用改良過的 Pictet-Spengler 反應將L-tryptophan、L-tryptophan ester及L-tryptophan amide與glyoxal化合物以一步驟合成得到一系列1-取代及1,3-二取代-β-carboline 衍生物。利用此方法成功地合成了從呂宋青藤（Illigera luzonensis）所分離得到的化合物 luzongerine A（56b）；從銀柴胡（Stellaria dichotoma L. var. lanceolata Bge.）根部所分離得到的 stellarine A（58），亦利用此方法成功地合成出單一產物；以往合成1-(4-methoxy-benzoyl)-9H-β-carboline-3-carboxylic acid methyl ester（60）的步驟複雜，應用本方法亦成功地一步驟合成出來。
合成得到的1-取代及1,3-二取代-β-carboline化合物進行細胞毒殺活性測試及以LPS刺激巨噬細胞RAW264.7產生前列腺素E2（PGE2）及一氧化氮（NO）之模式進行抗發炎活性試驗。除了化合物（10c）、（37c）及（40c）之外，其他化合物對四株受測癌細胞沒有顯著的細胞毒殺活性。化合物luzongerine A抑制誘導一氧化氮合成酶（iNOS）的效果與濃度成線性關係。大部份受測化合物可以有效抑制PGE2與NO的生成，其中化合物（39a）與（36b）能有效地降低iNOS與COX-2蛋白質的表現，這樣的結果顯示合成得到的β-carboline衍生物在轉譯階段確實抑制NO及PGE2的產生。除此之外，化合物（10a）、（10c）、（35a）、（37a）~（40a）、（40c）、（42b）、（43a）、（44a）、（45b）、（46a）、（47b）、（47c）與（58），與對照組indomethacin比較，對於超氧陰離子與彈性蛋白酶具有顯著的抑制效果，其中化合物（39a）效果最佳。化合物（39a）進一步利用西方墨點法觀察其對於fMLP誘發的嗜中性白血球中之JNK與AKT的磷酸化所造成的影響，結果fMLP誘發的嗜中性白血球中之JNK與AKT的磷酸化很明顯地受到化合物（39a）的抑制，因此可以確認化合物（39a）確實藉由調控JNK與AKT的訊息傳遞路徑達到抑制嗜中性白血球的活性。因此合成所得到之1-benzoyl-3-carboxy β-carboline類化合物具有開發為抗發炎藥物的潛力。
從冬蟲夏草菌絲體的抗發炎劃分共分離得到50個化合物，並經光譜分析與化學方法鑑定確認其結構，其中有5個為天然界首次分離得到的化合物，分別為cordysinin A (338)、cordysinin B (339)、cordysinin C (340)、cordysinin D (341)及cordysinin E (342)。分離得到的化合物中，ergosteryl-3-O-β-D-glucopyranoside（228）及1-(5-hydroxymethyl-2-furyl)-β-carboline（331）對於超氧陰離子與彈性蛋白酶具有顯著的抑制效果，顯示這些化合物為冬蟲夏草菌絲體中具有抗發炎活性的成分。

A one-step conversion of L-tryptophan, L-tryptophan ester and L-tryptophan amide with glyoxals directly to various 1-substituted and 1,3-disubstituted β-carboline derivatives under modified Pictet-Spengler conditions was described. Moreover, practical applicatios for the synthesis of some β-carbolines, including luzongerine A (56b) purified from Illigera luzonensis, stellarine A (58) identified from Stellaria dichotoma L. var. lanceolata Bge., and 1-(4-methoxy-benzoyl)-9H-β-carboline-3-carboxylic acid methyl ester (60) were also successfully carried out utilizing this protocol.
The synthetic compounds were examined for cytotoxicity and anti-inflammatory activity, as measured by the inhibition of prostaglandin E2 (PGE2) production and nitric oxide (NO) production in LPS/IFN-γstimulated RAW 264.7 macrophage cells. Among the testes compounds, only three compounds 10c, 37c and 40c showed marginal cytotoxicity against four human cancer cell lines. Luzongerine A displayed significant dose-dependent inhibition of inducible nitric oxide synthase (iNOS). Most of the tested compounds exhibited potent inhibitory activity of both NO and PGE2 production. Compounds 39a and 36b significantly reduced the expression of inducible nitric oxide synthase (iNOS) and cyclooxygenase 2 (COX2), suggesting that β-carboline analogs can inhibit NO and PGE2 production at the translational level. In addition, several of the β-carboline derivatives (10a, 10c, 35a, 37a-40a, 40c, 42b, 43a, 44a, 45b, 46a, 47b, 47c and 58) displayed significant inhibitory activity of superoxide anion generation or elastase release compared to the reference compound, indomethacin, with 39a being the most potent. N-Formyl-L- methionyl-phenylalanine (FMLP)-induced phosphorylation of c-Jun N-terminal kinase (JNK) and protein kinase B (AKT) were also inhibited by 39a, suggesting that it suppresses human neutrophil functions by inhibiting the activation of JNK and AKT signaling pathways. Therefore, the synthetic 1-benzoyl-3-carboxy β-carboline analogs may have great potential to be developed as anti-inflammatory agents.
The chemical investigation for the bioactive fractions of the mycelia of Cordyceps sinensis has resulted in the characterization of fifty compounds, including five constituents, cordysinins A-E (338-342) reported from the natural source for the first time. The chemical structures of cordysinins A-E (338-342) were comprehensively established with the NMR spectroscopic and mass spectrometric analyses, and by the Mosher’s method. In addition, some isolates were examined for their anti-inflammatory bioactivities. Among these tested compounds, ergosteryl-3-O-β-D-glucopyranoside (228) and 1-(5-hydroxymethyl-2-furyl)-β-carboline (331) displayed significant inhibition of superoxide anion generation and elastase release. These results indicated that these compounds should be the anti-inflammatory principles in the mycelia of C. sinensis.

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