 1D-, 2D-NMR, mass data and other physicochemical properties, as well as by comparison of the spectral data with the literature. They were identified as (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-glucopyranoside (1), (2Z,6R) -6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-(6’-O-acetyl)-O-β-D-glucopyranoside (2), (-)-(4R)-4,7-dihydroxy-1-menthene 7-O-β-D-glucopyranoside (3), 5-hydroxymethyl-2-furaldehyde (4), 5-hydroxymaltol (5), protocatechuic acid (6), 6-methoxy-7-hydroxycoumarin (7), quercetin-3-O-β-D-glucopyranoside (8), quercetin-3-O-β-D-galactopyranoside (9), rutin (10), kaempferol-3-O-β-D-glucoside (11), kaempferol-3-rutinoside (12), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), 3,4-di-O-caffeoyl-quinic acid (16), 3,5-di-O-caffeoyl-quinic acid (17), 4,5-di-O-caffeoyl-quinic acid (18), methyl chlorogenate (19), (-)-pinoresinol 4-O-β-D-glucopyranoside (20), (+)-simplexoside (21), (-)-sesamin (22), (-)-kobusin (23), rosin (24), phenylmethyl-β-D-glucopyranoside-6'-O-acetate (25), 3,4-dihydroxy-p-menth-1-ene (26), (4R)-p-menth-1-en-4,7-diol (27), (2E,6S)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D-glucopyranoside (28), (2Z,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-β-D-glucopyranoside (29), (2Z,6R)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D-glucopyranoside (30), (2E,6R)-2,6-dimethyl-2,7-octadiene-1,6-diol (31), (2E,6R)-6-hydroxy-2,6-dimethyl-2,7-octadien-1-yl-β-D-glucopyranoside (32), (2E,6R)-1-hydroxy-2,6-dimethyl-2,7-octadien-6-yl-β-D-glucopyranoside (33), (+)-(3S,4S,6R)-3,6-dihydroxy-1-menthene (34), (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 6-O-β-D-glucopyranoside (35), (-)-(3S,4S,6R)-3,6-dihydroxy-1-menthene 3-O-β-D-glucopyranoside (36), oleanolic acid-3-O-β-D-glucuronopyranoside (37), styraxlignolide E (38), and styraxlignolide D (39), respectively. Among them, the inhibitory effects of 17 selected compounds on LPS-stimulated NO production in BV2 and RAW264.7 cells were investigated. Compound 23 showed significant inhibitory effect against LPS-induced NO production in BV2 and RAW264.7 cells with IC50 values of 14.25 ± 2.69 and 36.35 ± 6.27 μM, respectively. The results showed that (-)-kobusin (23) has the potential anti-neuroinflammatory and anti-inflammatory activities. In addition, the phytochemical study on the roots of A. henryi led to the discovery of twenty compounds, also, their chemical structures were elucidated by the analysis of 1D-, 2D-NMR, mass data and other physicochemical properties, as well as by comparison of the spectral data with the literature. They were identified as 6-methoxy-7-hydroxycoumarin (7), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), (-)-sesamin (22), helioxanthin (40), savinin (41), taiwanin C (42), behenic acid (43), 3-O-caffeoyl-quinic acid (44), 5-O-caffeoyl-quinic acid (45), (+)-threo-(7R,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (46), (+)-erythro-(7S,8R)-guaiacylglycerol-β-coniferyl aldehyde ether (47), ferulic acid (48), caffeic acid (49), stigmasterol (50), β-sitosterol (51), adenosine (52), syringin (53), and trans-coniferin (54), respectively. Among these isolates, compound 41 showed significant inhibitory effect against lipopolysaccharide (LPS)-induced nitric oxide and prostaglandin E2 production with IC50 values of 2.22 ± 0.11 and 2.28 ± 0.23 μM, respectively. These effects of compound 41 were associated with the suppression of LPS-induced expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase-2 (COX-2) protein. Furthermore, compound 41 negatively regulated the production of interleukin (IL)-1β and tumor-necrosis factor (TNF)-α at the transcriptional level in LPS-stimulated BV2 microglial cells. These anti-neuroinflammatory effects of compound 41 was mediated by p38 mitogen-activated protein kinase (MAPK). The phytochemical investigation on the stems of A. henryi based on LPS-induced macrophages RAW264.7 and microglia BV2 as the bioactivity guided model resulted in eighteen compounds were obtained and their chemical structures were identified as 6-methoxy-7-hydroxycoumarin (7), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), (-)-sesamin (22), 3-O-caffeoyl-quinic acid (44), 5-O-caffeoyl-quinic acid (45), caffeic acid (49), stigmasterol (50), β-sitosterol (51), p-hydroxybenzoic acid (55), trans-p-hydroxycinnamic acid (56), (E)-caffeic acid methyl ester (57), trans-coniferyl aldehyde (58), syringaldehyde (59), vanillin (60), trans-sinapaldehyde (61), and undecanedioic acid, monomethyl ester (62), respectively. Among them, the inhibitory effects of selected compounds on lipopolysaccharide (LPS)-stimulated NO production in RAW264.7 and BV2 cells were investigated. Compound 57 showed significant inhibitory effect against LPS-induced NO production in RAW264.7 and BV2 cells with IC50 values of 1.28 ± 0.11 and 12.18 ± 2.85 μM, respectively. The results showed that isolate 57 has the potential anti-inflammatory and anti-neuroinflammatory activities. The phytochemical investigation on the flowers of A. henryi led to thirteen compounds were obtained, and the chemical structures were identified as quercetin-3-O-β-D-glucopyranoside (8), rutin (10), kaempferol-3-O-β-D-glucoside (11), kaempferol-3-rutinoside (12), 1,3-di-O-caffeoyl-quinic acid (13), 1,4-di-O-caffeoyl-quinic acid (14), 1,5-di-O-caffeoyl-quinic acid (15), kaempferol-3-O-α-L-rhamnoside (63), kaempferol (64), dihydrosesamin-9-O-β-D-glucopyranoside (65), eugenol glucoside (66), 3,5-dicaffeoylquinic acid methyl ester (67), and 3,4-dicaffeoylquinic acid methyl ester (68), respectively. Among them, the inhibitory effects of selected compounds on LPS-stimulated NO production in RAW264.7 and BV2 cells were investigated. Compound 68 showed significant inhibitory effect against LPS-induced NO production in RAW264.7 cells with IC50 value of 38.69 ± 2.91 μM. The results showed that compound 68 possess the potential anti-inflammatory activity.
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