Active Substances from Callicarpa nudiflora Exert Anti-Cervicitis Effects and Regulate NLRP3-Associated Inflammation

Luohuazizhu suppository is a Traditional Chinese Medicine used in clinic to treat cervicitis, which is prepared from Callicarpa nudiflora Hook. et Arn (C. nudiflora), an herbal Chinese medicine named Luohuazizhu. This study aimed to figure out the active constituents of C. nudiflora and the potential mechanism for its anti-cervicitis effect. The ethanol extract in C. nudiflora (CNE) and the different fractions of CNE extracted by petroleum ether (CNE-p), dichloromethane (CNE-d), and n-butanol (CNE-b) were tested in vivo for their anti-cervicitis effects. Then the isolated compounds from the CNE-p were tested in vitro for their anti-inflammatory activities. The results displayed that CNE-p, CNE-d, and CNE-b exhibited adequate anti-cervicitis effects, with CNE-p showing the highest efficacy. Further experiment demonstrated that CNE-p could significantly inhibit the expression of NLRP3 in vitro. Six diterpenoids obtained from the CNE-p showed the ability to regulate inflammatory factor levels in vitro. Among these compounds, compounds 1 (callicarpic acid A) and 2 (syn-3,4-seco-12S-hydroxy-15,16-epoxy-4(18),8(17),3(16),14(15)-labdatetraen-3-oic acid) were the most effective agents, and they also inhibited the expression level of NLRP3 in vitro. The results confirmed that C. nudiflora has significant anti-cervicitis effects and the diterpenoids were most likely to be its active components. These data provide scientific support for the clinic usage of Luohuazizhu suppository and the development of new agents in treating cervicitis.     

Two New Diterpenoids from Callicarpa pedunculata

Two new diterpenoids, pedunculatic acid A (= (4R,5α,7α)‐7‐ethoxy‐9β,13β‐dioxyabiet‐8(14)‐en‐18‐oic acid; 1 ) and pedunculatic acid B (= (4S,5α,12β)‐8β,14β‐epoxy‐12‐hydroxy‐11‐oxototaran‐19‐oic acid; 2 ), together with three known sesquiterpenoids, were isolated from the Chinese medicinal herb Callicarpa pedunculata R. Brown . Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR, and by high‐resolution mass spectrometry.     

裸花紫珠抗炎作用及增强免疫功能的实验研究

研究了裸花紫珠的抗炎作用及对小鼠免疫功能的影响。结果表明,裸花紫珠能明显抑制二甲苯所致的小鼠耳廓肿胀和角叉菜胶所致的大鼠足跖肿胀,表明其具有良好的抗炎作用;裸花紫珠能增加小鼠碳粒廓清指数,表明其可增强机体免疫能力。     

Three new labdane-type diterpenoids from Callicarpa macrophylla Vahl.

Three new labdane-type diterpenoids, callicapene M3-M5 (1–3) were isolated from the Callicarpa macrophylla Vahl. Their structures were identified by spectroscopic method. The isolated compounds were evaluated for inhibitory activity on NO production in LPS-activated RAW 264.7 macrophage cells by using MTT assays. Compounds 1–3 showed potent inhibitory activity, with IC₅₀ value of 48.15, 46.31 and 38.72?μM respectively.     

Lignanoids and Diterpenoids from Callicarpa furfuraceae

The three new lignanoids 1 – 3 and the five new phyllocladane diterpenoids 7 – 11 were isolated from the leaves of Callicarpa furfuraceae, together with two known lignanoids, lariciresinol ( 4 ) and (+)‐sesamin ( 5 ), and five known diterpenoids, 17‐norphyllocladane‐3,16‐dion ( 6 ), calliterpenone ( 12 ), calliterpenone 17‐acetate ( 13 ), (3β,16α)‐phyllocladane‐3,16,17‐triol ( 14 ), and (3β,16α)‐phyllocladane‐3,16,17‐triol 17‐acetate ( 15 ). Their structures were established by spectral‐data interpretation.     

Two New Phenylethanoid Glycosides from Callicarpa longissima

Two new phenylethanoid glycosides, longissimosides A and B ( 1 and 2 , resp.), together with eight structurally related known compounds, were isolated from the EtOH extract of leaves and stems of Callicarpa longissima (Hemsl .) Merr . The structures of 1 and 2 were elucidated as 2‐(3,4‐dihydroxyphenyl)ethyl O‐(α‐L ‐rhamnopyranosyl)‐(1→3)‐O‐(2‐O‐syringoyl‐β‐D ‐xylopyranosyl)‐(1→6)‐ 4‐O‐[(E)‐caffeoyl]‐β‐D ‐glucopyranoside ( 1 ) and 2‐(3‐hydroxy‐4‐methoxyphenyl)ethyl O‐(α‐L ‐rhamnopyranosyl)‐(1→3)‐O‐(β‐D ‐apiofuranosyl)‐(1→6)‐4‐O‐[(E)‐isoferuloyl]‐β‐D ‐glucopyranoside ( 2 ) on the basis of spectroscopic data and acid hydrolysis.     

Two New Diterpenoids from Isodon rubescens

In order to further study on minor diterpenoid constituents of lsodon rubescens, wereinvestigated this species, which was collected in Taibai mountain, Shaanxi Province.TWo new diterpenoids, taibairubescensins A (l) and B (2), were isolated. In this paper,we present the structure elucidation of these two new diterpenoids.Taibairubescensin A (l ), C,.H,#O, (FABMS m/z 435[M 11 ), an amorphous powder,showed UV and iR absorption bands for the existence of hydroxyl, acetoxyl and a fivemembe…     

Nine New Norlabdane Diterpenoids from the Leaves of Austroeupatorium inulifolium

Nine new norlabdane diterpenoids were isolated from the leaves of Austroeupatorium inulifolium collected in Indonesia. All of them have an acyl‐furan unit connected to C(11), and oxygenated functions at C(2) and C(3). The structure elucidations and the assignment of the absolute configurations of the isolated natural products were carried out by extensive spectroscopic analysis and the extended Mosher method, as well as chemical correlations. Antimicrobial activities and cytotoxicity against HL‐60 cells were determined using bioassays.     

Two New ent-Kaurane Diterpenoids from Isodon xerophilus

In continuation of our research on diterpenoids in the Isodon species, several newcompounds"' were obtained from the leaves oflsodon xerophilus (C. Y. Wu et H. W. Li)H. Hara (Labiatae), a perennial shrub native to Yunnan province. Further fractionation ofthe EtOAc extract led to the isolation of tWo new enl-kauranoids, xerophilusin E (l) andxerophilusin F (2). This paper deals with the structUral elucidation of the newcompounds.Xerophilusin E (l), a minor constitUent, was obtained as p…     

Two New Diterpenoids and Other Constituents from Isodon japonicus

Two new ent‐kaurene diterpenoids, 15α,20‐dihydroxy‐6,7‐seco‐entkaur‐16‐ene‐7,1α(6,11α)‐diolide ( 1 ), 6β‐butyroxy‐3β‐hydroxy‐6,7‐seco‐6,20‐epoxy‐7,1α‐olide‐entkaur‐16‐en‐15‐one ( 2 ), together with 25 known compounds, 3 – 27 , were isolated from the leaves of Isodon japonicus. Their structures were established by spectroscopic methods, including 2D‐NMR techniques.     

Two New Abietane Diterpenoids from Coleus xanthanthus

In our previous paper1, we reported a novel sesquiterpenoid from the EtOAc part of Coleus xanthanthus. The continuous work for the investigation of the petroleum part of C. xanthanthus led to the isolation of two new abietane diterpenoids which were identified as 11-acetoxy-coleon U(1) and 11,16-diacetoxy-coleon U(2) by spectral methods. Figure 1 The structures of 1 and 2 1 2 R= H OAcCompound 1 was obtained as pale yellow cubic crystals, mp:190.5-1920C; [(]+ 20.50 (c=0.875, CHCl3). Its…     

Two New ent-Kaurane Diterpenoids from Isodon adenantha

As a medicinal herb locally used for the treatment of enteritis and dysentery in Yunnan province2, Isodon adenantha (Diels) Hara has been previously studied, which led to the isolation of several ent-kaurane diterpenoids including a new one3-5. In continuation of our research on the bio-active constituents from Isodon species6, two new ent-kaurane diterpenoids, adenanthins B (1) and C (2), were isolated from I. adenantha collected in Dali, Yunnan. In this paper, we report the structural el…     

A Rare New Cleistanthane Diterpene from the Pericarp of Trewia nudiflora

A minor, unprecedented diterpene, 3β,17‐dihydroxycleistantha‐12,15‐dien‐2‐one ( 1 ), was isolated from the CHCl₃‐soluble part of the EtOH extract of the pericarp of Trewia nudiflora. The structure of 1 was elucidated by means of 1D‐ and 2D‐NMR spectroscopic analyses as well as by HR‐MS. Also isolated were two known triterpenes, glutin‐5‐en‐3‐ol and olean‐18‐en‐3‐one (germanicone), as well as three known sterols, (22E,24R)‐5α,8α‐epidioxyergosta‐6,22‐dien‐3β‐ol, (22E,24R)‐5α,8α‐epidioxyergosta‐6,9(11),22‐trien‐3β‐ol, and (22E,24R)‐6‐methoxyergosta‐7,22‐dien‐3,5‐diol.     

New Diterpenoids from Coleus forskohlii

Two new diterpenoids, forskolin G and H were isolated from the chloroform extract of the roots of Coleus forskohlii, and based on spectroscopic data,their structures were identified as 1α-hydroxy-6β,7β-diacetoxy-8,13-epoxylabd-14-ene-11-one(1),and 1α，6β-diacetoxy-8,13-epoxy labd-14-ene-11-one (2),respectively.     

Three New ent‐Trachylobane Diterpenoids from Co‐cultures of the Calli of Trewia nudiflora and Fusarium sp. WXE

Five diterpenoids, including three new ent‐trachylobane diterpenoids, i.e., (3α)‐3‐hydroxy‐ent‐trachylobane‐17,19‐dioic acid 19‐methyl ester ( 1 ), ent‐trachylobane‐17,19‐dioic acid 19‐methyl ester ( 2 ), ent‐trachylobane‐17,19‐dioic acid ( 3 ), and two known atisane‐type ones, i.e., (16α)‐16,17‐dihydroxy‐ent‐atisan‐19‐oic acid methyl ester ( 4 ), and 17‐hydroxy‐ent‐atisan‐19‐oic acid methyl ester ( 5 ), were isolated from the co‐culture extract of the calli of Trewia nudiflora and its endophytic fungus Fusarium sp. WXE. Their structures were elucidated by spectroscopic analyses, including 1D‐ and 2D‐NMR experiments, and HR‐Q‐TOF mass spectrometry. The antitumor and antibacterial properties of the new compounds were evaluated.     

Three New Diterpenoids from Isodon Eriocalyx

Isodoneriocalyxisknowntoberichinent-kaurenoids.Inspiteofthatmanyent-kaurenoidswereisolated,newent-kaurenoidswerestillisolatedfromcollectionindifferentregions'-,o.FromthedriedleavesofthisspeciescollectedinHeqingcounty,Yunnan,threenewcompounds,eriocalyxinsC-El-3,wereisolated.Inthispaper,wereportthestructureelucidationofthesenewcompoundsbyspectralanalysis.EriocaIyxinClC22H2sO7(HRMS4O4.l825calc4O4.1835),ElMS(7OeV)In/z(reI.Int%)t4O4[M1 (lO),386[M-H2O] 'lO),368IM-2H,O] (2O),344(l00),32…     

New Casbane Diterpenoids from the Hainan Soft Coral Sinularia Species

Six new casbane diterpenoids, sinularcasbanes G–L ( 1 – 6 , resp.) were isolated from the soft coral Sinularia sp. Their structures were established by extensive spectroscopic analyses, especially 2D‐NMR and HR‐ESI‐MS. The configuration was confirmed by CD analyses and by comparison with data reported in the literature. The compounds were evaluated for cytotoxicity against ten human cancer cell lines (H1975, U937, K562, BGC823, MOLT‐4, MCF‐7, A549, HeLa, HL60, and Huh‐7) and showed no activity.     

Four New Diterpenoids from Isodon leucophylla

IsodonleucoPhyll(Dunn)Hara(Labiatae),distributedinthenorthwestareaofYunnanProvince,isusedasfolkmedicineforitsantibacterialandanti-inflanimatoryactivitybylocalpractitioners'.Fromtheleavesofthisplant,fournewent-kauranetypediterPenoids,baiyecrystalA'C1'3andePi-baiyecrystalC4,wereisolated.Thispaperpresentstheirsimctureelucidation.BaiyecrystalA1C26H34O1owasdeterminedbyHRMS(5O6.2157,calc5o6.2l52).Itsmassspectrumshowedthatthemolecularion(wt5O6)was58amumorethanthatofeffusaninD5',aknownkaureno…     

Anti-NLRP3 inflammasome abietane diterpenoids from Callicarpa bodinieri and their structure elucidation

Callica rpabodinieri is a Chinese traditional medicine herb with anti-inflammatory activity in clinic.Herein,we report two new 9,10-seco and etherified abietane diterpenoids bodinieric acids J and K(1 and 2) and one known compound(3) isolated from the leaves and twigs of this plant.Their chemical structures were elucidated by detailed spectrometry data analysis and DP4+NMR calculation methods.Hypothetical biosynthetic pathways of 1-3 were preliminarily speculated.Compound 3 inhibited inflammasome activation and exhibited blockage of NLRP3 inflammasome activation at non-cytotoxic concentrations in vitro.     

Two New Abietane Diterpenoids from the Stems of Clerodendrum kaichianum P. S. Hsu

Two new abietane diterpenoids, named 17‐hydroxyteuvincenone G ( 1 ) and 17‐hydroxyteuvincen‐5(6)‐enone G ( 2 ), together with four known diterpenoids, were isolated from the stems of Clerodendrum kaichianum P. S. Hsu . Their structures were elucidated by extensive NMR and MS analyses, and by comparison with literature data. The new compounds showed significant cytotoxicities against the HL‐60 and A‐549 tumor cell lines.